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Location: Washington, DC metro; hybrid with regular work at customer sites and in secure facilities
Clearance: Active TS/SCI required; CI or full-scope polygraph strongly preferred
Reports to: VP, Federal Sales
Travel: Approximately 30%, primarily within the National Capital Region and to customer sites
Why this role exists
Maritime activity connects some of the Intelligence Community’s most complex challenges: great-power competition, sanctions evasion, narcotics trafficking, and illicit proliferation networks. Understanding that activity requires connecting fragmented data, detecting deceptive behavior, and identifying relationships that are difficult to see at scale.
Windward’s AI-powered maritime intelligence platform helps analysts address these challenges. With existing adoption across U.S. government organizations, including Intelligence Community customers, we have a foundation for broader growth.
We are looking for a Director of Sales who can expand that foundation across mission centers, directorates, and programs—turning demonstrated analytical value into funded, enduring adoption.
What you’ll own
- A named IC account portfolio. Lead account mapping, mission discovery, champion development, technical validation, procurement strategy, negotiation, close, and expansion.
- Executive access and sponsorship. Build relationships with senior intelligence executives, directorate and mission-center leaders, technology leaders, and program executives. Connect analyst demand with senior sponsorship and budget authority.
- Mission-set fluency. Work with targeters, all-source analysts, collection managers, and program teams to understand workflow gaps. Partner with Solution Engineering to demonstrate how Windward supports their requirements.
- The procurement path. Identify viable contract vehicles, funding sources, acquisition strategies, and teaming arrangements. Incorporate security, integration, and authorization dependencies into the pursuit plan.
- Account expansion. Turn a successful deployment into adoption across additional teams, directorates, and mission sets. Partner with Customer Success and delivery teams to establish evidence of value.
- A productive teaming network. Develop relationships with primes, systems integrators, and cleared partners that support access, procurement, and delivery.
- Forecast integrity. Apply MEDDPICC, maintain accurate CRM records, and surface risks early. Build forecasts grounded in validated requirements, funding, decision processes, and customer commitments.
- Voice of the customer. Bring actionable mission requirements and market insight to product and leadership teams while setting realistic customer expectations.
What we’re looking for
Required
- Active TS/SCI clearance.
- Five or more years selling software, data, or analytics into the Intelligence Community, with closed opportunities you can discuss at an unclassified level.
- Demonstrated ownership of full-cycle federal sales, including engagement with acquisition and contracting stakeholders.
- A record of meeting sales targets and expanding strategic accounts.
- Experience securing executive sponsorship and advancing opportunities with senior intelligence leaders.
- Understanding of federal procurement, funding cycles, contract vehicles, and the security and authorization requirements that influence deployment.
- Ability to discuss data fusion, analytical outputs, false positives, and integration requirements with technical customers.
- Experience growing an initial foothold into adoption across multiple teams or directorates.
Preferred
- CI or full-scope polygraph.
- Prior intelligence experience in maritime analysis, targeting, GEOINT, MASINT, collection management, or all-source analysis.
- Experience as a government user of commercial data or analytics.
- Relationships with IC-focused primes, systems integrators, and cleared partners.
- Familiarity with customer requirements concerning corporate ownership, facility clearances, supply-chain provenance, and data handling.
- Practical use of MEDDPICC or an equivalent qualification methodology.
What success looks like
You deepen customer relationships, establish senior sponsorship, and develop qualified opportunities across your account portfolio. You convert mission needs into funded deployments and build a repeatable path to broader adoption.
Why Windward
- Substantive intelligence challenges. Help customers understand deceptive maritime activity and complex global networks.
- An established starting point. Build on existing government and IC adoption.
- Direct customer influence. Bring mission insight into product development and go-to-market decisions.
- Opportunity to shape the business. Play a central role in expanding Windward’s Intelligence Community presence.
Windward is an equal opportunity employer. All qualified applicants will receive consideration without regard to any characteristic protected by law.
Skills Required
- Active TS/SCI clearance
- 5+ years selling software or analytics into the Intelligence Community with closed deals speakable at unclassified level
- Ownership of full-cycle federal sales, including navigating contracting and procurement shops end-to-end
- Command of federal procurement mechanics (contract vehicles, color of money, POM cycles, ATO/accreditation timelines)
- Proven ability to sell and close at SES/flag officer or mission-center director level
- Credible technical fluency on data fusion, model outputs, false positives, and integration architecture
- Track record building an account from single foothold into multi-directorate adoption
- Ability to travel ~30% (primarily NCR, COCOM HQs, customer sites)
- Prior service or experience in maritime, targeting, MASINT/GEOINT, or all-source roles
- Familiarity with FOCI, cleared resellers/primes, and supply-chain provenance advantages
- Fluency and practical use of a rigorous qualification discipline (MEDDPICC or equivalent)
- Comfort working in an early-stage federal business environment and helping write process
What We Do
Windward is the leading Maritime AI™ company delivering full visibility across the seas through sensor-agnostic intelligence and agentic workflows that turn ocean data into decisive action to anticipate threats, protect critical assets, and stay in control at sea.
