Senior Software Engineer, Developer Enablement at Fleetio

Ruby on Rails; United States; Remote; USD 140,000 - 180,000; Full time

Benefits offered by this job

Health and dental coverage

Vision insurance

Stock options

401(k) match

PTO 4 weeks

Holidays + floating

Parental leave

Wellbeing fund

Tech stipend and equipment

Job summary

Fleetio is seeking an experienced Senior Software Engineer to join our Developer Enablement team. You will own and evolve Fleetio’s public API, webhooks, and Developer Portal to empower customers and partners to connect, extend, and automate Fleetio’s platform.

You will collaborate with Product Managers, Designers, and Engineers to deliver high-quality software with robust API design, clear documentation, and developer-focused tooling.

Qualifications

• 5+ years experience with Ruby on Rails.
• 2+ years experience with ReactJS, TypeScript.
• Experience designing, building, and maintaining public REST APIs with authentication (OAuth), versioning and rate limiting.
• Experience with webhooks, event-driven systems, or third-party integrations.
• Collaborates with product teams to architect solutions and maintain API quality.
• Strong attention to detail in API design, consistency, and documentation.
• Excellent written and verbal communication; comfortable in asynchronous environments.

Responsibilities

• Deliver well-tested, maintainable, and performant code.
• Design and implement improvements to Fleetio’s public API, webhooks, and Developer Portal.
• Architect features with engineering peers; drive API standards across teams.
• Document APIs with OpenAPI specs and examples; create developer-friendly tooling.
• Contribute to prototypes and spikes to validate feasibility.
• Participate in on-call rotation to ensure reliability.

Skills

Ruby on Rails

ReactJS

TypeScript

REST APIs

OAuth

OpenAPI

Webhooks

API design

Unit tests

Documentation

Job description

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
Description
Fleetio is seeking an experienced Senior Software Engineer to join our Developer Enablement team. The Developer Enablement team owns Fleetio’s public API, webhooks, Developer Portal, and the tools that let customers and partners build on Fleetio. You will be a key player in making our API reliable, well-documented, and easy to build on, so that customers and integration partners can connect, extend, and automate Fleetio on their own.

If you are passionate about leveraging technology to drive meaningful impact, excel in problem-solving, and possess a keen eye for developer experience, we encourage you to apply and join us in shaping the future of fleet management software.

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
The ideal candidate for this role will demonstrate a strong proficiency in backend development and API design, with a proven track record of delivering high-quality software solutions. You are passionate about building APIs and developer tools with clean, consistent design and scalable architecture. You should be an effective communicator and be comfortable working in an asynchronous environment with your team. You are product-minded and team-oriented, willing to hear others' opinions and educate on best practices.

Your Impact
You will collaborate closely with Product Managers, Designers, and other Engineers to consistently deliver high-quality software.
You will take part in planning, designing, and implementing improvements to Fleetio’s public API, webhooks, and Developer Portal.
You will engage in collaborative design and architecture of features.
You will deliver well-tested, maintainable, and performant code.
You will research and implement prototypes and spikes as necessary to validate assumptions and technical feasibility.
You will possess a strong voice in development and planning processes.
You will thoroughly review your peers’ code to ensure quality and consistency and to share knowledge.
You will set and uphold API standards, and guide engineers across Fleetio as they design and review changes to our public API.
You will improve the experience of developers who build on Fleetio through clear documentation, examples, sandbox environments, and tooling.
You will help prepare our API for AI-driven use, so that AI assistants and agents can work with Fleetio data safely.
You will help customers and integration partners succeed with our API, and take part in the team’s on-call rotation to keep our API, webhooks, and integrations reliable.

Your Experience
5+ years experience with Ruby on Rails
2+ years experience with ReactJS, Typescript
Varied experience building full-stack web-based systems and features
Experience designing, building, and maintaining public REST APIs, including authentication (such as OAuth), versioning, rate limiting, and documentation (such as OpenAPI)
Experience with webhooks, event-driven systems, or third-party integrations
Previous experience working closely with a product team to architect solutions
Strong attention to detail in API design, consistency, and documentation
Excellent written and verbal communication skills
Experienced writing unit, integration, and API tests
Experience with developer portals, SDKs, or AI tooling is a plus
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