VP of External Sales

Role Overview

• This role exists to win new cities, starting immediately, with you carrying deals and to build the outside sales organization that scales it: hire and ramp hunters, open new states, and create a system a new hire can execute without anyone else in the room.
• You’ll recruit, hire, and ramp your own reps and carry deals yourself while you do it.
• If your success story starts with “marketing handed us leads,” this isn’t your job.
• You’ll close the biggest deals yourself, step into your team’s late-stage deals, and report the truth good or bad to leadership every week.
• A hired, ramped team running the qualification and outbound system with a repeatable onboarding path behind them
• Active pipeline in at least three new states
• Pipeline, stages, and forecast in HubSpot that You, the CEO, CFO, and board take at face value
• no haircuts, no surprises.
• First closed-won in each new state and a documented playbook for the state after that.
• New-logo results that clearly outpace what founder-led sales delivered
• Qualification, demo standards, and cadence discipline a new hire can run after 90 days without anyone else in the room.

Requirements

• You've done this before, at least once.
• Self-sourced new-logo wins you can walk us through deal by deal, a territory or market you opened from zero, and sellers you've hired and ramped as a first sales leader or a player-coach.
• You know what a strong motion looks like because you've built one, not just worked inside one.
• You can operate in public-sector buying or prove you'll learn it fast.
• Direct govtech or municipal software experience is the fast path.
• A track record winning long-cycle, committee-driven, procurement-heavy deals (healthcare, edtech, public safety, enterprise) is the credible alternative.
• Either way, RFPs, cooperative purchasing, and city attorney redlines don't scare you.
• You can make complex software make sense to normal people.
• You're disciplined in the unglamorous parts.
• CRM hygiene, written follow-up, cadence you actually run because you'll hold your team to a standard you model yourself.
• Devoted to the craft, not just disciplined at it.
• We hire sellers for devotion over discipline
• curiosity about the buyer, the market, and their own performance.
• We expect the person leading them to embody it: you study your losses, you can self-critique without flinching, and you're still getting better at this.

Benefits

• Uncapped commission and upside tied to what you build, not a slot in a 50-person org chart
• Real ownership. You own the number, the team, and the plan and you’re in the room for every conversation about growth.
• Real mission. Our software is how a small town pays its employees, bills its water, and runs its court. When we win, a city clerk gets their weekends back. It’s not saving the world, but it’s honest work that matters to real communities.