Sales director – Fed Civilian

Windward Ltd.; Washington (District of Columbia); Hybrid; USD 150,000 - 210,000; Full time

Job summary

Windward Ltd. invites a Director of Sales to drive federal civilian opportunities and funding-aligned engagements in Washington, DC area, with hybrid client-site engagement. You will lead strategy across agencies, build executive sponsorship, and guide complex deals from prospecting to close.

The role emphasizes MEDDPICC-based sales, enterprise analytics offerings, and collaboration with engineering and legal teams to ensure compliant, funded deployments. Travel around 30% is expected.

Qualifications

• Five or more years selling enterprise software, data, or analytics to federal civilian agencies.
• A demonstrated record of meeting sales targets and closing complex federal opportunities.
• Full-cycle sales experience, including new opportunity creation, procurement strategy, negotiation, and award.
• Experience building executive relationships and developing champions across mission, technology, and acquisition teams.
• Working knowledge of federal budgeting, purchasing processes, contract vehicles, and agency security and authorization requirements.
• Ability to translate technical capabilities into measurable mission outcomes and a compelling business case.
• Experience expanding adoption across offices, bureaus, or programs.
• Ability to meet suitability, access, and security requirements for assigned customers.

Responsibilities

• Lead account strategy, prospecting, opportunity development, qualification, technical validation, procurement, negotiation, close, and expansion for a named federal civilian account portfolio.
• Understand the priorities of assigned agencies and identify where maritime intelligence can improve investigations, risk assessment, enforcement, and operational efficiency.
• Build relationships with senior agency leaders, program executives, CIO and CDO organizations, mission owners, and acquisition teams; connect frontline needs with enterprise priorities and funding.
• Define use cases, success criteria, and evaluations tied to measurable customer value in partnership with Solution Engineering.
• Identify budget owners, purchasing pathways, contract vehicles, and partners early; plan for agency budget cycles, security reviews, privacy considerations, and integration requirements.
• Expand successful deployments across offices, bureaus, regions, and related mission teams; work with Customer Success to build adoption and demonstrate results.
• Engage systems integrators, resellers, and other partners that strengthen access, procurement, and implementation.
• Apply MEDDPICC, maintain accurate CRM records, and manage customer action plans with clear owners, milestones, and risks.
• Bring agency requirements to product, delivery, legal, and finance teams and shape proposals that balance customer needs with successful execution.

Job description

Location: Washington, DC metro; hybrid with regular customer-site engagement

Clearance: No active clearance required at hire unless specified for assigned accounts; ability to meet applicable agency suitability, public trust, or security clearance requirements

Reports to: VP, Federal Sales

Travel: Approximately 30%, including agency headquarters, field offices, and customer sites

Why this role exists

Federal civilian agencies face maritime challenges that span border security, customs enforcement, sanctions enforcement, trade, transportation, and protection of natural resources. Their teams need to identify risk, investigate complex networks, and prioritize action across large volumes of fragmented information.

Windward’s AI-powered maritime intelligence platform helps agencies turn that information into actionable insights. We are expanding our federal civilian business by connecting our capabilities to clear agency priorities and measurable outcomes.

We are looking for a Director of Sales who can build relationships across mission, technology, and acquisition teams—and turn agency needs into funded programs and long-term customer growth.

What you’ll own

• A named federal civilian account portfolio. Lead account strategy, prospecting, opportunity development, qualification, technical validation, procurement, negotiation, close, and expansion.

• Agency mission alignment. Understand the priorities of your assigned agencies and identify where maritime intelligence can improve investigations, risk assessment, enforcement, and operational efficiency.

• Executive sponsorship. Build relationships with senior agency leaders, program executives, CIO and CDO organizations, mission owners, and acquisition teams. Connect frontline needs with enterprise priorities and funding.

• Outcome-based selling. Partner with Solution Engineering to define use cases, success criteria, and evaluations tied to measurable customer value.

• Funding and procurement strategy. Identify budget owners, purchasing pathways, contract vehicles, and partners early. Plan for agency budget cycles, security reviews, privacy considerations, and integration requirements.

• Account growth. Expand successful deployments across offices, bureaus, regions, and related mission teams. Work with Customer Success to build adoption and demonstrate results.

• Partner development. Engage systems integrators, resellers, and other partners that strengthen access, procurement, and implementation.

• Forecast and execution discipline. Apply MEDDPICC, maintain accurate CRM records, and manage customer action plans with clear owners, milestones, and risks.

• Cross-functional coordination. Bring agency requirements to product, delivery, legal, and finance teams and shape proposals that balance customer needs with successful execution.

Required

• Five or more years selling enterprise software, data, or analytics to federal civilian agencies.

• A demonstrated record of meeting sales targets and closing complex federal opportunities.

• Full-cycle sales experience, including new opportunity creation, procurement strategy, negotiation, and award.

• Experience building executive relationships and developing champions across mission, technology, and acquisition teams.

• Working knowledge of federal budgeting, purchasing processes, contract vehicles, and agency security and authorization requirements.

• Ability to translate technical capabilities into measurable mission outcomes and a compelling business case.

• Experience expanding adoption across offices, bureaus, or programs.

• Ability to meet suitability, access, and security requirements for assigned customers.

Preferred

• Experience selling to agencies responsible for homeland security, customs, law enforcement, sanctions, transportation, trade, or natural resources.

• Familiarity with maritime intelligence, investigations, supply-chain analysis, or risk analytics.

• Experience navigating cloud security reviews, FedRAMP requirements, and agency authorization processes.

• Relationships with federal civilian systems integrators and channel partners.

• Experience converting evaluations into funded enterprise deployments.

• Practical use of MEDDPICC or an equivalent qualification methodology.

What success looks like

You build a qualified pipeline around agency priorities, establish executive sponsorship, and close opportunities with clear funding and procurement paths. Your customers demonstrate measurable value, expand adoption, and become a foundation for sustainable growth.

Why Windward

• Broad public-sector impact. Support missions that protect borders, strengthen enforcement, and improve visibility into global maritime activity.

• Compelling analytical challenges. Help agencies connect data and prioritize the activity that matters.

• Room to build. Develop new use cases and expand relationships across the federal civilian market.

• A visible role in our growth. Help shape account strategy, partnerships, and the evolution of Windward’s federal business.

Windward is an equal opportunity employer. All qualified applicants will receive consideration without regard to any characteristic protected by law.