4 Fleetio Ceo Jobs Hiring Near You

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

Fleetio is writing a new chapter. We are moving from a well-loved product in a category we helped define to a brand that fleet operators, technicians, and executives recognize at first sight and trust on instinct. We put our name on a NASCAR race. We have a car on track with 23XI Racing. We are rebuilding the company narrative around where fleet operations are actually going - not where it has been.
What we need now is the person who makes it all feel like one thing.
As Senior Director of Brand, you own how Fleetio looks, sounds, and shows up - everywhere. Our visual identity. Our editorial voice. Our social presence and video work. Our earned media. The creative expression of the company story across every surface a customer, a candidate, or an analyst will ever touch. You will lead a talented in-house team and a set of agency partners, and report directly to the CMO on a marketing leadership team being rebuilt for the next stage of growth.
This is a builder's role, not a caretaker's. The narrative foundation is being set now. You get to define the expression of it.
Fleetio has a product customers love and a story the market has not yet fully heard. Closing that gap is the single highest-leverage thing marketing can do for this company right now. This seat is where that work lives.
What You'll Own

• Brand system and creative. Visual identity, creative direction, and design standards across web, campaign, product surfaces, events, and sponsorship - the system that makes Fleetio recognizable in a category where most brands look interchangeable.
• Content and thought leadership. Editorial strategy and the content engine - thought leadership, long-form, owned research, and the always-on content that builds authority with fleet leaders and feeds organic and AI-driven search.
• Social and multimedia. Organic social and video as a real channel, not an afterthought - the presence that keeps Fleetio in the conversation between sales cycles.
• Communications and PR. Earned media strategy in partnership with our PR agency, executive visibility programs, awards, and the messaging discipline that holds across every external moment.
• Brand activation. Turning our 23XI Racing partnership and our field presence into a year-round content and storytelling engine - not a logo on a car.
• Team and partners. Hiring, developing, and leading the brand and content team; owning agency relationships, creative operations, and the intake and prioritization system that lets a small team punch far above its weight.

What Success Looks Like
In your first year:

• The new Fleetio narrative is live and consistent everywhere - from the homepage to the trade show booth to the sales deck - and it looks and sounds unmistakably like us.
• Awareness and share of voice move measurably in our favor in the fleet management category.
• The content engine runs at a cadence demand generation, and sales can actually build on, anchored by at least one owned research franchise, the industry cites.
• The NASCAR partnership produces story, not just impressions - with a content calendar behind every race weekend.
• The brand and content team is stronger, clearer on standards, and doing the best work of their careers.

Who You Are

• 10+ years in brand leadership, including 4+ years leading and developing teams.
• You have taken a B2B brand - ideally SaaS, ideally at meaningful scale - through a narrative or identity evolution, and shipped it into market. Not just designed it. Shipped it.
• You have real taste, editorial and visual, and the judgment to know when good enough ships and when it does not.
• You are comfortable being measured. Awareness, share of voice, engagement, content-influenced pipeline - you can hold a number and defend it in front of a CEO.
• You are a genuine partner to product marketing, demand generation, events, and customer marketing. Brand does not work in a room by itself.
• You have managed agencies well - gotten more out of them than the retainer suggested.
• You like real-world industries. Our buyers are fleet managers, technicians, and operations leaders. They are not marketers, and they can smell marketing from a mile away.

Nice to Have

• Sponsorship, partnership, or experiential activation experience - sports, motorsport, or large-scale events.
• Experience building or running an in-house creative studio.
• Challenger-brand or category-creation experience against a larger, better-funded incumbent.
• Fluency in how content strategy is changing under AI-driven search and answer engines.

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.