Head of Sales (Player-Coach) - GovSignals
TLDR
Lead the sales strategy for GovSignals, significantly impacting government contracting processes while building and mentoring a high-performing sales team.
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.
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
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)
Benefits
Health Insurance
100% employer-paid medical, vision, and dental (Bronze coverage)
Unusual Ventures is an AI-first company building systems that enhance human judgment and accountability while machines excel at pattern recognition. Specifically, our EnFi platform is transforming the FinTech landscape by streamlining complex credit risk assessment and portfolio monitoring, allowing lenders to make smarter decisions with AI-driven automation across their operations.
- Founded
- Founded 2018
- Employees
- 11-50 employees
- Industry
- Diversified Financial Services