Fleetio seeks an Engineering Manager to lead the Payments engineering team, partnering with Product and Engineering to deliver reliable, well-tested payment and billing systems. The role includes technical leadership, coaching and developing engineers, guiding tradeoffs around reliability and maintainability, driving roadmap outcomes, and recruiting talent. Candidates should have 2–3+ years leading engineering teams in SaaS and experience in payments, billing, subscription platforms or fintech; Ruby on Rails experience is strongly preferred and experience with Stripe, Recurly, or Chargify is desirable.

Lead Growth 1 and Growth 2 engineering squads (initially ~7 direct reports) to run structured experimentation programs and deliver measurable product and business outcomes. Requires 2+ years as an engineering manager or technical people leader, deep experience with experimentation and analytics (e.g., Snowflake, Segment, Growthbooks), and familiarity with SaaS web application stacks (Ruby on Rails and React preferred). Role partners closely with Product, Design, and Data to prioritize and translate experiment learnings into engineering work.

Fleetio is hiring a Director of Engineering to lead the Leverage Pod (Foundations Engineering, Builder Experience, Solutions Engineering). The role owns strategy, roadmap, budget, and outcomes to increase the speed and quality of Product & Engineering, manages agency partners and SOWs, drives adoption of shared frameworks and developer tooling (including AI-assisted/agentic development), and hires and develops managers and senior ICs. Requires 3+ years as a Director or Senior Engineering Manager and experience leading platform/foundations or developer-productivity teams; Ruby on Rails and React experience is listed as a plus.