Head of Sales

Sitreps 2 Steercos; Washington, Baltimore (District of Columbia, MD); On-site; USD 150,000 - 165,000; Full time

Benefits offered by this job

Health benefits

401(k)

Commuting benefits

Lunch in office

Job summary

Sitreps 2 Steercos in Washington, DC is seeking a relentless, customer-facing seller to own our direct sales motion in a founding team capacity. You will field engagements with operators and staffs, run demos, shape requirements, and close agreements to build a security-focused AI platform for defense customers.

You will need a live network across DoD units and contracts, with a proven ability to originate and close deals while managing a dynamic, early-stage environment.

Qualifications

• Experience selling to DoD or government agencies.
• Track record of originating and closing government deals.

Responsibilities

• Direct sales: own new business from first contact to award.
• Engage with operators, staffs, and program offices, run demos and shape requirements.
• Drive opportunities through contracting pathways (OTAs, CSOs, IDIQs, etc.).
• Maintain a current pipeline and forecast honestly.

Skills

Defense contracting

Sales to government

Customer-facing selling

Demo software to operators

Travel readiness

Clearance eligibility

Job description

Location: Washington, DC / Northern Virginia. In person, Rosslyn office.

Compensation: $150,000 to $165,000 base, plus uncapped commission and equity to be

Commission: Structure and ramp are flexible with this founding direct sales role.

Role Type: Full-Time Employee

Travel: Up to 40%, to be in front of customers

Clearance: Must be eligible to obtain and maintain a U.S. security clearance

About the Client

We're on a mission to ensure warfighters are prepared for every challenge they face. We are committed to assembling a world-class team of exceptional problem solvers, combining expert engineering talent with deep experience in National Security.

We build AI for the most important problem in defense: making sure the force is ready to fight. Our software is deployed and in use with DoD partners today. The office is in Rosslyn.

About the Role

We're looking for a relentless, customer-facing seller to own our direct sales motion. This role is for someone who moves fast, gets in front of operators and staffs, and converts conversations into signed work. You'll spend your time in front of units, commands, and program offices, running demos, shaping requirements, and closing.

If you want a defined territory and an inherited playbook, this isn't it. If you want to build a pipeline from zero and win, it is.

Exercise planning and operational planning are the initial focus areas for this seat, so knowledge or experience in either is a real advantage.

Responsibilities

• Direct Sales. Own new business from first contact through award. Prospect, qualify, demo, and close across services, combatant commands, and operational units.
• Field Engagement. Get in the room. Work exercises, industry days, wargames, and conferences to generate qualified demand and build durable operator relationships.
• Deal Execution. Drive opportunities through the fastest available contracting pathway, including O&M sales, CSOs, OTAs, consortium vehicles, and simplified acquisitions.
• Pipeline Discipline. Maintain an accurate, current pipeline. Forecast honestly, kill dead deals early, and communicate what engineering needs to know and when.
• Voice of the Customer. Translate operator problems into clear product feedback, and translate capabilities into language a staff officer or contracting officer can act on.

Requirements

Must-Haves

• Prior military service inside a DoW organization.
• A track record of originating and closing government business, with specific deals you can point to and describe.
• A live network across DoW operational units, staffs, or program offices that you can activate in your first 30 days.
• Working fluency in defense contracting pathways (OTAs, CSOs, IDIQs, consortium structures) and the ability to pick the right one under time pressure.
• Comfort demoing software yourself, without an engineer in the room.
• High tolerance for ambiguity and a bias toward action in an early-stage environment.
• Willingness to travel up to 40% to be in front of customers.
• Must be eligible to obtain and maintain a U.S. security clearance.

Nice-to-Haves

• Experience selling software or AI/ML products into defense, not services or hardware.
• Familiarity with exercise planning cycles, wargaming, and operational assessments.
• Experience at an early-stage defense tech or govtech company.
• Active U.S. security clearance.
• Competitive salary and equity to share in our success
• The chance to join a founding team and directly shape the future of the company
• The opportunity to work with cutting-edge AI technology in a defense context
• Full health and dental benefits, 401(k), commuting benefits, lunch when in office
• Office in Washington, DC / Northern Virginia

On how you get paid.

We have deliberately put the emphasis on earning through closing rather than on collecting a salary. Commission is uncapped and the structure is genuinely open: if you have thrived under a model before, we want to hear it, and the rate can go above the usual range on larger deals. We are also flexible on ramp. The right person for this seat should be confident they can do very well on incentives.