[All remote jobs](https://jobicy.com/jobs.md)[![Fleetio logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2023/07/e571b83c37e0ed5371754d319be16e76.jpeg)](https://jobicy.com/company/fleetio.md)[Fleetio](https://jobicy.com/company/fleetio.md) # Senior Software Engineer, Developer Enablement AI Summary Fleetio is hiring a Senior Software Engineer for its Developer Enablement team to improve the public API, webhooks, Developer Portal, and integration tooling. The role requires strong backend and full-stack experience, particularly Ruby on Rails, React, and TypeScript. The engineer will set API standards, build reliable and well-documented developer experiences, and support customers and partners using Fleetio integrations. This remote role also includes architecture collaboration, code reviews, testing, prototyping, and participation in an on-call rotation. Candidates must be eligible to work remotely from the United States, Canada, or Mexico.[Apply for this job](#job-application)[View company](https://jobicy.com/company/fleetio.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md), [Canada](https://jobicy.com/job-region/canada.md), [Mexico](https://jobicy.com/job-region/mexico.md)SalaryUndisclosedDepartment[Software Engineering](https://jobicy.com/categories/engineering.md)EmploymentFull TimeExperienceSeniorPublished12 Nov 2026Apply before12 Dec 2026Listing views45Application actions3Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. Opportunity details ## About this role. A little about us…[Fleetio](https://jobicy.com/company/fleetio.md) 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](https://rubyonrails.org/foundation)! More about our team and company: * Fleetio overview video: [https://www.youtube.com/watch?v=YoXyXTFWbkg](https://www.youtube.com/watch?v=YoXyXTFWbkg) * Our careers page: [https://www.fleetio.com/careers](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](https://fleet.io/culture) * Engineering culture, interview process and videos:[https://www.fleetio.com/careers/engineering](https://www.fleetio.com/careers/engineering) * Fleetio Go overview video:[https://www.fleetio.com/go](https://www.fleetio.com/go) * More about the Fleetio platform: [https://www.fleetio.com/features](https://www.fleetio.com/features) * API docs: [developer.fleetio.com](https://developer.fleetio.com/) * Test drive Fleetio to get an even better feel for what we’re building: [https://www.fleetio.com/register](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 * Fully stocked kitchen with tons of drinks & snacks (BHM only) * Remote working friendly since 2012 #LI-Remote 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. Show more [Apply now >](https://jobicy.com/jobs/161529-senior-software-engineer-developer-enablement.md) > Annual salary information is not provided for this position. Explore salary ranges for similar roles in our [Salary Directory ›](https://jobicy.com/salaries.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 4/5EasyHard ### Pace & Pressure 4/5RelaxedFast-paced ### Autonomy Level 4/5GuidedFull ownership ### Communication Load 4/5IndependentCollaborative AI insightThis is a senior-level platform engineering role requiring deep API design expertise, production reliability ownership, and cross-functional technical leadership. The scope spans public integrations, developer experience, security-minded API design, and on-call support. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Market rate$155,000US market range (per year)$135k–$180k0$198.00k AI insightThe yearly pay period is inferred from the job context; it was not explicitly stated by the employer. No employer base salary was disclosed. The annual compensation estimate is inferred for a senior remote software engineer focused on Ruby on Rails, public APIs, developer tooling, and platform reliability in the US market. ## Core skills Skills and capabilities most closely associated with this opportunity. [Ruby on Rails](https://jobicy.com/jobs?search_keywords=Ruby%20on%20Rails.md)[React](https://jobicy.com/jobs?search_keywords=React.md)[TypeScript](https://jobicy.com/jobs?search_keywords=TypeScript.md)[REST API design](https://jobicy.com/jobs?search_keywords=REST%20API%20design.md)[OAuth](https://jobicy.com/jobs?search_keywords=OAuth.md)[OpenAPI](https://jobicy.com/jobs?search_keywords=OpenAPI.md)[Webhooks](https://jobicy.com/jobs?search_keywords=Webhooks.md)[Event-driven architecture](https://jobicy.com/jobs?search_keywords=Event-driven%20architecture.md)[API versioning](https://jobicy.com/jobs?search_keywords=API%20versioning.md)[Rate limiting](https://jobicy.com/jobs?search_keywords=Rate%20limiting.md)[Integration testing](https://jobicy.com/jobs?search_keywords=Integration%20testing.md)[Developer experience](https://jobicy.com/jobs?search_keywords=Developer%20experience.md)[Technical documentation](https://jobicy.com/jobs?search_keywords=Technical%20documentation.md)[Code review](https://jobicy.com/jobs?search_keywords=Code%20review.md)[On-call support](https://jobicy.com/jobs?search_keywords=On-call%20support.md) Sample interview questionsHow would you design a public REST API that can evolve without breaking existing customer integrations?I would establish consistent resource conventions, clear versioning rules, stable response contracts, and a documented deprecation policy. I would favor additive changes, use feature flags where appropriate, provide migration guides, and monitor usage before retiring endpoints. What practices would you use to make webhooks reliable for third-party consumers? I would use signed payloads, unique event identifiers, retries with exponential backoff, idempotency guidance, delivery logs, and clear failure visibility. I would also document event schemas and provide a sandbox or replay mechanism so partners can safely test integrations. How have you balanced product delivery speed with API quality and consistency? I use lightweight design reviews, reusable API patterns, contract tests, and clear ownership standards to prevent inconsistent decisions early. This keeps delivery moving while ensuring that public interfaces remain predictable, secure, and maintainable. How would you improve the experience of developers integrating with Fleetio for the first time? I would review the onboarding path end to end, identify points of confusion in authentication, endpoint discovery, and error handling, then improve quick-start guides and practical examples. A sandbox environment, API explorer, OpenAPI specification, and integration templates would reduce time to first successful request. Describe your approach to participating in an on-call rotation for public APIs and integrations. I prioritize observability, actionable alerts, documented runbooks, and blameless incident reviews. During an incident, I communicate impact and progress clearly, mitigate customer disruption quickly, and turn the root cause into durable improvements such as tests, monitoring, or architectural safeguards. Next step ## Apply now. Follow the employer’s application method and review Jobicy’s safety guidance before sharing personal information. 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