Staff Software Engineer, Leverage

About the role

Fleetio is seeking a Staff Software Engineer to be the founding engineer on our new Leverage team. The Leverage team's mandate is to make every person at Fleetio more productive by building the knowledge infrastructure that connects our internal data to the AI tools employees already use every day. At other companies, this work falls under "productivity engineering" or "internal tools." We call it Leverage because the scope is broader: serve the entire company, not just engineering. This is not a blank slate. Fleetio engineers are already using AI tools daily, and an organic ecosystem of shared skills and integrations has emerged across the engineering org. You will build on that momentum, not start from zero. Your job is to add the enterprise capabilities this ecosystem needs to scale: identity and auth, structured access to internal data, governance, and quality standards. You will design and build the context layer that connects Fleetio's distributed knowledge to the AI tools our team already uses. You will work directly with the Leverage team lead, and together you will define the technical direction for everything this team builds. This is a remote opportunity open to candidates in the United States, Canada, or Mexico. More About Our Team and Company 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.

Responsibilities

• Design and build the knowledge infrastructure that gives AI tools at Fleetio structured access to company context. The form this takes (an API layer, a CLI, an SDK, agent configuration, protocol servers, or something new) is a decision you will help make.
• Build integrations that connect Fleetio's internal knowledge sources (project management, documentation, code, data warehouses, communication tools) into a consistent, secure context layer with identity passthrough.
• Design the system so other teams can extend it. Whether that means spoke templates, plugin architectures, or shared configuration patterns, the goal is to scale beyond what a small team can maintain directly.
• Take ownership of CI/CD intelligence, making pipelines fast, reliable, and trustworthy as AI-accelerated development increases code velocity.
• Define and own the measurement framework for AI adoption and internal tool impact across the company. Track what works, surface what doesn't.
• Champion AI-first documentation practices: structure internal docs so AI tools can consume them effectively (coding examples, machine-parseable formats, clear interface descriptions).
• Collaborate closely with the Platform/SRE team (they own infrastructure

Requirements

• You are product-minded and team-oriented, willing to hear others' perspectives and educate on best practices. Excellent communication skills, particularly written, are essential.

Benefits

Additional Information

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

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