VP of External Sales

This is a fully remote position, open to applicants in Texas.

📋 Description

• This position is designed to acquire new cities immediately, with you managing deals and establishing an outside sales organization that can scale: recruiting and training hunters, expanding into new states, and developing a system that allows new hires to operate independently.

• You will be responsible for recruiting, hiring, and training your own representatives while also managing deals yourself during this process.

• If your success narrative begins with “marketing provided us leads,” then this role is not for you.

• You will close the largest deals personally, become involved in your team's late-stage negotiations, and provide honest updates—good or bad—to leadership every week.

• A trained and ramped team will manage the qualification and outbound system, supported by a repeatable onboarding process.

• Maintain an active pipeline in at least three new states.

• Your pipeline, stages, and forecasts in HubSpot will be trusted by you, the CEO, CFO, and board—no adjustments, no unexpected changes.

• Successfully close the first deal in each new state and create a documented playbook for subsequent operations in that state.

• Deliver new-logo results that significantly surpass those achieved through founder-led sales efforts.

• Establish qualification, demo standards, and cadence discipline that a new hire can execute after 90 days without requiring assistance.

⛳️ Requirements

• You have experience in a similar role, having done this at least once before.

• You can present self-sourced new-logo wins in detail, including a territory or market you developed from scratch, and sellers you have hired and trained as a first sales leader or as a player-coach.

• You understand what constitutes a strong sales motion because you have built one rather than simply operated within one.

• You can navigate public-sector purchasing or demonstrate your ability to learn quickly.

• A background in govtech or municipal software will expedite your path.

• A proven history of winning long-cycle, committee-driven, procurement-heavy deals (in sectors such as healthcare, edtech, public safety, or enterprise) serves as a credible alternative.

• In any case, RFPs, cooperative purchasing, and city attorney revisions do not intimidate you.

• You have the ability to simplify complex software concepts for everyday users.

• You are disciplined in the less glamorous aspects of the job.

• Maintain CRM hygiene, provide written follow-ups, and adhere to a cadence that you personally enforce, setting an example for your team.

• You are dedicated to your craft, not merely disciplined in it.

• We seek sellers who are passionate about their work rather than just disciplined; curiosity about the buyer, the market, and personal performance is essential.

• We expect the leader to embody this mindset: you analyze your losses, can self-evaluate without hesitation, and continually strive for improvement.

🏝️ Benefits

• Uncapped commission and potential rewards linked to your contributions, rather than being confined to a position within a 50-person organizational chart.

• Genuine ownership. You will have authority over the numbers, the team, and the strategy, and you will be included in every discussion regarding growth.

• A meaningful mission. Our software facilitates how a small town pays its employees, manages its bills, and operates its court. When we succeed, a city clerk can reclaim their weekends. While it's not about saving the world, it is fulfilling work that impacts real communities.