Director of Engineering (Leverage)

Fleetio is seeking a Director of Engineering to lead the Leverage Engineering Pod, which aims to multiply the delivery capacity of all of Product & Engineering. The role involves setting the strategy for measuring leverage across Product & Engineering, managing agency partners, and overseeing the Pod's vision, roadmap, and investment case. The Director will report directly to the VP of Engineering and sit on the Product & Engineering Senior Leadership Team.

• Lead and be accountable for the strategy and execution of the Leverage Engineering Pod, overseeing three Squads: Foundations Engineering, Builder Experience, and Solutions Engineering.
• Set the strategy for how leverage is measured across Product & Engineering, driving adoption of shared frameworks and services, and proving the multiplier effect with data.
• Own the Pod's vision, roadmap, and investment case end to end, prioritizing a portfolio across three very different Squads, and making the case for the investment each deserves.
• You're an engineering leader who gets more satisfaction from making twenty teams faster than from shipping one team's feature
• You're comfortable in commercial territory: choosing partners, structuring statements of work, and holding outside teams to an inside standard
• 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'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
• Exceptional written and verbal communication: you can make an investment case to executives and a technical case to Staff engineers
• A track record of attracting, developing, and retaining strong engineers and future leaders
• You use AI development tools daily and have changed how a team builds software with them
• You've led a platform, foundations, or developer-productivity organization whose customers were other engineering teams, and you can show how you measured and grew its impact
• You've delivered meaningful work through outside partners: selecting agencies or outsourced teams, managing statements of work, and keeping quality and ownership clean through handoff
• You've led engineering through real scale, growing teams while a business expanded from roughly $100M to $300M in revenue, and you know what has to change in people, process, and architecture along the way
• 3+ years leading engineering organizations as a Director or Senior Engineering Manager, including managing managers
• Be sure to mention "coffee" in your application so we know you read th
• Experience standing up a professional services, field engineering, or partner delivery function inside a product company
• Experience treating an internal platform as a product: adoption metrics, internal customer discovery, deprecation management
• Familiarity with native mobile development (we ship iOS and Android apps supported by a cross-cutting Mobile chapter)
• Experience building applications with Ruby on Rails and React