Head of Sales (Player-Coach)

Overview Head of Sales (Player-Coach) GovSignals Washington, D.C. or New York, NY • Full-time • Hybrid, in-office when not traveling About GovSignals We are shaping the future of government contracting with breakthrough AI‑driven solutions. We are disrupting a multi‑billion dollar industry and enabling private‑sector technologies to secure government contracts faster than ever, strengthening national security and driving economic growth. GovSignals has built the most advanced government‑contracting AI platform available. From small businesses to Fortune 500 enterprises, our platform multiplies the opportunities contractors can pursue and empowers them to deliver fully compliant, winning proposals in hours instead of months. As one of the largest aggregators of U.S. government data, we set trends rather than follow them. About the Role We’re at an inflection point. The product is the best on the market, the market is responding, and now we need someone who will take our existing processes and layer in the sales machine that takes us to the next level. This is a role for a rare kind of leader—someone who has done this before. Not just managed a team, but built them. Designed the process from scratch, hired the early reps, written the playbook, and driven revenue through sheer force of will and operational discipline. You know what great looks like because you’ve created it. Now you want to do it again, in a category that’s being invented in real time. Reporting directly to the CRO co-founder, you’ll be a true partner in shaping our next wave of go-to-market strategy, sales process, and team architecture. You’ll spend roughly 60% of your time carrying and closing your own book of business—leading from the front—and 40% building the team and systems underneath you. When your reps get stuck, you get on the call. When a deal needs architecture, you draw the map. When the process breaks, you fix it. This is not a role for someone who is ready to step back from work. If your best days selling are behind you, this isn’t the right seat. But if you’re an operator who loves the craft of selling as much as the craft of building, and you want the total compensation upside to match the effort—we should talk. Key Responsibilities Carry and close your own enterprise pipeline end-to-end: prospecting, discovery, demos, deal structure, and close Partner with the CRO on GTM strategy, sales process design, pricing, and competitive positioning Hire, onboard, and develop a team of elite Account Executives who sell consultatively and close with conviction Jump into your reps’ deals—diagnose what’s stuck, sharpen the narrative, and help close alongside them Build and continuously refine sales playbooks, qualification frameworks, onboarding programs, and coaching rhythms Approve quotes, structure creative deals, and navigate complex multi-stakeholder buying processes across the team’s pipeline Own pipeline reporting, forecasting accuracy, and CRM discipline for the full sales organization, including all conference pipeline Collaborate with Marketing, Product, and Client Success to tighten positioning, improve feedback loops, and accelerate revenue Engage existing clients to deepen relationships and unlock expansion opportunities Represent GovSignals at industry events, conferences, and in senior prospect conversations Who You Are You’ve built a sales org—not just inherited one. You’ve hired the early reps, figured out what worked, and scaled a repeatable motion from early traction through meaningful revenue. You’ve made the mistakes that come with building at speed and learned from them. Your instincts on hiring, process, and pipeline are sharp because they were forged in the field. You’re a consultative seller to your core. You ask question after question to diagnose a prospect’s problem without telling them what you think -- until you know what problem you’re solving. You lead prospects to water rather than force a sale. Your reps will learn to sell the way you sell. You’re a systems thinker who sees the whole board—how the right qualification criteria changes pipeline quality, how a better demo flow shortens sales cycles, how comp design shapes rep behavior. You connect those dots and build accordingly. You’re not looking for a 9-to-5. You’re looking for a mission—and the ownership stakes to go with it. Required Qualifications Proven track record of building and scaling a sales team from early stage through meaningful revenue milestones—you’ve designed the system, not just run inside one Strong personal selling record: history of closing six- and seven-figure enterprise SaaS deals as an individual contributor Experience as a founder, early sales hire, or sales leader at a high-growth startup where ambiguity was the norm and you thrived anyway Deep expertise in consultative, value-based selling—you diagnose before you prescribe Ability to operate as a strategic partner to leadership on pricing, positioning, and GTM design Strong hiring instincts: you know how to find, assess, and close elite sales talent Exceptional executive presence and C-suite engagement skills Proficiency in CRM systems and a belief in rigorous pipeline discipline Government contracting familiarity preferred but not required What This Is Not This is not a role for a sales leader who is ready to step back from the work. If you need a large team beneath you before you can drive revenue, this isn’t the right fit. If your approach to management is reviewing calls and dashboards from a distance, this isn’t the right fit. If “startup hours” sounds like a red flag rather than a rallying cry, this isn’t the right fit. We need someone who runs toward the complexity, thrives in the uncertainty, and measures success in closed deals—not just team size. Compensation & Benefits Base Salary: $150K–$250K Commission + Bonus: $75K–$150K expected Total Target Compensation: $225K–$400K+ OTE Equity: Meaningful stake in a well-funded, fast-growing startup—we want you to win big when we win big Benefits: 100% employer-paid medical, vision, and dental (Bronze coverage) #J-18808-Ljbffr