Director of Customer Success – U.S. Public Sector

Windward • Washington, DC

3d • Hybrid

About The Position

We are seeking a Director of Customer Success to lead our U.S. Public Sector CS organization. In this leadership role, you will be responsible for defining and executing the customer success strategy for our federal and governmental portfolio. You will lead a department of CSMs, ensuring that Windward’s technology is deeply integrated into the mission-critical operations of U.S. government agencies. As a Director, you will not only oversee relationships but also drive the scalable growth of the department, influence the product roadmap, and serve as a key member of the regional leadership team.

Requirements

• Experience: 8+ years in Customer Success or Account Management in a SaaS environment, with at least 3-4 years in a senior leadership role (Director or Senior Manager), managing a team with a book of business of tens of million USD.
• Public Sector Expertise: Proven track record of managing and scaling CS operations within the U.S. Federal or Government sector (Must).
• Security Clearance: Active High Security Clearance (Must/Highly Preferred).
• Strategic Mindset: Proven ability to handle complex, multi-million dollar renewals and expansion initiatives.
• Leadership: Experience working with global teams, and collaborating with other managers to achieve goals
• Can do approach and hands-on approach - you will lead strategic customers\partnership directly and support your team in escalations
• Travel: Ability to travel up to 30-40% for on-site customer engagements and events, primarily within the U.S.

Nice To Haves

• Domain Knowledge: Deep familiarity with the Maritime Domain and/or Intelligence Operations (OSINT, SIGINT, etc.) is a significant advantage.

Responsibilities

• Strategic Leadership: Define and implement the long-term CS strategy for the U.S. Public Sector, aligning department goals with global company objectives and ARR targets.
• Scaling & Mentorship: Build and develop a high-performing CS organization. Lead, mentor, and coach Team Leads and CSMs, fostering a culture of high performance, accountability, and mission-driven excellence.
• Executive Relationship Management: Act as the executive sponsor for strategic federal accounts, building long-term partnerships with senior government officials and C-level stakeholders.
• Lifecycle & Retention Ownership: Accountable for overall retention (GRR) and expansion (NRR) targets across the U.S. government portfolio.
• Cross-Functional Influence: Partner with Sales, Product, and R&D to ensure the "Voice of the Government Customer" shapes the future of the Windward platform.
• Operational Excellence: Optimize CS methodologies, including onboarding playbooks, health-scoring models, and proactive risk mitigation strategies tailored to federal requirements.
• Procurement & Compliance Navigation: Oversee the alignment of CS strategies with U.S. Federal acquisition, regulatory (FedRAMP, etc.), GOV cloud and compliance requirements.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 51-100 employees