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Director of Engineering, Leverage

Remote - USA, CAN, MEX

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!

More about our team and company:

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

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 and statement-of-work oversight alongside our commercial teams, and running the handoff protocol that turns contracted work into owned, maintained product
  • 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 and as a model for the rest of engineering
  • Run a disciplined intake: this Pod exists to multiply the organization, and you will protect its 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 on the seam between infrastructure and application frameworks, and with our Design System team on the front-end foundation
  • 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
  • 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
  • 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 use AI development tools daily and have changed how a team builds software with them
  • A track record of attracting, developing, and retaining strong engineers and future leaders
  • Exceptional written and verbal communication: you can make an investment case to executives and a technical case to Staff engineers
  • 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: 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)

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
  • Fully stocked kitchen with tons of drinks & snacks (BHM only)
  • Remote working friendly since 2012 #LI-Remote

Fleetio provides equal employment opportunities to all employees and applicants and prohibits discrimination and harassment. We celebrate diversity and are committed to creating an inclusive environment for all. All employment is decided on the basis of qualifications, merit and business need.

This application is not intended to and does not create a contract or offer of employment. Employment with Fleetio is at will.

If you have a disability or a special need that requires an accommodation to fill out the online application, please let us know by calling (205) 718-7500.

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We use AI-assisted tools to support our application review process. These tools help us assess qualifications and assist our recruiting team in identifying candidates whose skills and experience closely match the job requirements we selected for this role. If you’d prefer to opt out of profiling, you can contact us at recruiting@fleetio.com, and we’ll review your application without AI assistance.

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