Director, Federal Civilian Sales

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

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.