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Director of Product Management, FleetOS

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:

We’re looking for a Director of Product Management to lead FleetOS — the operating system that powers how fleets operate, communicate, and scale. This is a remote opportunity and is open to candidates in the United States, Canada, or Mexico.

About FleetOS

FleetOS is the foundation that helps Fleetio evolve from a system of record to a system of results. It is how we:

  • Standardize fleet maintenance and operations data so it is trustworthy, comparable, and actionable.
  • Orchestrate workflows across people, partners, and systems via APIs, integrations, and automation.
  • Deliver guidance, recommendations, and next best actions that help fleets improve uptime, reduce costs, and stay compliant.

Who you are

You will be accountable for setting the strategy and driving the execution of FleetOS. You will partner with leaders across Fleetio on strategy, planning, and execution, and you will ensure we are continuously delivering the right platform capabilities at the right time. You are a people-first leader who sets a high bar while building an environment where PMs do their best work. You coach, hire, and develop talent, and you foster a culture of clarity, ownership, collaboration, and customer empathy. This role is part of the Product Leadership team and will report to the VP of Product.

Your impact

  • Define and own a differentiated, data-informed vision, strategy, goals, and roadmap for FleetOS.
  • Drive measurable outcomes for fleets by turning data + workflows into results (uptime, cost savings, compliance leverage), not just features.
  • Treat the platform as a product: own strategy across APIs, extensibility, automation primitives, and partner-facing surfaces.
  • Make Fleetio the orchestration layer for third-party tools and machine-to-machine workflows.
  • Advance data standardization and intelligence so FleetOS can provide guidance, benchmarking, and next best actions.
  • Lead and scale a team of PMs to maximize their effectiveness and support career growth.
  • Hire and develop PM leaders, provide clear expectations, and create space for teams to take smart risks and learn.
  • Foster a culture of impact, experimentation, iteration, collaboration, learning, and sound decision-making.
  • Create strong cross-functional alignment by setting crisp goals, making principled tradeoffs, and communicating clearly.
  • Collaborate with Engineering to optimize product development practices and delivery predictability.
  • Collaborate with Design to deliver a coherent, high-quality platform experience (including developer and admin experiences).
  • Collaborate with Product Marketing to position FleetOS capabilities, support launches, and evolve packaging and monetization where appropriate.
  • Collaborate with Marketing, CX, Sales, Enablement, and customer-facing teams to improve awareness, win rates, and retention.
  • Serve as an ambassador for FleetOS and the product team, and roll up your sleeves.

What success looks like

  • FleetOS capabilities are adopted by internal teams and customers, and they unlock new product experiences across Fleetio.
  • Ecosystem health improves: more high-quality integrations, higher integration adoption, and stronger partner outcomes.
  • Platform leverage increases: more workflows are automated and fewer critical processes depend on manual data entry.
  • Data quality and standardization improve in ways that unlock guidance and measurable customer outcomes.

Your experience

  • 8+ years in product management, shipping and scaling modern B2B SaaS applications.
  • 4+ years leading empowered product teams.
  • Product leadership experience in platform products (APIs, developer-facing surfaces, integrations ecosystems, extensibility).
  • Experience shipping products where data quality, standardization, and instrumentation are first-class requirements.
  • Strong cross-functional leadership with GTM teams and technical stakeholders (platform engineering, data engineering, security/privacy as needed).
  • Comfort operating in hybrid UI + non-UI product environments (automation, machine-to-machine, workflows).
  • Experience with hybrid PLG (product-led growth) and SLG (sales-led growth) motions.
  • Excellent writing, speaking, presentation, collaboration, prioritization, and persuasion skills.
  • Strategic, analytical, creative, and data-informed in how you work and inform decisions.
  • Embody our core values of intelligence, intensity, integrity, and ownership.
  • Bachelor's degree in Business, Engineering, Design, Computer Science, or relevant field.

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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