Director of AI Transformation

Description Windward is the leading Maritime AI™ company, fusing data and Generative AI to empower global leaders with mission-grade intelligence. We help organizations anticipate threats and make high-stakes decisions with confidence. This is a role for someone who wants to build the org of the future, where agents and people work side by side, and is ready to own the program that gets a company there! You're taking over the leadership of Windward's AI Transformation: the internal AI work across every function. You'll own the program end-to-end. Your Mission Make Windward AI-native in how it operates. Not a faster version of today — a different way of working, with AI in the loop in every function, measured by hours saved, adoption, and platform leverage. How the Team Works We move fast, ship continuously, and care more about outcomes than titles or process. We have low tolerance for politics, status-game meetings, and passive operators. If you need a roadmap committee to feel safe, this isn't the place. If you have a bias for action, enjoy being hands-on, and naturally prioritize value, this is the team for you. What You'll Do? Run the three pillars (Adoption, Infrastructure, Builds) and the foundation that ties them together. Adjust as we learn, and make it real on the ground. Lead the change, not just the tooling — the hard part isn't building the agent, it's getting people to change how they worked for years. You'll drive that change, build trust with VPs, and push where it matters. Manage and grow the team — both direct reports and dotted line champions. You'll grow the team from there as the program scales. Run the prioritization machine — choose what’s the right effort, from vertical low hanging fruit and all the way to horizontal initiatives. Make "agents as employees" real — every agent has a manager, a cost, a performance review, and a forward plan. Managers are measured and rewarded on how their agents perform. Measure and report impact — hours saved, adoption, leverage and metrics you define and instrument. Report up. Adjust the program based on what the numbers say. Stay hands-on — this isn't a role for someone who only writes plans. You build agents and workflows yourself when it makes sense, sit in proposal reviews with the PM, weigh in on architecture with the Engineer, and ship things when needed. Requirements Who Are You? 6+ years in product, operations, or engineering leadership. You've run a function, owned a meaningful program, and managed people. Bonus if you've run an internal transformation before - AI, automation, ops, or otherwise. Understand AI deeply - agentic systems, the build-vs-buy landscape, what's hard and what's easy. You're familiar with agent frameworks, workflow builders, and no-code/low-code AI tools. You can hold your own in an architecture conversation and you have informed opinions about the stack. A strong people manager - You've hired senior ICs, set goals, given hard feedback, and grown people. You know when to lead and when to get out of the way. A natural cross-functional operator- You build trust with VPs and department heads. You can push back, make a case, and earn cover when you need it. Comfortable in executive rooms. A program builder - You can design and run something that touches every function in the company without it collapsing under its own weight. You care deeply about change management - You know that getting people to change how they work is harder than building the thing they're supposed to use — and you're patient enough to do both. You can write and present at every level - board update, all-hands, one-on-one with a VP, manifesto-style doc for the team. You've owned company-level metrics and moved them. English at a professional level. Advantage You've founded a company, or led a 0-to-1 function inside a larger org. You've worked on AI products or AI transformation programs in production. You have a technical background — engineer, data scientist, or PM on a deeply technical product. Location: Tel Aviv. Hybrid