Staff Software Engineer
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Job Description
Staff Software Engineer at Fleetio focused on enhancing productivity by building knowledge infrastructure for AI tools. Collaborate across teams and drive company-wide technical standards.
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.
- 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)
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