Remote
US
💻Engineering
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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!
Fleetio is looking for an Engineering Manager to lead our Payments engineering team. In this role, you’ll guide a team responsible for building and maintaining complex, high-stakes payment systems that support Fleetio’s customers and business operations.
You’ll partner closely with Product, Engineering, and cross-functional stakeholders to deliver reliable, well-tested, and maintainable solutions in a domain where accuracy, systems thinking, and attention to detail are critical. You’ll also coach and develop engineers, support technical decision-making, and help the team balance delivery speed with engineering quality.
If you are an engineering leader with strong technical expertise, excellent leadership skills, and experience leading teams in payments, billing, subscription platforms, fintech, or similarly high-accountability domains, we would love to connect with you.
This is a remote opportunity and is open to candidates in the United States, Canada, or Mexico.
The ideal candidate for this role possesses a blend of technical expertise, leadership skills, business acumen, and strong systems thinking. You have experience leading SaaS web application engineering teams and are comfortable operating in complex, financially oriented systems where quality, reliability, and maintainability matter.
You have meaningful experience with payments, billing, subscription platforms, fintech, or similar high-stakes product areas. Experience with tools or platforms such as Stripe, Recurly, Chargify, or similar payment processing or billing systems is strongly desired. Ruby on Rails experience is strongly preferred, and React or comparable web application framework experience is helpful.
Your leadership experience includes successfully managing and inspiring engineering teams, developing talent, driving roadmap outcomes, and fostering a collaborative, accountable engineering culture. You communicate clearly, reason well through tradeoffs, and help teams deliver high-quality outcomes without losing sight of customer and business impact.
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.
Health Insurance
Dental Insurance
Vision Insurance
Flexible Spending Account (FSA)
Health Savings Account (HSA)
Disability Insurance
Life Insurance
Wellness Programs
Employee Assistance Program
401(k) / Retirement Plan
401(k) Match
Stock Options
Performance Bonus
PTO / Vacation
Paid Holidays
Bereavement Leave
Company Equipment
Parental Leave
Learning & Development Budget
Defined Career Pathways
Team Events & Social Budget
Paid Trial
Free Snacks & Drinks
Fleetio's job board labels roles three ways: "Remote - USA, CAN, MEX" on most engineering and product roles, "Remote - USA" on marketing, sales and business operations roles, and plain "Remote" on a couple of others. A Software Engineer posting states it directly: "This is a remote opportunity open to candidates in the United States, Canada, or Mexico." Fleetio publishes no EMEA, APAC or work-from-anywhere language, so the widest stated zone is North America. Fleetio works remotely by default, and one posting frames the Birmingham HQ as an alternative rather than a requirement: you can work "remotely from anywhere in the U.S. or from our HQ in Birmingham, AL."
Four stages, published on the engineering page. First a one-hour lead interview with the Lead Software Engineer and/or hiring manager. Then a small coding project that Fleetio pays you for: "We value your time and commitment to the project, so we will pay you for it!" Then a two-hour team interview with several engineers, covering a walkthrough of your project plus technical and team-fit discussion. Finally a conversation with the CTO, then an offer. Read postings closely: some ask you to "mention coffee in your application so we know you actually read this." Fleetio has not published an equivalent process for non-engineering roles.
The wellbeing fund is the distinctive one: $150 every quarter to spend on whatever supports your wellbeing. Time off runs to four weeks of PTO, increasing at year two, plus 12 company holidays and 2 floating holidays. Health and dental premiums are covered at 100% for the employee and 50% for family. Fleetio also sets aside community service funds for team members, which it lists alongside its benefits rather than as a separate volunteering program.
No. No open Fleetio posting carries a compensation range, including US-remote roles, and no pay-transparency or pay-equity statement appears on the careers, culture or engineering pages. The comp signals Fleetio does publish are non-numeric: incentive stock options for all team members, and commission language on sales roles such as "uncapped earning potential."
It does not say. There is no published core-hours policy, meeting policy, timezone-overlap requirement, documentation-first statement or employee handbook anywhere on the careers, culture or engineering pages. The closest thing to a stated norm is the Work-Life Balance tenet, which is about focusing intensely to get things done at work and then leaving work behind. Working norms are worth asking about per team, since they are not set company-wide in public.
One perk does. The stocked kitchen with drinks and snacks is marked "BHM only," and Fleetio states no remote equivalent for it. Birmingham is also where the company's civic presence sits, including sponsorship of area tech events. No other office is disclosed, and every open role is labeled remote.
