Engineering Manager, Payments

Fleetio

9d•Remote

About The Position

Fleetio is looking for an Engineering Manager to lead its Payments engineering team. This role involves guiding a team responsible for building and maintaining complex, high-stakes payment systems that support Fleetio’s customers and business operations. The manager will 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. Additionally, the role includes coaching and developing engineers, supporting technical decision-making, and helping the team balance delivery speed with engineering quality. This is a remote opportunity open to candidates in the United States, Canada, or Mexico.

Requirements

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.

Nice To Haves

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.

Responsibilities

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.

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