Sales Director

Account Executive — Intelligence Community Location: Washington, DC metro (hybrid; SCIF access required) Clearance: Active TS/SCI required. CI or FS poly strongly preferred. Reports to: VP, Federal Sales Travel: ~30%, primarily NCR, COCOM headquarters, and customer site job that is used for creating requisitions 'from scratch' Why this role exists Maritime is where great-power competition, sanctions evasion, narcotics trafficking, and illicit proliferation networks all converge — and it is the domain where the intelligence problem is hardest. Vessels go dark. Identities get laundered through shell registries. Ship-to-ship transfers happen at 3 a.m. in a gap between AIS coverage. Windward built the AI platform that resolves those problems at scale, and the U.S. Intelligence Community is already using it. We are in 24 U.S. government organizations, including three IC elements. Our analytics have contributed materially to CENTCOM operations, with recognition at the highest levels of the U.S. government. Our INDOPACOM program is our flagship past performance. We are not looking for someone to open the IC. We are looking for someone to take a validated beachhead and turn it into a portfolio — new mission centers, new directorates, new programs of record. What you'll own A named IC account set. You own the full lifecycle across your agencies: account mapping, mission-set discovery, champion development, technical validation, procurement strategy, award, and expansion. There is no hand-off to a farmer. You keep what you close. Access at the top. This is a senior-level sale. You will be in front of SES/SIS civilians, flag and general officers, directorate and mission-center chiefs, CTOs and CDOs, and program executives — and you will be expected to earn a second meeting on the strength of the first. Analyst enthusiasm creates pilots; senior sponsorship creates programs of record. You will build both, and you will not mistake one for the other. Mission-set fluency, not feature pitching. You will sit with targeters, all-source analysts, collection managers, and program managers and translate their actual workflow gaps into deployed capability. The demo is a means, not the meeting. The procurement path. You will architect how the money moves — existing IDIQs, OTAs, GSA, SBIR/CSO on-ramps, sole-source justifications, contractor and SI teaming. You will know which vehicle is real and which one is a mirage before your champion does. A teaming network. Primes, SIs, and cleared resellers who can carry Windward on their paper into places we can't reach directly. You identify, vet, and manage them. Forecast integrity. MEDDPICC-disciplined qualification and a forecast senior leadership can plan against. We would rather hear "this slips a quarter" in July than in September. Voice of the customer. Requirements you surface shape the product roadmap. You are the customer's advocate inside the building, not just our advocate outside it. Requirements What we're looking for Required Active TS/SCI. Non-negotiable — this role cannot be performed at a lower level. 5+ years selling software or analytics into the Intelligence Community, with closed deals you can speak to at an unclassified level. Demonstrated ownership of full-cycle federal sales, including navigating the contracting shop — not just building the relationship and handing it off. Command of federal procurement mechanics: contract vehicles, color of money, POM cycles, ATO and accreditation timelines, and how a good-idea-fairy meeting becomes a funded requirement. Proven ability to sell at the executive level. You have carried a deal to an SES, flag officer, or mission-center director and closed it — and you can describe how you got the meeting, not just what happened in it. Credible technical range. You can hold your own on data fusion, model outputs, false positives, and integration architecture with a customer engineer in the room. Track record of building an account from a single foothold into multi-directorate adoption. Strong signals Prior service in a maritime, targeting, MASINT/GEOINT, or all-source role — or time as a government customer of commercial analytics. Experience selling in an environment where the government cares who owns you. Windward's U.S. operations run through Prominent Edge, which holds a facility clearance, and our parent is a U.S. entity. FOCI and supply-chain provenance are advantages here, and you should know how to use them. Fluency with a real qualification discipline (MEDDPICC or equivalent) that you actually apply rather than back-fill into the CRM on Fridays. Comfort in a company where the U.S. federal business is still being built and process is something you help write. What this role is not Not a relationship-only seat. A rolodex without a procurement thesis will not carry you here. Not a farming role on existing renewals. Not a position where you can wait for RFPs. Most of what you close, you will have shaped 12 months earlier. Not for someone who needs a large support apparatus. You will have a Sales Engineer, marketing, and executive air cover — and you will still be the one who figures it out. Why Windward The mission is real. Our outputs appear in intelligence products and drive operational decisions. You will be able to point at things that happened. Cleared, U.S.-based infrastructure. FCL, cleared personnel, and a U.S. corporate parent — a materially cleaner posture than the foreign-owned alternatives in this market. Agentic AI that is deployed, not demoed. Analysts use it daily to compress hours of manual research into minutes. Early enough to matter. The U.S. federal organization is being built now. Your fingerprints will be on it. Serious upside against achievable numbers. Quotas here are set to be beaten, not to be survived. The pipeline is real, the product is differentiated, and the commission structure is built so that a strong year is a life-changing one rather than a rounding error. A team of closers. Small, senior, and high-performing. Everyone on this team has carried a federal number and hit it. There is no dead weight to compensate for and no one you will have to drag. Windward is an equal opportunity employer. All qualified applicants will receive consideration without regard to any characteristic protected by law. #J-18808-Ljbffr