Enterprise Sales Director

About us At Sierra, we’re building a platform to enable every company in the world to build better, more human customer experiences with AI. We partner with industry leaders such as SoftBank, Uber, Rivian, CLEAR, and Sutter Health. 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 Family. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. About the Public Sector team Sierra recently received 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 Build Sierra’s public sector business: Own a portfolio of strategic Federal, state or local government accounts, develop territory and account plans, build qualified pipeline, and consistently achieve or exceed revenue targets. Create opportunities around mission outcomes: Develop trusted relationships with agency leaders, program executives, technology teams, procurement officials, and other stakeholders. Translate priorities such as constituent access, service delivery, workforce effectiveness, and program integrity into compelling AI agent opportunities. Lead complex sales cycles from discovery through award: Orchestrate executive alignment, solution development, business cases, security and legal reviews, pricing, proposal strategy, negotiation, and close across long, multi-stakeholder government buying processes. Design the path to contract: Understand how each customer can buy and shape a practical acquisition strategy early. Navigate direct awards, competitive solicitations, pilots, task orders, and contract vehicles—including GSA schedules, GWACs, IDIQs, BPAs, state schedules, and cooperative purchasing agreements—as relevant to the opportunity. Build and execute capture plans: Qualify opportunities with discipline; map decision-makers, influencers, incumbents, competitors, funding sources, fiscal-year timing, acquisition milestones, and win themes; and lead the internal cadence required to move from early demand to award. Develop Sierra’s partner ecosystem: Build productive relationships with prime contractors, systems integrators, resellers, distributors, small-business partners, and other technology providers. Know when Sierra should sell directly, participate as a subcontractor, establish a teaming arrangement, or pursue a partner-led transaction—and align incentives and responsibilities accordingly. Shape prime and teaming relationships: Identify where Sierra can strengthen a prime contractor’s solution and where partners can provide customer access, past performance, implementation capacity, or a procurement pathway. Negotiate clear account alignment, deal registration, workshare, and go-to-market plans that create durable value for the customer and Sierra. Run high-quality bids and proposals: Partner with public sector leadership, legal, security, product, engineering, and delivery teams on RFIs, RFPs, sources sought, oral presentations, and other procurement responses. Make thoughtful bid/no-bid recommendations and ensure every submission is compliant, differentiated, and precise. Operate as part of the customer’s team: Earn trust across senior agency leadership and working teams by understanding the mission, communicating candidly, and remaining accountable from the first meeting through deployment and expansion. Help build the public sector go-to-market motion: As an early member of the team, improve our account segmentation, capture process, partner strategy, contract-vehicle roadmap, forecasting, and repeatable sales playbooks. Bring market signals back to product and company leadership to help shape Sierra’s platform and public sector strategy. Operate as an AI-native seller: Use AI throughout the sales cycle—from account research and personalized outreach to call synthesis, opportunity planning, proposal development, and forecasting—so you can spend more time on judgment, strategy, and customer relationships. What you'll bring Meaningful enterprise technology sales or business development experience, including significant experience selling software, cloud, data, or AI solutions to U.S. government customers. A demonstrated record of building pipeline, exceeding quota, and closing complex six- and seven-figure opportunities with long sales cycles and multiple technical, mission, executive, and procurement stakeholders. 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. Even better... Experience helping launch or scale a public sector business for a high-growth software company. Established relationships across Federal civilian agencies, state governments, or the government contractor and systems integrator ecosystem. Familiarity with the FAR and related acquisition frameworks, government cloud and security requirements, and the commercial implications of FedRAMP High. Experience shaping and closing outcome-based, usage-based, or other nontraditional software agreements in the public sector. Experience with AI, conversational systems, customer experience technology, contact centers, or digital government services—and the ability to speak credibly with both mission and technical leaders. Experience operating alongside founders or senior executives in high-stakes customer and partner engagements. Our values Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. What we offer We want our benefits to reflect our values and offer the following to full-time employees: Flexible (unlimited) paid time off Medical, dental, and vision benefits for you and your family Life insurance and disability benefits Retirement plan dependent on country of employment Parental leave Fertility and family building benefits through Carrot Lunch, as well as delicious snacks and coffee to keep you energized Discretionary benefit stipend giving people the ability to spend where it matters most Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. Be you, with us We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class. #J-18808-Ljbffr