Fleetio, a leading fleet maintenance and optimization platform, appointed Leslie Henthorn to the company’s executive leadership team as its first Chief Marketing Officer, marking a strategic inflection point as the company scales its enterprise presence and deepens its impact in heavy equipment and multi-location fleet management.
Henthorn brings more than two decades of high-tech marketing leadership to Fleetio, with a proven track record of building powerful brands and revenue engines at industry-defining companies like Ironclad and Twilio. Her arrival marks a significant milestone as Fleetio continues to transform fleet operations with smarter, more connected tools that empower fleet professionals on the front lines.
The appointment aligns with Fleetio’s sustained, nationally recognized growth, ranking as the 295th fastest-growing company in North America on the 2025 Deloitte Technology Fast 500™ and placing 28th on The Software Report’s Top 50 Software Companies of 2025. These recognitions reflect the company’s rapid momentum, driven by delivering practical and innovative solutions that lead to better decisions, stronger performance, and measurable results in the field.
With the acquisition of Auto Integrate earlier this year, Fleetio now operates one of the industry’s richest connected maintenance datasets—powering more than 9 million vehicles annually and supporting over 8,000 customers worldwide. This foundation enables Fleetio’s evolution from a system of record into an intelligent fleet operations platform that surfaces the right insights, recommends the best next action, and automates routine decisions. By learning from millions of repair and maintenance patterns across its network, Fleetio helps fleet teams save time, reduce downtime, and proactively address issues before they impact the business.
Recent innovations, including early access features such as Smart Uploads and intelligent repair order assessments, streamline data entry and expedite critical workflows. Fleetio remains focused on eliminating busywork and empowering customers to make faster, more confident decisions—while always staying in control. Guiding these efforts into the next era of growth, Henthorn brings a builder’s mindset and a human-centered leadership style that prioritizes empathy, resilience, and alignment to drive transformation. With sharp focus and strategic clarity, her leadership will strengthen Fleetio’s position at the forefront of innovation in fleet technology.
“Leslie is the ideal leader to take our marketing organization to the next level,” said Jon Meachin, Chief Executive Officer of Fleetio. “Her ability to scale world-class teams and deliver real results speaks for itself. As Fleetio steps into its next chapter of scaling our impact and shaping the future of fleet, we’re excited to have Leslie accelerating that momentum.”
Prior to joining Fleetio, Henthorn more than doubled Ironclad’s inbound new business pipeline, strategically scaled the marketing team to focus on upmarket, and positioned the company as the leading AI-driven contract lifecycle management platform. At Twilio, she aligned global marketing initiatives, championed community-driven engagement, transformed the company’s annual conference into a premier industry event with 40,000+ attendees, and helped drive the evolution of the go-to-market strategy toward enterprise expansion.
“Fleetio has a powerful product, a passionate customer community, and a team deeply committed to growth,” said Henthorn. “What drew me here was the rare combination of product strength, culture, customer obsession, and market momentum. Marketing is about creating clarity, connection, and trust, and I’m honored to help bring in a new energy and experience to ensure the market understands Fleetio’s vision to innovate and scale.”
