Director of Engineering, Leverage

Fleetio

8d•Remote

About The Position

Fleetio is seeking a Director to lead its Leverage Engineering Pod, a division focused on multiplying the delivery capacity of all of Product & Engineering. This role involves leading three Squads: Foundations Engineering (building shared frameworks and services), Builder Experience (modernizing the Product Development Lifecycle with a focus on AI-assisted and agentic development), and Solutions Engineering (accelerating roadmap commitments for key accounts through agency partners). The primary customers are internal teams within Product & Engineering, aiming to increase their speed and quality. The role also has a commercial aspect, managing agency partners and statements of work for the Solutions Engineering Squad. The Director will report to the VP of Engineering, sit on the Product & Engineering Senior Leadership Team, and own the Pod's vision, roadmap, and investment case, requiring both product judgment and engineering leadership.

Requirements

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, and know what has to change in people, process, and architecture along the way
Led a platform, foundations, or developer-productivity organization whose customers were other engineering teams, and can show how you measured and grew its impact
Delivered meaningful work through outside partners: selecting agencies or outsourced teams, managing statements of work, and keeping quality and ownership clean through handoff
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: can make an investment case to executives and a technical case to Staff engineers
Mention "coffee" in your application

Nice To Haves

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)

Responsibilities

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

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