Engineering Manager, Payments - Fleetio

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!

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.

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.

• 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.
• Ruby on Rails experience is strongly preferred, and React or comparable web application framework experience is helpful.
• Track record of managing and inspiring engineering teams, developing talent, and fostering a collaborative culture.

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 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.
• Recruit and hire strong engineering talent as the team scales.
• Foster a positive, accountable, and high-quality engineering culture.

Your experience

• 2–3+ years of experience leading engineering teams as an Engineering Manager or technical people leader.
• Experience managing web application engineering teams in a SaaS environment.
• Experience working in payments, billing, financial systems, fintech, subscription platforms, or similarly complex/high-stakes domains.
• Experience with payment processing or billing platforms such as Stripe, Recurly, Chargify, or similar.
• Experience with Ruby on Rails strongly preferred; React or comparable web application frameworks also helpful.
• Excellent written and verbal communication skills.