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Location: San Francisco, CA; US - Remote; New York, NY; Atlanta, GA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE CONSUMER BUSINESS SERVICES TEAM - Sierra partners with the businesses that power everyday life for consumers and enterprises alike — from the CPG brands on every shelf to the logistics networks that get products there, the real estate and facilities teams that manage the buildings people live and work in, and the energy and utility providers that keep the lights on. Our agents handle everything from order tracking and account management to field service scheduling and billing support, tuned to the voice and workflows of each business. - This vertical spans a wide range of industries — consumer products, commercial real estate, automotive & mobility, transportation & logistics, industrial manufacturing, information & data services, consumer electronics, professional services, facilities management, construction, energy, and utilities — giving you the breadth to build relationships across some of the largest and most established companies in the world. - Join us to bring AI agents to the businesses that quietly run the economy — and help build technology that makes these essential services faster, more reliable, and more human for everyone who depends on them. WHAT YOU'LL DO - Be the primary partner to your Sales counterparts helping to win deals and grow customers - Go from first discovery to a tailored, working agent in days, not weeks, across prospects and existing customers - Work with every team involved in the decision: CX, IT, security, procurement, and executive sponsors - Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle - Mentor newer SEs and contribute reusable assets for your industry or team - Stay with the account after the sale, through the Agent Development handoff, launch, and expansion to new use cases - Go deep on your industry, the patterns, and winning motions to scale your work WHAT YOU'LL BRING - 4-6+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales - Experience in leading the sales process with large Enterprise customers with deal sizes ranging $500-$1M - Past experience in demo building, and presenting, and working with customers or clients in the GTM function - Experience in relationship-building with prospects, including executives and technical leaders - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it - Experience growing accounts past initial sale - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience EVEN BETTER... - Experience translating code, technical logic and user requirements to product and engineering requirements - Selling a technical AI product 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 - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; US - Remote; New York, NY; Atlanta, GA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE CONSUMER BUSINESS SERVICES TEAM - Sierra partners with the businesses that power everyday life for consumers and enterprises alike — from the CPG brands on every shelf to the logistics networks that get products there, the real estate and facilities teams that manage the buildings people live and work in, and the energy and utility providers that keep the lights on. Our agents handle everything from order tracking and account management to field service scheduling and billing support, tuned to the voice and workflows of each business. - This vertical spans a wide range of industries — consumer products, commercial real estate, automotive & mobility, transportation & logistics, industrial manufacturing, information & data services, consumer electronics, professional services, facilities management, construction, energy, and utilities — giving you the breadth to build relationships across some of the largest and most established companies in the world. - Join us to bring AI agents to the businesses that quietly run the economy — and help build technology that makes these essential services faster, more reliable, and more human for everyone who depends on them. WHAT YOU'LL DO - Be the primary partner to your Sales counterparts helping to win deals and grow customers - Go from first discovery to a tailored, working agent in days, not weeks, across prospects and existing customers - Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle - Work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy - Go deep on your industry, the patterns, and winning motions to scale your work WHAT YOU'LL BRING - 3-4+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales - Experience in leading the sales process with Enterprise customers with deal sizes ranging $200-$500k - Past experience in demo building, and presenting, and working with customers or clients in the GTM function - Experience in relationship-building with prospects, including executives and technical leaders - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it - A track record of handling a high number of deals concurrently without cutting quality, and comfortable switching between sub-industries and use cases - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience EVEN BETTER... - Experience translating code, technical logic and user requirements to product and engineering requirements - Selling a technical AI product 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 - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; US - Remote; New York, NY; Atlanta, GA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE CONSUMER BUSINESS SERVICES TEAM - Sierra partners with the businesses that power everyday life for consumers and enterprises alike — from the CPG brands on every shelf to the logistics networks that get products there, the real estate and facilities teams that manage the buildings people live and work in, and the energy and utility providers that keep the lights on. Our agents handle everything from order tracking and account management to field service scheduling and billing support, tuned to the voice and workflows of each business. - This vertical spans a wide range of industries — consumer products, commercial real estate, automotive & mobility, transportation & logistics, industrial manufacturing, information & data services, consumer electronics, professional services, facilities management, construction, energy, and utilities — giving you the breadth to build relationships across some of the largest and most established companies in the world. - Join us to bring AI agents to the businesses that quietly run the economy — and help build technology that makes these essential services faster, more reliable, and more human for everyone who depends on them. WHAT YOU'LL DO - Go deep on a few accounts. Learn each customer's business well enough that you could be wearing their badge in their hallways - Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle - Decide when to bring in Agent Development, Product, Security, Legal, and Sierra leaders, and what each of them needs to do. You keep everyone aimed at the same goal - Raise the bar for the SE team: mentor others, set standards for demos and pilots, and write the playbooks for Strategic deals and GTM processes - Stay with the account after the sale, through the Agent Development handoff, launch, and expansion to new use cases - Share what you see across your largest accounts with Product leadership and inform roadmap WHAT YOU'LL BRING - 7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales - Experience in leading the sales process with Strategic customers with deal sizes of $1M+ consistently - Past experience in demo building, and presenting, and working with customers or clients in the GTM function - Strong experience in relationship-building with prospect stakeholders, including C-suite executives and technical leaders - Experience leading architecture, integration, and security discussions with enterprise architects, engineering leaders, and security teams - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it - Experience growing accounts past initial sale and defining customer roadmaps to facilitate growth - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience EVEN BETTER... - Experience translating code, technical logic and user requirements to product and engineering requirements - Selling a technical AI product 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 - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; US - Remote; New York, NY; Atlanta, GA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. 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 - Be the primary partner to your Sales counterparts helping to win deals and grow customers - Go from first discovery to a tailored, working agent in days, not weeks, across prospects and existing customers - Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle - Work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy - Go deep on your industry, the patterns, and winning motions to scale your work WHAT YOU'LL BRING - 3-4+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales - Experience in leading the sales process with Enterprise customers with deal sizes ranging $200-$500k - Past experience in demo building, and presenting, and working with customers or clients in the GTM function - Experience in relationship-building with prospects, including executives and technical leaders - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it - A track record of handling a high number of deals concurrently without cutting quality, and comfortable switching between sub-industries and use cases - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience EVEN BETTER... - Experience translating code, technical logic and user requirements to product and engineering requirements - Selling a technical AI product 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 - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; US - Remote; New York, NY; Atlanta, GA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. 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 - Go deep on a few accounts. Learn each customer's business well enough that you could be wearing their badge in their hallways - Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle - Decide when to bring in Agent Development, Product, Security, Legal, and Sierra leaders, and what each of them needs to do. You keep everyone aimed at the same goal - Raise the bar for the SE team: mentor others, set standards for demos and pilots, and write the playbooks for Strategic deals and GTM processes - Stay with the account after the sale, through the Agent Development handoff, launch, and expansion to new use cases - Share what you see across your largest accounts with Product leadership and inform roadmap WHAT YOU'LL BRING - 7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales - Experience in leading the sales process with Strategic customers with deal sizes of $1M+ consistently - Past experience in demo building, and presenting, and working with customers or clients in the GTM function - Strong experience in relationship-building with prospect stakeholders, including C-suite executives and technical leaders - Experience leading architecture, integration, and security discussions with enterprise architects, engineering leaders, and security teams - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it - Experience growing accounts past initial sale and defining customer roadmaps to facilitate growth - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience EVEN BETTER... - Experience translating code, technical logic and user requirements to product and engineering requirements - Selling a technical AI product 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 - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; US - Remote; New York, NY; Atlanta, GA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. 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 - Go deep on a few accounts. Learn each customer's business well enough that you could be wearing their badge in their hallways - Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle - Decide when to bring in Agent Development, Product, Security, Legal, and Sierra leaders, and what each of them needs to do. You keep everyone aimed at the same goal - Raise the bar for the SE team: mentor others, set standards for demos and pilots, and write the playbooks for Strategic deals and GTM processes - Stay with the account after the sale, through the Agent Development handoff, launch, and expansion to new use cases - Share what you see across your largest accounts with Product leadership and inform roadmap WHAT YOU'LL BRING - 7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales - Experience in leading the sales process with Strategic customers with deal sizes of $1M+ consistently - Past experience in demo building, and presenting, and working with customers or clients in the GTM function - Strong experience in relationship-building with prospect stakeholders, including C-suite executives and technical leaders - Experience leading architecture, integration, and security discussions with enterprise architects, engineering leaders, and security teams - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it - Experience growing accounts past initial sale and defining customer roadmaps to facilitate growth - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience EVEN BETTER... - Experience translating code, technical logic and user requirements to product and engineering requirements - Selling a technical AI product 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 - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; US - Remote; New York, NY; Atlanta, GA; Washington, D.C. Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE PUBLIC SECTOR TEAM - Sierra recently received FedRAMP High https://sierra.ai/blog/certified-fedramp-high certification, enabling us to bring our industry-leading technology to partners in the US public sector. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry. - Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies. - We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions. - In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do. WHAT YOU'LL DO - Be the primary partner to your Sales counterparts helping to win deals and grow customers - Go from first discovery to a tailored, working agent in days, not weeks, across prospects and existing customers - Work with every team involved in the decision: CX, IT, security, procurement, and executive sponsors - Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle - Mentor newer SEs and contribute reusable assets for your industry or team - Stay with the account after the sale, through the Agent Development handoff, launch, and expansion to new use cases - Go deep on your industry, the patterns, and winning motions to scale your work WHAT YOU'LL BRING - 4-6+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales - Experience in leading the sales process with large Enterprise customers with deal sizes ranging $500-$1M - Past experience in demo building, and presenting, and working with customers or clients in the GTM function - Experience in relationship-building with prospects, including executives and technical leaders - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it - Experience growing accounts past initial sale - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience EVEN BETTER... - Experience translating code, technical logic and user requirements to product and engineering requirements - Selling a technical AI product 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 - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

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. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO - Design and build a structured onboarding program for new Account Executives and Sales Engineers, with role-specific tracks - Deliver onboarding live and asynchronously: cohort sessions, workshops, certifications, and role-plays - Introduce what AI Fluency means at Sierra and how to incorporate it into daily sales activities (account research, call prep, call recaps, pipeline updates, etc.) - Make sure every seller can explain, demo and stand behind how Sierra uses AI, so they can speak credibly with customers who are learning to deploy AI themselves - Establish baseline ramp metrics (time to first meeting, first deal, quota attainment, SE readiness) and set targets for reducing them - Use AI tools to scale enablement itself: faster content creation, AI-driven role-play and call coaching, and self-serve answers to seller questions - Partner with Product, Marketing, Sales Leadership, and Sales Engineering to keep content accurate as the product and market change - Recruit subject-matter experts, including top sellers and SEs, to teach and coach in the program - Gather feedback from new hires and managers, and iterate on the program quarterly - Build the global program so it can be adapted for regional teams, including our London office WHAT YOU’LL BRING - 6+ years in sales enablement at a high-growth B2B software company, with hands-on onboarding or training experience and experience managing cross-functional programs - Experience designing and delivering onboarding for both quota-carrying sellers and technical sellers - Track record of prioritizing competing requests from senior stakeholders and saying no with data - Track record of tying enablement work to business outcomes, not just completion rates - Strong facilitator, comfortable teaching experienced sellers and executives - Willing to do the hands-on work in the early months, not just manage it, and comfortable building from scratch with limited process and few resources - Able to learn a technical product ([AI agents / enterprise software]) well enough to teach it credibly - Hands-on, daily use of AI tools in your own work, and experience teaching others to adopt new tools and change how they work EVEN BETTER… - Experience running sales kickoff or product launch enablement - Experience selling or supporting sales in AI, SaaS, or enterprise software - Familiarity with enablement platforms (e.g., [Highspot, Seismic, Salesforce, Gong]) - Experience running onboarding through rapid headcount growth, or handing a program to a successor 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 - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

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. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. What you’ll do We are looking for a Compensation Partner to join our Compensation team. In this role, you'll play a critical part in supporting and evolving our global compensation programs through robust analysis, scalable processes, AI-native workflows, and cross-functional collaboration. You will serve as a trusted compensation subject matter expert to stakeholders and employees as we continue to grow. - Conduct detailed compensation analysis and modeling, leveraging AI and automation to support program design and decision-making. - Lead market benchmarking efforts globally, building scalable workflows for market reviews and ongoing evaluation of internal equity and external competitiveness. - Manage the execution of our compensation planning cycles, with a focus on data accuracy, analysis, and process optimization. - Partner with the Recruiting team to optimize offer processes, providing market intelligence and internal equity insights. - Support stock plan administration, partnering with Legal to manage equity grant processes and improve the accuracy and employee experience of equity operations. - Develop and maintain compensation tools, dashboards, and self-service experiences that enable Recruiting, People, and business leaders to access compensation insights. - Champion AI-native workflows by integrating AI tools and automation into compensation processes to improve operational efficiency and surface sharper insights. WHAT YOU’LL BRING - 5+ years of compensation or total rewards experience in high-growth technology environments. - Proven experience developing and maintaining compensation bands, including sales OTE and equity frameworks, and job architectures at scale. - Strong understanding of global compensation practices, with experience supporting international markets. - Hands-on experience with equity compensation, including RSUs and stock options, and comfort navigating equity administration processes and platforms such as Carta. - Highly collaborative, with a track record of building strong cross-functional partnerships, particularly with Recruiting, Legal, and People teams. - Skilled in leveraging compensation data platforms such as Pave, Radford, and Levels.FYI http://Levels.FYI, and HRIS platforms such as Workday to generate insights and inform decision-making. - An AI-native operating mindset: you instinctively look for ways to use AI, automation, and technology to improve how work gets done rather than defaulting to manual processes. EVEN BETTER… - You've supported compensation programs spanning multiple geographies, including navigating local pay regulations, statutory requirements, and regional market data. - You have experience at a large or high-growth technology company and understand how to design scalable compensation programs and processes. - You’ve built AI-powered or automated workflows that replaced manual operational processes or created new self-service capabilities. 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 - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

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. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO You’ll join a full-stack data team building the systems making our AI agents measurably smarter with every interaction, building the real-time pipelines, analytics products, and deep personalization primitives that turn millions of conversations into business outcomes. You’ll work across these areas: - Data Foundations: Architect and build our core platform to handle data at scale with low latency. This includes our real-time eventing infrastructure, streaming and batch ETL pipelines, and our Iceberg-based data lakehouse. You will own the systems for interactive OLAP querying, orchestration, and experimentation, ensuring our data is trustworthy, fast, and easy to use for the entire organization. - Memory & Personalization: Power the next generation of intelligent experiences. You will develop the systems for long-term agent memory, build reusable Customer Data Platform (CDP) primitives, and implement the optimization loops that allow our agents to personalize interactions and demonstrably lift business outcomes. WHAT YOU'LL BRING We’re excited to meet candidates who bring depth in one of these areas: Platform Engineering - You have designed, built, and operated large-scale data systems, processing terabytes or petabytes of data with technologies like Spark, Flink, Trino/Presto, and data lakehouse formats like Iceberg or Hudi. - You possess strong backend and distributed systems fundamentals in a language like Go, Scala, or Python. You understand the trade-offs of different storage engines, query plans, and data serialization formats. - You have a history of implementing pragmatic data governance, lineage, and testing. You’ve built platforms that are cost-aware, highly operable, and a delight for other engineers to build upon. - You're well-versed in data modeling best practices (dimensional modeling, star/snowflake schemas, slowly changing dimensions) and know how to optimize analytical query patterns for both traditional OLAP systems and modern cloud data warehouses. Product Engineering - You have a portfolio of shipped data products, including analytics dashboards, data visualization tools, or alerting and exploration systems. - You are a skilled full-stack engineer (e.g., TypeScript/React and a service layer like Go), with a keen eye for performance, API design, and polish. - You excel at turning ambiguous questions into clear, intuitive interfaces. You have strong product sense around information architecture, handling empty states, and making complex data explainable. - You have practical experience with ML-powered product features, such as personalization, recommendations, or classification systems. Shared Qualities - Strong software engineering background with 4-7+ years of hands-on development experience in building and shipping production systems or products. - A passion for being on the frontier of AI products. - High agency and a bias to action in a high-autonomy environment. - Degree in Computer Science or related field, or equivalent professional experience.   EVEN BETTER... - Deep experience with event streaming platforms (e.g., Kafka, Kinesis) and real-time data processing. - Experience with modern data visualization libraries (e.g., ECharts, D3.js) and the principles of building performant, reusable charting components for complex data. - Production experience with recommender systems or optimization loops (e.g., multi-armed bandits, ranking). - A track record of leading complex technical projects or mentoring other engineers. 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 - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

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. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO - Build Sierra’s enterprise platform capabilities. You’ll design and build the foundational systems and capabilities that enable Sierra to serve the world’s largest and most demanding enterprises. This includes the identity, access management, integration points, and extensibility that enterprise customers require to allow customers to embed Sierra into their existing ecosystems. - Scale with our largest customers. Our enterprise customers have complex environments, strict security requirements, and high expectations for reliability. You’ll ensure Sierra’s platform scales across organizations, regions, and use cases while maintaining performance and simplicity. - Form the foundation of trust. Enterprise customers trust Sierra with their most sensitive workflows and data. You’ll help set and uphold a high bar for security, compliance readiness, reliability, and operational excellence across the platform. WHAT YOU’LL BRING - A passion for being on the frontier of AI products. - Pride in building reliable, maintainable, and secure systems that scale. - Motivation and high-agency to drive outcomes - we have a high-autonomy culture and each team member has lots of agency to overcome obstacles and achieve customer impact. - Alignment to our company values throughout your work, notably finding a balance between Craftsmanship, Customer Obsession, and Competitive Intensity. - 4+ years hands-on experience building production products and systems. - Degree in Computer Science or related field, or equivalent professional experience. EVEN BETTER… - Experience building enterprise features such as SSO, RBAC, IAM, audit logs, or compliance-adjacent systems. - Experience with integrations, APIs, and working with complex customer environments. - Backend-leaning full-stack experience building enterprise SaaS applications. - Security-adjacent experience (e.g., auth, permissions, data isolation, threat modeling). - Experience building AI-powered products or platforms. 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 - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

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. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO - Build primitives for self improvement: Create the feedback loops, evaluation systems, memory, signals, and decisioning infrastructure that help long-running agents learn from outcomes and improve over time. - Build the future of long-horizon agents: Design and ship agents that pursue complex business outcomes over days, weeks, or months across voice, SMS, email, and other channels. - Turn 0-to-1 work into a platform: Identify patterns and build reusable systems, abstractions, and tools that make future Horizon agents faster and easier to launch. - Solve technically complex problems: Build across orchestration, integrations, data, memory, signals, decisioning, observability, and multi-channel engagement. - Shape the Horizon product: Surface platform gaps through hands-on implementation and work with product and engineering to define Horizon’s architecture and roadmap. - Create a clean path beyond the POC: Once a solution is validated, translate what you built into durable product capabilities and enable a successful handoff for continued deployment. WHAT YOU’LL BRING - Experience building and scaling end-to-end production systems. - Strong platform and systems engineering fundamentals. - The ability to move between customer problems, product design, and technical implementation. - Strong technical judgment in ambiguous, fast-changing environments. - A builder’s mindset and the ability to take products from zero to one. - Comfort working directly with customers and understanding complex business processes. - High agency, adaptability, and clear communication. - At least two years of professional software engineering experience - Experience with Python, TypeScript, or Go and React. EVEN BETTER... - Experience as a founder, founding engineer, or early engineer at a startup. - Experience building workflow, orchestration, event-driven, or distributed systems. - Experience developing platforms or reusable infrastructure for other engineers. - Experience building or deploying AI and LLM-powered products. - Familiarity with enterprise integrations, APIs, data pipelines, and systems of record. - Experience working in complex industries such as financial services or healthcare. 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 - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

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. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO The agent must collect and use a card number but can never see it. This work sits across four hard technical domains: payments, security, real-time voice, and LLMs. Voice is the core challenge. A caller speaks or types a card number in a live, low-latency audio stream, and the digits must never reach the model, while the model stays on the call. Sierra owns every system that touches card data, and one small team owns it end to end across three workstreams: Platform, Product, and Safety & Integrity. Customers keep their own telephony and payment gateways. Payments is live in production for some of the largest consumer enterprises, on a platform that handles hundreds of millions of calls a year. The platform is certified to PCI DSS Level 1. - Build real-time card capture for voice: intercept keypad and spoken digits in a live audio stream, upstream of the agent runtime in a network-segmented environment, while the LLM stays live on the call. Make it work across every telephony provider and protocol Sierra supports. - Build and extend the tokenization platform: agents receive and send short-lived tokens, and the platform swaps a token for the real value only when it calls the customer's payment gateway. - Own the payments egress control plane: every destination for card data is approved, versioned with the agent release, and enforced by infrastructure below the application, not by convention. - Make payment actions correct: an at-most-once action primitive in the Agent SDK, validated amounts and items, and monitoring that compares what the agent said about a payment with what really happened. - Keep card data out of places it should not be: deterministic detection in the agent's hot path that catches what general-purpose models miss. No LLM, including any we build ourselves, ever sees a plaintext card number. - Make payments self-serve: one payments API across Agent Studio, the Agent SDK, and Ghostwriter, Sierra's agent-building agent; gateway middleware that developers write against tokens; and support for single-tenant and customer-cloud deployments. Any team can add payments to an agent without a payments engineer in the loop. - Grow the platform beyond cards: extend tokenization into a privacy vault for all PII. WHAT YOU'LL BRING - 5+ years building backend, platform, or infrastructure systems, with a track record of shipping and operating high-reliability services in production. - A deep security instinct. You design as though every component will eventually be compromised, and you reason naturally about blast radius, least privilege, and making bad states impossible rather than reacting to them. - Rigor about correctness under failure: retries, idempotency, at-most-once behavior, and clear handling of timeouts and unclear results from external systems. - Fluency in a systems language (we use Go) and comfort owning critical systems end to end, from design through production and on-call. - Range and ownership. You like a small team with broad scope, you build clean abstractions over messy external systems, and you're never satisfied solving a problem once per customer. - Clear communication. You can explain a design or a risk to other engineering teams and to non-engineers. - Degree in Computer Science or a related field, or equivalent professional experience. You don't need payments experience. The engineers who built this platform came from backend, infrastructure, and security work, not payments. We care more about how you build correct, secure systems than about the word "payments" on your resume. EVEN BETTER… - Real-time or streaming systems: voice, telephony, media, or low-latency pipelines. - Applied cryptography and key management, network isolation, egress control, or cloud security. - Platforms other engineering teams build on, such as APIs, SDKs, and self-serve developer services. - Deployments into customer-owned clouds or single-tenant environments. - Customer-facing technical work, such as architecture reviews with customers. - Setting technical direction on ambiguous, high-stakes problems. - Payments, fintech, or another sensitive-data domain such as healthcare or identity. 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 - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

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. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO When someone calls an airline, texts a retailer, or opens their bank's app and talks to a Sierra agent, our systems carry that conversation. Phone calls, SMS, WhatsApp, email, and the chat inside our customers' apps all run through this team. AI voice, chat, and messaging agents are new and they must operate with global communication networks. Nobody has fully solved how to make the two work together at the speed of a real conversation. We have to solve it for millions of calls, and you will be building the future of how entire industries will operate with AI agents. Demo: Finding the perfect stay https://sierra.ai/resources/videos/demo-finding-the-perfect-stay Demo: Flight disruption recovery https://sierra.ai/resources/videos/demo-flight-disruption-recovery - Multi-modal: Make one conversation work across voice, text, and screen. A customer can start by talking, switch to typing on a crowded train, send a photo of a broken part, and get a link or a form back on screen. The agent remembers everything, whichever way the customer talks and personalizes it. You will build on the frontier here, and decide what it should feel like. - Make AI voice feel like a real conversation. Every call crosses carriers, telephony networks, and contact centers around the world before it reaches our agent. Making AI agents feel lively and real across global infrastructure is a critical problem to get right for end users. - Give personal AI agents a safe way in. More people now have their own AI assistants. Today a company can either block them or hand them the user’s full account access. The Personal Agent Protocol https://personalagentprotocol.org/ is an open standard that offers a better option: a safe way for personal agents to work with a company and its Sierra agent. You’ll help build it. - Build the agent experience inside the app. ChatKit is our library of native iOS, Android, and web components for talking to an agent. It covers voice controls, live waveforms, transcripts, and chat. Customers use it to build an agent experience inside a customer’s flagship app, not like a widget added on top. You decide what those components are and how they behave. - Get every call to the right agent. You’ll build and own our global telephony stack: SIP, WebRTC, the Sierra Voice Protocol and our integrations with major contact-center platforms. That means millions of calls and messages, and every one of them reaching the right agent. - Put Sierra on every channel. SMS, WhatsApp, RCS, email, LINE, Messenger and Instagram. You’ll build the tools that let developers launch a new channel on their own, delivering value in hours not weeks. WHAT OWNERSHIP LOOKS LIKE - A bias for shipping. You move fast, and you finish what you start. - Curiosity about the hard parts. You go deep where other engineers avoid going: protocols, edge cases, and end to end multi-modal experiences. - An AI-native way of building. You not only use AI tools every day, it is ingrained in the way you operate and think. You’ve deleted all old priors and re-invented the way you and your teams work from the ground up. Come ready to tell us about something you built that you couldn’t have built 6 months ago. - An obsession with the details. When one call in ten thousand fails, you want to know why. You obsess about the product experience and pixels as much as you do latency and reliability. - Strong backend fundamentals. You can also work comfortably across backend, infra, mobile and web. - 3+ years building production software that real users depend on. WHAT YOU'LL BRING - A passion for being on the frontier of AI products. - Pride in building reliable, maintainable, and secure systems that scale. - Motivation and high-agency to drive outcomes in a high-autonomy culture. - 4+ years hands-on experience building production systems. - Degree in Computer Science or related field, or equivalent professional experience. EVEN BETTER... - Experience building AI products for enterprise or consumers - Experience building native SDKs for iOS (Swift) or Android (Kotlin) - Experience building messaging apps, voice apps or voice agents - Experience with SIP, WebRTC, Twilio or contact-center platforms - Experience with real-time, low-latency distributed systems None of these are required. If the problems above excite you, we’d love to hear from you. 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 - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

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. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO - Reporting & Experimentation: Build a system for analyzing and visualizing millions of data points about agent performance. Enable agent developers to run A/B test their agents to make data-driven decisions about agent behavior. - Data Exploration: Build Explorer, the equivalent of ChatGPT + AI-powered clustering over conversational data. - Monitoring: Build systems for proactively monitoring agents for defects or new patterns. WHAT YOU'LL BRING - A passion for being on the frontier of AI products. - Motivation and high-agency to drive outcomes - we have a high-autonomy culture and each team member has lots of agency to overcome obstacles and achieve customer impact. - Alignment to our company values throughout your work, notably finding a balance between Craftsmanship, Customer Obsession, and Competitive Intensity. - 4+ years hands-on experience building production products and systems. - Experience and comfort to build and ship full-stack solutions. - Degree in Computer Science or related field, or equivalent professional experience. EVEN BETTER... - Experience building AI-powered products. - A sharp eye for design. - Experience with Go and Typescript. - Experience building developer tooling, programming languages, or databases. - Leadership experience on technical projects or teams. 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 - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

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. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO - Simulation & Benchmarking: How can we craft a simulation platform to test AI agents against every real-world scenario imaginable? (See 𝜏-Bench https://sierra.ai/blog/benchmarking-ai-agents) - Content Management: How do we create intuitive, no-code tools that allow anyone to guide and test AI agents? - Agent Development Lifecycle: How do we adapt traditional software development methodologies to accommodate AI agents’ non-deterministic behavior, natural language interactions, and reliance on large language models? (See Sierra’s ADLC https://sierra.ai/blog/agent-development-life-cycle) - Generative Agent Development: How do we accelerate agent creation using generative tools like Cursor and Claude Code? Can we build self-improving systems based on real-world interactions, customer-driven feedback, and self-play? WHAT YOU'LL BRING - A passion for being on the frontier of AI products. - Motivation and high-agency to drive outcomes - we have a high-autonomy culture and each team member has lots of agency to overcome obstacles and achieve customer impact. - Alignment to our company values throughout your work, notably finding a balance between Craftsmanship, Customer Obsession, and Competitive Intensity. - 4+ years hands-on experience building production products and systems. - Experience and comfort to build and ship full-stack solutions. - Degree in Computer Science or related field, or equivalent professional experience. EVEN BETTER... - Experience building AI-powered products. - A sharp eye for design. - Experience with Go and Typescript. - Experience building developer tooling, programming languages, or databases. - Leadership experience on technical projects or teams. 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 - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

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. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO - Build the core systems that power agents. You’ll work on the Agent SDK — the orchestration engine, runtime, and primitives that define how agents reason, take actions, and interact with users and systems. - Design the agentic loop. What primitives do we need to build agents that are steerable and verifiable, while still conversational and adaptive? You’ll help define how agents operate in real-world environments. - Improve retrieval and grounding. You’ll build systems that ensure agents provide accurate, trustworthy responses by effectively retrieving and using knowledge. - Build evaluation systems. You’ll design frameworks that allow us and our customers to measure and improve agent quality over time. WHAT YOU'LL BRING - A passion for being on the frontier of AI products. - Strong software engineering fundamentals and experience building production systems. - Motivation and high-agency to drive outcomes in a high-autonomy culture. - 4+ years hands-on experience building production products and systems. - Degree in Computer Science or related field, or equivalent professional experience. EVEN BETTER - Experience building AI-powered systems or agent frameworks. - Experience with retrieval, evaluation systems, or LLM-based applications. - Experience building developer platforms or SDKs. - Experience with Go and Typescript. 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 - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: London Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. As a Software Engineer Intern, Agent, you'll work directly on production AI agents for Sierra's customers. You'll gain hands-on experience contributing to the design and development of AI agents, shipping features, and learning from real-world use cases at scale. If you're hungry to shape and learn from the most important technological wave in history, come build at Sierra.   WHAT YOU'LL BRING - Pursuing a bachelor's or master's degree in computer science or a related field - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences EVEN BETTER - Experience building or deploying AI/LLM systems in production - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering - Prior experience with React, TypeScript, and/or Go INTERN QUALIFICATIONS - The intern program is open to students graduating December 2027 - June 2028 - Note: The full benefits listed below are available only to full-time employees. Interns are eligible for a monthly stipend for health insurance, daily lunch, and, of course, free alphorn lessons. 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 - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.