Key Account Director, Corrections

Skydio is the leading US drone company and the world leader in autonomous flight, the key technology for the future of drones and aerial mobility. The Skydio team combines deep expertise in artificial intelligence, best-in-class hardware and software product development, operational excellence, and customer obsession to empower a broader, more diverse audience of drone users, from utility inspectors to first responders, soldiers in battlefield scenarios, and beyond.

About the Team: Public safety is where drone technology faces the highest stakes. Agencies across the country are standing up Drone as First Responder (DFR) programs that put an aircraft over an emergency within seconds of a call. As drone programs move from the age of tools to the age of infrastructure, we are expanding our public safety sales team to meet that demand.

About the role: As a Key Account Director, Corrections at Skydio, you will lead a national team of Key Account Leaders selling into State Departments of Corrections and state-funded Port Authorities. This is a first-line leadership role, and the job comes down to three things: recruiting the right people, coaching them into great sellers, and keeping them here.

You will not carry your own accounts. Your number is your team’s number, and you will hit it by making each person on the team better: sharpening deal strategy, getting into the field on their most competitive pursuits, and building the territory, pipeline, and forecast discipline that makes a segment predictable. You will work alongside peer Directors leading other segments and geographies, and across Channel, Sales Engineering, Business Development, Marketing, Strategic Relationships, Government Relations, and Mission Success.

Corrections is one of our least penetrated markets, so building the Skydio brand with DOC leadership is part of the job alongside building the team.

You will also set the standard for how the team works, not only what it sells. We sell autonomous flying robots and the artificial intelligence that powers them. Every seller here uses AI tools as a normal part of running a territory, and you will model that, coach to it, and hire for it.

This is a highly competitive market, and much of the work happens alongside our channel. Your team will sell against incumbent platforms and well-funded challengers, and you will set the standard for how they win.

Location: National (Remote, United States)

How we work

These are the standards we hire to, and as a leader you own them for your segment. You set the bar in who you hire, what you coach to, and what you tolerate.

• High integrity. Public safety is a tight-knit community. Corrections leaders talk to each other, and a reputation for straight answers travels fast. We sell what the ecosystem is actually capable of, we are clear about where the product is today and where it’s headed, and we win on our own merits. There’s no compromise here.

• Sales is a team sport. One team. No lone wolves. Deals are won by account leaders, sales engineering, business development, channel, marketing, strategic relationships, government relations, and mission success pulling in the same direction, and our partners are part of that team, not a channel to be managed around. The best people here care more about the collective number than their own slice of it.

• Great conversationalists. This is the craft of the job: asking better questions than anyone else in the room, listening for what a corrections leader isn’t saying, real curiosity about how an agency operates. Not polish, not a rehearsed pitch. Trust in this market is built one honest conversation at a time, and it is the thing competitors cannot copy.

• Curious, and fluent with the tools. Everyone on this team uses AI as a normal part of their work: researching agencies, preparing for meetings, analyzing pipeline, drafting and then editing. That takes taste more than technical skill: knowing what a quality result looks like, describing a problem precisely enough to get it, and catching the tool when it is confidently wrong. The same muscle makes a great seller. Discovery is specifying the problem; qualification is checking the output. We hire people who are curious about how things work, whether that’s an agency’s budget, a legislature’s appropriations cycle, or the aircraft’s autonomy, and who have spent the last two years embracing AI rather than waiting to be told to use it.

How you’ll make an impact

Recruit

• Own hiring for your segment: build a continuous talent pipeline, run a fast and rigorous process, and personally close the candidates you want

• Hire to the bar above: integrity, team instinct, conversational craft, and fluency with the tools matter as much as a closed-won history

• Screen for evidence, not adjectives: attainment stated year by year with the misses included, deal stories with the mechanics of how the customer bought, and something the candidate has built or changed in how they work in the last two years

• Run a structured process: the same core questions for every candidate, a live working session, independent scoring, and a debrief that decides on evidence

• Onboard and ramp new Key Account Leaders with a clear path from first day to first award, and hold the ramp accountable

Coach

• Run 1:1s and deal reviews that build judgment rather than just inspect pipeline

• Get in the field: join demos, customer meetings, and executive conversations, then debrief with specific, usable feedback

• Coach the competitive game: POV strategy, shaping requirements early, framing Skydio’s unique differentiators, displacement plays, and defending accounts under attack

• Build MEDDPICC rigor, channel fluency, and forecast honesty into how the team works, not just what they report

• Raise the team’s fluency with AI tools: build shared workflows for customer research, call prep, RFP response, and pipeline analysis, and hold the line that nothing AI-drafted reaches a customer unreviewed

Retain

• Build a team that people don’t want to leave: clear expectations, real development paths, and recognition that lands

• Own territory and quota design so assignments are achievable, equitable, and worth staying for

• Have honest career conversations early, address disengagement before it becomes a resignation, and be the escalation path your team trusts to clear obstacles

Run the segment

• Own the segment number: pipeline coverage, forecast accuracy, linearity across the quarter, and the analysis behind them

• Partner with Channel on partner strategy, joint planning, and the deal structures that get customers to yes

• Act as executive sponsor on your team’s largest and most competitive pursuits: present in the room, without taking the deal over

• Represent your segment’s customer insight, competitive intelligence, and product gaps to Marketing and Product

• Coordinate and attend the national events that drive growth in this market (CLA, ACA, and others)

What makes you a good fit

Required

• 3+ years leading quota-carrying sellers as a first-line manager, with team attainment you can state year by year, including the year you missed and what you changed

• 4+ years total in enterprise software, hardware, or SaaS sales, including personal success closing complex, multi-stakeholder deals

• Demonstrated success recruiting sellers: a real network, a clear point of view on what good looks like, a structured process you can describe, and the ability to close candidates

• A coaching approach you can articulate, with specific examples of people who got measurably better working for you

• Strong voluntary retention history, a record of developing people into larger roles, and the judgment to move quickly when someone isn’t right for the seat

• Experience selling or leading teams into SLED customers, with working knowledge of procurement vehicles and budget and grant cycles

• Experience selling or leading teams into State Department of Corrections customers, with working knowledge of their procurement and budget cycles

• Fluency selling with and through channel partners

• 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 (we will ask you to show it, not describe it)

• Executive presence with both customer leadership and your own team, and high personal integrity under quota pressure

• Ability to travel at least 50% of the time; this role can be based anywhere in the United States

Preferred

• Experience in public safety, specifically corrections, and relationships across the CLA and ACA communities

• Experience building a team from a small base rather than inheriting a mature one

• You have built something with AI that other people use, whether a research tool, an analysis, or a team workflow, and you can talk about what the first version got wrong

• Curiosity that shows: you can explain how something outside sales works (an agency budget, an airspace waiver, the aircraft’s autonomy) in plain language, and you learn fast

• Familiarity with MEDDPICC, Salesforce, Clari, BGov, GovWin, Slack, and Google Workspace

• UAV, robotics, or emerging technology background, and comfort in a fast-moving environment

What to expect from our process

We run a structured process and we tell you what it is. A 30-minute conversation with the hiring manager. A deep dive on your leadership record: hiring, coaching, retention, and the team number, year by year. A working session where you use your own AI tools on a realistic problem from this segment and walk us through your choices. A panel on the public safety market and how you would run the segment. A conversation about how you think. References with people who worked for you and with you. Every interviewer scores independently against the same rubric before we compare notes.

On AI in the process: draft your resume yourself and refine it with AI if you like; we want your real experience, well expressed. Use whatever tools you want to prepare. Expect to use them in the working session. Leave them off during the conversational interviews so we can see how you think in real time. We use AI to draft job descriptions like this one and to take notes, and a human makes every hiring decision.

Compensation: At Skydio, our compensation packages for regular, full-time employees include competitive base salaries, equity in the form of stock options, and comprehensive benefits packages. Compensation will vary based on factors, including skill level, proficiencies, transferable knowledge, and experience. Relocation assistance may also be provided for eligible roles. The annual base salary range for this position is $144,000- $200,000 + commission. Fundamentally, we believe that equity is the key to long-term financial growth, and we ensure all regular, full-time employees have the opportunity to significantly benefit from the company's success. Regular, full-time employees are eligible to enroll in the Company’s group health insurance plans. Regular, full-time employees are eligible to receive the following benefits: Paid vacation time, sick leave, holiday pay and 401K savings plan. This position and all associated benefits are subject to applicable federal, state, and local laws, as well as the Company’s policies and eligibility criteria.

*Compensation for certain positions may vary based on the position’s location.

#LI-WM1

At Skydio we believe that diversity drives innovation. We have created a multidisciplinary environment that embraces the power of diverse perspectives to create elegant solutions for complex problems. We are committed to growing our network of people, programs, and resources to nurture an inclusive culture.

Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, protected veteran status, or other characteristics protected by federal, state or local anti-discrimination laws.

For positions located in the United States of America, Skydio, Inc. uses E-Verify to confirm employment eligibility. To learn more about E-Verify, including your rights and responsibilities, please visit https://www.e-verify.gov/