Director of Engineering, Leverage - Fleetio

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, Builder Experience, and Solutions Engineering.

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, and the role carries a commercial edge as well, selecting and managing agency partners through Solutions Engineering.

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.

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 and statement-of-work oversight alongside our commercial teams, and running the handoff protocol
• Modernize our Product Development Lifecycle through Engineering: pursue step changes in how we deliver software, leading the shift from AI-assisted to agentic development on your own Squads first
• Run a disciplined intake: protect the Pod's charter rather than let it become a catch-all for unowned work
• Hire, develop, and retain engineering managers and senior individual contributors; own performance, succession, and engagement across the Pod
• Partner with the VP of Engineering and CTO on vision, with our Platform Engineering Pod, and with our Design System team
• Own the Pod's budget across tooling and agency spend, and be accountable for the throughput it buys

Your experience

• 3+ years leading engineering organizations as a Director or Senior Engineering Manager, including managing managers
• Led engineering through real scale, growing teams while a business expanded from roughly $100M to $300M in revenue
• Led a platform, foundations, or developer-productivity organization whose customers were other engineering teams
• Delivered meaningful work through outside partners: selecting agencies or outsourced teams, managing statements of work, and keeping quality clean through handoff
• Use AI development tools daily and have changed how a team builds software with them
• Track record of attracting, developing, and retaining strong engineers and future leaders
• Exceptional written and verbal communication skills
• Be sure to mention "coffee" in your application so we know you read this

Considered a plus

• Experience building applications with Ruby on Rails and React
• Experience standing up a professional services, field engineering, or partner delivery function inside a product company
• Experience treating an internal platform as a product
• Familiarity with native mobile development (iOS and Android)

Benefits

• Multiple health/dental coverage options (100% coverage for employee, 50% for family)
• Vision insurance
• Incentive stock options
• 401(k) match of 4%
• PTO - 4 weeks (increases at year two!)
• 12 company holidays + 2 floating holidays
• Parental leave - birthing parent (16 weeks paid) non-birthing (4 weeks paid)
• FSA & HSA options
• Short and long-term disability (short term 100% paid)
• Community service funds
• Professional development funds
• Wellbeing fund - $150 quarterly
• Business expense stipend - $125 quarterly
• Mac laptop + new hire equipment stipend