Director of Engineering, Leverage

Remote - USA, CAN, MEX

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: builds the shared frameworks and services every Product Squad builds on
• Builder Experience: 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
• 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: fleet.io/culture
• Engineering culture, interview process and videos: fleetio.com/careers/engineering
• More about the Fleetio platform: fleetio.com/features
• API docs: 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 and statement-of-work oversight alongside our commercial teams,
• 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,
• you will protect its charter rather than let it become a catch-all for unowned work
• Hire,

develop,

• retain engineering managers and senior individual contributors;

own performance, succession, engagement across the Pod

• Partner with VP of Engineering & CTO on vision,

Platform Engineering Pod on infrastructure/application seam, Design System team on front-end foundation

• Own Pod's budget across tooling & agency spend; accountable for throughput it buys

Your experience

• 3+ years leading engineering organizations as Director or Senior Manager including managing managers
• Led engineering through real scale growing teams while business expanded $100M-$300M revenue; know changes needed in people/process/architecture along way
• Led platform/foundations/developer-productivity orgs serving other engineering teams; can show impact measurement/growth
• Delivered meaningful work through outside partners selecting agencies/outsourced teams managing statements-of-work keeping quality/ownership clean via handoff
• Use AI development tools daily; changed how team builds software with them
• Track record attracting/developing/retaining strong engineers/future leaders
• Exceptional written/verbal communication; can make investment case to execs & 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 & React
• Experience standing up professional services/field engineering/partner delivery function inside product company
• Experience treating internal platform as product adoption metrics...