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Salary: USD 172,800 - 216,000 / annual
Skydio is the leading US autonomous drone company, serving defense, public safety, and enterprise customers. This Director role leads the Community Safety sales organization, which sells into municipal and county law enforcement agencies across two segments: Mid-City (41–100 sworn personnel) and Small Cities (below 41). You will manage Key Account Directors who run each segment and their teams.
This is a second-line leadership role focused on building and developing leaders and sellers rather than running deals directly. Your core responsibilities span four areas:
**RECRUIT**: Own hiring across both levels—Key Account Directors and individual sellers. Recruiting is a first-order responsibility, not delegated. You will source actively, maintain a live network, participate in interview loops, and close top candidates who need time with you to commit. You will hire for coaching ability in leaders, not just closing ability. Build the bench before you need it by identifying and developing your next two or three Directors. Hold a consistent evidence bar across both segments: year-by-year attainment (including misses), retention history, deal mechanics, and evidence of what candidates have built or changed in their own work.
**COACH**: Coach your Directors on their judgment and leadership, not just pipeline. Sit in on their 1:1s, deal reviews, and forecast calls. Develop each Director's weakest area deliberately. Stay in the field a few times per quarter with sellers to maintain a first-hand read on the business. Raise AI fluency across both segments through shared workflows for agency research, call prep, RFP response, and pipeline analysis.
**RETAIN**: Build an organization people don't want to leave. Own quota and territory architecture so the math is achievable and equitable. Own the career path from Small Cities to Mid-City, including promotion mechanics and account handoffs. Fix structural causes of attrition—bad territory design, unclear compensation, or ineffective leadership—rather than only addressing individual departures.
**RUN THE BUSINESS**: Own the combined number across both segments: pipeline coverage, forecast accuracy, and linearity. Manage two different motions on their own terms—Small Cities runs on volume and velocity; Mid-City on complexity and cycle length. Represent the business to Skydio leadership through forecasts, business reviews, headcount planning, and unvarnished assessments of what is working and what is not. Own the segment model end-to-end, including the upmarket handoff from Small Cities to Mid-City.
**BUILD STRATEGIC PARTNERSHIPS**: Own executive relationships with the largest channel and technology partners at their leadership level. Run joint business planning with partner leadership. Be the escalation point when relationships are strained and the sponsor when they are working.
You will also set the standard for how the organization works. Every seller uses AI tools as a normal part of running their territory. You will model that, coach to it, and hire for it. This is a highly competitive market; your teams will sell against incumbent platforms and well-funded challengers. You will set the standard for how they win.
The role requires 50% travel. FAA Part 107 certification is strongly encouraged within the first 60 days and required for certain positions.
**REQUIREMENTS**
- 3+ years in sales leadership including experience leading other managers, OR a strong first-line leader with a clear, evidenced case for the step up
- 6+ years total in enterprise software, hardware, or SaaS sales, including personal success closing complex, multi-stakeholder deals
- A record of hiring at both levels: managers you developed, and sellers you personally sourced, interviewed, and closed
- Team attainment you can state year by year, including the year you missed and what you changed
- Experience owning a number across more than one sales motion or segment, with a point of view on how they should be managed differently
- Executive relationship experience with channel or technology partners at a leadership level, including joint planning and results
- Comfort representing a business upward: forecast, capacity planning, and honest assessment of what is and is not working
- Experience selling or leading teams into SLED (State, Local, Education) customers, with working knowledge of procurement vehicles, budget and grant cycles, and what it takes to get a program approved by a council or commission
- Daily, systematic use of AI tools in your own work, and at least one workflow, analysis, or tool you built or changed in the last two years that made you or your team measurably better (you will be asked to show it, not describe it)
- Strong voluntary retention history and judgment to move quickly when a leader is not right for the seat
- Executive presence with agency leadership, partner executives, and your own organization, and high personal integrity under quota pressure
- Ability to travel at least 50% of the time
**PREFERRED**
- Experience in public safety, specifically law enforcement, fire, or emergency management
- Experience standing up or scaling a segment model that runs more than one motion
- You have built something with AI that other people use (research tool, analysis, team workflow) and can discuss what the first version got wrong
- Curiosity that shows: you can explain how something outside sales works (agency budget, airspace waiver, aircraft autonomy) in plain language and learn fast
- Familiarity with MEDDPICC, Salesforce, Palantir, Anthropic, Cursor, Slack, Google Workspace
- UAV, robotics, or emerging technology background and comfort in a fast-moving environment
About Skydio
Defense / GovTech; Industrial — autonomous drones for defense, public safety, and enterprise.
