Senior Software Engineer, Developer Enablement - Fleetio

About Fleetio

Fleetio is a modern software platform that helps thousands of organizations worldwide manage their fleet operations. Transportation technology is a rapidly growing market, and Fleetio is leading the charge with raving fans and new customers signing up every day. We raised $450M in our Series D funding round in March 2025 and are a proud founding member of the Rails Foundation.

About the Role

Fleetio is seeking an experienced Senior Software Engineer to join our Developer Enablement team. The Developer Enablement team owns Fleetio’s public API, webhooks, Developer Portal, and the tools that enable customers and partners to build on Fleetio. You will play a key role in making our API reliable, well-documented, and easy to build on, ensuring customers and integration partners can connect, extend, and automate Fleetio independently.

This is a fully remote opportunity open to candidates in the United States, Canada, or Mexico.

Who You Are

• Strong proficiency in backend development and API design with a proven track record of delivering high-quality software solutions
• Passionate about building APIs and developer tools with clean, consistent design and scalable architecture
• Effective communicator who excels in an asynchronous work environment
• Product-minded and collaborative, eager to share best practices and learn from teammates

Your Impact

• Collaborate closely with Product Managers, Designers, and other Engineers to consistently deliver high-quality software
• Plan, design, and implement improvements to Fleetio’s public API, webhooks, and Developer Portal
• Engage in collaborative design and system architecture for new features
• Deliver well-tested, maintainable, and performant code
• Research and implement prototypes and spikes to validate technical feasibility
• Provide thorough peer code reviews to ensure quality, consistency, and knowledge sharing
• Set and uphold API standards, guiding engineers across the organization on public API changes
• Improve developer experience with clear documentation, code examples, sandbox environments, and tooling
• Prepare APIs for safe AI-driven use by assistants and autonomous agents
• Support customers and integration partners, participating in the on-call rotation to maintain high platform reliability

Your Experience

• 5+ years of experience with Ruby on Rails
• 2+ years of experience with ReactJS and TypeScript
• Broad experience building full-stack web-based applications
• Proven experience designing, building, and maintaining public REST APIs (including OAuth, versioning, rate limiting, and OpenAPI)
• Experience with webhooks, event-driven architectures, or third-party integrations
• Experience collaborating with product teams to architect scalable solutions
• Strong attention to detail regarding API consistency and documentation
• Experience writing comprehensive unit, integration, and API tests
• Experience with developer portals, SDKs, or AI tooling is a plus
• Note: Be sure to mention “coffee” in your application so we know you reviewed the details carefully.

Benefits

• Multiple health and dental coverage options (100% coverage for employee, 50% for family)
• Vision insurance
• Incentive stock options
• 401(k) match up to 4%
• 4 weeks PTO (increases at year two)
• 12 company holidays plus 2 floating holidays
• Parental leave: 16 weeks paid for birthing parents, 4 weeks paid for non-birthing parents
• FSA & HSA options
• Short-term (100% paid) and long-term disability
• Professional development and community service funds
• Quarterly wellbeing fund ($150) and quarterly business expense stipend ($125)
• Mac laptop plus new hire equipment stipend