Location: 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.
WHAT YOU'LL DO
- Scale The Function: Lead, coach, and develop a high-caliber SE team, providing guidance, assigning projects and ensuring technical excellence. Conduct regular performance evaluations, foster professional growth, and coach team members to reach their full potential.
- Player-Coach: Be a true player-coach who stays in the work: own your own enterprise deals as an individual contributor, running discovery, demos, and technical deep dives alongside your team, while leading and growing a team of high-growth enterprise SEs. Set the bar by example, jump into the most strategic cycles, and turn what you learn in the field into coaching and playbooks that raise the whole team. As the team grows, become a strategic leader and more manager focused.
- GTM Technical Expert: Guide your team in designing and delivering compelling technical demos and proofs of concept for Sierra’s platform, providing technical solutions to customer challenges, and addressing technical questions throughout the sales cycle.
- Cross-Functional Work: Partner closely with Sales, Product, and Agent Engineering teams to define best practices, playbooks, and repeatable processes that enable your team and partnership to scale beyond 1:1 customer interactions.
- Lead & Support Customers: Act as a technical leader in early-stage customer conversations, helping your team understand, anticipate, and solve customer needs to advance Sierra’s industry-leading AI solutions.
WHAT YOU'LL BRING
- 5-7+ years of experience in Sales Engineering, Solutions Engineering, or customer-facing technical sales, with at least 3+ years in a leadership capacity.
- Experience developing frameworks for how SEs partner with Sales, Product, and Engineering to deliver impact efficiently across accounts.
- History of establishing metrics and systems that measure SE impact on pipeline health, win rates, and customer adoption.
- Track record of leading presales processes and supporting enterprise and strategic sales cycles from discovery through close.
- Ability to translate customer business problems into Sierra’s technical solutions and clearly communicate to both technical and non-technical stakeholders across complex organizations.
EVEN BETTER
- Experience building Sales Engineering orgs in emerging categories (e.g., AI, data, security).
- Comfort with workflows, AI and ML concepts, APIs/webhooks, and JSON.
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.
This is one of the first Customer Success Managers at RETR, and you will own a book of our enterprise customers end to end: the relationships, the value they get, the renewal, and the growth. What you own.
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
- Lead & develop a high-performing sales team - Hire, onboard, and develop Enterprise/Strategic AEs covering Southeast Asia. Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team.
- Own regional performance - Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights.
- Be deeply involved in deals - Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy.
WHAT YOU'LL BRING
- 10- 15+ years of experience in an Enterprise customer-facing sales role, identifying and closing large accounts.
- People Leadership Experience: 5+ years managing, mentoring, and developing a high performing enterprise sales team.
- Enterprise Experience: Experience managing a $1M+ quota, and running end-to-end complex deals.
- Strong Communication Skills: Exceptional verbal and written communication abilities.
- Analytical Mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
EVEN BETTER...
- Industry Knowledge: Familiarity with the AI landscape, key players, and emerging trends.
- Experience Building GTM Strategies: Building sales teams and sales motions from scratch, or from early stage growth.
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.
This role is open to MBA students graduating in spring 2027.
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.
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 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: Bournemouth, United Kingdom
Location:
London
Reporting Line:
Head of Partner Advocacy & Growth
Department:
Marketing
Employment Type:
Full-time
We are looking for an experienced B2B acquisition marketer with deep digital expertise to drive new mortgage brokers into the OneDome Growth Partners network.
This is a cross-channel role where you will be responsible for identifying, reaching, and converting mortgage brokers primarily through performance digital channels, while also amplifying impact through PR, events, and referral initiatives.
Reporting into the Head of Partner Advocacy & Growth, you will be the chief digital evangelist of the Growth Partners value proposition – using paid media, SEO, email, and automation to drive a predictable, scalable pipeline of new broker partners.
Key Responsibilities
Digital-First Broker Acquisition Strategy
Design and execute a multi-channel acquisition plan to drive a steady pipeline of new mortgage broker partners.
Own and optimise the full funnel – from awareness through to application.
Develop a referral initiative that includes digital tracking, automated incentives, and broker-friendly sharing tools.
Performance Marketing & Optimisation
Manage acquisition budgets with a CPA focus, continuously testing ad creative, landing pages, audience segments, and offers.
Implement retargeting campaigns to nurture brokers who have shown interest but not yet joined.
Work with analytics teams to set up conversion tracking.
Run regular A/B tests on messaging through deep understanding of our value proposition
Test channel mix to improve conversion rates.
Channel & Campaign Integration
Work closely with the PR team to amplify trade media coverage – using earned media as fuel for paid and owned campaigns.
Partner with the Events Manager to create hybrid event strategies: identifying where to be seen and how to maximise our presence.
Spend time with internal partnership and sales teams to map the broker’s digital journey from first click to first completed application.
Own the Growth Partners website landing pages for acquisition, optimising for SEO and conversion (CRO).
Develop a compelling narrative around the Growth Partners community and create acquisition-focused digital assets and content to drive engagement
Performance Reporting & Optimisation
Track, measure, and report on digital acquisition KPIs: new broker sign-ups, CPA, CTR, conversion rate (landing page to application), ROI by channel, and referral conversion rates.
Produce weekly dashboards for the Head of Partner Advocacy & Growth, making data-backed recommendations to reallocate spend.
Feed digital learnings back into the broader growth strategy to continuously improve broker acquisition efficiency.
Key Skills and Experience
5+ years of B2B marketing experience, with at least 3 years in a digital marketing or performance marketing role.
Proven track record of growing memberships or acquiring partners preferably in a professional services environment.
Hands-on experience with: Google Analytics, Google Ads, LinkedIn Campaign Manager, email marketing platforms and content management tools.
Demonstrable success in creating innovative acquisition campaigns across multiple channels.
You are digitally obsessive and commercially savvy: You love data and can model LTV:CAC and argue for incremental budget based on channel performance.
A collaborative operator, you’ll enjoy working as part of a team whilst being equally at home leading a solo project.
About OneDome
OneDome
is a UK-based
housing and fintech technology platform
building an
AI-powered platform
to simplify life’s biggest financial decisions — from buying a first home to building and protecting long-term wealth.
The platform brings together property discovery, mortgage origination, legal and transaction services, insurance, and financial planning into a single, end-to-end digital experience. OneDome’s flagship
HomeBuyer Service
reimagines home ownership as a retail-style product, bundling everything required to purchase a home into one transparent, fixed-price offering. Beyond home purchases, the platform supports customers across the full lifecycle of home ownership and personal finance.
OneDome operates at scale, working with a nationwide network of over 500 mortgage brokers and arranging approximately
$1.4 billion in mortgage volume per month
,
positioning the company among the largest housing and mortgage platforms in the UK.
The company is
profitable
and has been recognised for rapid, capital-efficient growth, including being ranked the
4th fastest-growing fintech
and
17th fastest-growing technology company
by the
Deloitte Fast 50
in 2025, and the
6th fastest-growing tech company
by the
Sunday Times Tech 100
in 2026.
Backed by Channel 4 Ventures and family offices across the UK, Saudi Arabia, the United States, and Australia, OneDome is building the next generation
housing and fintech super-platform
, replacing fragmented, manual processes with a modern, data-driven, AI-enabled consumer experience.
Salary: £40,000 – £45,000 / year
Location: London
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
As a Partnerships Development Lead, you’ll play a critical role in building and nurturing a robust ecosystem of partners and stakeholders around Sierra, amplifying our reach and market impact.
- Industry Partnerships: Develop and grow partnerships with key industry players and technology platforms
- Strategic Customer Channels: Explore and cultivate alternative customer acquisition channels beyond traditional sales, leveraging Sierra’s ecosystem of investors, partners, and industry influencers to drive inbound interest and adoption
- GTM Strategy & Collaboration: Align partnership efforts with Sierra’s broader GTM approach, collaborating closely with Sales and Marketing
- Investor & VC/PE Engagement: Build and deepen relationships with VCs and PE firms to position Sierra as a strategic AI partner across their portfolios. Proactively identify opportunities to introduce Sierra to portfolio companies that would benefit from our agents
- Industry & Market Expansion: Gather market intelligence, share insights to inform product development, and explore opportunities for potential growth across new market segments and geographies
WHAT YOU’LL BRING
- 8+ years in business development, strategic partnerships, or related roles in tech
- Strong understanding of the VC/PE landscape and experience working with investors
- Proven track record of structuring and closing high-value partnerships with senior stakeholders
- Ability to engage and maintain relationships with C-level executives, investors, and key decision-makers
- Analytical mindset to evaluate partnership opportunities and align them with Sierra’s long-term vision
- Ability to navigate ambiguity in a fast-moving startup environment
EVEN BETTER…
- Prior experience at a high-growth AI or enterprise SaaS startup
- Deep expertise in a few of our key industries: financial services, healthcare, telecommunications, media, travel, transportation and hospitality, retain and consumer goods, and/or technology
- Experience structuring and managing ecosystem partnerships
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; 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.
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
- Language fluency - professional fluency in both Spanish and English
- 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
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
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
- Run the monthly and quarterly commission cycle, from pulling data and calculating commissions to validating payouts, getting approvals and handing off to payroll.
- Investigate rep questions, document what you find, recommend fixes, and clear issues quickly so reps trust their payouts.
- Work with Salesforce and data owners to keep source data clean, map new fields and deal types, and find upstream problems before they turn into payout errors.
- Reconcile and audit payouts against payroll, bookings and plan terms every cycle.
- Model the cost and payout impact of proposed plan changes and set up new plans in the system.
- Automate manual steps, tighten SLAs and build reporting on attainment, payout cost and comp effectiveness.
WHAT YOU’LL BRING
- 5+ years in sales compensation, commissions operations or a closely related finance/RevOps role.
- A track record of managing commission cycles across multiple regions, currencies, and payroll schedules, from data collection through payout validation, approvals, and payroll handoff.
- Strong analytical skills, including payout modeling, data reconciliation, and investigating discrepancies against compensation plan terms.
- Experience using Salesforce to pull and review sales data for commission calculations.
- Ability to configure sales compensation tools to calculate, validate, and report commission payouts.
- Clear, calm communication with sellers and leaders, including during difficult payout conversations.
EVEN BETTER…
- Familiarity with commission accounting, including accruals, journal entries, and month-end close.
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
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
You'll own the operational backbone that connects what we sell to what we bill: turning executed contracts and agent usage into accurate bookings and reports, and turning the data behind both into critical insights the business acts on. This role sits at the center of the company’s business model and works across Sales, Finance, Legal, Pricing, GTM Systems, and Agent Development.
Own Order Management across the Customer Lifecycle
- Own the path from signature to booking: build, verify, and book quotes across the customer lifecycle, capturing all critical commercial terms
- Collaborate across GTM Operations, Finance, and Sales Compensation to ensure bookings flow accurately into all downstream systems and reporting
- Leverage and spearhead order management guides and best practices, influencing policies and processes as new terms and products emerge
Accelerate usage tracking and reporting
- Partner with Agent Development to set up, verify, and maintain outcome-based usage tracking across agents
- Run the monthly consumption reporting and billing cycle for our growing customer base, delivering key reports to the company and to the Customer
- Serve as the owner for usage questions from customers, Sales, and Agent Development
Support our Deal Operations and Velocity
- Draft, review, and execute order forms, working with our Pricing team to align on commercial negotiation, deal forecast, and downstream operability
- Partner with Sales, Legal, Pricing, and Finance across the deal lifecycle to execute deals cleanly and drive scalability over time
Build the Operational Machine with us
- Continuously identify repetitive processes across the order management lifecycle and collaborate across the Go-to-Market Operations team to automate and scale them
- Work with Revenue Operations and GTM systems to define billing processes and policies for new products and pricing models
- Ramp from running standard processes to owning complex and ambiguous scenarios
WHAT YOU’LL BRING
- 2–4 years in deal desk, order management, billing operations, or revenue operations at a B2B SaaS company
- Experience owning an operational booking and/or billing queue end-to-end with high accuracy against monthly deadlines
- Experience with CRMs (e.g., Salesforce) and a CPQ or billing system; comfortable reading a contract and translating terms into system fields
- Strong attention to detail and clear written communication skills to collaborate with Sales, Finance, Legal, and customers
- Ability to identify areas for improvement and build solutions using AI tooling
- Based in San Francisco and able to work in-office with the team
EVEN BETTER…
- Experience with usage-based billing (commitments, overages, credits, true-ups)
- Familiarity with Quoting and Contract Lifecycle Management tools
- SQL or spreadsheet modeling skills
- Exposure to sales compensation, revenue recognition, or partner and reseller billing
- Experience at a high-growth company where you helped stand up a process from scratch
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
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.
Sierra’s Applied Research team advances the quality, speed, and cost efficiency of the models powering our agents across a wide range of tasks. Our work spans post-training open-weight models for specialized capabilities and pioneering new approaches to voice AI, turning research breakthroughs into reliable production systems.
WHAT YOU’LL DO
- Tackle unsolved applied AI and ML problems. Pushing the boundaries of post-training, voice AI, and long-horizon task execution, building agents that can reason, adapt, and reliably carry out complex tasks for customers.
- Determine when to build specialized models and when to use externally provided frontier intelligence, balancing quality, speed, and cost to deliver customer value.
- Turn ambiguous product and customer problems into well-framed machine learning problems.
- Develop, fine-tune, evaluate, and deploy models that improve Sierra’s customer-facing AI agents.
- Advance our post-training work, from supervised fine-tuning toward reinforcement learning and long-horizon optimization.
- Build rigorous evaluations that connect model performance to real-world agent quality.
- Work with large-scale, proprietary datasets spanning text and audio interactions.
- Collaborate across Sierra while taking ideas from experimentation through production deployment and customer impact.
WHAT YOU’LL BRING
- Strong experience building and deploying production machine learning and AI systems. We welcome backgrounds across applied ML, including search, ranking, recommendations, advertising, language, and speech.
- Excellent judgment in framing product problems as ML tasks and selecting the simplest & most effective approach.
- Experience working deeply with data, experimentation, evaluation, and model iteration.
- A practical, evidence-driven approach to ML, with strong judgement around when a problem calls for modeling and when a simpler solution will deliver the best outcome.
- The ability to operate with high agency and work across the stack when needed to deliver an outcome.
- Alignment with Sierra’s values, including Craftsmanship, Customer Obsession, and Competitive Intensity.
- A degree in computer science, machine learning, or a related field, or equivalent professional experience.
EVEN BETTER…
- Experience with supervised fine-tuning or reinforcement learning.
- Experience in search, ranking, recommendations, or advertising systems.
- Experience training and deploying language, speech, or multimodal models.
- Experience designing model evaluations tied to real-world product outcomes.
- Experience working with large-scale consumer datasets or high-volume ML products.
- Contributions to applied ML research or benchmarks.
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
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 ROLE
Sierra’s AI agents depend on foundation models to reason and act in real time. The Inference team builds the systems that make those models fast, reliable, and efficient at scale.
As a Software Engineer on Inference, you’ll help define Sierra’s inference architecture across both self-hosted models and third-party inference providers. You’ll work on the systems responsible for serving and routing inference, managing capacity and quota, and optimizing for latency, reliability, and cost.
This is a systems-first role at the intersection of distributed infrastructure and AI. You don’t need to be an ML researcher—we’re looking for engineers who love complex systems problems and are excited to apply that expertise to one of the fastest-moving areas of AI infrastructure.
WHAT YOU'LL DO
- Partner with frontier labs and providers. At our scale, we rely on frontier labs, and inference providers to supply capacity, training and inference infrastructure.
- Shape Sierra’s inference architecture. Design how inference traffic flows across models, infrastructure, and providers, including new serving and proxy layers as Sierra scales.
- Build for low latency and high reliability. Develop systems for routing, failover, capacity management, and quota that keep inference performant and available across large-scale production workloads.
- Build and operate self-hosted inference. Run models on GPU infrastructure, from building containers and operating inference engines to managing the underlying compute capacity.
- Optimize inference performance. Work with the Applied Research team on techniques such as speculative decoding and serving-engine optimizations that improve latency, throughput, and cost.
- Build across a hybrid inference stack. Work with both Sierra-managed infrastructure and leading inference platforms, making architectural decisions about where and how workloads should run.
- Push the serving stack forward. Work closely with inference providers to tune engines and infrastructure for Sierra’s workloads.
- Support the broader model lifecycle. Contribute to infrastructure that enables post-training while partnering closely with our Models and Agent Runtime teams.
WHAT YOU'LL BRING
- Deep systems thinking and strong distributed systems fundamentals.
- Experience designing, building, and operating large-scale production systems.
- Strong judgment around tradeoffs involving latency, reliability, capacity, and cost.
- Experience taking ownership of complex infrastructure from architecture through production operation.
- Excitement about applying systems expertise to AI infrastructure and learning quickly as the underlying technology evolves.
EVEN BETTER
- Experience with ML infrastructure, MLOps, or production inference systems.
- Experience serving LLMs or other large models at scale.
- Experience operating self-hosted inference and GPU infrastructure.
- Familiarity with inference frameworks such as vLLM or SGLang.
- Experience with post-training infrastructure or inference-performance optimization.
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
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.
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: London
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
- Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
- Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
- Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
- Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
- Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds.
- Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
WHAT YOU'LL BRING
- 10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
- Strong communication skills: Exceptional verbal and written communication abilities in English, with fluency in Swedish, Norwegian, or Danish.
- Enterprise experience: Experience managing a $1M+ quota, and running end-to-end complex deals.
- Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
- Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
EVEN BETTER...
- Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
- Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.
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.
Knock is looking for a proven sales leader to own the performance and growth of Knock's Account Executive organization. You will be accountable for delivering the company plan for leads and loan applications across Account Executives, Senior Account Executives, and Wholesale Account Executives.
Location: Tokyo
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
- Set the standard for great marketing and PR in a hyper growth, founder-led company.
- Work cross functionally to raise awareness of Sierra.
- Maintain overall responsibility for local marketing as well as press, public speaking and social media.
- Be a key part of Sierra’s global Marcomms team — pitching in as needed.
WHAT YOU’LL BRING
- Deep knowledge of Japan and the Japanese tech/business environment.
- Entrepreneurial and scrappy — you like to try new things, and you lean into risk.
- A problem solver — you roll up your sleeves and solve what’s thrown at you.
- Fast and calm — you move quickly and are poised under pressure.
- Strong execution — you deliver what you promise, to a high standard.
- Creative — you can set the standard for what drives conversation in enterprise PR.
- Excellent communicator — you have strong written and verbal communications.
- Great team player — you’re low ego and enjoy working with people at every level. You are good at building and maintaining relationships, internally and externally.
- Understanding of marketing, the press and social media — either from working at a company, in government or as a journalist.
- Good judgement and professionalism — you can navigate ambiguity and can be trusted with sensitive or confidential initiatives.
EVEN BETTER
- Proven track record working in a fast paced company.
- Strong written and spoken English and Japanese.
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 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 pioneers 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 not only to deliver exceptional customer experiences, but also to drive meaningful growth for their businesses.
- 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 for what it means to go beyond your role, and help build the travel industry of the future.
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.
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: Cape Town, South Africa
Job Description:
Dedicated Adviser Support Executive
Location:
CBD Cape Town, South Africa (Office-based, on-site)
UK-aligned Hours:
Mon-Fri (10am-7pm winter / 11am-8pm summer)
Reports to:
Head of Mortgage Customer Success
Department:
Customer Success
Type:
Full-time
Company Information
OneDome is an award-winning next generation property marketplace (one stop shop housing ecosystem). We are a market disruptor enabling home movers to conduct an end-to-end property transaction via a single platform. The OneDome platform makes transactions faster, more assured and allows customers to have greater control over their transactions.
Our goal is to challenge market norms and to reshape the property industry to better reflect the consumer demands of the 21st century.
We are growing as a business and as such we are seeking entrepreneurial and collaborative individuals who are simplifiers. We need our people to help us work towards our mission of revolutionising home moving.
OneDome achieved Gold for the Best Use of Digital in Property market and won the title of the Most Innovative Company in the 2021 Best Business Awards in the UK.
Role Overview
We are looking for a highly organised and proactive Dedicated Adviser Support Executive to provide one-to-one support to a Senior Adviser across mortgages, protection and later-life business.
This is a varied role combining mortgage administration, application processing, case support and general adviser administration.
You will work closely with the Adviser on a daily basis, taking ownership of time-consuming administrative and processing activities so the Adviser can focus on client relationships and providing advice.
A key part of the role will be developing a strong understanding of the Adviser's working style, clients and processes and becoming a reliable point of support across their day-to-day workload.
Key Responsibilities
Mortgage Application & Processing Support
Key mortgage applications accurately using lender portals and internal systems
Prepare mortgage applications for submission, ensuring all required information has been entered accurately and documentation is in place
Work closely with the Adviser when keying more complex applications or where additional information is required
Support the Adviser with residential, remortgage and other mortgage applications
Check client information, income and supporting documentation before applications are progressed
Maintain accurate client and application information across internal systems
Complete relevant mortgage administration and internal forms
Identify missing information or documentation and follow up where required
Case & Client Administration
Support with the ongoing administration of mortgage cases
Request outstanding documents and information from clients
Review documentation such as bank statements, income evidence and budget information against agreed processes
Keep internal systems and case notes accurate and up to date
Complete routine administrative and case checks
Follow up on outstanding actions and ensure important tasks are not missed
Communicate professionally with clients and relevant third parties by email and telephone where required
Help manage the Adviser's pipeline and keep track of outstanding actions and priorities
Later Life & Protection Support
Provide administrative support across later-life and protection business
Assist with gathering client information, including income and supporting documentation
Support with basic data input and case preparation on relevant systems
Complete administrative sections of internal, compliance and provider forms
Contact providers and Business Development Managers to obtain factual information, criteria and case updates where required
Support the Adviser with research and preparation for more complex later-life cases
Follow up on outstanding requirements and maintain accurate records
Training and guidance will be provided for specialist processes where
required.
Dedicated Adviser Support
Work closely with the Adviser on a one-to-one basis and develop a strong understanding of their preferred way of working.
Help organise and prioritise outstanding actions across the Adviser's workload.
Monitor the Adviser's diary and upcoming priorities where appropriate.
Maintain consistent communication through agreed channels, including email and telephone.
Proactively identify administrative tasks that can be completed without requiring Adviser involvement.
Help ensure information is organised and readily available when the Adviser needs it.
Adapt to the Adviser's working processes while helping develop efficient and consistent ways of working.
What We're Looking For
We are looking for someone who:
Is highly organised, reliable and proactive.
Has excellent attention to detail and accuracy.
Is comfortable working closely with one Adviser and building a strong one-to-one working relationship.
Has excellent written and verbal English communication skills.
Can process and organise detailed financial information accurately.
Is confident working across multiple systems and lender portals.
Can manage several tasks and priorities without losing track of outstanding actions.
Is comfortable communicating with clients, lenders, providers and other professional third parties.
Takes ownership and follows tasks through to completion.
Is adaptable and comfortable learning new processes.
Can work independently while recognising when something needs to be escalated.
Is patient, methodical and comfortable supporting complex cases.
Experience
Previous mortgage administration, mortgage processing or financial services experience is highly desirable.
A good understanding of the UK mortgage application process would be advantageous.
Previous experience keying mortgage applications or using lender portals would be particularly beneficial.
Experience using mortgage CRM or financial services systems would be advantageous.
Previous experience within later life, equity release or protection would be beneficial but is not essential.
Full training will be provided on internal systems and specialist processes where required.
About OneDome
OneDome is a UK-based
housing and fintech technology platform
building an
AI-powered platform
to simplify life’s biggest financial decisions — from buying a first home to building and pro-tecting long-term wealth.
The platform brings together property discovery, mortgage origination, legal and transaction ser-vices, insurance, and financial planning into a single, end-to-end digital experience. OneDome’s flagship
HomeBuyer Service
reimagines home ownership as a retail-style product, bundling every-thing required to purchase a home into one transparent, fixed-price offering. Beyond home pur-chases, the platform supports customers across the full lifecycle of home ownership and personal finance.
OneDome operates at scale, working with a nationwide network of over 500 mortgage brokers and arranging approximately
$1.4 billion in mortgage volume per month
, positioning the compa-ny among the largest housing and mortgage platforms in the UK.
The company is
profitable
and has been recognised for rapid, capital-efficient growth, including being ranked the
4th fastest-growing fintech
and
17th fastest-growing technology company
by the Deloitte Fast 50 in 2025, and the 6th fastest-growing tech company by the
Sunday Times Tech 100
in 2026.
Backed by Channel 4 Ventures and family offices across the UK, Saudi Arabia, the United States, and Australia, OneDome is building the next generation
housing and fintech super-platform
, re-placing fragmented, manual processes with a modern, data-driven, AI-enabled consumer experience.
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
ОфисSingapore
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