Account Executive, Mid-Market [Remote]

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.)

A little about us…Fleetio is a modern software platform that helps thousands of organizations around the world 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 Series D in June 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:
• Our careers page:

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 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

Your experience

• 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

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 View phone number on swooped.co.