Engineering Manager, Payments

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: Fleetio overview video: https://www.youtube.com/watch?v=YoXyXTFWbkg Our careers page: https://www.fleetio.com/careers Description 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. More About Our Engineering Team Watch our culture videos: https://fleet.io/culture Engineering culture, interview process and videos: https://www.fleetio.com/careers/engineering Fleetio Go overview video: https://www.fleetio.com/go More about the Fleetio platform: https://www.fleetio.com/features API docs: developer.fleetio.com Test drive Fleetio to get an even better feel for what we're building: https://www.fleetio.com/register This is a remote opportunity and is open to candidates in the United States, Canada, or Mexico. Who you are 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 trad