---
title: 'Director, Joint Planning at Sitreps'
canonical: 'https://feeny.ai/job/director-joint-planning-sitreps-washington-539d7jmjvnwc'
type: 'job'
last_seen: '2026-09-11'
---

# Director, Joint Planning at Sitreps

- **Company:** Sitreps
- **Location:** Washington, DC / Northern Virginia
- **Work type:** onsite
- **Posted:** 2026-08-14
- **Last confirmed live:** 2026-09-11
- **Apply:** https://job-boards.greenhouse.io/sitrepsllc/jobs/4370075009

## Job description

Director of Joint Planning

Company: Early-Stage Defense Tech Software Location: Rosslyn, Arlington, VA (Washington, DC metro area). In person. Compensation: $160,000 to $190,000 base, plus equity Role Type: Full-Time Employee Reports To: Head of Mission Travel: Roughly 4 to 5 days a month on average, worldwide Clearance: Active TS/SCI preferred

## 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 are hiring a joint planning expert onto the mission team. This is a domain seat, not a program management seat. You are being hired because you know the Joint Planning Process cold, you have built and defended real staff products, and you can walk into a combatant command, a joint task force, or an exercise planning conference and be immediately credible.

Two things make this role unusual. First, you will be out with real units, at real events, doing real planning work, and then translating what you saw into product. Second, we no longer separate the person who understands the mission from the person who designs the software. Our mission people use the tools available today to design what the product should look like themselves, off their own expertise, and then work directly with engineers to build it. If you have opinions about how planning ought to work and have never had a way to act on them, this is that seat.

You will work alongside our head of mission, an expert joint planner who has planned both operations and exercises and can hold a room at any rank in any service. That is the standard for this role.

## Responsibilities

- Own an effort end to end: initial meeting, scoping, product design, training, and ongoing support. There is no staff behind you and no process to inherit.
- Go out to real-world operations and exercises worldwide. Sit in IPCs, MPCs, CPXs, and in headquarters during operations. Participate as a planner, not as an observer.
- Embed with a unit and train them hands-on, from an E-4 analyst to a general or flag officer.
- Design what the product should be. Use the AI tools available to you to build the concept yourself, then take it to engineering: here is the problem, here is what I built, tell me what breaks.
- Build and critique real staff products, including orders, annexes, IPOE, and MSELs.
- Bring operator judgment into the product portfolio. Where does this fit, what should exist next, what are we getting wrong.

## Requirements

Must-Haves

- Around 10 years of active-duty military experience, with an operations background: Army fires or maneuver, Navy unrestricted line, or operational Air Force, whether flying or deep in ops workflows.
- Expert command of the Joint Planning Process and of service-specific operational planning workflows. You can build and critique staff products without a staff behind you.
- At least one tour of real-world staff planning at a joint force headquarters, such as a JTF or a combatant command, or as an enabler such as JECC.
- Tier 1 or Tier 2 exercise experience and fluency in the Joint Exercise Life Cycle. You have planned and executed as a trusted agent, in the white cell, in EXCON or HICON, and participated in multiple iterations.
- Daily use of current AI tools, in the department or commercially. Not aware of them, using them.
- Genuine curiosity about product design and UI/UX. You want a hand in shaping what we build.
- Credibility at any rank and in any service, plus the presence to brief a GO/FO and then teach a junior analyst an hour later.
- Startup fit: high ownership, comfort with ambiguity, and the willingness to move fast without being told what to prioritize.
- Comfort working alongside engineers and translating operator needs into product.
- In person in Washington, DC or Northern Virginia, and ready to travel worldwide, sometimes on short notice.

Nice-to-Haves

- Active TS/SCI.
- Advanced planning education: Service War College, JAWS, SAMS, SAW, or JPME II.
- Experience at a defense technology or govtech company where you sat between operators and engineers.
- Familiarity with AI and machine learning products in operational planning or decision support.

## 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 travel. Nothing about this schedule is rigid. Some months there is no travel at all. A typical month is 4 to 5 days. A heavy month, built around a two-week event, might be 10 days. You are not forward deployed and you are not stationed next to a customer. You go where the event is, do the work, and come home.

## 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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