---
title: 'Director of Defense Sales at Sitreps'
canonical: 'https://feeny.ai/job/director-of-defense-sales-sitreps-washington-mqjtqp8fb779'
type: 'job'
last_seen: '2026-09-11'
---

# Director of Defense Sales at Sitreps

- **Company:** Sitreps
- **Location:** Washington, DC
- **Work type:** onsite
- **Posted:** 2026-09-04
- **Last confirmed live:** 2026-09-11
- **Apply:** https://job-boards.greenhouse.io/sitrepsllc/jobs/4395856009

## Job description

Director of Defense Sales

Company: Early-Stage Defense Tech Software Location: Washington, DC / Northern Virginia. In person, Rosslyn office. Compensation: $150,000 to $165,000 base, plus uncapped commission and equity 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.

## Compensation & Benefits

- 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.

## About Sitreps

## Company Overview
- **One-liner**: Sitreps is a veteran-founded recruiting agency and defense technology company that connects elite military talent with high-impact roles and builds software-driven maritime intelligence platforms for the U.S. Department of Defense.
- **Entity Type**: Private (startup stage; no public funding rounds disclosed)
- **Headquarters**: Arlington, Virginia, USA (multiple job postings list Arlington, VA as primary location; also offices in New York City and Litchfield, VA)
- **Founded**: 2019
- **Founders**: Kyle Eberly, Wyatt Frasier, Max Cormier (co-founders)

## Core Business
- **Primary Industries**: Defense Technology, Professional Services (Veteran Recruiting & Staffing), Software & Analytics
- **Target Customers**: U.S. Department of Defense (DoD) and federal civilian agencies (B2G); defense-focused enterprises and technology companies (B2B) seeking veteran talent
- **Mission/Purpose**: Leveraging a deep-rooted community of military veterans to help world-class businesses scale, while also transforming commercial fleets into persistent sensing assets for national security.

## Products & Services
- **Sitreps Talent (Recruiting Agency)**: A curated recruiting service that sources, vets, and places high-performing military professionals into roles at partner companies. Serves 10+ industries including defense tech, software, AI, fintech, and private equity. Places roles such as product managers, account executives, engagement managers, and sales directors.
- **Maritime Intelligence Platform (Defense Tech Software)**: A next-generation software platform that transforms global commercial fleets into persistent sensing assets for the United States. Used by Navy strategic programs; includes analytics, data integration (SQL/Python/R), and implementation services.
- **AI & Agentic Solutions (Emerging)**: Design, prototype, and deploy scalable AI and agentic workflows for defense acquisition challenges, embedding with clients to productionize models.

## Market Standing
- **Valuuation / Funding**: Not publicly disclosed. The company appears to be privately funded (no public rounds recorded). A Head of Sales job description references growing revenue from ~$2M to $5M+ (with a path to $30M), suggesting current annual revenue in the low single-digit millions.
- **Key Metrics**: 150+ veterans placed, 40+ partner companies, 95% retention rate, serving 10+ industries (source: [sitreps.com/about/clients](https://www.sitreps.com/about/clients))
- **Notable Investors / Partners**: Not listed publicly. Partner companies are not named on the website, but the client portfolio includes defense tech, software, HVAC, real estate, AI, fintech, private equity.
- **Growth Signals**:
  - Scaling sales team from ~$2M to $30M target
  - Active hiring for senior roles: VP of Engagement, Head of Intelligence, Chief Operating Officer, Forward Deployed Data Scientists
  - Expanding into AI/agentic solutions for defense acquisition
  - Multiple office locations and remote/hybrid work options

## Competitive Advantages
- **Authentic Veteran Community**: Sitreps began as a viral online community for veterans transitioning to business roles — now the “largest community of veterans in business in the USA,” providing unmatched access to, and credibility with, military talent.
- **Dual Capability**: Combines a staffing agency with in-house defense tech software development, allowing cross-pollination of talent insights and mission understanding.
- **High Retention**: 95% placement retention rate indicates strong matching and support processes.
- **Clearance and Domain Expertise**: Many roles require active security clearances and deep knowledge of naval strategic programs, DoD acquisition, and intelligence — creating a high barrier for competitors.

## Strategic Focus
- **Scale Revenue**: Formalizing sales processes (CRM, commissions, segmentation) with a goal of growing from ~$2M to $5M+ in the near term and eventually $30M.
- **Productize Defense Tech**: Expand the maritime intelligence platform and AI/agentic solutions for broader DoD adoption.
- **Deepen Government Relationships**: Hiring Engagement Directors and Account Executives for each military branch (Air Force, Navy, Army, Coast Guard, Marine Corps).
- **Build Internal Infrastructure**: Transitioning from QuickBooks to an audit-ready ERP, adding financial controls and federal contract audit compliance.

## Why Work Here
- **Mission-Driven Work**: Directly support national security and veteran employment — two high-impact, purpose-rich areas.
- **Hybrid & Remote Flexibility**: Many roles offer remote options (U.S.-based); some positions require on-site presence in Arlington, VA, New York, or Litchfield, VA; a hybrid workspace is the norm.
- **Career Growth**: Early-stage company where leaders are expected to build functions from scratch and grow into C-level roles (e.g., Head of Sales → CRO path).
- **Diverse Roles**: Opportunities span professional services, engineering (forward deployed, data science), intelligence analysis, sales, and operations — appealing to both veterans and civilians.
- **Culture**: Described as “authentic, expertise-driven, and grounded in real connection” — not a typical corporate recruiter but a community-first organization.

## Sources
1. [builtin.com](https://builtin.com/company/sitreps-llc) – Company overview, perks, culture, job listings
2. [job-boards.greenhouse.io](http://job-boards.greenhouse.io/sitrepsllc) – Official careers page with all current openings
3. [sitreps.com/about/team](https://www.sitreps.com/about/team) – Founders and team profiles
4. [sitreps.com/about/clients](https://www.sitreps.com/about/clients) – Client metrics, industries served, roles filled
5. [builtin.com](https://builtin.com/company/sitreps-llc/jobs) – Detailed job descriptions (Head of Sales, Implementation Engineer, etc.)

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