VP Customer Success IL

As the VP Customer Success at Windward, you will be the primary architect of the customer journey for a global portfolio of hundreds of enterprise accounts. You will lead a Customer Success organization focusing on both Commercial customers and Public Sector intelligence agencies to derive maximum value from Windward’s Maritime AI platform.

You will sit at the intersection of commercial growth and operational excellence, managing a complex landscape of diverse business lines across the US, EU, UK, and International markets.

Core Responsibilities

1. Strategic Leadership & Portfolio Management

• Segmented Strategy: Oversee a diverse portfolio of 300+ enterprise customers, developing bespoke success strategies for two distinct pillars:
• Commercial: Energy majors, bunkering, commodity traders, and ship owners.
• Government: Coast guards, Law Enforcement Agencies (LEA), Customs, and Intelligence organizations.
• Revenue Accountability: Primary Drive Customer satisfaction, Gross Retention Rate (GRR) and Net Retention Rate (NRR). Identify and act upon expansion opportunities (upsell/cross-sell) in partnership with the Sales team.
• Global Scale: Manage and scale localized teams across various time zones to provide seamless support for international markets.

2. Complex Implementations & Product Adoption

• Operational Excellence: Oversee complex, large-scale implementations that involve integrating Windward’s AI into existing customer workflows and technical ecosystems.
• Value Realization: Define and track "Success Outcomes" for customers, ensuring that maritime intelligence translates into actionable insights for risk management, compliance, and national security.
• Feedback Loop: Serve as the "Voice of the Customer" to the Product and Engineering teams, ensuring the roadmap reflects the evolving needs of both commercial and government sectors.

3. Executive Relationship Management

• Trusted Advisor: Act as an executive sponsor for "Tier 1" accounts, building relationships with C-suite executives in the private sector and high-ranking officials in the public sector.
• Crisis Management: Navigate high-stakes maritime or geopolitical events where customers rely on Windward for real-time intelligence and support.

Required Experience & Qualifications

• Leadership: 10+ years in a senior leadership role (VP or similar) within Customer Success, Account Management, or Professional Services.
• Multi-Business Line Leadership: Proven track record of managing both Commercial (SaaS/Enterprise) and Government (Public Sector/Defense) business lines simultaneously
• Maritime Domain Expertise: Deep understanding of the maritime ecosystem (shipping, trade and security) is a huge advantage. You must speak the language of data & insights, sanctions compliance, and maritime risk.
• Scale: Experience managing a portfolio of hundreds of Enterprise customers with a structured approach to high-touch vs. tech-touch engagement.
• Global Exposure: Significant experience operating across US, EU and UK and international markets, with an understanding of the differing regulatory and business landscapes.
• Implementation Depth: Expertise in managing long-cycle, complex technical implementations involving AI, Data and API integrations.