Staff Software Engineer, Leverage
Fleetio · United States
- Hybrid
- Full-time
- $150,000 / year
- United States
Job highlights
- Founding engineer for new Leverage team.
- Build knowledge infrastructure for AI tools.
- Integrate internal data and SaaS APIs.
- Focus on developer productivity and adoption.
- Remote role in US, Canada, or Mexico.
About the role
About Fleetio
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!
Fleetio overview video: https://www.youtube.com/watch?v=YoXyXTFWbkg
Our careers page: https://www.fleetio.com/careers
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.
Who You Are
- A staff-level, systems-minded engineer who gets energy from building tools that make other people more effective.
- Deep experience integrating across SaaS APIs and comfortable navigating inconsistent auth models, pagination, rate limits, and data formats.
- Prefers building one system that enables 50 integrations over building 50 one-off integrations.
- Comfortable operating in ambiguous, cross-functional spaces; talks to users before writing code.
- Cares about adoption and understands that internal tools fail with bad UX or no adoption strategy.
- Brings strong opinions about developer productivity, loosely held, and communicates clearly with engineers and non-technical stakeholders.
- Product-minded and team-oriented, willing to hear others' perspectives and educate on best practices.
- Excellent communication skills, particularly written.
Your Impact
- Design and build the knowledge infrastructure for AI tools at Fleetio to access company context.
- Build integrations connecting internal knowledge sources into a consistent, secure context layer.
- Design the system for extensibility by other teams.
- Partner with teams across Fleetio to identify friction points and build integrations.
- Take ownership of CI/CD intelligence, ensuring fast, reliable, and trustworthy pipelines.
- Define and own the measurement framework for AI adoption and internal tool impact.
- Champion AI-first documentation practices for effective AI tool consumption.
- Collaborate closely with Platform/SRE, Product Managers, Designers, and Engineers.
- Produce well-tested, maintainable, and performant code; thoroughly review peer code.
- Contribute enterprise-grade capabilities to Fleetio's internal AI tooling ecosystem.
- Establish technical standards for the Leverage team, setting the bar for architecture, tooling, and code quality.
Your Experience
- 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.
- Full-stack capabilities: building backend services, CLI tools, and internal UIs.
- Experience with identity and access management (Okta, SSO, or similar) and passing user identity through to downstream systems.
- 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.
Considered a Plus
- 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 understanding of their effectiveness.
- 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.
- Familiarity with AI agent skill/tool architectures (Codex skills, MCP tools, function calling patterns).
- Experience with Snowflake, PostgreSQL, or similar data platforms.
- Knowledge of the fleet management industry.
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).
- Remote working friendly since 2012.
Equal Opportunity
Fleetio provides equal employment opportunities to all employees and applicants and prohibits discrimination and harassment. We celebrate diversity and are committed to creating an inclusive environment for all. All employment is decided on the basis of qualifications, merit and business need.
This application is not intended to and does not create a contract or offer of employment. Employment with Fleetio is at will.
If you have a disability or a special need that requires an accommodation to fill out the online application, please let us know by calling (205) 718-7500.
Key skills/competency
- Staff Software Engineer
- Integration Engineering
- SaaS APIs
- Authentication
- Developer Productivity
- AI Tools
- Internal Tools
- System Design
- Full-Stack Development
- CI/CD
Skills & topics
- Staff Software Engineer
- Software Engineer
- Integration Engineering
- SaaS APIs
- AI Tools
- Developer Productivity
- Internal Tools
- Systems Engineering
- Full-Stack Development
- Remote
- Rails
- Identity and Access Management
- API Design
- Developer Platforms
How to get hired
- Tailor your resume: Highlight your 5+ years of production software experience, integration skills, and work with APIs, SaaS, and identity management.
- Showcase your impact: Emphasize your ability to build scalable systems, improve developer productivity, and drive adoption of internal tools.
- Mention "coffee": Include the word "coffee" in your application to demonstrate you've read the job description carefully.
- Demonstrate product mindset: Discuss your experience working cross-functionally, talking to users, and prioritizing UX and adoption strategies in your cover letter or interviews.
- Prepare for technical and behavioral questions: Be ready to discuss your system design, API integration experience, and how you approach ambiguous problems and collaboration.
Technical preparation
Behavioral questions
Frequently asked questions
- What is the primary goal of the Leverage team at Fleetio?
- The primary goal of the Leverage team at Fleetio is to enhance company-wide productivity by building the knowledge infrastructure that connects internal data to AI tools used by employees. This role is focused on "productivity engineering" or "internal tools" with a broader scope to serve the entire company.
- What kind of technical challenges will a Staff Software Engineer on the Leverage team face at Fleetio?
- A Staff Software Engineer on the Leverage team will tackle challenges such as integrating across numerous SaaS APIs with inconsistent authentication, pagination, and rate limits. They will also focus on building enterprise capabilities like identity and auth, structured data access, governance, and designing scalable systems for internal AI tools.
- Is this a remote position, and where can candidates be located?
- Yes, this is a remote opportunity open to candidates located in the United States, Canada, or Mexico.
- What experience is essential for the Staff Software Engineer role at Fleetio?
- Essential experience includes 5+ years of professional production software development, strong integration engineering skills with various APIs and authentication schemes, full-stack capabilities, and experience with identity and access management. Excellent written communication skills are also crucial.
- What does Fleetio offer in terms of benefits for employees?
- Fleetio offers comprehensive benefits including multiple health/dental coverage options, vision insurance, incentive stock options, 401(k) match, generous PTO, 12+ holidays, paid parental leave, FSA/HSA options, disability insurance, and stipends for professional development, wellbeing, and business expenses.
- What is the significance of mentioning "coffee" in the application for this Staff Software Engineer role?
- Mentioning "coffee" in your application is a specific instruction from Fleetio to ensure candidates have read the job description thoroughly. It's a small detail that shows attention to detail and genuine interest in the role.
- How does Fleetio support diversity and inclusion?
- Fleetio is committed to providing equal employment opportunities and prohibits discrimination and harassment. They celebrate diversity and strive to create an inclusive environment where all employment decisions are based on qualifications, merit, and business need.
- What is the company's funding status and growth trajectory?
- Fleetio raised $450M in their Series D funding round in March 2025 and is described as being on an exciting trajectory, indicating significant growth and investment.
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