Sierra has filed one layoff notice in the last twelve months, covering 242 workers, most recently September 2026. These are public filings with state labor departments, and an open role can sit alongside them. See the filings

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About the job

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 and were awarded our first contract with a federal agency. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry.

- Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies.

- We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions.

- In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.

WHAT YOU'LL DO

- Build and lead Sierra’s public sector sales team: Recruit, develop, and lead a team of account executives serving strategic federal, state, or local government accounts. Set clear expectations, coach for performance, and build a culture of customer obsession, accountability, and consistent execution.

- Own revenue growth and territory strategy: Translate Sierra’s public sector ambitions into territory coverage, account priorities, pipeline goals, and revenue plans. Allocate resources thoughtfully, maintain rigorous forecasts, and drive the team to consistently achieve or exceed revenue targets.

- Create opportunities around mission outcomes: Build executive relationships with agency leaders and help your team translate priorities such as constituent access, service delivery, workforce effectiveness, and program integrity into compelling AI agent opportunities. Serve as an executive sponsor for strategic accounts.

- Guide complex sales cycles from discovery through award: Coach account executives through long, multi-stakeholder government buying processes and engage directly at critical moments. Mobilize cross-functional support for executive alignment, solution development, business cases, security and legal reviews, pricing, proposal strategy, negotiation, and close.

- Shape acquisition and capture strategy: Ensure every priority opportunity has a credible path to contract and a disciplined capture plan. Help the team navigate funding, fiscal-year timing, competitive dynamics, and procurement pathways—including GSA schedules, GWACs, IDIQs, BPAs, state schedules, and cooperative purchasing agreements. Lead deal reviews that surface risks early and turn strategy into clear next steps.

- Scale Sierra’s partner ecosystem: Partner with public sector and partnerships leadership to build productive relationships with prime contractors, systems integrators, resellers, distributors, small-business partners, and technology providers. Guide decisions about direct sales, subcontracting, teaming, and partner-led transactions to expand customer access and accelerate growth.

- Lead strategic prime and teaming relationships: Establish executive alignment with key partners and help shape account ownership, deal registration, workshare, and joint go-to-market plans. Ensure partnerships bring meaningful customer access, past performance, implementation capacity, or procurement pathways—and translate into qualified pipeline and successful delivery.

- Drive disciplined pursuit and proposal decisions: Partner with the Public Sector GM on bid/no-bid recommendations and prioritize resources across strategic pursuits. Align sales, legal, security, product, engineering, and delivery teams to produce procurement responses that are compliant, differentiated, and precise.

- Stay accountable for customer success: Build trust with senior agency leaders, establish strong handoffs from sales to delivery, and remain engaged through deployment and expansion. Help resolve escalations and ensure commitments made during the sales process support lasting customer relationships.

- Build a repeatable public sector go-to-market motion: Work with public sector leadership to refine account segmentation, hiring and capacity plans, capture processes, partner strategy, contract-vehicle priorities, and sales playbooks. Bring market signals and customer feedback to product and company leadership to shape Sierra’s platform and public sector strategy.

- Lead an AI-native sales organization: Embed AI into how the team researches accounts, develops outreach, synthesizes calls, plans opportunities, creates proposals, and forecasts. Model effective use, share successful practices, and help account executives spend more time on judgment, strategy, and customer relationships.

WHAT YOU'LL BRING

- 15+ years of selling experience: Extensive experience in enterprise customer-facing sales role, specifically selling to the U.S. government.

- People leadership experience: 10+ years managing, mentoring, and developing a high-performing enterprise sales team.

- Enterprise experience: You've run and managed end-to-end complex deals ($1M+).

- Strong fluency in government acquisition and procurement, including funding and budget cycles, competitive solicitations, proposal processes, task orders, and common Federal or state contract vehicles.

- Experience developing and executing capture strategies before a solicitation is released—not simply responding once an RFP is public.

- A strong network and demonstrated ability to work with government technology partners, including prime contractors, systems integrators, resellers, distributors, and small-business teaming partners.

- Sound judgment about direct, channel, prime/subcontractor, and teaming models, with the ability to select and execute the right path for a particular agency and opportunity.

- The ability to build credibility with agency executives, program leaders, contracting and procurement officials, security teams, and technical stakeholders—and to align those groups around a shared path forward.

- Excellent executive communication, negotiation, account planning, and forecasting skills. You are rigorous about details, procurement milestones, and next steps.

- A passion for public sector work and a belief in the potential of government institutions to improve outcomes for the people they serve.

- Comfort operating with high ownership in an early-stage business: you create structure where it does not yet exist, move with urgency, and collaborate deeply across functions.

OUR VALUES

- Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.

- Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.

- Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.

- Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.

- Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.

WHAT WE OFFER

We want our benefits to reflect our values and offer the following to full-time employees:

- Flexible (unlimited) paid time off

- Medical, dental, and vision benefits for you and your family

- Life insurance and disability benefits

- Retirement plan dependent on country of employment

- Parental leave

- Fertility and family building benefits

- 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.