Staff Software Engineer, Leverage

Fleetio is a modern software platform that helps organizations manage their fleet operations. They are seeking a Staff Software Engineer to build the knowledge infrastructure that connects internal data to AI tools, enhancing productivity across the company.

Responsibilities:

• Design and build the knowledge infrastructure that gives AI tools at Fleetio structured access to company context
• 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
• Partner with teams across Fleetio to identify where missing context creates the most friction, and build the integrations that close those gaps
• 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
• Champion AI-first documentation practices: structure internal docs so AI tools can consume them effectively
• Collaborate closely with the Platform/SRE team and with Product Managers, Designers, and Engineers across the organization
• Produce well-tested, maintainable, and performant code
• Contribute enterprise-grade capabilities to Fleetio's existing internal AI tooling ecosystem
• Establish the technical standards for the Leverage team

Requirements:

• 5+ years of professional experience building production software
• Strong integration engineering skills: comfort working across dozens of APIs, authentication schemes (OAuth, API keys, SAML, service accounts), data formats, and rate limits
• Experience with protocol-based architectures (MCP, LSP, or similar), SDKs, CLI tooling, or developer platform design. You understand how to expose structured data to client tools in a way that scales
• Full-stack capabilities: you will build backend services, CLI tools, and internal UIs
• Experience with identity and access management (Okta, SSO, or similar) and understanding of how to pass user identity through to downstream systems
• Experience building and consuming APIs and working with external integrations
• Solid experience solving challenging architecture problems with good design
• Experience with unit testing frameworks and CI/CD pipelines
• Excellent communication skills, particularly written
• Be sure to mention 'coffee' in your application so we know you actually read this
• Comfort working in a Rails shop
• Experience building internal tools, developer platforms, or developer experience tooling
• Track record integrating across multiple SaaS APIs, with firsthand knowledge of inconsistent auth, pagination, and rate limiting
• Experience on a small team (2-5 people) where you owned significant portions of the product
• Hands-on experience with AI coding tools (Copilot, Codex) and an understanding of what makes them effective vs. ineffective
• Experience at a company that invests seriously in internal tooling (Stripe, Shopify, Block, etc.)
• Familiarity with workflow automation platforms (n8n, Zapier, Workato, or similar)
• Experience contributing to or maintaining shared developer tooling ecosystems (internal package registries, shared libraries, plugin systems)
• Familiarity with AI agent skill/tool architectures (Codex skills, MCP tools, function calling patterns)
• Experience with Snowflake, PostgreSQL, or similar data platforms
• You know a thing or two about the fleet management industry