Fleetio

Staff Software Engineer

Fleetio

full-time

Posted on:

Location Type: Remote

Location: California • New York • United States

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Job Level

Lead

About the role

  • 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.
  • Partner with teams across Fleetio to identify where missing context creates the most friction, and build the integrations that close those gaps. This is not engineering-only: Product Managers need AI tools that understand product strategy and customer data; designers need access to design systems and user research; Customer Success needs account history and help center content.
  • 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; we build the tooling and knowledge layer on top) and with Product Managers, Designers, and Engineers across the organization.
  • Produce well-tested, maintainable, and performant code. Thoroughly review your peers' code to ensure quality, maintain consistency, and share knowledge.
  • Contribute enterprise-grade capabilities to Fleetio's existing internal AI tooling ecosystem: identity and auth for protected systems, governed data access, cross-system queries, and quality patterns that help the ecosystem scale.
  • Establish the technical standards for the Leverage team. As the founding engineer, your decisions on architecture, tooling, and code quality will set the bar for everyone who follows.

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
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)
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
integration engineeringAPI developmentauthentication schemesprotocol-based architecturesSDK developmentCLI toolingfull-stack developmentidentity and access managementunit testing frameworksCI/CD pipelines
Soft Skills
excellent communicationcollaborationownershipproblem-solvingdocumentation practices