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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. 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 RETAIL TEAM - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice. - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line. - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone. WHAT YOU'LL DO - 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 - 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: Woburn, United States About Huzzle At Huzzle, we connect exceptional talent with top opportunities at leading companies across the UK, US, Canada, Europe, and Australia. Our clients include fast-growing startups and established businesses in SaaS, MarTech, FinTech, and EdTech. Unlike traditional outsourcing, you’ll be placed directly with a client as a core member of their team—giving you real ownership, career progression, and long-term stability. Salary: $45,000 base + uncapped commission. Most reps earn $55K-$70K in year one. Role Type: Full-time Location: Woburn, MA. On-site for your first 90 days, then hybrid About the Company Our client is one of the leading outsourced sales development companies in the US. They build and run phone-first sales teams for B2B tech companies, from fast-growing startups to names like Honeywell, PTC, SurveyMonkey and OpenText. Inc. 5000 fastest-growing private company five years in a row Employee-owned, so the team shares in the company’s success 170+ people across offices in Woburn, MA and Fort Lauderdale, FL Promote-from-within culture, with promotion reviews at 90 days and 6 months A great place to start a career in tech sales and grow fast. Job Summary We are looking for a driven, results-oriented B2B Sales Development Representative (SDR) to join a fast-growing company in a full-time, on-site position. In this role, you'll be responsible for identifying potential business customers, generating qualified leads, and booking meetings for the sales team through strategic outbound prospecting. The ideal candidate has proven experience in B2B outbound sales, excellent communication skills, and the ability to engage decision-makers through cold calling, email outreach, and LinkedIn prospecting. Key Responsibilities Identify and research potential B2B clients within target industries and markets. Conduct high-volume outbound prospecting through cold calls, personalized emails, and LinkedIn outreach. Engage key decision-makers, including founders, executives, and department heads. Qualify leads based on customer needs, budget, authority, and buying intent. Book qualified sales meetings and product demonstrations for Account Executives or senior sales representatives. Maintain accurate prospect records, sales activities, and pipeline updates in CRM platforms such as HubSpot, Salesforce, or Pipedrive. Handle objections confidently and communicate the company's value proposition effectively. Collaborate closely with the on-site sales and marketing teams to optimize outreach strategies and improve conversion rates. Consistently meet or exceed KPIs related to outreach activity, qualified leads, and meetings booked. Requirements 1–3+ years of experience in B2B sales, sales development, lead generation, or appointment setting. Proven track record of successful outbound prospecting and booking qualified B2B meetings. Excellent written and spoken English with strong interpersonal and communication skills. Confidence in cold calling and engaging senior-level decision-makers. Experience using CRM tools such as HubSpot, Salesforce, or Pipedrive. Familiarity with sales prospecting tools such as Apollo, LinkedIn Sales Navigator, Instantly, or similar platforms. Strong objection-handling, relationship-building, and negotiation skills. Self-motivated, organized, and comfortable working in a fast-paced, office-based sales environment. Ability to work collaboratively with colleagues and managers on-site. Willingness and ability to commute to the office daily. Nice to Have: Experience selling SaaS, technology solutions, professional services, or other B2B offerings. Familiarity with multichannel outbound sales sequences. Experience working with international clients, particularly in the UK or US. Understanding of sales methodologies such as BANT, SPIN, or consultative selling. Benefits 🚀 Opportunity to work with a growing, ambitious sales team. 🤝 Structured onboarding, hands-on support, and team collaboration. 💼 Long-term career opportunities with a high-growth business. 🏢 Collaborative, on-site working environment.

Location: Ethiopia About Huzzle At Huzzle, we connect exceptional talent with top opportunities at leading companies across the UK, US, Canada, Europe, and Australia. Our clients include fast-growing startups and established businesses in SaaS, MarTech, FinTech, and EdTech. Unlike traditional outsourcing, you’ll be placed directly with a client as a core member of their team—giving you real ownership, career progression, and long-term stability. Role Type: Full-time Engagement: Independent Contractor Job Summary We are hiring experienced and results-driven Sales Development Representatives (SDRs) for full-time remote opportunities with growing international companies. As an SDR, you'll be responsible for identifying potential business customers, generating qualified leads, conducting outbound prospecting, and booking meetings for sales teams. The ideal candidate has at least 2 years of proven B2B outbound sales experience, excellent communication skills, and the confidence to engage business decision-makers across international markets. Fluent English and previous B2B sales experience are mandatory requirements for this role. Key Responsibilities Conduct high-volume B2B outbound prospecting through cold calls, emails, and LinkedIn outreach. Research and identify target businesses, key stakeholders, and decision-makers. Generate and qualify B2B leads based on business needs, budget, authority, and buying intent. Schedule qualified meetings and product demonstrations for Account Executives and sales teams. Manage and maintain accurate prospect information in CRM platforms such as HubSpot, Salesforce, or Pipedrive. Execute personalized outreach sequences to improve response rates and conversions. Consistently meet or exceed KPIs related to outreach activity, qualified leads, and meetings booked. Collaborate with sales and marketing teams to refine targeting and outreach strategies. Follow up with prospects professionally and maintain strong relationships throughout the B2B sales pipeline. Requirements Minimum 2 years of professional B2B sales experience, preferably in an SDR, BDR, or outbound sales role. Proven B2B outbound prospecting experience is mandatory. Candidates with exclusively B2C sales experience will not be considered. Fluent English (written and spoken) is mandatory, with excellent pronunciation, comprehension, and professional communication skills. Demonstrated success in B2B cold calling, cold emailing, lead generation, and appointment setting. Experience engaging business owners, managers, executives, and other key decision-makers. Proven ability to generate qualified B2B leads and book sales meetings. Experience using CRM systems such as HubSpot, Salesforce, Pipedrive, or similar platforms. Strong objection-handling, negotiation, and relationship-building skills. Confidence communicating with international business clients. Self-motivated, target-driven, and comfortable working independently in a remote environment. Strong organizational skills and the ability to manage multiple prospects and follow-ups. Reliable internet connection and a professional remote working setup. Nice to Have Experience selling into US, UK, or other international B2B markets. Previous experience in B2B SaaS, technology, digital marketing, or professional services. Familiarity with prospecting tools such as Apollo, LinkedIn Sales Navigator, Lemlist, or Instantly. Experience working in fast-paced startups or high-growth sales teams. Benefits 🌎 Fully remote role with flexible working hours 🚀 Work with high-growth international companies 📈 Clear career progression to Account Executive and beyond 🎯 Performance-based bonuses and incentives 🧠 Ongoing training, mentorship, and sales development support

Location: Fort Lauderdale, United States About Huzzle At Huzzle, we connect exceptional talent with top opportunities at leading companies across the UK, US, Canada, Europe, and Australia. Our clients include fast-growing startups and established businesses in SaaS, MarTech, FinTech, and EdTech. Unlike traditional outsourcing, you’ll be placed directly with a client as a core member of their team—giving you real ownership, career progression, and long-term stability. Salary: $45,000 base + uncapped commission. Most reps earn $55K-$70K in year one. Role Type: Full-time Location: Fort Lauderdale, FL. On-site for your first 90 days, then hybrid About the Company Our client is one of the leading outsourced sales development companies in the US. They build and run phone-first sales teams for B2B tech companies, from fast-growing startups to names like Honeywell, PTC, SurveyMonkey and OpenText. Inc. 5000 fastest-growing private company five years in a row Employee-owned, so the team shares in the company’s success 170+ people across offices in Woburn, MA and Fort Lauderdale, FL Promote-from-within culture, with promotion reviews at 90 days and 6 months A great place to start a career in tech sales and grow fast. Job Summary We are looking for a driven, results-oriented Sales Development Representative (SDR) with proven B2B sales experience to join a fast-growing company in an on-site position. In this role, you will be responsible for identifying potential business customers, conducting outbound prospecting, engaging decision-makers, and booking qualified meetings for the sales team. The ideal candidate has hands-on experience in B2B lead generation, cold calling, email outreach, and CRM management. You should be confident communicating with business professionals and comfortable working in a target-driven, office-based sales environment. Key Responsibilities Conduct outbound prospecting through cold calls, emails, and LinkedIn outreach. Identify and engage key decision-makers within target businesses. Generate and qualify B2B leads based on ideal customer profiles. Book qualified meetings and discovery calls for Account Executives or senior sales representatives. Manage and maintain accurate prospect information within CRM systems. Follow up consistently with prospects to nurture relationships and drive conversions. Collaborate with the on-site sales team to improve outreach strategies and pipeline generation. Meet or exceed weekly and monthly KPIs, including outreach activity, qualified leads, and meetings booked. Requirements Previous B2B sales experience is mandatory. Proven experience in an SDR, BDR, outbound sales, or B2B lead generation role. Strong cold calling and outbound prospecting skills. Experience engaging business owners, managers, and senior decision-makers. Excellent written and spoken English communication skills. Familiarity with CRM platforms such as HubSpot, Salesforce, or Pipedrive. Experience using sales prospecting tools such as LinkedIn Sales Navigator, Apollo, or similar platforms. Strong objection-handling, relationship-building, and negotiation skills. Ability to work effectively in a fast-paced, office-based sales environment. Must be able to work on-site full-time. Benefits 🚀 Opportunity to work with a growing, ambitious sales team. 🤝 Structured onboarding, hands-on support, and team collaboration. 💼 Long-term career opportunities with a high-growth business. 🏢 Collaborative, on-site working environment.

Location: United States; Canada (BC & ON only) Workplace: Remote Webflow is the agentic web marketing platform for modern marketing teams, helping organizations build, manage, and optimize high-performing web experiences that drive predictable growth and strengthen brand trust. Building at Webflow will need grit, because we move fast, without ever sacrificing craft or quality. We’re looking for a Financial Analyst, GTM to serve as the primary finance partner to our Sales, Marketing, and Customer Success leadership. This is a high-visibility, high-impact role sitting right at the center of GTM decisions, helping leadership decide where to invest, improve productivity, and drive predictable ARR growth. ABOUT THE ROLE: - Location: Remote-first (United States; BC & ON, Canada) - Full-time - Permanent - Exemption status: Exempt (US Only) - The cash compensation for this role is tailored to align with the cost of labor in different geographic markets. We've structured the base pay ranges for this role into zones for our geographic markets, and the specific base pay within the range will be determined by the candidate’s geographic location, job-related experience, knowledge, qualifications, and skills. - United States (all figures cited below are in USD and pertain to workers in the United States) - Zone A: $112,000 - $135,000 - Zone B: $105,000 - $126,000 - Zone C: $98,300 - $118,000 - Canada (figures cited below are in CAD and pertain to workers in ON & BC, Canada) - $123,000 - $147,000 This role is also eligible to participate in Webflow's company-wide bonus program. Target amounts are a percentage of base salary and vary by career level. Payouts are based on company performance against established financial and operational goals. Please visit our Careers page https://webflow.com/careers#pay-zones for more information on which locations are included in each of our geographic pay zones. However, please confirm the zone for your specific location with your recruiter. - Application Information: - Application deadline: applications accepted on an ongoing basis until position is closed and filled - This posting is for an existing vacancy - Reporting to the Director of Corporate Finance As a Financial Analyst, GTM, you’ll: - Own the GTM expense plan and forecast, covering headcount and non-headcount spend, and turn it into executive-ready commentary for Sales, Marketing, and Customer Success leaders on variances, risks, and investment tradeoffs - Manage GTM headcount planning and capacity, including hiring plans, ratios such as quota-carrying reps to sales support, and attrition, and flag drift from targets before it affects the forecast - Reduce manual effort in planning by improving Workday and Adaptive Planning workflows, removing manual tagging, and setting materiality thresholds so non-headcount forecast updates focus on spend that moves the outlook - Own the single source of truth for ARR and ATR across our Sales and Self-Serve models, auditing the ARR in Salesforce and the data warehouse, documenting metric definitions, and resolving breaks with Revenue Operations, Data and/or Accounting - Run the monthly churn, renewal, and write-off review with GTM partners, preparing the analysis, root-cause commentary, and forecast implications leaders use to make decisions - Synthesize multi-source data from Salesforce, the data warehouse, Workday, and NetSuite into clear metrics, KPIs, and business narratives that inform GTM leadership decisions - Build working relationships across Finance, Accounting, Procurement, and GTM to drive alignment without formal authority, and automate recurring reporting with SQL, spreadsheets, and AI tools ABOUT YOU: Requirements: - BS / BA college degree in Finance, Accounting, Economics, or a related field, or relevant experience - 3+ years of experience in FP&A, corporate finance, investment banking, consulting, or public accounting; experience in SaaS or a subscription business is preferred - Strong proficiency in Excel or Google Sheets, including building models from raw data You’ll thrive as a Financial Analyst, GTM if you: - Have a working understanding of SaaS metrics such as ARR, NRR, GRR, churn, and renewals, and can trace them back to source data in Salesforce and the data warehouse - Enjoy partnering with Sales, Marketing, and Customer Success leaders and can explain financial results in plain terms to non-finance audiences - Notice manual work and fix it, whether with SQL, spreadsheet automation, or AI tools - Bring accounting fluency, including accruals and the monthly close; a CPA and a Big 4 background is preferred - Stay curious and open to growth — demonstrating a proactive embrace of AI, and actively building and applying fluency in emerging technologies to elevate how we work, drive faster outcomes, and expand collective impact. OUR CORE BEHAVIORS - Build lasting customer trust. We build trust by taking action that puts customer trust first. - Win together. We play to win, and we win as one team. Success at Webflow isn't a solo act. - Reinvent ourselves. We don't just improve what exists, we imagine what's possible. - Own it all the way. We move fast because the moment demands it, and we hold ourselves accountable to deliver outcomes — for each other, and for customers.   BENEFITS - Ownership in what you help build. Every permanent Webflower receives equity (RSUs) in our growing, privately held company. - Health coverage that actually covers you. Comprehensive medical, dental, and vision plans for full-time employees and their dependents, with Webflow covering most premiums. - Support for every stage of family life. 12 weeks of paid parental leave for all parents and 6+ weeks of additional paid leave for birthing parents. Plus inclusive care for family planning, menopause, and midlife transitions. - Time off that’s actually off. Flexible vacation, paid holidays, and a sabbatical program to help you recharge and come back inspired. - Wellness for the whole you. Access to mental health resources, therapy and coaching. - Invest in your future. A 401(k) with 100% employer match (up to $6,000/year) in the U.S., and support for retirement savings globally. - Stipends to support our distributed team. Localized support for cell, Wi-Fi, and WFH expenses to help you settle into your best remote life. - Bonus for building together. All full-time, permanent, non-commission employees are eligible for our annual WIN bonus program.   Temporary employees may be eligible for paid holiday and time off, statutory leaves of absence, and company-sponsored medical benefits depending on their Fixed Term Contract and their country/state of employment.   BE YOU, WITH US At Webflow, equality is a core tenet of our culture. We are an Equal Opportunity (EEO)/Veterans/Disabled Employer and are committed https://webflow.com/diversity-equity-inclusion to building an inclusive global team that represents a variety of backgrounds, perspectives, beliefs, and experiences. Employment decisions are made on the basis of job-related criteria without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other classification protected by applicable law. Pursuant to the San Francisco Fair Chance Ordinance, Webflow will consider for employment qualified applicants with arrest and conviction records.   STAY CONNECTED Not ready to apply, but want to be part of the Webflow community? Consider following our story on our Webflow Blog https://webflow.com/blog, LinkedIn https://www.linkedin.com/company/webflow-inc-/, X (Twitter) https://twitter.com/webflow, and/or Glassdoor https://www.glassdoor.com/Reviews/Webflow-Reviews-E890506.htm.   PLEASE NOTE: We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, to perform essential job functions, and to receive other benefits and privileges of employment. Upon interview scheduling, instructions for accommodation requests will be administered. To join Webflow, you'll need a valid right to work authorization depending on the country of employment. If you are extended an offer, that offer may be contingent upon your successful completion of a background check, which will be conducted in accordance with applicable laws. We may obtain one or more background screening reports about you, solely for employment purposes. Webflow uses AI tools to assist in screening and evaluating applications. AI does not make final hiring decisions. For details on how we process your personal information, see Webflow’s Applicant Privacy Notice https://webflow.com/legal/applicant-privacy-notice.

Location: Oakland, California, United States, AMER From Fivetran’s founding until now, our mission has remained the same: to make access to data as simple and reliable as electricity. With Fivetran, customer data arrives in their warehouses, canonical and ready to query, with no engineering or maintenance required. We’re proud that more organizations continue to leverage our technology every day to become truly data-driven. About the role The Principal of Marketing Insights sits at the intersection of growth strategy, investment planning, and performance analytics. You’ll partner with the office of CMO, marketing leadership, and cross-functional analytics teams to determine where we invest, how we improve performance, and what it will take to achieve our growth targets. You’ll translate business goals and performance insights into clear priorities, resource decisions, and coordinated action across Marketing. This includes shaping pipeline strategy, evaluating investment tradeoffs, and identifying opportunities to improve conversion, velocity, and efficiency across regions, segments, and growth motions. This is a high-visibility leadership role during a period of significant organizational change. We’re looking for someone who brings structure to ambiguity, challenges assumptions with sound business judgment, and drives decisions through to measurable results. You’ll work closely with marketing leaders, Finance, GTM Operations, Technical Marketing Ops, and Central Analytics to connect strategy, investment, and execution. What you’ll do Growth strategy & planning: Translate company growth targets into marketing plans with clear priorities, investment requirements, and performance assumptions. Lead the analytical foundation for annual and quarterly planning, developing scenarios that evaluate growth opportunities, resource needs, and tradeoffs. Own marketing’s pipeline planning models and assumptions, coordinating inputs across regions, segments, channels, and motions. Identify the highest-impact opportunities to improve pipeline generation, conversion, and velocity; partner with functional leaders to turn those opportunities into action. Investment strategy & efficiency: Shape recommendations for allocating resources across programs, channels, regions, and segments based on expected business impact. Evaluate tradeoffs between headcount and program investment, partnering with Finance and marketing leaders to improve resource productivity. Identify where to scale, reduce, or reallocate spend, and measure whether those decisions improve pipeline yield and marketing efficiency. Develop models that connect marketing investment to pipeline and revenue outcomes, making assumptions and uncertainties clear. Program management & accountability: Lead weekly and monthly marketing performance reviews, focusing leadership on the decisions and actions needed to achieve targets. Proactively identify performance risks, diagnose root causes, and align leaders on corrective actions, owners, and timelines. Track actions and assess their impact, adjusting the approach when results fall short. Lead cross-functional initiatives across Marketing, XDR, Sales, Finance, and Analytics, resolving dependencies and escalating decisions when needed. Insights & measurement: Set the strategic analysis agenda around the business questions most consequential to marketing growth and efficiency. Define the metrics, scorecards, and decision tools marketing leaders need to manage performance. Partner with Analytics to deliver scalable reporting and with Marketing Ops to ensure consistent definitions, reliable tracking, and data quality. Translate complex analysis into clear executive narratives that explain what is happening, why it matters, and what action to take. Skills we’re looking for 8+ years experience in marketing strategy, GTM analytics, or business performance within B2B SaaS, with scope and impact consistent with director-level leadership. A demonstrated record of influencing investment decisions and delivering measurable improvements in pipeline, conversion, or marketing efficiency. Experience developing growth plans, pipeline models, investment scenarios, and performance assumptions. Strong business judgment and a clear point of view, with the confidence to challenge senior stakeholders constructively and build alignment around difficult tradeoffs. Proven ability to lead cross-functional initiatives and drive recommendations through to execution and results. Ability to independently structure ambiguous problems and balance speed with analytical rigor. Deep understanding of B2B SaaS metrics, including pipeline, ARR, conversion, velocity, acquisition costs, and attribution. Hands-on fluency with SQL and BI tools such as Looker, enabling independent investigation and effective partnership with Analytics. Working knowledge of Salesforce and marketing automation platforms such as Marketo. Clear executive communication, with the ability to connect detailed analysis to business decisions. Bonus Skills Experience navigating a merger, organizational integration, or significant GTM transformation. Experience with experiment design, incrementality measurement, predictive modeling, or cohort analysis. Familiarity with the modern data stack, including Fivetran, dbt, Snowflake, and Looker. Background in data infrastructure, developer tools, or analytics software. The compensation range displayed on this job posting reflects the minimum and maximum target for new hire compensation for the target position and level, and may include sales incentives or target bonuses depending on the role.  Our compensation ranges are determined by role, level, and location. Our job titles may span more than one career level. Within the range, individual compensation is determined by additional factors, including job-related skills, experience, relevant education or training, business need, market demands. The compensation range is subject to change and may be modified in the future. Your recruiter can share more about the specific compensation range for your location during the hiring process. Oakland Pay Range $179,670 — $224,587 USD Perks and Benefits 100% employer-paid medical insurance * Generous paid time away from work, including paid vacation or flexible/unlimited vacation depending on role and country, plus paid sick time, inclusive parental leave, paid holidays, including a year-end Global Week of Rest, and volunteer days off. RSU stock grants* Professional development and training opportunities Company virtual happy hours, free food, and fun team-building activities Monthly cell phone stipend Access to an innovative mental health support platform that offers personalized care and resources in areas such as: therapy, coaching, and self-guided mindfulness exercises for all covered employees and their covered dependents. * May vary by country and worker type - please reach out to your recruiter for more information Click here to learn more about Fivetran's Benefits by Region. We’re honored to be valued at over $5.6 billion , but more importantly, we’re proud of our core values of Get Stuck In, Do the Right Thing, and One Team, One Dream . Read about us in Forbes . Fivetran brings together high-quality talent across the globe to make data access as easy and reliable as electricity for our customers. We value and recognize that our customers benefit from having innovative teams made of people from many backgrounds, experiences, and identities. Fivetran promotes diversity, equity, inclusion & belonging through attracting, recruiting, developing, and retaining a diverse workforce, not only because it is the right thing to do, but because it helps us build a world-class company to better serve our customers, our people and our communities. To learn more about Fivetran’s culture and what it’s like to be part of the team, click here and enjoy our video. To learn more about our candidate privacy policy, you can read our statement here . We are committed to ensuring that all candidates have an equal opportunity to participate in our interview process. If you require accommodations at any stage of the process due to a disability, medical condition, or any other circumstance, please don't hesitate to submit your request by filling out this form . We will work with you to provide reasonable accommodations to facilitate your participation and ensure a fair and accessible interview experience. Your request and any information provided will be kept confidential and will not impact your candidacy. We look forward to hearing from you and accommodating your needs to the best of our ability.

Location: Denver, Colorado, United States, AMER From Fivetran’s founding until now, our mission has remained the same: to make access to data as simple and reliable as electricity. With Fivetran, customer data arrives in their warehouses, canonical and ready to query, with no engineering or maintenance required. We’re proud that more organizations continue to leverage our technology every day to become truly data-driven. About the role The Principal of Marketing Insights sits at the intersection of growth strategy, investment planning, and performance analytics. You’ll partner with the office of CMO, marketing leadership, and cross-functional analytics teams to determine where we invest, how we improve performance, and what it will take to achieve our growth targets. You’ll translate business goals and performance insights into clear priorities, resource decisions, and coordinated action across Marketing. This includes shaping pipeline strategy, evaluating investment tradeoffs, and identifying opportunities to improve conversion, velocity, and efficiency across regions, segments, and growth motions. This is a high-visibility leadership role during a period of significant organizational change. We’re looking for someone who brings structure to ambiguity, challenges assumptions with sound business judgment, and drives decisions through to measurable results. You’ll work closely with marketing leaders, Finance, GTM Operations, Technical Marketing Ops, and Central Analytics to connect strategy, investment, and execution. What you’ll do Growth strategy & planning: Translate company growth targets into marketing plans with clear priorities, investment requirements, and performance assumptions. Lead the analytical foundation for annual and quarterly planning, developing scenarios that evaluate growth opportunities, resource needs, and tradeoffs. Own marketing’s pipeline planning models and assumptions, coordinating inputs across regions, segments, channels, and motions. Identify the highest-impact opportunities to improve pipeline generation, conversion, and velocity; partner with functional leaders to turn those opportunities into action. Investment strategy & efficiency: Shape recommendations for allocating resources across programs, channels, regions, and segments based on expected business impact. Evaluate tradeoffs between headcount and program investment, partnering with Finance and marketing leaders to improve resource productivity. Identify where to scale, reduce, or reallocate spend, and measure whether those decisions improve pipeline yield and marketing efficiency. Develop models that connect marketing investment to pipeline and revenue outcomes, making assumptions and uncertainties clear. Program management & accountability: Lead weekly and monthly marketing performance reviews, focusing leadership on the decisions and actions needed to achieve targets. Proactively identify performance risks, diagnose root causes, and align leaders on corrective actions, owners, and timelines. Track actions and assess their impact, adjusting the approach when results fall short. Lead cross-functional initiatives across Marketing, XDR, Sales, Finance, and Analytics, resolving dependencies and escalating decisions when needed. Insights & measurement: Set the strategic analysis agenda around the business questions most consequential to marketing growth and efficiency. Define the metrics, scorecards, and decision tools marketing leaders need to manage performance. Partner with Analytics to deliver scalable reporting and with Marketing Ops to ensure consistent definitions, reliable tracking, and data quality. Translate complex analysis into clear executive narratives that explain what is happening, why it matters, and what action to take. Skills we’re looking for 8+ years experience in marketing strategy, GTM analytics, or business performance within B2B SaaS, with scope and impact consistent with director-level leadership. A demonstrated record of influencing investment decisions and delivering measurable improvements in pipeline, conversion, or marketing efficiency. Experience developing growth plans, pipeline models, investment scenarios, and performance assumptions. Strong business judgment and a clear point of view, with the confidence to challenge senior stakeholders constructively and build alignment around difficult tradeoffs. Proven ability to lead cross-functional initiatives and drive recommendations through to execution and results. Ability to independently structure ambiguous problems and balance speed with analytical rigor. Deep understanding of B2B SaaS metrics, including pipeline, ARR, conversion, velocity, acquisition costs, and attribution. Hands-on fluency with SQL and BI tools such as Looker, enabling independent investigation and effective partnership with Analytics. Working knowledge of Salesforce and marketing automation platforms such as Marketo. Clear executive communication, with the ability to connect detailed analysis to business decisions. Bonus Skills Experience navigating a merger, organizational integration, or significant GTM transformation. Experience with experiment design, incrementality measurement, predictive modeling, or cohort analysis. Familiarity with the modern data stack, including Fivetran, dbt, Snowflake, and Looker. Background in data infrastructure, developer tools, or analytics software. #LI-JC1 #LI-Hybrid The compensation range displayed on this job posting reflects the minimum and maximum target for new hire compensation for the target position and level, and may include sales incentives or target bonuses depending on the role.  Our compensation ranges are determined by role, level, and location. Our job titles may span more than one career level. Within the range, individual compensation is determined by additional factors, including job-related skills, experience, relevant education or training, business need, market demands. The compensation range is subject to change and may be modified in the future. Your recruiter can share more about the specific compensation range for your location during the hiring process. Denver Pay Range $173,573.50 — $216,966.75 USD Perks and Benefits 100% employer-paid medical insurance * Generous paid time away from work, including paid vacation or flexible/unlimited vacation depending on role and country, plus paid sick time, inclusive parental leave, paid holidays, including a year-end Global Week of Rest, and volunteer days off. RSU stock grants* Professional development and training opportunities Company virtual happy hours, free food, and fun team-building activities Monthly cell phone stipend Access to an innovative mental health support platform that offers personalized care and resources in areas such as: therapy, coaching, and self-guided mindfulness exercises for all covered employees and their covered dependents. * May vary by country and worker type - please reach out to your recruiter for more information Click here to learn more about Fivetran's Benefits by Region. We’re honored to be valued at over $5.6 billion , but more importantly, we’re proud of our core values of Get Stuck In, Do the Right Thing, and One Team, One Dream . Read about us in Forbes . Fivetran brings together high-quality talent across the globe to make data access as easy and reliable as electricity for our customers. We value and recognize that our customers benefit from having innovative teams made of people from many backgrounds, experiences, and identities. Fivetran promotes diversity, equity, inclusion & belonging through attracting, recruiting, developing, and retaining a diverse workforce, not only because it is the right thing to do, but because it helps us build a world-class company to better serve our customers, our people and our communities. To learn more about Fivetran’s culture and what it’s like to be part of the team, click here and enjoy our video. To learn more about our candidate privacy policy, you can read our statement here . We are committed to ensuring that all candidates have an equal opportunity to participate in our interview process. If you require accommodations at any stage of the process due to a disability, medical condition, or any other circumstance, please don't hesitate to submit your request by filling out this form . We will work with you to provide reasonable accommodations to facilitate your participation and ensure a fair and accessible interview experience. Your request and any information provided will be kept confidential and will not impact your candidacy. We look forward to hearing from you and accommodating your needs to the best of our ability.

Location: New York, NY (HQ); San Francisco, CA Workplace: Hybrid ABOUT RAMP Ramp is building the smart infrastructure for finance teams, embedded in the transaction flow of every dollar a business spends. We automate how over $275B in annualized spend flows in and out of 85,000+ companies: authorizing payments, flagging risk, categorizing spend, and closing books. The problems are high-stakes, data-dense, and unforgiving. We hire people with high agency and high urgency. We look for slope over intercept. We care less about where you trained and more about what you’ve built. At Ramp, everyone is a builder who owns problems end to end and makes consequential decisions that shape the outcome. The median Ramp customer saves 7.5% and grows revenue 16% in their first year – far in excess of businesses operating without Ramp. We believe every ambitious company deserves the same. If you want to build systems that directly shape how companies move and manage billions, Ramp is the place to do it. ABOUT THE ROLE You will be a front-line manager to a group of 6-8 CSMs, who each manage ~60 Activations at a given time in Ramp’s Mid Market portfolio. You will be responsible for developing and standardizing implementation best practices, 1:1 coaching and mentoring, building a repeatable and scalable customer activation motion that enables growth without proportional increases in team size, and working closely with leaders across Sales, Marketing, Operations, Risk, and Product to drive positive outcomes for this segment. As a key member of the Mid Market CSM leadership team, you will have the opportunity to help build and refine Ramp’s customer success and onboarding motion. WHAT YOU'LL DO - Set and maintain a high-performing culture and morale by managing a group of exceptional CSMs to drive thorough and efficient onboarding and product activation for Ramp’s medium/large customers - Oversee the daily activities and quota performance management of individual CSMs to ensure team exceeds product onboarding and spend activation goals, while maintaining strong CSAT - Refine best practice playbooks for the CSM team, and improve team output and efficiency over time by optimizing systems and processes - Develop and execute career development and leadership plans for direct reports; inclusive of but not limited to daily 1:1 mentoring, coaching on sales skills, enhancing product knowledge, providing call feedback, and running enablement sessions - Act as a voice of the customer and key contributor retaining and expanding Ramp’s Mid Market segment - Build and leverage internal AI tools and Salesforce dashboards to monitor the success of our customers and the performance of the team - Report on team performance and forecast to senior leadership - Represent the CSM team cross-functionally with leaders of other departments WHAT YOU NEED - 5+ years of implementation, CSM or AM experience as an individual contributor, with a proven, consistent track record exceeding goals - 3+ years of experience building and leading implementation or CSM teams with a proven track record of exceeding goals - Prior demonstrated success in fast-paced, results-oriented GTM environments, ideally at SaaS companies - Ability to identify trends, translate company strategy into team-level priorities, and drive initiatives that improve team metrics and organizational outcomes - Proven ability to coach teams on selling the full platform, not just individual products; experience driving multi-product adoption, cross-sell, and upsell across a book of business - Track record of pushing pace on input metrics, building repeatable playbooks, and optimizing systems and processes to improve team output - Strong collaboration and influencing skills across Sales, Product, Operations, and other GTM teams; demonstrated ability to represent Customer Success at a leadership level - Comfort with and curiosity about AI tools and their application to CS workflows; ability to lead a team through AI-driven process transformation and evaluate how AI can augment CSM productivity and customer outcomes - Strong understanding of customer financial workflows, including AP/AR, spend controls, and month-end close processes; ability to coach CSMs on ROI-grounded conversations with controllers and finance leaders - Proficiency in data analytics tools (Salesforce, Looker, and Excel) with the ability to leverage data to drive decisions, create systems, and identify process improvements. NICE TO HAVES - CPA or equivalent accounting certification, or deep working knowledge of accounting software (e.g. NetSuite, QuickBooks, Xero, Sage) - Experience with financial services sales or selling into finance and accounting personas - Experience at a high-growth startup in an enterprise or mid-market customer success environment - Familiarity with contribution profit models or usage-based revenue metrics - Experience leading teams through AI adoption or workflow automation initiatives BENEFITS AVAILABLE TO ALL FULL-TIME RAMP EMPLOYEES (GLOBAL) - Flexible PTO - Centralized home-office equipment ordering - Health and wellness stipend - Budget for intra-office travel - Weekly coffee stipend UNITED STATES - 100% medical, dental & vision insurance coverage for you, with partial coverage for dependents - One Medical annual membership - 401(k), including employer match on contributions made while employed by Ramp - Fertility HRA (up to $10,000 per year) - Parental leave: up to 16 weeks (birthing + bonding) or 8 weeks (bonding only) at 100% pay - Pet insurance - In-office perks: lunch, snacks, drinks, and more - Relocation expense coverage to NYC or SF (if needed) CANADA - Group medical, dental, and vision coverage through Sun Life - Life, AD&D, and disability coverage - Fertility drug coverage (up to $4,000 lifetime) - Group Retirement Plan with employer match (RRSP + DPSP) - Parental leave: up to 16 weeks (birthing + bonding) or 8 weeks (bonding only) at 100% pay, with additional time available at reduced pay - Employee Assistance Program and virtual care through Lumino Health UNITED KINGDOM - Private medical insurance through Freedom Elite - Virtual GP and at-home care via eMed x Livi - Workplace pension through Penfold, with salary sacrifice option - Parental leave: up to 16 weeks (birthing + bonding) or 8 weeks (bonding only) at 100% pay with additional time available at reduced pay REFERRAL INSTRUCTIONS If you are being referred for the role, please contact that person to apply on your behalf.   OTHER NOTICES Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.   Beware of recruiting scams: Ramp will only contact you through official @Ramp.com http://Ramp.com email addresses and will never ask for payment or sensitive personal information during the hiring process.   Ramp Applicant Privacy Notice https://ramp.com/legal/applicant-privacy-notice

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.