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](https://rubyonrails.org/foundation)! **More about our team and company:** - Fleetio overview video: https://www.youtube.com/watch?v=YoXyXTFWbkg - Our careers page: https://www.fleetio.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. ## More About Our Team and Company - Watch our culture videos: http://fleet.io/culture - Engineering culture, interview process and videos: http://fleetio.com/careers/engineering - More about the Fleetio platform: http://fleetio.com/features - API docs: http://developer.fleetio.com ## 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. ## Your impact - Own the strategy and outcomes for a portfolio spanning shared frameworks, developer tooling, and partner delivery; define what good looks like for each Squad and hold that bar - Make the rest of Product & Engineering measurably faster: drive adoption of shared frameworks and services, retire duplicated effort across Pods, and prove the multiplier effect with data - Stand up our Solutions Engineering Squad: accelerate the roadmap commitments that win and retain key accounts by building the agency bench, owning contracting an…