SMB Account Executive at Fleetio - Remote USA — Columbus
Traveler-Friendly Insight
Fleetio has been remote-friendly since 2012, making this a well-established remote culture rather than a pandemic-era afterthought. The SMB Account Executive role is open to anyone based anywhere in the U.S., which means full domestic location flexibility — you can work from a beach town in Florida, a mountain cabin in Colorado, or a co-working space in Austin.
However, there are meaningful timezone and schedule constraints to be aware of. Sales roles require synchronous availability: you'll be making calls, running live demos, and following up in real time with U.S.-based SMB prospects. Expect to work standard U.S. business hours (likely Central or Eastern), which limits flexibility for overseas travel. This is not an async-friendly role — reliable internet and a professional call environment are essential daily.
- Visa consideration: This role requires U.S. work authorization. Digital nomad visas in other countries won't help here unless you maintain a U.S. base for tax/payroll purposes.
- Perks for nomads: The $125/quarter business expense stipend and new hire equipment stipend help with remote setup costs. The $150/quarter wellbeing fund could offset co-working memberships.
- Domestic travel flexibility: You can relocate freely within the U.S. — cities like Medellín and Lisbon are off the table, but low-cost U.S. hubs like Tucson, AZ or Chattanooga, TN let you stretch your commission earnings further.
Bottom line: great for U.S.-based remote workers who want flexibility of location within the country, but not suited for international nomads.
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 high-earning potential based on performance? Are you well-versed in prospecting and closing? If so, you might be our next SMB Account Executive selling to small & medium businesses.
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 are
You'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 small and medium 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
Your Experience
- 2 years SaaS sales experience (not necessarily in a closing role)
- 1 year of closing experience preferred
- Consistent employment with no large gaps
- Can-do attitude focused on ideas and ways to make it work, not reasons it will not
- 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
- Resourceful and determined, yet not afraid to ask for help
- Excited by technology and its ability to make you more productive
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 (Birmingham, AL office 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.
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.
Frequently Asked Questions
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