About this role.
Fleetio seeks an Engineering Manager to lead its Payments engineering team for a remote role open in the United States, Canada, and Mexico. The manager will own delivery and technical direction for reliable payment, billing, and related financial systems while balancing quality, risk, scalability, and speed. Key responsibilities include coaching engineers, partnering with Product and Engineering leaders on roadmap priorities, communicating tradeoffs, and recruiting talent. The ideal candidate has 2–3+ years of people-leadership experience in SaaS engineering and meaningful exposure to payments, billing, fintech, or subscription platforms. Ruby on Rails is strongly preferred, with React or a comparable web framework as a helpful additional background.
Role DNA
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Job Complexity
4/5Pace & Pressure
4/5Autonomy Level
4/5Communication Load
5/5Salary analysis
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Core skills
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Sample interview questions
I start by making the risk explicit: customer impact, financial exposure, reversibility, and operational burden. I then work with the team to define the smallest safe increment, including testing, monitoring, rollout controls, and clear ownership. This enables progress without treating quality work as optional.
I use regular one-on-ones to understand each engineer’s goals, strengths, and growth areas, then align stretch opportunities with team priorities. I provide timely, specific feedback and establish clear expectations for scope, technical judgment, collaboration, and ownership. I also create mentoring and review practices that help growth happen through everyday work.
I would partner with Product, Finance, Support, and technical leaders to evaluate customer value, compliance or financial risk, revenue impact, urgency, and engineering effort. I would make tradeoffs visible, reserve capacity for reliability work, and use measurable outcomes to revisit priorities. The goal is a roadmap that protects core payment operations while continuing to deliver customer value.
I would first map the workflow, dependencies, data flows, and highest-risk failure paths with the team. We would add targeted observability and characterization tests before changing critical behavior, then prioritize remediation based on impact and likelihood. I would communicate the risk clearly and stage improvements behind controlled releases where possible.
I frame the discussion around outcomes, risks, options, costs, and the decision needed rather than implementation detail alone. For example, I explain how a reliability investment reduces payment failures or support load, and what feature timing it affects. I ensure stakeholders understand uncertainty and agree on the rationale, owner, and next steps.
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 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.
- 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.
- Track record of leading teams through delivery of roadmap initiatives and measurable outcomes.
- Strong judgment around technical quality, risk, system complexity, and customer/business impact.
- Strong passion and track record for attracting, developing, and retaining engineering talent.
- Excellent written and verbal communication skills.
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.
Annual salary information is not provided for this position. Explore salary ranges for similar roles in our Salary Directory ›
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