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Location: Tokyo, Japan Workplace: Hybrid WHO WE ARE Notion is the collaborative AI workspace where teams and agents think together https://www.youtube.com/watch?v=vkpYpWfEK5s. We're building one place where your knowledge, projects, meetings, and AI tools live side by side, so work is faster, clearer, and less fragmented. Millions of individuals, small teams, and large companies run their work on Notion. Notinos (our employees) are customer zero in bringing this future of work to life. We care about craft, building things that last, and the belief that great work is still fundamentally human. Our goal isn’t to ship the next feature. Each and every team of Notinos is working to set the standard for how humans work together in the AI era. From building a business’s system of record to making and managing AI agents to automating away the busy work, we care deeply about giving our customers more time for their life’s work. ABOUT THE ROLE: The Solutions Consultant Manager is the person who makes our GTM motion real on the ground. As an in-region leader directly managing a team of Solutions Consultants, you'll own your team's full commercial output—new logo, expansion, and renewals—and be accountable for both the results and the quality of execution that produces them. This isn't a traditional pipeline-management role. The best SC Managers are coaches first: they know what a great first meeting looks like, can watch a live build and tell a rep exactly what to change, and build the operating rhythm and inspection cadence that makes consistent execution possible across the team. If you're a builder who loves developing people as much as winning deals—and you want to lead a regional team in a go-to-market model that's genuinely new—this is the role. WHAT YOU'LL ACHIEVE: - Own the commercial performance of your team across new logo ARR, expansion ARR, and UBP outcomes—accountable for both the headline numbers and the quality of execution that drives them - Coach SCs on the GTM builder motion: what great looks like in a first meeting (workflow diagnosis, current → future architecture), a second meeting (live build in Notion + value narrative), and through the full cycle to adoption hand-off - Contribute to and participate in the regional operating cadence: weekly pipeline reviews, deal support sessions, call reviews against the motion quality rubric, and forecast calls with senior leadership - Hire, onboard, and certify new SCs to the GTM builder motion—driving readiness from ramp through consistent execution, and managing performance with clarity when expectations aren't met - Partner with the regional BDR manager on pipeline strategy, outbound targeting, and qualification standards to ensure the team's book of business is healthy and growing - Partner with Outcomes leadership on adoption hand-offs, at-risk account management, and renewal strategy—owning the overall commercial arc for the region while collaborating on the execution that follows close - Represent your team or region in leadership forums with clear signal on what's working, what needs investment, and where execution is breaking down SKILLS YOU'LL NEED TO BRING: - Track record as a quota-carrying B2B seller with direct experience in workflow design, live demos, or technical sales—you can coach the builder motion because you've run it yourself - Frontline sales management experience: built an operating cadence, ran performance management, and developed talent from onboarding through consistent overperformance - Strong coaching orientation: you can watch a demo or deal review and identify specifically what to change—not just whether the outcome was good, but why, and what the rep should do differently next time - Commercial instincts at the team level: able to read pipeline health, identify risk early, and drive urgency across a team without micromanaging individual deals - You don't need to be an AI expert, but you have a strong interest in the evolving AI landscape, stay closely attuned to industry trends and developments, and are curious and willing to adopt AI tools to work smarter and deliver better results. - Native or bilingual level fluency Japanese and business-level English proficiency across speaking, listening, and reading, including the ability to support team members with global communication NICE TO HAVES: - Experience selling or managing in a consumption or usage-based business where adoption signals matter as much as closed ARR - Track record building high-performing regional teams from an early stage: hiring to profile, structured onboarding, certification, and performance management - Experience in a shared account ownership model—able to navigate the SC/CSA hand-offs and hold the commercial arc across the full customer lifecycle A NOTE ON AI You don’t need deep AI expertise for every role, but we do expect every Notino to be intellectually curious, drawn to tinkering and discovery, and excited to use AI as a real collaborator in their work. For some roles, AI fluency is a core requirement — when that’s the case, we'll say so explicitly in the qualifications. People who thrive here don’t treat AI as a novelty. They use it to think better, and make their work easier for others to build on. EQUAL OPPORTUNITY & ACCOMMODATIONS We hire talented people from a wide range of backgrounds. If you’re excited about this role but don’t meet every bullet, we still encourage you to apply. Notion is an equal opportunity employer and does not discriminate on the basis of any legally protected characteristic. Consistent with applicable law, we will consider for employment qualified applicants with arrest and conviction records. Notion provides reasonable accommodations during the application process; if you need one, please let your recruiter know. Notion is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Notion considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Notion is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If you need assistance or an accommodation due to a disability, please let your recruiter know.

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 is growing fast, and product marketing sits at the center of how we go to market. You'll make sure customers and prospects understand what we build, why it matters to their industry and role, and why Sierra is the right choice. You'll own positioning, messaging, launches, sales enablement, and content, working closely with product, sales, agent development and the rest of marketing. WHAT YOU'LL DO - Shape how we tell our story. You’re a passionate product marketer, energized by messaging and positioning and skilled at building a message for a feature, product, industry or buyer. One day you may update web copy, the next you build an event session, craft a sales narrative, write a launch blog post, or create content for a campaign. - Lead product launches. When a product or new feature ships, you lead how we go to market - the messaging, the assets, and the sales enablement. Sometimes this means translating to industries or buyers. - Arm our sales team. You build and maintain the playbooks and assets our GTM teams use to sell including slide decks, landing pages, demos and more. - Build with AI-first. You’re AI fluent, and your first instinct is to self-serve and improve how you work. You’ll help build the automations, templates, and systems that keep our work consistent across industries and workstreams. - Go wide and deep. You flex across channels and activations, and you can go deep on one area, such as an industry vertical, a persona, or our web strategy. You’re comfortable with ambiguity and a fast pace, and you like to build. WHAT YOU'LL BRING - 4+ years of B2B or B2C product marketing experience. - Expertise in positioning and messaging, leading product or feature launches, and building sales-facing and customer-facing assets for different audiences and industries. - Strong operational instincts. You think in process, systems, and repeatable frameworks, and you’re comfortable building structure where none exists. - Fluency with tools like ChatGPT or Claude to work faster and automate where it makes sense. - A passion for storytelling and experience building presentations in Google Slides. - Comfort being on a lean team that’s still being defined, and enthusiasm for shaping how it works. SAMPLE PROJECTS - Take a new product from roadmap to launch: positioning, messaging, sales assets, enablement, and demo. - Go deep on an industry and understand how our product can help that segment, build messaging that resonates, and downstream assets. 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: Canada - Remote Workplace: Remote ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE RETAIL TEAM - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice. - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line. - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone. WHAT YOU'LL DO - 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. - 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. - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow. WHAT YOU'LL BRING - 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts. - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. - Strong communication skills: Exceptional verbal and written communication abilities. - 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. 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: US - Remote; San Francisco, CA; New York, NY; Atlanta, GA Workplace: Remote ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE RETAIL TEAM - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice. - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line. - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone. WHAT YOU'LL DO - 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. - 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. - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow. WHAT YOU'LL BRING - 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts. - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. - Strong communication skills: Exceptional verbal and written communication abilities. - 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. 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: Canada - Remote Workplace: Remote ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE HEALTHCARE TEAM - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system. - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms. - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone. WHAT YOU'LL DO - 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. - 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. - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow. WHAT YOU'LL BRING - 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts. - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. - Strong communication skills: Exceptional verbal and written communication abilities. - 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. 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: US - Remote; San Francisco, CA; New York, NY; Atlanta, GA Workplace: Remote ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE HEALTHCARE TEAM - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system. - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms. - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone. WHAT YOU'LL DO - 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. - 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. - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow. WHAT YOU'LL BRING - 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts. - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. - Strong communication skills: Exceptional verbal and written communication abilities. - 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. 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: US - Remote; San Francisco, CA; New York, NY; Atlanta, GA Workplace: Remote ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. 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. - 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. - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow. WHAT YOU'LL BRING - 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts. - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. - Strong communication skills: Exceptional verbal and written communication abilities. - 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. 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: Canada - Remote; Toronto Workplace: Remote ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. 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. - 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. - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow. WHAT YOU'LL BRING - 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts. - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. - Strong communication skills: Exceptional verbal and written communication abilities. - 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. 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: Canada - Remote Workplace: Remote ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE FINANCIAL SERVICES TEAM - Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity. - Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one. - Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone. WHAT YOU'LL DO - 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. - 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. - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow. WHAT YOU'LL BRING - 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts. - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. - Strong communication skills: Exceptional verbal and written communication abilities. - 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. 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: US - Remote; San Francisco, CA; New York, NY; Atlanta, GA Workplace: Remote ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE FINANCIAL SERVICES TEAM - Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity. - Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one. - Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone. WHAT YOU'LL DO - 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. - 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. - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow. WHAT YOU'LL BRING - 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts. - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. - Strong communication skills: Exceptional verbal and written communication abilities. - 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. 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: Canada - Remote Workplace: Remote ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE RETAIL TEAM - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice. - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line. - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone. WHAT YOU'LL DO - Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction. - Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams. - Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise. - Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction. - Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org. - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow. WHAT YOU'LL BRING - 10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts. - Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies. - Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. - Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers. - Mastery of complex deal structuring, risk navigation, and pricing. - Exceptional executive communication and a reputation for precision and trust. EVEN BETTER... - Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike. - Experience operating alongside founders/executives in front of strategic customers. 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: US - Remote; San Francisco, CA; New York, NY; Atlanta, GA Workplace: Remote ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE RETAIL TEAM - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice. - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line. - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone. WHAT YOU'LL DO - Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction. - Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams. - Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise. - Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction. - Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org. - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow. WHAT YOU'LL BRING - 10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts. - Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies. - Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. - Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers. - Mastery of complex deal structuring, risk navigation, and pricing. - Exceptional executive communication and a reputation for precision and trust. EVEN BETTER... - Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike. - Experience operating alongside founders/executives in front of strategic customers. 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: Canada - Remote; Toronto Workplace: Remote ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. WHAT YOU'LL DO - Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction. - Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams. - Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise. - Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction. - Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org. - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow. WHAT YOU'LL BRING - 10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts. - Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies. - Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. - Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers. - Mastery of complex deal structuring, risk navigation, and pricing. - Exceptional executive communication and a reputation for precision and trust. EVEN BETTER... - Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike. - Experience operating alongside founders/executives in front of strategic customers. - 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: US - Remote; San Francisco, CA; New York, NY; Atlanta, GA Workplace: Remote ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. WHAT YOU'LL DO - Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction. - Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams. - Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise. - Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction. - Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org. - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow. WHAT YOU'LL BRING - 10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts. - Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies. - Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. - Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers. - Mastery of complex deal structuring, risk navigation, and pricing. - Exceptional executive communication and a reputation for precision and trust. EVEN BETTER... - Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike. - Experience operating alongside founders/executives in front of strategic customers. 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: United States, San Mateo, CA Why Sony Interactive Entertainment? Sony Interactive Entertainment isn’t just the Best Place to Play — it’s also the Best Place to Work. Sony Interactive Entertainment (SIE) is the company behind the PlayStation brand. As a subsidiary of Sony Group Corporation, we’re part of a proud legacy of innovation and excellence. SIE is a dynamic technology company, delivering cutting-edge hardware and network services to more than 100 million people and an entertainment leader, home to some of the most beloved and recognizable intellectual properties (IP) in the world. Our role at SIE is to create and nurture the experiences under the PlayStation brand, a name synonymous with entertainment excellence and creativity. Why PlayStation Our team is innovating and crafting the next generation of gaming experiences on PlayStation! You will work alongside partners in engineering, product, design, and research to build tools and technologies that keep our players safe.  PlayStation Network currently has more than 100 million monthly active users. This is a phenomenal opportunity to join our high leverage team working on building outstanding new experiences! You will lead a passionate engineering team responsible for developing Microsoft Windows® PC based software for the PlayStation® and other applications/devices. You will be responsible for providing strong technical leadership in highly secure and performant PC-based software design and development. Role Responsibilities Lead, coach, mentor, grow, and empower your team to achieve their goals Strong understanding of software engineering methodologies Collaborate with colleagues to develop, implement, and uphold SDK and application security features for PC applications Create technical specifications as a Product Owner Guide the team technically to build high quality products on PC Participate in code reviews and documentation Lead day-to-day activities of the team using Agile/Scrum methodologies Collaborate with geographical diverse teams to coordinate development activities Contribute to engineering-wide initiatives as a member of PlayStation's engineering management team Qualifications 2+ years of people management experience A bachelor’s degree in computer science, or equivalent experience Experience with requirements gathering and analysis, design and development of scalable code with unit tests across multiple technology stacks Experience in building high-performance SDKs or Frameworks Knowledge of client-side Operating System security fundamentals and features Experience with securing consumer client-side applications Extensive experience with C/C++ Experience or knowledge of cryptographic algorithms and ciphers Experience recruiting and building great teams Ability to work with a high level of autonomy and responsibility Excellent written and verbal communication skills Passion for supporting team members’ career growth Nice-to-Have Skills Similar experiences with security engineering on non-PC platforms Experience with low-level engineering tools (e.g. disassemblers/decompiling) Experience with game development or game engine development Experience with securing PC games Experience or knowledge of anti-cheat and/or anti-tamper concepts and products Experience with codesigning and certificate verification workflows Experience or knowledge with data integrity checking Experience or knowledge of binary obfuscation Experience securing IPC traffic Experience using tools such as Ghidra, IDA or x64Dbg At SIE, we consider several factors when setting each role’s base pay range, including the competitive benchmarking data for the market and geographic location. Please note that the base pay range may vary in line with our hybrid working policy and individual base pay will be determined based on job-related factors which may include knowledge, skills, experience, and location. In addition, this role is eligible for SIE’s top-tier benefits package that includes medical, dental, vision, matching 401(k), paid time off, wellness program and coveted employee discounts for Sony products. This role also may be eligible for a bonus package. Click here to learn more. The estimated base pay range for this role is listed below. $201,400 — $302,000 USD Please note, Sony Interactive Entertainment conducts background checks at the offer stage for all new employees (which may include criminal background checks for some roles) and will need to process personal information to support these checks. Please refer to our Candidate Privacy Notice for more information about what personal information we collect, how we use it, who we share it with, and your data protection rights. Equal Opportunity Statement: Sony is an Equal Opportunity Employer. All persons will receive consideration for employment without regard to gender (including gender identity, gender expression and gender reassignment), race (including colour, nationality, ethnic or national origin), religion or belief, marital or civil partnership status, disability, age, sexual orientation, pregnancy, maternity or parental status, trade union membership or membership in any other legally protected category. We strive to create an inclusive environment, empower employees and embrace diversity. We encourage everyone to respond. Sony Interactive Entertainment is a Fair Chance employer and qualified applicants with arrest and conviction records will be considered for employment.

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 - Drive high-impact security and infrastructure initiatives end-to-end. Lead complex, cross-functional programs spanning cloud infrastructure, platform security, identity and access management, detection and response, vulnerability management, and secure software delivery from problem definition through execution and sustained outcomes. - Own execution, planning, and program health. Be accountable for sequencing work, managing dependencies, tracking risk, and ensuring delivery of Sierra’s most critical security programs, with clear milestones and outcomes. - Help shape Sierra’s security strategy. Partner with security and engineering leadership to define priorities, investment areas, and execution plans that align risk reduction with platform growth, customer trust, and long-term scalability. - Build and strengthen security foundations. Drive programs that establish durable security primitives such as identity boundaries, access controls, logging and detection baselines, incident readiness, and secure defaults that future teams and features can confidently build on. - Translate ambiguity into clear execution. Decompose loosely defined security, risk, and compliance challenges particularly in emerging AI domains into structured programs, prioritized workstreams, and measurable outcomes. - Lead communication and alignment. Provide clear updates to leadership on program health, risks, dependencies, and tradeoffs; surface issues early and drive cross-functional alignment. WHO YOU'LL WORK WITH - Engineering: Infrastructure, Data Platform and Agent SDK engineers to shape technical requirements, manage dependencies, and deliver resilient systems. - Security & GRC: Security engineering, risk, compliance, and privacy partners to align on threat models, control strategy, audits, and risk management in a rapidly evolving AI landscape. - Product and GTM: Product, Agent Development, and Sales to operationalize security commitments and respond to sophisticated customer and regulator expectations. - Legal: On security terms, third-party risk, and contractual obligations. - Executive Leadership: Senior leaders who rely on you for clarity, prioritization, and confidence in Sierra’s security strategy and execution. WHAT YOU'LL BRING - Experience running security-focused technical programs in fast-growing SaaS or platform environments. - Strong technical fluency across cloud infrastructure, IAM, infrastructure as code, observability, secure CI/CD, and incident response. - Ability to execute through ambiguity, prioritize effectively, and keep teams moving. - Comfort operating in environments where things aren’t fully built yet and helping decide what needs to be built first. - Clear, concise communication with senior technical and business leaders. - A collaborative, pragmatic style with high ownership and high agency. EVEN BETTER... - Experience scaling security programs globally in AI-first or data-intensive SaaS environments. - Exposure to emerging AI risk, data governance, or agent and model-related security considerations. - Experience supporting security initiatives in public-sector, regulated and/or multi-cloud environments (AWS, GCP, Azure). - Relevant security, cloud, AI or technical program management certifications. - Familiarity with regulatory and compliance frameworks (ISO 27001, PCI DSS, FedRAMP, HIPAA) 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: Bulgaria; Poland; Serbia Would you like to build a career in a leading multinational IT company? We’re looking for an AI Adoption Officer to lead AI transformation across the organization. You’ll help teams integrate AI into their daily work by identifying high-impact use cases, improving business processes, reducing manual work, and driving productivity through practical AI solutions. Since 2007, MMDSmart has been a leading supplier in cloud communications, delivering game-changing IT products to businesses in over 100 countries. Our success is fueled by the inspiration and innovative ideas of our team members, encouraging their growth and impacting our Messaging and Voice solutions. These empower our clients to communicate more effectively with their customers. Don’t miss this chance to excel in a rapidly expanding tech company, where your potential and ambitions are not just recognized, but celebrated. You’ll work closely with business leaders to identify opportunities, implement AI tools, establish best practices and governance, and ensure employees are confident in adopting AI. Key Responsibilities: Develop and execute the organization's AI strategy and roadmap aligned with business objectives. Identify, prioritize, and implement high-impact AI use cases to optimize business processes and improve productivity. Lead the evaluation, deployment, and continuous optimization of AI tools and solutions across the organization. Drive AI adoption through employee training, change management, and the development of AI best practices. Establish and maintain AI governance, ensuring responsible, secure, and ethical AI usage. Define and monitor KPIs, measure business impact, and provide data-driven recommendations to leadership. Stay informed on emerging AI technologies and identify opportunities to drive innovation and competitive advantage. Requirements Qualifications: Bachelor's degree in Business, Information Technology, Computer Science, or equivalent practical experience. Experience leading AI adoption, digital transformation, business transformation, or process improvement initiatives. Strong understanding of Generative AI technologies and productivity platforms (e.g., ChatGPT, Microsoft Copilot, Google Gemini, Claude, or similar). Experience implementing AI solutions within business environments. Experience training and supporting non-technical users in adopting new technologies. Strong understanding of business process analysis and workflow optimization. Experience leading cross-functional projects and organizational change initiatives. Ability to evaluate AI solutions based on business value and return on investment. Excellent analytical, communication, presentation, and stakeholder management skills. Curiosity about emerging AI technologies and a passion for continuous learning. Benefits Why do talents choose and stay at MMDSmart? Embrace the opportunity to work in a company that cares about: Your Wellness: Access to mental health programs, comprehensive medical insurance, and a sports card*. Your Happiness: Enjoy the company of cool teammates, a friendly atmosphere, a strong mentorship, and a variety of bonuses & corporate gifts. Your Development: Benefit from free educational events & courses, and English classes with native speakers. Your Career: Focus on your professional development in a supportive environment Think this role’s got your name on it? Go ahead and apply, we’d love to see what you’ve got! Equal-Opportunity Employment We are an equal opportunity employer committed to creating a diverse and inclusive work environment. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status.

Location: Europe; United States Workplace: Remote ABOUT CANTINA: Cantina is a new social platform founded by Sean Parker with the most advanced AI character creator. Our bots are lifelike, social creatures that can interact wherever people are online—across voice, video, and text. Create yourself, imagine someone new, or choose from thousands of characters to share infinitely scalable, personalized content and seamless group chat. If you’re excited about how AI can shape creativity and social interaction, come help us build what’s next.   ABOUT THE ROLE: We’re looking for a Research / ML Engineer to join our Speech Team to build state-of-the-art speech systems end-to-end—from data specs through production inference. You’ll drive the model ↔ data ↔ eval flywheel for VC and adjacent tasks (controllable TTS, voice design and more), partnering closely with research, data, and infra to ship fast, reliable, and cost-aware models. In this role, you will work at the intersection of cutting-edge research and practical engineering, contributing to the development of safe, steerable, and trustworthy AI systems. You will thrive in this role if you: - See research and engineering as two sides of the same coin and enjoy owning work end-to-end. - Are results-oriented, flexible, and willing to pick up whatever moves the needle. - Like collaborating closely with infra, data, and product to ship measurable improvements. - Enjoy designing experiments, listening tests, and metrics that correlate with user-perceived quality. - Eager to learn every-day, find and solve unique large-scale problems. WHAT YOU’LL DO: - Model Building: Architect, implement, pre-train, fine-tune, and post-train/alignment (e.g., GRPO/DPO) for large-scale speech models. - Experimental Design: Design, run, and analyze scientific experiments to advance our understanding of the models. - Tool Development: Develop and improve dev tooling to enhance team productivity. - Full-Stack Contribution: Contribute to the entire stack, from low-level optimizations to high-level model design. - Data Ownership: Define data requirements and collaborate on acquisition, curation, augmentation, labeling quality, and synthetic data strategies. - Rigorous Evaluation: Design automated objective/subjective evaluations—listening tests, SV/WER/ASR-based metrics, robustness & bias checks, and red-team studies. - Pipeline Delivery: Harden the training → evaluation → inference pipeline; profile latency, memory, and cost; and meet production SLAs with robust monitoring and rollback. - Safety & Responsibility: Contribute to safety/consent guardrails and to misuse/abuse mitigation for responsible speech technology.   WHAT YOU’LL BRING: - Exceptional research/development experience with large-scale audio models (>8B parameters, >500k hours of data). - Deep hands-on experience with diffusion and/or flow-matching transformers, including practical knowledge of samplers, schedules, conditioning mechanisms, and distillation. - Deep hands-on experience training audio VAEs, neural audio codecs, and vocoders latent/tokenizer design, reconstruction and perceptual objectives, adversarial training. - Strong experience with multi-node, multi-GPU distributed training (FSDP/DeepSpeed or equivalent). - Strong software engineering skills with a proven track record of building complex systems. - Strong with PyTorch and performance work (profiling, CUDA/Triton/C++ as needed) and writing reliable production-quality code. - Shipped large-scale speech/audio or multimodal generative models to production. - Background in working with large-scale ML data, and the ability to iterate on data and triangulate quality using both subjective and objective signals. - Experience with voice cloning, speech control/steerability, or expressive speech generation. - Notable publications and/or open-source contributions in speech/audio/ML. COMPENSATION: When determining compensation, a number of factors will be considered, including skills, experience, job scope, location, and competitive compensation market data.   BENEFITS FOR U.S.-BASED ROLES: - Competitive salary and generous company equity - Medical, dental, and vision insurance – 99.99% of premiums covered by Cantina - 42 days of paid time off, including: - 15 PTO days - 10 sick days - 15 company holidays - 2 floating holidays - Generous parental leave & fertility support - 401(k) retirement savings plan - Lifestyle spending account – $500/month to use however you’d like - Complimentary lunch and snacks for in-office employees - One Medical membership, and more!