[Hiring] Director of Engineering, Leverage @Fleetio

Role 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: Modernizes our Product Development Lifecycle, focusing on AI-assisted and agentic development.
• Solutions Engineering: Accelerates roadmap commitments to win and retain key accounts, extending 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, including cadence, expectations, and evidence of improvement. The role carries a commercial edge as well, overseeing agency partners and ensuring contracted work meets Fleetio standards.

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, requiring product judgment and engineering leadership.

Qualifications

• 3+ years leading engineering organizations as a Director or Senior Engineering Manager, including managing managers.
• Experience leading engineering through real scale, growing teams while a business expanded from roughly $100M to $300M in revenue.
• Experience in platform, foundations, or developer-productivity organizations whose customers were other engineering teams.
• Experience delivering meaningful work through outside partners, managing statements of work, and ensuring quality and ownership.
• Daily use of AI development tools and experience changing 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.

Requirements

• Own the strategy and outcomes for a portfolio spanning shared frameworks, developer tooling, and partner delivery.
• Make the rest of Product & Engineering measurably faster by driving adoption of shared frameworks and services.
• Stand up the Solutions Engineering Squad to accelerate roadmap commitments.
• Modernize the Product Development Lifecycle through Engineering.
• Run a disciplined intake to protect the Pod's charter.
• Hire, develop, and retain engineering managers and senior individual contributors.
• Partner with the VP of Engineering and CTO on vision.
• Own the Pod's budget across tooling and agency spend.

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.