Director of Engineering, Leverage

A little about us…Fleetio is a modern software platform that helps thousands of organizations worldwide manage their fleet operations. Transportation technology is a hot market, and we’re leading the charge with raving fans and new customers signing up every day. We raised $450M in our Series D funding round in March of 2025 and are on an exciting trajectory as a company.

Fleetio is also a proud founding member of the Rails Foundation ! com/careers Description Fleetio is looking for a Director to lead our Leverage Engineering Pod, a Division within Engineering whose mission is to multiply the delivery capacity of all of Product Engineering. You will lead and be accountable for the Pod's strategy and execution through three Squads: Foundations Engineering, which builds the shared frameworks and services every Product Squad builds on; Builder Experience, which exists to modernize our Product Development Lifecycle, pursuing step changes in our ability to deliver software rather than incremental gains, with AI-assisted and agentic development as its current focus; and Solutions Engineering, a new Squad chartered to accelerate the roadmap commitments that win and retain key accounts, extending our capacity through vetted agency partners.

Your customers are mostly internal: the Product and Platform Pods whose speed and quality your Squads exist to raise. You will set the strategy for how leverage is measured across Product Engineering: the cadence, the expectations, and the evidence that your Squads are making every other Pod faster. The role carries a commercial edge as well: through Solutions Engineering you will select and manage agency partners, oversee statements of work, and make sure contracted work lands as first-class Fleetio code with a clean handoff to a long-term owner.

You will report directly to the VP of Engineering and sit on the Product Engineering Senior Leadership Team. You will own the Pod's vision, roadmap, and investment case end to end, which means bringing product judgment as well as engineering leadership: discovering what your internal customers need, prioritizing a portfolio across three very different Squads, and making the case for the investment each deserves.

Who You Are

You're an engineering leader who gets more satisfaction from making twenty teams faster than from shipping one team's feature. You've run a platform, foundations, or developer-productivity organization, and you know its failure modes: the ivory tower nobody adopts, the dumping ground that absorbs every unowned problem, the tooling team that optimizes for novelty instead of adoption. You hold a high bar through data and judgment rather than process, and you're personally fluent in AI-assisted development, with a grounded point of view on where agentic development is taking the discipline.

You're comfortable in commercial territory: choosing partners, structuring statements of work, and holding outside teams to an inside standard.