Key Account Leader, Corrections

Skydio

7d•$120,000 - $180,000•Remote

About The Position

Skydio is hiring a Key Account Leader to own a territory within a national segment of State Departments of Corrections and state-funded Port Authorities. This is a full-cycle, quota-carrying sales role responsible for identifying opportunities, building pipeline, running deals, and closing business. The role involves building Skydio’s presence in a relatively untapped market, including engaging agencies that may never have considered a drone program, and helping customers get programs funded, approved, and deployed. The position is national and remote within the United States, with at least 50% travel. The leader reports to the Key Account Director, Corrections, and works closely with Sales Engineering, Business Development, Channel, Marketing, Strategic Relationships, Government Relations, and Mission Success. The role sells autonomous flying robots and artificial intelligence, and requires daily use of AI tools for territory research, meeting preparation, RFP responses, and pipeline analysis. The annual base salary range is $120,000–$180,000, plus commission. Eligible regular, full-time employees receive stock options and comprehensive benefits; relocation assistance may be provided for eligible roles.

Requirements

At least 5 years carrying an individual quota in enterprise software, hardware, or SaaS sales, with year-by-year attainment information, including an account of a missed year and what was changed afterward.
Personal success running full-cycle, multi-stakeholder deals from first conversation to signed contract.
A record of building a personal pipeline and a clear understanding of the proportion of closed business that was self-sourced.
Disciplined qualification and a forecast that a manager can trust.
Fluency selling with and through channel partners.
Daily, systematic use of AI tools in work.
At least one AI workflow, analysis, or tool built or changed in the last two years that measurably improved performance, with willingness to demonstrate it.
Ability to engage credibly with agency leadership and maintain high personal integrity under quota pressure.
Ability to travel at least 50% of the time.
Ability to be based anywhere in the United States.

Nice To Haves

Experience in public safety, especially corrections, and relationships across the CLA and ACA communities.
Experience selling into state agencies and working knowledge of state procurement and appropriations cycles.
Having built an AI tool, analysis, or workflow used by others, and being able to discuss what the first version got wrong.
Demonstrated curiosity and ability to explain how a subject outside sales works in plain language, such as an agency budget, airspace waiver, or aircraft autonomy.
Familiarity with MEDDPICC, Salesforce, Clari, BGov, GovWin, Slack, and Google Workspace.
UAV, robotics, or emerging technology background and comfort working in a fast-moving environment.

Responsibilities

Own and maintain a territory plan, including understanding the agencies in the territory and their likelihood of moving forward.
Generate pipeline through outbound sales, events, and partners rather than relying on inbound demand.
Engage early with agencies and shape the criteria they use to make purchasing decisions.
Run full-cycle deals from initial conversation through discovery, demonstration, proof of value, proposal, procurement, and approval.
Qualify opportunities using MEDDPICC rigor and exit deals that are not viable.
Build consensus among facility leadership, DOC leadership, state IT, state procurement, and legislators who fund programs.
Compete against incumbent platforms and challengers by communicating Skydio’s differentiators, running displacement plays, and defending accounts.
Sell with and through channel partners and structure deals to help customers reach a decision.
Coordinate Sales Engineering, Business Development, Government Relations, and Mission Success around shared deal outcomes.
Hand off awarded accounts to Mission Success and remain engaged to support account growth.
Maintain honest forecasts and clean pipeline records that the Director can rely on.
Use AI tools daily for agency research, call preparation, RFP response, and pipeline analysis; review AI-generated work before it reaches customers.
Share field intelligence with the team, including competitive information, product gaps, and changes in agency purchasing practices.
Represent Skydio at national market events, including CLA and ACA.