Chief of Staff, Head of Product Strategy & GTM

Remote - USA 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=IlvIbwZT3oU
Our careers page: https://www.fleetio.com/careers

About Fleetio & Auto Integrate Fleetio is a modern fleet operations platform used by thousands of organizations worldwide to manage vehicles, equipment, and drivers. Auto Integrate, acquired by Fleetio in 2025, is a leading global maintenance authorization network that supports fleets that choose to outsource their service, maintenance, and repair needs. The business is managed by a small, global team within Fleetio, combining the resources of a scaled SaaS company with the agility of a niche market leader. Who you are We are hiring a senior leader to serve as the chief of staff to the business unit president and to own product strategy and go-to-market for Fleetio’s Auto Integrate proprietary maintenance authorization network. This role reports to the president of the business unit and will operate in a small, entrepreneurial environment while being responsible for enhancing and appropriately pricing a service that supports many of the US’s largest fleets. You will support end-to-end product strategy, monetization, and go-to-market for all Auto Integrate products. You will partner closely with Sales, Product, Engineering, Finance, and Operations leadership to set the multiyear vision, define and execute pricing and packaging changes, and drive adoption of all new product functionality in the market. You must be located in Eastern Standard Time. Key objectives:

Define and evangelize the 3-year growth strategy for Auto Integrate, including segment, use case, and geographic expansion.
Lead pricing, packaging, and monetization strategy to appropriately balance customer value delivery with revenue maximization, while remaining simple and scalable.
Support product marketing, positioning, and go-to-market motions to drive new logo acquisition, product activation, and expansion/upsell.

Your Impact Chief of staff & product strategy

Prepare materials and recommendations for executive team and board-level discussions on business unit strategy, including product, pricing, and market expansion.
Define and maintain executive dashboards, KPI frameworks, and leading indicators to monitor product performance, pricing impact, and GTM effectiveness.
Support setting the product vision and multiyear roadmap for Auto Integrate, working with executive leadership and Product to align on strategic bets and sequencing.
Define target customer segments, use cases, and vertical focus; clarify where we win versus competitors and adjacent solutions in fleet, logistics, and broader B2B SaaS.
In partnership with the product team. ensure market...