How Israeli Startups Actually Break Into the DoW – A conversation with Sean Singleton, Oglethorpe Capital

Sean’s career runs the entire DoD gauntlet: Air Force acquisitions officer, JP Morgan investment banker, DIU leader, and now Managing Director at Oglethorpe Capital. He’s seen the system from every angle, and his message to Israeli startups was incredibly consistent: the companies that win aren’t the ones with the most impressive demos — they’re the ones who know how to navigate the machinery.

His biggest lessons for founders:

Solve a priority problem, not a requirement list.

DIU’s success came from flipping the model: find a real operational pain point, solve it, and get the customer to commit to scaling if it works. Israeli startups thrive here, but only if they stop pitching and start listening.

You can’t parachute into the U.S. market.

If you want to sell to DoD, you need a real presence in the U.S. Someone on your team must live and breathe the ecosystem — not fly in twice a quarter.

Partner early with systems integrators.

Lockheed, Raytheon, and Booz Allen have the contract vehicles and congressional ground game founders can’t replicate. Fighting them is pointless. Collaborating with them is leverage.

Build the political strategy early.

Professional staffers matter more than cabinet secretaries. If you’re not in their ear, someone else is.

For Israeli founders, the takeaway is simple: winning in the U.S. defense market isn’t about the tech — it’s about understanding the system. Learn the system, and the doors open. Ignore it, and nothing moves