Sales Enablement Manager

We are hiring a Sales Enablement Manager to build and run a modern, AI-forward enablement function for our global sales organization.

This is a hands-on individual contributor role responsible for onboarding, certification, sales coaching, enablement content, tools, and continuous learning. You will partner closely with Sales, Product, Product Marketing, Marketing, Revenue Operations, and Customer Success to ensure our field teams are equipped to sell Windward’s platform with clarity, confidence, and urgency.

The role may be based in Washington, DC or London and will support commercial, government, and defense go-to-market teams.

What You’ll Do

• Build and manage onboarding programs for new sellers, GTM personnel and sales leaders, with clear 30/60/90-day milestones tied to ramp, product mastery, and sales execution.
• Develop a sales competency and certification framework covering product knowledge, use cases, discovery, demo delivery, value selling, methodology, and competitive positioning.
• Embed AI tools into seller workflows, including call analysis, deal coaching, content discovery, role-play simulations, and rep self-service.
• Work with cross functional teams to develop, create and maintain enablement content, including playbooks, battlecards, talk tracks, demo guides, discovery guides, objection-handling materials, and manager toolkits.
• Partner with Product, Product Marketing, Marketing, RevOps, Customer Success, and Sales leadership to keep messaging, content, and training aligned to the buyer journey and seller needs.
• Run coaching programs, pitch certifications, deal clinics, call reviews, office hours, and skill-building sessions for reps and frontline managers.
• Establish an always-on learning rhythm for product launches, new use cases, competitive updates, and messaging changes.
• Build field fluency around Windward’s Maritime AI platform, translating complex AI, maritime, compliance, intelligence, and operational capabilities into clear customer value.
• Define and track enablement KPIs such as ramp time, certification completion, content usage, win rate, sales cycle progression, quota attainment, and manager feedback.
• Treat enablement as a product: gather feedback, prioritize based on revenue impact, iterate quickly, and continuously improve.

What You’ll Bring

• 4+ years of experience in sales enablement, revenue enablement, sales, or a related GTM role, ideally in B2B SaaS.
• Experience supporting enterprise, technical, complex, or mission-driven sales motions.
• Proven ability to build or scale enablement programs, including onboarding, certification, coaching, competency frameworks, and sales content.
• Hands-on curiosity and experience using AI tools to improve seller productivity, learning, or enablement workflows.
• Strong instructional-design instincts and the ability to make complex products easy to understand, learn, and sell.
• Excellent cross-functional partnership skills across Sales, Product, Marketing, RevOps, and Customer Success.
• Data-driven approach to measuring impact and improving programs over time.
• Comfort operating as a hands-on individual contributor in a fast-moving, global environment.
• Strong communication, facilitation, and executive presence.