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
Do you have a passion for sales and a desire to join a fast-growing and profitable software company? Are you an overachiever who wants a high-earning potential that’s based on performance? Are you well-versed in prospecting and closing? If so, you might be our next Mid-Market Account Executive.
In this role, you'll work with a mix of inbound and outbound leads and close new customers using sales tactics (emails, phone calls, web-based demos, etc.)
Who you areYou’re a driven, results-oriented sales professional who thrives in a fast-paced environment and is motivated by uncapped earning potential. You’re excited by the opportunity to work with fascinating customers and prospects across a wide range of industries—because nearly every organization that operates a fleet is a potential Fleetio customer. You’ll be responsible for sourcing and closing new business, influencing and owning the sales process while driving meaningful outcomes and ARR growth. You know how to leverage cross-functional teams to convert high-impact prospects into long-term customers, and you’re eager to join a team of “A” players who are passionate, supportive, and committed to success. Whether you’re working remotely from anywhere in the U.S. or from our HQ in Birmingham, AL, you’ll find a collaborative, customer-centric culture where your contributions matter and your success is celebrated.
Your impact- Know our software inside and out - you’ll be a solution expert for Fleetio and fleet management
- Conduct consultative sales to help Medium and Large organizations understand how Fleetio can help them
- Generate new pipeline through strategic outbound outreach (calls, emails, etc.)
- Perform web-based demos and presentations for prospects around the world
- Proactive and consistent follow-up via phone and email with prospects
- Negotiate pricing & close opportunities
- 3+ years of SaaS sales experience
- Experience owning customer engagements end-to-end, from prospecting and qualification to close
- Experience in pipeline generation as well as inbound pipeline management and managing different types of buyers
- Experience selling to a broad array of decision-makers within an organization
- Strong verbal and written communication skills
- Excellent presentation and negotiation skills
- Ability to remain focused and disciplined with your time
- Driven by results. Outstanding work ethic and hustle
- Ability to travel 20% of the time
- Resourceful and determined, yet not afraid to ask for help
- Excited by technology and its ability to make you more productive
- 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.
Skills Required
- 3+ years of SaaS sales experience
- Own customer engagements end-to-end from prospecting and qualification to close
- Experience generating pipeline through outbound outreach and managing inbound pipeline
- Experience selling to a broad array of decision-makers within an organization
- Strong verbal and written communication skills
- Excellent presentation and negotiation skills, including web-based demos
- Ability to remain focused and disciplined with your time
- Driven by results with an outstanding work ethic and hustle
- Ability to travel 20% of the time
- Proactive and consistent follow-up via phone and email; strong prospecting skills
- Excited by technology and its ability to increase productivity
Fleetio Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Fleetio and has not been reviewed or approved by Fleetio.
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Healthcare Strength — Health coverage includes multiple medical and dental options with full employee-premium coverage, plus vision, HSA/FSA, and employer-paid short-term disability. Core health benefits are consistently presented as comprehensive across official listings.
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Leave & Time Off Breadth — Time off includes PTO that increases with tenure, company holidays, and floating holidays. Paid parental leave is offered for both birthing and non-birthing parents.
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Wellbeing & Lifestyle Benefits — Extras include quarterly wellbeing and business-expense stipends, professional development funds, community service support, and remote-work setup assistance. These perks augment the core package and are emphasized across employer materials.
Fleetio Insights
What We Do
Our software helps organizations around the world track, analyze and improve their fleet operations. We're passionate about making it easy to manage a fleet so our customers can spend more time focusing on their mission.
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