Sales Director, Site Security

About the Team

Physical Site Security is transforming at a rapid pace. Historically guards have been the primary force behind Site Security. Today, the largest enterprises in the country are looking towards deployment of technology, robotics, and AI to augment and improve their security posture. Many are now putting Skydio Docks over their fulfillment centers, data centers, distribution hubs, and campuses to patrol perimeters, respond to alarms, and put eyes on an incident in seconds. Security is the fastest-growing part of Skydio's commercial business and is now a standalone team. Our largest site security customers include some of the biggest names in retail, logistics, and technology, and the account base behind them is thousands of companies wide.

About the role

As Sales Director, Site Security, you will lead nine quota-carrying sellers: six Strategic Account Managers on the largest enterprises and three Enterprise Account Executives on the next tier. Five of the nine are new seats you will hire. Each seller is paired with Solutions Engineering, and three dedicated BDRs that build net-new pipeline for the team. This team carries the largest number in Commercial Sales and is planned to grow several-fold over the next three years.

This is a build, not a harvest. The team works a book of thousands of large enterprises where only a small fraction are customers today. Your job is to turn a handful of flagship wins into a repeatable motion: one team, one playbook, every facility type. A perimeter is a perimeter. A win at a data center should teach the team how to win at a distribution center, a hospital, or a stadium. One rep owns each logo, and we never put two account teams on one account.

Much of this market is already held by the contract security firms that staff guard posts at these sites. They own the relationships, the master contracts, and the budget line. We grow with them, not around them. You will make sure your team sells with these partners, and that the rep who owns the account gets credit when a partner carries the deal.

You will work alongside peer leaders in Utilities and Emerging markets, and closely with Strategic Partnerships, Solutions Engineering, Customer Success, Deployment, Product, and Marketing. We sell autonomous flying robots and the AI that powers them, and every seller here uses AI tools as a normal part of running a territory. You will model that, coach to it, and hire for it.

How we work

High integrity. Security leaders talk to each other, and a reputation for straight answers travels fast. We sell what the product can do today, including uptime, SLAs, and how much of the operation is autonomous, we are clear about where it's headed, and we win on our own merits.

Sales is a team sport. No lone wolves. Site security programs are won by account leaders, solutions engineering, partnerships, contract security firms, customer success, and deployment pulling in the same direction. The best people here care more about the collective number than their own slice of it.

Great conversationalists. Ask better questions than anyone else in the room. Listen for what a Chief Security Officer isn't saying. Be curious about how a security operations center actually runs: its alarm volumes, its guard contracts, its incident reports. Trust is built one honest conversation at a time.

Curious, and fluent with the tools. Everyone on this team uses AI to research accounts, prepare for meetings, analyze pipeline, and draft and then edit. That takes judgment more than technical skill: knowing what a good result looks like and catching the tool when it is confidently wrong.

How you'll make an impact

Recruit

• Fill the open seats fast: the team is growing and every week a seat sits empty moves revenue out of the year

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

• Hire for integrity, team instinct, conversational skill, and fluency with the tools as much as for a closed-won history

• Onboard and ramp new sellers so they start with a book, relationships, and identified opportunities, not an empty list

Coach

• Run 1:1s and deal reviews that build judgment, not just inspect pipeline

• Get in the field: join executive meetings, site walks, and pilot reviews, then give specific, usable feedback

• Coach the site security sale: building the ROI case against the guard contract, then stacking value beyond guard reduction through facility inspection, EHS, and operations use cases

• Coach selling with partners: when to lead direct, when a contract security firm or integrator carries the deal, and how to keep the account relationship either way

• Build MEDDPICC rigor and forecast honesty into how the team works: current close dates, current notes, no duplicate or stale opportunities

• Raise the team's fluency with AI: shared workflows for account research, call prep, RFP response, and pipeline analysis, with nothing AI-drafted reaching a customer unreviewed

Retain

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

• Design territories and quotas that are achievable, fair, and worth staying for

• Have honest career conversations early, and be the escalation path your team trusts to clear obstacles

Run the security business

• Own the security number: pipeline coverage, forecast accuracy, linearity, and the analysis behind them, presented to executive leadership every month

• Convert flagship programs into enterprise-wide rollouts across hundreds of sites

• Route accounts cleanly: hand companies under $1B to Inside Sales, and keep one rep on every logo

• Build coverage across the book: use account scoring to focus the team on the enterprises where docks fit best, starting with data centers, logistics, and distribution

• Partner with Strategic Partnerships on contract security firm relationships, joint pursuits, and the deal structures that get customers to yes

• Act as executive sponsor on the team's largest pursuits, present in the room without taking the deal over

• Bring customer insight, competitive intelligence, and product gaps back to Product and Marketing, including SLAs, multi-cloud requirements, and AI in the security operations center

What makes you a good fit

Required

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

• 7+ years in enterprise sales of hardware, software, or SaaS, with personal success closing complex, multi-site, multi-year deals with Fortune 500 companies

• Experience selling physical security technology or services to corporate security leaders: Chief Security Officers, VPs of Global Security, and GSOC leaders. Video surveillance, access control, security robotics, GSOC platforms, or guarding services all count

• A record of building a new market or category: creating demand, not only harvesting it

• Fluency selling with and through partners such as contract security firms, integrators, or resellers

• Demonstrated success recruiting sellers: a real network, a clear view of what good looks like, and the ability to close candidates

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

• Strong retention history and a record of developing people into larger roles

• Daily 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)

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

• Ability to travel at least 50% of the time

Preferred

• Corporate security, law enforcement, or military background

• Relationships with contract security firms and across the security industry, including ASIS and GSX

• Experience selling into data centers, logistics and distribution, retail, healthcare, or large campuses and venues

• Experience building a team from a small base, or scaling a team through rapid growth

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

• Curiosity that shows: you can explain how something outside sales works (a guard post staffing model, a GSOC alarm workflow, the aircraft's autonomy) in plain language

What to expect from our process

We run a structured process and tell you what it is. A 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 site security account problem and walk us through your choices. A panel on the security market and how you would run this team. References with people who worked for you and with you. Every interviewer scores independently against the same rubric before we compare notes.

Draft your resume yourself and refine it with AI if you like. Use whatever tools you want to prepare, and expect to use them in the working session. Leave them off during conversational interviews so we can see how you think in real time. 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 $172,000- 240,000 + 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.

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