Senior Forward Deployed Engineer

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!

Description

As a Forward Deployed Engineer you'll help us land key accounts by working closely with Sales and Customer Success to translate urgent, high-stakes needs into high-quality product work — shipped as durable Fleetio product that can be supported like the rest of the platform.

If you're excited by high-impact, high-visibility engineering work this could be a great fit. This team turns key account commitments into real, shippable products so Fleetio can win strategic deals and support those customers long-term. The engineers in this role will directly influence outcomes for key accounts and help close some of the largest deals at Fleetio.

More About Our Team and Company

This is a remote opportunity and is open to candidates in the United States, Canada, or Mexico.

Who you are

You’re a product-minded, delivery-oriented engineer who can operate in high-trust environments. You can take ambiguous problems and turn them into clear plans and high-quality shipped software. You’re comfortable collaborating directly with Sales and Customer Success partners to translate customer and deal context into product capabilities. This work includes quick discovery, rapid scoping, and clear communication about tradeoffs and timelines.

You’re independently successful: you take ownership from start to finish, stay tenacious through ambiguity, and consistently find a way to deliver.

You care about maintainability and operational excellence.

Your impact

• Ship high-leverage product improvements that unblock strategic deals and expand what Fleetio can confidently commit to for key accounts.
• Partner closely with Sales and Customer Success to understand constraints, timelines, and customer workflows; then, turn those needs into clear requirements and implementation plans.
• Drive work end-to-end: clarify the problem, align stakeholders, deliver iteratively, and ensure what you ship is production-ready and supportable.
• Partner with Product, Design, and Engineering peers to make pragmatic scope decisions and deliver iteratively.
• Build solutions that meet Fleetio's product and engineering standards: testing, observability, maintainability, documented
• Communicate proactively and clearly about tradeoffs, risks, and timelines.

Your experience

• 5+ years of experience with Ruby on Rails
• 2+ years with React
• Strong experience building and shipping production web applications with a focus on quality and maintainability.
• Experience collaborating with non-technical stakeholders, translating needs into technical plans, and managing expectations.
• Ability to decompose complex requests into milestones and deliver incrementally.
• Strong written communication and comfort working in a remote, async-friendly environment.

Nice to have

• Experience working on a large-scale Ruby on Rails application.
• Experience working on customer-facing platform/product capabilities that support enterprise accounts.
• Experience partnering with go-to-market teams (Sales, Customer Success) on delivery of time-sensitive commitments.

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

This application is not intended to and does not create a contract or offer of employment. Employment with Fleetio is at will.