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: youtube. com/watch? v=YoXyXTFWbkg - Our careers page: 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: io/culture - Engineering culture, interview process and videos: fleetio. com/careers/engineering - Fleetio Go overview video: fleetio. com/go - More about the Fleetio platform: fleetio.

com/features - API docs: developer. fleetio. com - Test drive Fleetio to get an even better feel for what we're building: 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 tradeoffs, and help teams deliver high-quality outcomes without losing sight of customer and business impact. Your impact - Lead the Payments engineering team in delivering reliable, high-quality web application experiences. - Partner with Product and Engineering leadership to prioritize roadmap work tied to payments, billing, and related customer/business outcomes. - Guide the team through complex technical tradeoffs involving reliability, maintainability, risk, and delivery speed. - Develop and mentor engineers through regular 1:1s, feedback, coaching, and performance conversations. - Work with senior technical leaders to ensure the team produces well-tested, maintainable, and performant code. - Help the team navigate existing system complexity and identify opportunities to improve reliability and scalability. - Communicate progress, risks, tradeoffs, and decisions clearly to relevant stakeholders. - Recruit and hire strong engineering talent as the team scales.