Account Executive, Enterprise

Job Description:

Description

Do you have a passion for technology sales and want to join a fast-growing and profitable software company? Are you an overachiever who wants a high-earning potential based on performance? Are you well-versed in prospecting and closing deals with large organizations? If so, you might be our next Enterprise Account Executive.

In this role, you'll create your business development plan and work to close new customers using strategic sales tactics (emails, phone calls, web-based demos, face-to-face meetings, 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 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=IlvIbwZT3oU
• Our careers page: https://www.fleetio.com/careers

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 within the Enterprise segment, 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

• Work with Fleetio’s largest Prospects and some of the world’s most well-known brands — all with over 1,000 vehicles in their fleet
• Develop a strategic territory business plan to source and close net new logos within a given territory
• Navigate complex organizational structures to identify and drive the sale process with multi-layer stakeholders in enterprise organizations: executive sponsors, champions, and buyers
• Research and understand the business objectives of your customers and perform a value-driven sales cycle
• Collaborate with internal partners to move deals forward and ensure customer success
• Consistently deliver ARR revenue targets and drive success through a metric-based approach
• Develop and execute sales strategies and tactics to generate pipeline, drive sales opportunities, and deliver repeatable and predictable bookings
• Provide timely and insightful input back to other corporate functions, including Product Management, Customer Success and Account Management
• Create ROI and business justification reports based on a data-driven approach
• Run tight POCs based on business success criteria

Your experience

• 5+ years of experience successfully closing Enterprise deals of $150k+
• 5+ years of experience carrying a $1mil + quota
• High proficiency in selling software as a service (SaaS) and cloud-based solutions to enterprise customers
• Proven experience building relationships and selling face-to-face to C-level executives
• Experience supporting Trials or Proof of Concepts
• Proven track record of success in building a direct customer strategy and creating relationships across customer departments
• Have clear examples of closing complex deals and selling into complex organizations
• Ability to learn, pitch, and demonstrate a technical product and have the ability to adapt in a fast-growing and changing environment
• Effectively use a repeatable method for uncovering greenfield opportunities and building out a new territory
• Previous experience working with cross-functional business partners, including Solutions Engineers, Sales Development Reps, Project Managers, Executives, Customer Experience leaders, etc.

Considered a plus

• Domain expertise in fleet management
• Experience selling in transportation, logistics, or construction

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