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Location: Azerbaijan; Ukraine About Onedome We're a UK fintech building high-throughput digital infrastructure for the mortgage and property space. Recently acquired Trussle. We're taking our platform to the next level: fully automated, self-healing, observable, and built to handle real traffic spikes (we have a TV launch coming up). The role You'll be our senior platform engineer. Not a traditional ops role. You'll treat infrastructure as a product, build the internal developer platform our engineers deploy through, and bring SRE discipline into the application tier when it's needed. You won't have a platform team to lean on. You'll be building that capability. We know exactly what we need. What you'll do Own 5 AWS accounts across the organisation (QA, Prod, Infra, plus two others) Architect and maintain infrastructure as code with Terraform. Replace the click-ops that's still around Stand up CI/CD pipelines engineers actually want to use. Blue/green and canary where it makes sense Run releases reliably and reduce key-person risk on the deploy process Set up monitoring, alerting, and incident response so we catch issues before customers do. Define SLIs and SLOs that map to real user journeys Lead incident response as the primary infra responder. Run blameless post-mortems Patch and harden the platform. We're a fintech, this matters. IAM least privilege, secrets management, vulnerability scanning, MFA enforcement Lead infrastructure work for the TV launch: traffic spikes, autoscaling, capacity planning, runbooks Partner with backend engineers when production issues cross into the app tier. JVM tuning, connection pools, async patterns, memory leaks Architect multi-region DR. Drive the platform toward self-healing Optimise cost across DynamoDB, Lambda, and the wider AWS footprint Set architectural guardrails with tech leads and SWEs. Mentor engineers as the platform capability grows You must have 6+ years hands-on AWS in production (VPC, IAM, EC2/ECS/EKS, Lambda, S3, CloudFront, Route53, RDS, DynamoDB, SQS) Production Terraform (Terragrunt a plus). Multi-environment state management Production Kubernetes and Docker. EKS specifically Strong CI/CD experience: GitHub Actions, GitLab, Jenkins, or ArgoCD. GitOps practices Strong infrastructure security: IAM least privilege, secrets, patching, vulnerability scanning, MFA enforcement Observability from scratch: CloudWatch, Datadog, Grafana, Prometheus, OpenTelemetry, or ELK Solid backend competency in Java (Spring Boot), Python, or Node. Understanding of JVM, concurrency, async systems Comfort being the senior infrastructure person. Self-directed, opinionated, disciplined about documentation B2/C1 Level English Nice to have Fintech or other regulated industry experience DynamoDB at scale (we run many tables with PITR and S3 exports, Lambda-driven daily incrementals) AWS cost optimisation track record Past experience as a first infrastructure hire at a small team Building internal developer platforms or self-service tooling AWS DevOps Pro, Solutions Architect Pro, or CKA Service mesh experience (Istio, Linkerd) and DevSecOps practices Firebase or GCP exposure (we have a small footprint there) What you won't get from us A platform team to lean on. You'll be building that capability Click-ops everywhere. You'll be replacing what exists with IaC Ambiguity about the work. We know exactly what we need Working setup UK working hours. Fully remote across the EU Tooling: Microsoft 365, Teams, Planner, Nuclino, GitHub aws-vault with MFA enforcement on all accounts Sustainable on-call rotation Salary: $4,000 – $5,000 / month

Location: Brazil About Huzzle At Huzzle, we connect exceptional talent with top opportunities at leading companies across the UK, US, Canada, Europe, and Australia. Our clients include startups, digital agencies, and tech platforms in industries such as SaaS, MarTech, FinTech, and EdTech. Unlike an outsourcing agency, we place you directly with a client where you’re hired in-house as a valued member of their team. Role Type: Full-time Engagement: Independent Contractor Job Summary We are looking for a high-level Media Buyer and Creative Strategist based in Brazil to take full ownership of 17 Meta ad accounts in the high-stakes mortgage and first-time homebuyer lead generation niche. You will be responsible for the entire performance loop: diagnosing funnel issues, architecting creative angles that crush existing controls, and managing significant budgets to drive high-quality SQLs. If you are a data-driven marketer who thinks in terms of business bottom lines rather than just platform metrics, this is your opportunity to lead expansion for a fast-growing team. Key Responsibilities Own the end-to-end performance of 17 Meta ad accounts, focusing on lead generation for the mortgage industry Lead the creative strategy process by originating ad angles, hooks, and scripts that outperform current controls Diagnose performance bottlenecks by analyzing the interplay between CPL, CTR, CVR, and CAC to determine if the issue lies in the offer, the funnel, or the creative Write comprehensive creative briefs and manage the production workflow independently Lead client-facing calls in English, presenting data, insights, and strategic pivots with confidence Manage daily optimizations, scaling successful campaigns, and maintaining strict cost-per-booked-call targets Work synchronously with the US-based team during Pacific Standard Time hours Requirements 3+ years hands-on Meta Ads experience, ideally agency or multi-brand. Must be based in Brazil Proven ownership of campaign performance and business results, not just setup/optimization. Background in lead generation, service-based businesses, agencies, or info products. Experienced managing multiple accounts simultaneously. Strong Meta Ads expertise, including testing, optimization, creative angles, hooks, and concepts. Proven ability to beat existing controls with new creative strategies, backed by measurable results. Able to diagnose whether performance issues stem from the offer, funnel, creative, audience, or campaign structure. Strong understanding of CPL, CTR, CVR, CAC, cost per booked call, and cost per SQL. Must be able to interpret performance data and explain the next action, not simply report metrics. Benefits 💰 Competitive salary: Tailored based on skillset and experience 🌎 Fully remote: Work from anywhere with a flexible schedule. 🚀 Growth-oriented environment: Join a young, creative, and fast-scaling marketing team. 🎨 Creative freedom: Work on innovative campaigns for diverse clients.

Location: US - Remote; San Francisco, CA; New York, NY; Washington, D.C. Workplace: Remote ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE PUBLIC SECTOR TEAM - Sierra recently received FedRAMP High https://sierra.ai/blog/certified-fedramp-high certification and were awarded our first contract with a federal agency. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry. - Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies. - We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions. - In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do. WHAT YOU'LL DO - Build and lead Sierra’s public sector sales team: Recruit, develop, and lead a team of account executives serving strategic federal, state, or local government accounts. Set clear expectations, coach for performance, and build a culture of customer obsession, accountability, and consistent execution. - Own revenue growth and territory strategy: Translate Sierra’s public sector ambitions into territory coverage, account priorities, pipeline goals, and revenue plans. Allocate resources thoughtfully, maintain rigorous forecasts, and drive the team to consistently achieve or exceed revenue targets. - Create opportunities around mission outcomes: Build executive relationships with agency leaders and help your team translate priorities such as constituent access, service delivery, workforce effectiveness, and program integrity into compelling AI agent opportunities. Serve as an executive sponsor for strategic accounts. - Guide complex sales cycles from discovery through award: Coach account executives through long, multi-stakeholder government buying processes and engage directly at critical moments. Mobilize cross-functional support for executive alignment, solution development, business cases, security and legal reviews, pricing, proposal strategy, negotiation, and close. - Shape acquisition and capture strategy: Ensure every priority opportunity has a credible path to contract and a disciplined capture plan. Help the team navigate funding, fiscal-year timing, competitive dynamics, and procurement pathways—including GSA schedules, GWACs, IDIQs, BPAs, state schedules, and cooperative purchasing agreements. Lead deal reviews that surface risks early and turn strategy into clear next steps. - Scale Sierra’s partner ecosystem: Partner with public sector and partnerships leadership to build productive relationships with prime contractors, systems integrators, resellers, distributors, small-business partners, and technology providers. Guide decisions about direct sales, subcontracting, teaming, and partner-led transactions to expand customer access and accelerate growth. - Lead strategic prime and teaming relationships: Establish executive alignment with key partners and help shape account ownership, deal registration, workshare, and joint go-to-market plans. Ensure partnerships bring meaningful customer access, past performance, implementation capacity, or procurement pathways—and translate into qualified pipeline and successful delivery. - Drive disciplined pursuit and proposal decisions: Partner with the Public Sector GM on bid/no-bid recommendations and prioritize resources across strategic pursuits. Align sales, legal, security, product, engineering, and delivery teams to produce procurement responses that are compliant, differentiated, and precise. - Stay accountable for customer success: Build trust with senior agency leaders, establish strong handoffs from sales to delivery, and remain engaged through deployment and expansion. Help resolve escalations and ensure commitments made during the sales process support lasting customer relationships. - Build a repeatable public sector go-to-market motion: Work with public sector leadership to refine account segmentation, hiring and capacity plans, capture processes, partner strategy, contract-vehicle priorities, and sales playbooks. Bring market signals and customer feedback to product and company leadership to shape Sierra’s platform and public sector strategy. - Lead an AI-native sales organization: Embed AI into how the team researches accounts, develops outreach, synthesizes calls, plans opportunities, creates proposals, and forecasts. Model effective use, share successful practices, and help account executives spend more time on judgment, strategy, and customer relationships. WHAT YOU'LL BRING - 15+ years of selling experience: Extensive experience in enterprise customer-facing sales role, specifically selling to the U.S. government. - People leadership experience: 10+ years managing, mentoring, and developing a high-performing enterprise sales team. - Enterprise experience: You've run and managed end-to-end complex deals ($1M+). - Strong fluency in government acquisition and procurement, including funding and budget cycles, competitive solicitations, proposal processes, task orders, and common Federal or state contract vehicles. - Experience developing and executing capture strategies before a solicitation is released—not simply responding once an RFP is public. - A strong network and demonstrated ability to work with government technology partners, including prime contractors, systems integrators, resellers, distributors, and small-business teaming partners. - Sound judgment about direct, channel, prime/subcontractor, and teaming models, with the ability to select and execute the right path for a particular agency and opportunity. - The ability to build credibility with agency executives, program leaders, contracting and procurement officials, security teams, and technical stakeholders—and to align those groups around a shared path forward. - Excellent executive communication, negotiation, account planning, and forecasting skills. You are rigorous about details, procurement milestones, and next steps. - A passion for public sector work and a belief in the potential of government institutions to improve outcomes for the people they serve. - Comfort operating with high ownership in an early-stage business: you create structure where it does not yet exist, move with urgency, and collaborate deeply across functions. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Управлять производством контента от идеи до публикации. Один человек на short-form (Reels, Shorts), второй на YouTube long-form.

Location: Singapore Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. WHAT YOU'LL DO - GTM technical expert: Design and demo Sierra’s incredible Agent product, offering technical solutions to solve for our customer’s needs, and answering technical questions about our solutions. - Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy. - Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution. WHAT YOU'LL BRING - 5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales. - Past experience in demo building, and presenting, and working with customers or clients in the GTM function. - Experience in relationship-building with potential customers, including executives and technical leaders. - Experience in leading the sales process with Enterprise customers. - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience. EVEN BETTER... - AI-related experience (or experience in a similarly modern and highly technical industry). - Experience translating code, technical logic and user requirements to product and engineering requirements. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: Singapore Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. WHAT YOU'LL DO - Team leadership: Manage and mentor a team of Sales Engineers, providing support to help onboard and develop team members. This role reports to our Head of Sales Engineering. - Set clear performance expectations: Establish and communicate key performance indicators (KPIs) and objectives for the team. Monitor individual and team performance to ensure everyone is working towards meeting or exceeding goals. - GTM technical expert: Design and demo Sierra’s incredible Agent product, offering technical solutions to solve for our customer’s needs, and answering technical questions about our solutions. - Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy. - Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution. - Identify & strengthen partnerships: Identify opportunities and strengthen partnership between Sales Engineering and Sales teams to ensure alignment in objectives, seamless customer engagement, and efficient handoffs. Promote a culture of teamwork and shared goals, creating joint strategies to enhance both technical and commercial outcomes. - Lead across APJ: Build and lead the Sales Engineering team across Southeast Asia, Australia & New Zealand, Korea, and Japan. Adapt our technical sales motion to each market's customers, languages, and buying processes, and partner with regional Sales leaders to grow Sierra's presence across the region.   WHAT YOU'LL BRING - 6+ years experience in managing a team of Sales Engineers or Solutions Engineers. - Past experience in demo building, and presenting, and working with customers or clients in the GTM function. - Experience in relationship-building with potential customers, including executives and technical leaders. - Experience in leading the sales process with Enterprise customers. - A track record of deploying and leading Sales Engineering or Solutions Engineering teams across APJ markets, including Southeast Asia, ANZ, Korea, and Japan. - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: San Francisco, CA; New York, NY Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE TECH, MEDIA & TELECOM TEAM - We work with some of the world's most influential and recognizable companies, from global telecommunications providers and leading media brands to technology platforms that power businesses worldwide. - We build agents for the moments that matter, helping our customers rise to the occasion when service disruptions, major product launches, or global events like the World Cup https://www.linkedin.com/posts/claybavor_at-sierra-we-are-very-proud-to-have-partnered-activity-7491200203899760641-I27d?utm_source=share&utm_medium=member_desktop&rcm=ACoAABYjELMBZfjrg-wrv53M1tVXGe93FF3eTww drive millions of customer interactions. - We bring Sierra’s Horizon https://sierra.ai/product/horizon vision to TMT by building agents that transform the entire customer relationship: - Telecommunications: Turn one of the most frustrating customer experiences into one of the most personal, with agents that understand each subscriber, optimize their plan and savings, anticipate opportunities to add value, and earn their loyalty over time. - Media: Turn every subscription into an ongoing, personalized relationship, with agents that help each subscriber get the most from their experience through the right content, offer, plan, and support from their free trial through retention. - Technology: Bring the white-glove customer experience traditionally reserved for the largest enterprise accounts to every customer, helping them adopt the product, discover new ways to get value, expand their usage, and successfully renew. WHAT YOU’LL DO - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce. - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way. - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency. - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product. EXAMPLE PROJECTS These are some examples of projects that engineers on our team have worked on recently: - Create agents that pursue goals over weeks and months, reasoning about when to reach out, which channel to use, and what next action will move a customer relationship forward. - Develop personalization and experimentation systems powered by Sierra's Context Engine https://sierra.ai/blog/context-engine that combine customer data, behavior, prior conversations, and real-time context to determine the right offer or experience, then learn from every interaction and experiment to autonomously improve personalization over time. - Design conversational discovery agents that reason across huge content catalogs and rich subscriber context, using interests, history, entitlements, and the moment at hand to help someone quickly find something they'll actually want to watch, read, or listen to. - Build agents that troubleshoot deeply integrated telecommunications and connected-device experiences, reasoning across account, billing, network, and device systems to diagnose issues and take the actions needed to resolve them. - Experiment with new voice experiences and Voice Personas https://sierra.ai/blog/introducing-voice-personas tailored to each brand, customer, and moment, bringing the right empathy, energy, and conversational style to everything from navigating a frustrating telecom billing issue to helping someone discover their next favorite show or find the plan that's right for them. WHAT YOU'LL BRING - Experience building and scaling end-to-end production systems. - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments. - A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship. - Comfort working directly with customers to understand their needs and solve real-world problems. - Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences. - Excitement in the Tech, Media & Telecom space and a care for helping some of the world’s top brands continue to build brand loyalty with their customers. EVEN BETTER... - Experience building or deploying AI/LLM systems in production - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering - Prior experience with React, TypeScript, and/or Go - Previous roles where you interfaced with customers or led technical projects with external stakeholders OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: San Francisco, CA; New York, NY; Atlanta, GA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE TRAVEL, TRANSPORTATION AND HOSPITALITY TEAM - The Travel, Transportation and Hospitality (TTH) supports some of the largest airlines, hotel chains, rental car brands, cruise lines and travel tech companies in the world. Our customers are frontiers in the travel space, and are true thought partners in shaping our platform, helping reinvent what hospitality looks like in this new era. Our customers rely on us to not only deliver standout customer experiences, driving stronger growth in their business. - Our TTH team is constantly pushing the bounds of what is possible within this industry and beyond. We help support our customers in the moments that matter — whether that’s proactively encouraging new bookings to prepare for exciting events, or helping guests rebook their flights or stays during times of distress. We help our customers maximize the lifetime value of their guests and build products to delight guests at every touchpoint. - We’re a small and scrappy team, and we support each other with any deliverables we have to meet. Every engineer on TTH is also a product-led thinker; every PM on TTH is tinkering and developing tangible prototypes; and every strategist on TTH is capable of owning an agent end to end. As a part of this team, you’ll set the standard on what it means to go beyond your role, and help build the travel industry of the future. WHAT YOU’LL DO - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce. - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way. - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency. - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product. EXAMPLE PROJECTS These are some examples of projects that engineers on our team have worked on recently: - Building innovative multimodal experiences: Spearhead cross-cutting initiatives, partnering with the voice and Experience SDK teams to bring to life embedded voice mode in mobile apps. This brand new product allows users to talk, tap and text with our agents all in a single view — unlocking communication through rich visualizations, and accuracy in input collection with chat, with the ease and efficiency of voice. - Shipping complex booking experiences: Build personalized booking flows, including leveraging Google Maps APIs to support searching for properties via an embedded map view, developing a recommendation engine based on past reservations and orchestrating seamless payment collection to complete the full booking lifecycle. - Abstracting complex systems into packages: Modernize legacy reservations systems by creating Sierra packages that optimize querying and updating trips for customers across the board. You’ll be challenged to think deeply about how to orchestrate each step of these workflows to maximize efficiency while upholding reliability and accuracy. - Improving the capabilities of our built in integrations: Expand platform extensibility by introducing new capabilities to our existing integrations. An example is extending our MCP integrations to support MCP UI, which allows customers to dynamically host their custom UI resources on our embedded chat windows. WHAT YOU'LL BRING - Experience building and scaling end-to-end production systems. - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments. - A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship. - Comfort working directly with customers to understand their needs and solve real-world problems. - Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences. - Excitement in the travel space and a genuine care for helping improve the guest experience as a whole. Our customers care deeply about their guests, and we carry that through what we build every day. EVEN BETTER... - Language Fluency: Professional fluency in both Spanish and English. - Experience building or deploying AI/LLM systems in production - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering - Prior experience with React, TypeScript, and/or Go - Previous roles where you interfaced with customers or led technical projects with external stakeholders OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: San Francisco, CA; New York, NY; Atlanta, GA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE FINANCIAL SERVICES TEAM - Our financial services customers span insurers that provide protection for life’s most challenging moments, systemically important banks, neobanks committed to building more delightful banking software, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity. - Our Financial Services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle—the hours after a family discovers their home has been damaged by a wildfire and begins filing a claim; the difficult conversation following the loss of a loved one as beneficiaries navigate a life insurance claim; the frustration of dropping a phone, shattering the screen, and trying to quickly understand coverage and arrange for a repair or replacement. - Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone. WHAT YOU’LL DO - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce. - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way. - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency. - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product. EXAMPLE PROJECTS These are some examples of projects that engineers on our team have worked on recently: - Design and build AI agents for large insurance companies that consistently outperform human agents in filing claims quickly and consistently. - Develop and refine AI agents capable of navigating complex customer interactions, like generating a quote for insuring a modified 1960s Corvette. - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services! - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers WHAT YOU'LL BRING - Experience building and scaling end-to-end production systems. - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments. - A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship. - Comfort working directly with customers to understand their needs and solve real-world problems. - Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences. - Genuine interest in Financial Services and improving the end customer experience. Experience in insurance technology, implementations at financial institutions, working inside of these institutions or familiarity with financial services security and compliance requirements (coverage advice, PII handling, etc.) are a strong plus. EVEN BETTER... - Experience building or deploying AI/LLM systems in production - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering - Prior experience with React, TypeScript, and/or Go - Previous roles where you interfaced with customers or led technical projects with external stakeholders OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: San Francisco, CA; New York, NY; Atlanta, GA; Toronto Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE RETAIL TEAM - The Retail team on Agent Engineering supports some of the largest and most storied consumer brands in the world – including Gap, Wayfair, Sonos, and ADT. Together, we’re reinventing what commerce looks like in this new, AI-first era. Our customers rely on us to not only deliver novel experiences, but also host hundreds of millions of shopper and vendor interactions across web, app, phone, and in-store channels every year. - Our team supports our customers’ customers in the moments that matter – whether that's guiding a shopper to the right product during a limited drop or a Black Friday surge, locating a package that never arrived, or troubleshooting an appliance that stopped working. Always true to each brand’s voice, we create seamless experiences that resolve issues, drive revenue, increase lifetime value, and build lasting loyalty. - Our team supports our customers' customers in the moments that matter most, from product discovery and checkout to order tracking and troubleshooting. Always true to each brand’s voice, we create seamless experiences that resolve issues, drive revenue, increase lifetime value, and build lasting loyalty. - Every engineer on the Retail Team is a product-led thinker; every PM on Retail is also tinkering and developing tangible prototypes; and every strategist on Retail is capable of owning an agent end to end. As a part of this team, you'll set the standard on what it means to go beyond your role, and help build the groundwork for the retail industry in the future. WHAT YOU’LL DO - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce. - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way. - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency. - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product. EXAMPLE PROJECTS These are some examples of projects that engineers on our team have worked on recently: - Abstracting complex commerce systems into packages: Modernize the sprawl of order management, fulfillment, returns, and warranty systems behind the large retailer ecosystem by creating scalable packages that optimize looking up and updating orders for customers – from Shopify storefronts to decades-old homegrown Order Management System (OMS) and claims platforms. - Shipping the full discovery-to-checkout lifecycle: Build personalized shopping flows that carry a shopper from a vague idea to a completed order. This includes everything from building a recommendation engine that combines transcript-aware planning, structured filters, and semantic and keyword search to payment and order placement. - Building production-grade agents at a truly global scale: Sierra’s retail agents serve some of the world’s largest global brands, handling traffic at unprecedented volumes during the busiest times of the year and across all geographic locales. You will be building at the frontier of enterprise applied AI. WHAT YOU'LL BRING - Experience building and scaling end-to-end production systems. - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments. - A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship. - Comfort working directly with customers to understand their needs and solve real-world problems. - Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences. - Excitement in the retail space and a care for helping some of the world’s top brands continue to build brand loyalty with their customers. EVEN BETTER... - Experience building or deploying AI/LLM systems in production - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering - Prior experience with React, TypeScript, and/or Go - Previous roles where you interfaced with customers or led technical projects with external stakeholders OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: San Francisco, CA; New York, NY; Washington, D.C. Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE PUBLIC SECTOR TEAM - Sierra recently received FedRAMP High https://sierra.ai/blog/certified-fedramp-high certification, enabling us to bring our industry-leading technology to partners in the US public sector. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry. - Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies. - We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions. - In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do. WHAT YOU’LL DO - Design and build production-grade AI agents for government institutions at the Federal and state level. - Partner closely with industry leadership to build our public sector team, including our capture motion, market strategy, and product components to scale quickly. - Work closely with institutions to understand their most urgent needs and identify novel opportunities to expand our impact - for example through outbound contacts or long-horizon agents. - Build the future of the platform: Your direct work with public sector customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development. WHAT YOU'LL BRING - Full stack software development skills and familiarity with AI development processes. - A passion for public sector work and a faith in the potential of our institutions to transform outcomes for their constituents. - Comfort working directly with customers to understand their needs and solve real-world problems. A core part of the role is coordinating directly with public servants at our partners to understand their workflows. EVEN BETTER… - Experience building conversational or long-horizon agents using proprietary or open source frameworks. - Demonstrated track record ambiguity, for example as part of a founding team, new initiative at a large enterprise, forward deployed engineering, or elsewhere. - A prior understanding of government work and its complexities, including procurement, regulation, and patterns of partnership. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: San Francisco, CA; New York, NY; Atlanta, GA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE FINANCIAL SERVICES TEAM - Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity. - Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one. - Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone. WHAT YOU’LL DO - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce. - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way. - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency. - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product. EXAMPLE PROJECTS These are some examples of projects that engineers on our team have worked on recently: - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services! - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers WHAT YOU'LL BRING - Experience building and scaling end-to-end production systems. - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments. - A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship. - Comfort working directly with customers to understand their needs and solve real-world problems. - Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences. - Genuine interest in Financial Services and improving the end customer experience. Experience in financial technology, implementations at financial institutions, working inside of these institutions or familiarity with financial services security and compliance requirements (fair lending, PII handling, etc.) are a strong plus. EVEN BETTER... - Experience building or deploying AI/LLM systems in production - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering - Prior experience with React, TypeScript, and/or Go - Previous roles where you interfaced with customers or led technical projects with external stakeholders OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: New York, NY; San Francisco, CA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE HEALTHCARE TEAM - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system. - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms. - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone. WHAT YOU'LL DO - Design and deliver production-grade AI agents for healthcare: You'll build and ship highly performant, reliable, and empathetic AI agents that handle sensitive patient and member interactions. These agents help people understand their coverage, find providers, schedule appointments, navigate billing, and more—all while maintaining strict HIPAA compliance and the trust that healthcare demands. - Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments serving healthcare payers, providers, and platforms. - Partner with healthcare leaders: You'll work directly with executives and technical teams at health plans, provider networks, and healthcare technology companies to understand their most pressing challenges - from managing high call volumes to reducing administrative burden and building AI agents that transform how they operate at scale. - Navigate healthcare complexity: You’ll develop deep expertise in healthcare systems and workflows, including integrations across EHR and patient access platforms, payer and provider operations, and common healthcare data and interoperability standards. You’ll become fluent in the nuances of benefits and eligibility, claims and billing, scheduling and intake, and translate that understanding into exceptional, trustworthy AI experiences. - Build the future of the platform: Your direct work with healthcare customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development in healthcare. EXAMPLE PROJECTS These are examples of projects our healthcare team has worked on: - Build AI agents for major health insurance networks that handle detailed questions such as, "What's my co-pay for a primary care visit?" and "How many physical therapy sessions do I have left?" - Develop voice and chat agents for healthcare providers that help members find in-network specialists, check availability, and locate providers based on specialty or location; - Create AI agents for multi-site primary and urgent care providers that manage appointments and answer common questions across 30+ clinics; - Build agents that replace lengthy paper intake forms with conversational experiences, boosting pre-visit intake conversion rates; - Develop AI agents for healthcare financial platforms that help patients understand billing, payment status, explanations of benefits, and financial assistance eligibility - all while maintaining HIPAA compliance and strong PHI/data privacy safeguards. - Experiment with the latest voice models and integrate them at scale for healthcare enterprises requiring secure, compliant phone interactions; WHAT YOU'LL BRING - Experience building and scaling end-to-end production systems. - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments. - A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship. - Comfort working directly with customers to understand their needs and solve real-world problems. - Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences. - Genuine interest in healthcare and improving patient/member experiences. EVEN BETTER... - Experience in healthcare technology, health IT or working with healthcare organizations - Familiarity with healthcare systems: Major EHR ecosystems (e.g., Epic, Cerner/Oracle Health, athenahealth); X12 EDI transactions and clearinghouse workflows; scheduling/patient access, practice management, and contact center platforms. - Understanding of healthcare compliance requirements (HIPAA, PHI handling and healthcare data privacy). - Experience building or deploying AI/LLM systems in production. - Have been a founder or founding engineer—you know what it means to balance craft, ownership, and speed. - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering. - Prior experience with React, TypeScript, and/or Go. - Previous roles where you interfaced with customers or led technical projects with external stakeholders. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: San Francisco, CA; New York, NY; Washington, D.C. Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE PUBLIC SECTOR TEAM - Sierra recently received FedRAMP High certification, enabling us to bring our industry-leading technology to partners in the US public sector. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry. - Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies. - We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions. - In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do. WHAT YOU’LL DO As an Agent Strategist, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business. - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, evaluation, launch, and continuous iteration in production. Translate mission goals, policy requirements, and operational workflows into an agent that performs reliably in the real world. - Be a trusted strategic advisor to public sector leaders. Work shoulder-to-shoulder with agency executives and program leaders to define success, prioritize opportunities, and shape an AI strategy grounded in mission impact. - Partner with working teams day to day. Run working sessions with program, operations, technology, security, legal, and procurement stakeholders; resolve issues as they arise; and make the decisions that keep deployments moving toward launch. - Identify new ways to expand our impact. Understand our partners' most urgent needs and develop roadmaps for new use cases, including proactive outreach, multilingual access, and long-horizon agents that can support people across multi-step journeys. - Directly shape the product and our public sector strategy. Surface unmet needs from customer work, prototype new approaches, and partner with research, product, platform, and public sector leadership to influence Sierra's roadmap, market strategy, and repeatable solutions for government. EXAMPLE PROJECTS These are the kinds of projects that strategists on our public sector team have worked on recently: - Improve access to benefits and services. Launch an agent that helps residents understand eligibility, gather the right information, and navigate a complex application or recertification process across channels and languages. - Modernize constituent support. Design an agent that answers policy and program questions, provides case or application status, and routes sensitive or exceptional situations to the right public servant with full context. - Make critical reporting easier and safer. Build trusted conversational experiences for reporting fraud, safety concerns, or other high-stakes issues while meeting rigorous privacy, security, accessibility, and auditability requirements. - Enable proactive government services. Create a roadmap for outbound agents that remind people about deadlines, explain program changes, or help them complete important next steps before a benefit or service is interrupted. - Build repeatable public sector capabilities. Use a live agency deployment as a design partnership to shape new platform capabilities, evaluation standards, or implementation patterns that can serve institutions across federal, state, and local government. WHAT YOU’LL BRING - Ownership and delivery. A track record of leading multiple complex, high-visibility initiatives and driving cross-functional teams from an ambiguous starting point to measurable outcomes - for example as part of an early team, consultancy, or otherwise.. - Technical aptitude. Comfort engaging directly with technical concepts, including reading API documentation, understanding data models and system architecture, and following engineering and security tradeoffs in design discussions. - Commitment to public service. A passion for public sector work and a belief in the potential of institutions to improve outcomes for the people and communities they serve. - Communication. Clear, direct, and persuasive communication across executive, operational, policy, and technical audiences, with the ability to turn complexity into shared decisions. - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as policy, stakeholder, or implementation conditions change. EVEN BETTER... - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts. - Experience working in or with federal, state, or local government, including familiarity with procurement, security and compliance, accessibility, policy implementation, or systems integration. - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed. - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: San Francisco, CA; New York, NY Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE TECH, MEDIA & TELECOM TEAM - We work with some of the world's most influential and recognizable companies, from global telecommunications providers and leading media brands to technology platforms that power businesses worldwide. - We build agents for the moments that matter, helping our customers rise to the occasion when service disruptions, major product launches, or global events like the World Cup https://www.linkedin.com/posts/claybavor_at-sierra-we-are-very-proud-to-have-partnered-share-7491200202284945410-Bg79/?utm_source=share&utm_medium=member_desktop&rcm=ACoAABYjELMBZfjrg-wrv53M1tVXGe93FF3eTww drive millions of customer interactions. - We bring Sierra’s Horizon https://sierra.ai/product/horizon vision to TMT by building agents that transform the entire customer relationship: - Telecommunications: Turn one of the most frustrating customer experiences into one of the most personal, with agents that understand each subscriber, optimize their plan and savings, anticipate opportunities to add value, and earn their loyalty over time. - Media: Turn every subscription into an ongoing, personalized relationship, with agents that help each subscriber get the most from their experience through the right content, offer, plan, and support from their free trial through retention. - Technology: Bring the white-glove customer experience traditionally reserved for the largest enterprise accounts to every customer, helping them adopt the product, discover new ways to get value, expand their usage, and successfully renew. WHAT YOU'LL DO As an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business. - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome. - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there. - Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch. - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next. EXAMPLE PROJECTS These are the kinds of projects strategists on our TMT team work on: - Scope and launch a subscription-retention agent for a telecommunications or media company, then tune it to save more at-risk customers while preserving trust and brand voice. - Launch a top-of-funnel sales agent for a telecommunications provider that qualifies prospects, recommends plans and devices, and converts interest into new subscriptions. - Build a new-subscriber onboarding agent that activates service, ports numbers, configures devices, and reduces early-life churn. - Create a proactive, long-running agent that detects service or account issues, reaches out across channels, and manages resolution before the customer contacts support. - Develop a media growth agent that drives content discovery, trial conversion, plan upgrades, and subscription renewal. - Partner with Product to develop capabilities for TMT-scale traffic, including low-latency voice, multilingual experiences, proactive communications, and resilient performance during major launches or service events. WHAT YOU’LL BRING - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships. - Communication. Clear, direct, and persuasive across technical and non-technical audiences. - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast. - Technical aptitude. Comfortable engaging directly with technical concepts — reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion. - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes. - Interest in telecommunications, media, and technology. Experience in telecom, streaming and digital media, enterprise or consumer technology, or subscription businesses — and familiarity with customer care, billing, identity, content, or technical support systems — is a strong plus. EVEN BETTER... - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts. - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed. - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business. - Client-facing consulting, solutions, or strategy experience in a technically complex environment. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: San Francisco, CA; New York, NY Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE RETAIL TEAM - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice. - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line. - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone. WHAT YOU’LL DO As an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business. - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome. - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there. - Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch. - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next. EXAMPLE PROJECTS These are the kinds of projects that strategists on our team have worked on recently: - Launch an order management agent for a national apparel brand — order lookup, cancellations, returns, and exchanges — then hill-climb containment and CSAT week over week. - Partner with Product to build a shopping agent that plugs into a retailer’s existing search and recommendation systems to guide product discovery — turning the support channel into a revenue channel. - Stand up an in-store support voice agent for a big-box or grocery retailer, answering the stock-check and store-info calls that largely go unanswered today and converting them into store visits and sales. - Design a booking, payments, and outbound agent for a consumer services brand operating hundreds of locations. - Help a marketplace handle order status and buyer–seller disputes at enormous scale. - Launch outbound campaigns — cart recovery, win-back, churn saves, and subscription renewals — across voice and SMS. WHAT YOU’LL BRING - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships. - Communication. Clear, direct, and persuasive across technical and non-technical audiences. - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast. - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion. - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes. - Interest in retail and consumer experiences. Experience in e-commerce, retail technology, marketplaces, or consumer brands — and familiarity with commerce and CX stacks (e.g., commerce platforms, order management systems, contact center software) — is a strong plus. EVEN BETTER... - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts. - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed. - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: San Francisco, CA; New York, NY Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE FINANCIAL SERVICES TEAM - Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity. - Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one. - Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone. WHAT YOU’LL DO As an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business. - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome. - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there. - Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch. - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next. EXAMPLE PROJECTS These are the kinds of projects that strategists on our team have worked on recently: - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers. - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation. - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples. - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner. - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week. WHAT YOU’LL BRING - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships. - Communication. Clear, direct, and persuasive across technical and non-technical audiences. - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast. - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion. - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes. - Genuine interest in Financial Services and improving the end customer experience. Experience in financial technology, implementations at financial institutions, working inside of these institutions or familiarity with financial services security and compliance requirements (fair lending, PII handling, etc.) are a strong plus. EVEN BETTER... - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts. - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed. - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: San Francisco, CA; New York, NY Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE HEALTHCARE TEAM - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system. - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms. - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone. WHAT YOU’LL DO As an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business. - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome. - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there. - Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch. - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next. EXAMPLE PROJECTS These are examples of projects our healthcare team has worked on: - Lead the project for building AI agents for major health insurance networks that handle detailed questions like “what’s my co-pay for a primary care visit?” and “how many physical therapy sessions do I have left?” - Ideate and create a roadmap for growing value for large healthcare payers and providers. - Create AI agents for multi-site primary and urgent care providers that manage appointments and answer common questions across 30+ clinics. - Build agents that replace lengthy paper intake forms with conversational experiences, boosting pre-visit intake conversion rates. - Develop AI agents for healthcare financial platforms that help patients understand billing, payment status, explanations of benefits, and financial assistance eligibility. WHAT YOU’LL BRING - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships. - Communication. Clear, direct, and persuasive across technical and non-technical audiences. - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast. - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion. - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes. - Genuine interest in healthcare and improving patient/member experiences. Experience in healthcare technology, health IT or working with healthcare organizations and an understanding of healthcare compliance requirements (HIPAA, PHI handling and healthcare data privacy) are a strong plus. EVEN BETTER... - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts. - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed. - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.