Enterprise Sales Director - Majors, Public Sector

Sierra • San Francisco, CA

6d • $260,000 - $325,000 • Onsite

About The Position

Sierra is building a platform to enable every company in the world to build better, more human customer experiences with AI. The Public Sector team is focused on bringing Sierra's industry-leading technology to partners in the US public sector, having recently achieved FedRAMP High certification. This role will be part of the founding public sector team, aiming to redefine the relationship between the government and its citizenry. The company is explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their missions. Sierra is primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.

Requirements

• 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.

Nice To Haves

• 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.

Responsibilities

• 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.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed