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Senior Product Manager, Maintenance

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 an evidence-based, customer-centric, and inventive Senior Product Manager to join our product org. As a Senior PM on our Maintenance team, you'll own core areas of Fleetio's most widely used product domain. These workflows are what fleets rely on every day to keep their vehicles safe, compliant, and available for work. Your goal will be to deeply understand how fleets run maintenance across in-house teams and external vendors, and to build product experiences that make Fleetio the one place to run it all.

Reporting to the Director of Product Management - Maintenance, you should be thrilled at the prospect of tackling complex, high-usage workflows, delving into rich data for insight, formulating hypotheses, and turning them into value-driving features for our users. You'll partner with a cross-functional team of engineering, design, data, and go-to-market to plan, direct, approve, and optimize maintenance work — reshaping fleet management along the way.

Who You Are

Our ideal candidate for this role is insatiably curious and empathetic, passionate about and experienced collaborating with others, and skilled at turning messy, real-world operational problems into elegant product solutions. You have strong, loosely held opinions, are a proactive problem-solver and data-driven decision maker, and thrive in a fast-paced environment. You have extensive experience planning, designing, and iterating on end-to-end product features with cross-functional team members and executive leaders. You bring the judgment to own a core product area with significant customer impact. Where reliability and depth matter as much as velocity. Your ability to foster adoption and communicate effectively with technical and non-technical team members is key to your success.

Your Impact

  • Own the product strategy and roadmap for core maintenance workflows/ tools/ automations — spanning areas such as work orders, inspections, issues, service entries, preventive maintenance schedules, and parts & inventory.
  • Drive Fleetio's vision of running maintenance in one connected system, across in-house teams, external vendors, or both.
  • Collaborate cross-functionally with research, design, engineering, data science, marketing, and customer-facing teams to develop successful strategies and make informed decisions.
  • Ensure the evolution of Fleetio's maintenance experience is customer-driven, data-informed, and designed to help fleets automate coordination, control costs, and keep vehicles available for work.
  • Deeply understand the operational realities of both in-house shops and outsourced maintenance, and how they connect.
  • Balance depth and reliability in high-usage, mission-critical workflows with the pace of shipping new value.
  • Continuously generate and test hypotheses to iterate and improve the product experience.
  • Effectively communicate product vision, value proposition, trade-offs, risks, opportunities, learnings, insights, and roadmap updates to stakeholders, executives, and customers.
  • Work closely with your team to find ways to make our development process more efficient in delivering high-quality features to customers quickly.
  • Guide features through their entire creative cycle: discovery, ideation, specification, test, delivery, launch / GTM, analysis, and optimization.
  • Demonstrate initiative and ability to turn business priorities, key themes, and big ideas into a roadmap with minimal guidance.
  • Identify opportunities for differentiation, zero-to-one innovation, and revenue expansion.
  • Raise the bar for product quality based on strong evidence.

Your Experience

  • 5+ years in product management in modern B2B technology-driven SaaS environments, with a track record of owning core product areas end-to-end.
  • BA/BS/MS in Computer Science, Business, Design, or related equivalent field/experience.
  • Experience owning complex, workflow-heavy products where reliability and operational depth are critical.
  • In-depth knowledge of product management best practices and fluency with data.
  • Passion for customer & business success, shortening time to value, and the craft of PM.
  • A committed desire to understand our users and rally around the problems we're solving.
  • Effective at integrating feedback, facts, and needs into product recommendations, decisions, strategies, and launch execution across the product life-cycle.
  • Natural leadership skills: you influence and inspire others who love working with you.
  • A proven track record of strong cross-functional collaboration.
  • An entrepreneurial spirit: you are self-driven, accountable, and comfortable presenting to customers, prospects, partners, and stakeholders.
  • Egoless self-starter with great product sense, curiosity, attention to detail, and a growth mindset.
  • Talent for mediating across various needs and finding creative solutions.
  • Strong analytical and problem-solving skills, with the ability to translate data and insights into actionable product strategies and decisions.
  • Champion our core values of intelligence, intensity, integrity, and ownership.

Considered a plus

  • Experience in fleet / automotive / transportation software, vertical SaaS, or related space.
  • Domain knowledge of maintenance, field service, asset management, or shop operations.
  • Experience optimizing mature, high-usage products while also building zero-to-one.
  • Experience with marketplace or multi-sided products is also ideal.

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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