Engagement Manager

Sitreps 2 Steercos; Maryland; On-site; USD 160,000 - 190,000; Full time

Job summary

Early-Stage Defense Tech Software in the Washington DC / Northern Virginia area seeks a seasoned joint planning expert to field real-world mission planning work and translate insights into product with engineers. You will work directly with the mission head, balancing operator needs with software design, and travel to support events worldwide.

This is a high-ownership, fast-moving role requiring deep military planning background, comfort with ambiguity, and the ability to brief senior leaders

Qualifications

• Around 10 years of active-duty military experience.
• Expert command of the Joint Planning Process and service-specific planning workflows.
• At least one tour of real-world staff planning at a joint force headquarters (JTF or combatant command).
• Daily use of current AI tools in either department or commercial contexts.
• Genuine curiosity about product design and UI/UX; ability to translate operator needs into product.

Responsibilities

• Own an effort end to end: initial meeting, scoping, product design, training, and ongoing support.
• Go out to real-world operations and exercises worldwide and participate as a planner, not an observer.
• Embed with a unit and train hands-on from junior to senior ranks.
• Design the product concept using AI tools and collaborate with engineers to implement it.
• Build and critique real staff products, including orders, annexes, IPOE, and MSELs.
• Bring operator judgment into the product portfolio and identify future needs.

Job description

Company: Early-Stage Defense Tech Software

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.
• 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.