Key Account Leader, Corrections

Telemetry Today LLC; United States; Remote; USD 120,000 - 230,000; Full time

Job summary

Skydio is seeking a Senior Key Account Leader for Corrections to own a national territory within State Departments of Corrections and state-funded Port Authorities. This full-cycle, quota-driven role requires building pipeline, closing complex multi-stakeholder deals, and coordinating with channel, engineering, and government relations teams.

You will leverage MEDDPICC and AI-enabled selling to win in a highly competitive market, with travel up to 50% and a focus on strategic public safety

Qualifications

• 5+ years carrying an individual quota in enterprise software, hardware, or SaaS sales.

Responsibilities

• Own your territory plan and build pipeline.
• Run full-cycle deals from discovery to award, with multi-stakeholder engagement.
• Sell with and through channel partners and coordinate with Sales Engineering, BD, and Government Relations.
• Forecast honestly and maintain a clean pipeline for leadership review.
• Travel up to 50% across the United States as needed.

Skills

Enterprise sales (quota-bearing)

Full-cycle deals

Pipeline development

MEDDPICC qualification

Channel/partner selling

AI-enabled selling

Quota-driven integrity

Travel up to 50%

Tools

MEDDPICC

Salesforce

Clari

GovWin

Job description

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 Leader, Corrections at Skydio, you will own a territory within a national segment of State Departments of Corrections and state-funded Port Authorities. This is a full-cycle, quota-carrying role: you find the opportunities, run the deals, and close them. Your number is yours, and so is the territory plan behind it.

You will be the person an agency trusts with one of the most visible programs it will stand up this decade. That means understanding how the agency actually works, who has to say yes, and what it will take to get there, then running a process that gets the program funded, approved, and deployed. You will report to the Key Account Director, Corrections, and work alongside Sales Engineering, Business Development, Channel, Marketing, Strategic Relationships, Government Relations, and Mission Success.

Corrections is one of our least penetrated markets. You will be building the Skydio name with DOC leadership at the same time you are building pipeline, and many of your first conversations will be with agencies that have never considered a drone program.

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: researching agencies, preparing for meetings, responding to RFPs, and analyzing pipeline. We expect you to as well.

This is a highly competitive market, and much of the work happens alongside our channel. You will sell against incumbent platforms and well-funded challengers, and win on the merits.

Location:

National (Remote, United States)

How we work

These are the standards we hire to, and they describe how the best people on this team already work.

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

Build pipeline

• Own your territory plan: know the agencies in it, which are likely to move this year, and why
• Generate your own pipeline through outbound, events, and partners rather than waiting on inbound demand
• Get in early and shape the criteria the agency will use to make its decision

Win

• Run full-cycle deals from first conversation to award: discovery, demonstration, proof of value, proposal, procurement, and approval
• Qualify with MEDDPICC rigor, and walk away from deals that are not real
• Build consensus across the people who have to say yes: facility leadership, the DOC secretary or commissioner's office, state IT, state procurement, and the legislators who fund the program
• Sell against incumbents and challengers: frame Skydio's unique differentiators, run displacement plays, and defend accounts under attack

Partner

• Sell with and through channel partners, and structure deals that get customers to yes
• Bring in Sales Engineering, Business Development, Government Relations, and Mission Success at the right moment, and keep them pointed at the same outcome
• Hand off cleanly to Mission Success after award and stay close enough to the account to grow it
• Forecast honestly and keep your pipeline clean enough that your Director can trust it

What makes you a good fit

Required

• 5+ years carrying an individual quota in enterprise software, hardware, or SaaS sales, with attainment you can state year by year, including the year you missed and what you changed
• Personal success running full-cycle, multi-stakeholder deals from first conversation to signed contract
• A record of building your own pipeline, and a clear view of how much of your closed business you sourced
• Disciplined qualification and a forecast your manager could trust
• 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 measurably better (we will ask you to show it, not describe it)
• Presence with agency leadership 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 selling into state agencies, with working knowledge of state procurement and appropriations cycles
• You have built something with AI that other people use, whether a research tool, an analysis, or a 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 selling record: attainment year by year, how you built pipeline, and the mechanics of deals you won and lost. A working session where you use your own AI tools on a realistic problem from this territory and walk us through your choices. A panel where you run a discovery conversation and walk us through how you would win a deal in this segment. A conversation about how you think. References with people who managed you and worked alongside 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: