About this role.
Fleetio is seeking a full-time Mid-Market Account Executive to sell its fleet-management SaaS platform to medium and large organizations. The role owns the end-to-end sales process, combining inbound lead management with strategic outbound prospecting, web demonstrations, follow-up, pricing negotiation, and closing. Candidates need at least three years of SaaS sales experience and demonstrated ability to manage varied stakeholders and generate pipeline. This is a fast-paced, results-oriented role with uncapped earning potential and up to 20% travel. The position is remote for candidates anywhere in the United States, with an option to work from Fleetio’s Birmingham, Alabama headquarters.
Role DNA
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Job Complexity
4/5Pace & Pressure
5/5Autonomy Level
4/5Communication Load
5/5Salary analysis
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Core skills
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Cover letter sample
Dear Hiring Team,
I am excited to apply for the Mid-Market Account Executive role at Fleetio. With SaaS sales experience spanning prospecting, discovery, tailored demonstrations, negotiation, and closing, I can build pipeline while guiding complex stakeholders toward clear business outcomes.
I would bring a disciplined, consultative approach to selling Fleetio’s fleet-management platform and a strong focus on customer value, ARR growth, and consistent follow-through.
I am especially drawn to Fleetio’s fast-growing, customer-centric culture and would welcome the opportunity to contribute to the team’s continued success.
Sincerely,
Your Name
Sample interview questions
I start by defining the ideal customer profile and prioritizing accounts based on fleet size, operational complexity, likely pain points, and buying signals. I use a multi-channel cadence of calls, personalized emails, and relevant content, then track conversion metrics to refine messaging and focus on the highest-yield segments.
I use discovery to understand the prospect’s current workflows, operational costs, compliance concerns, stakeholders, and desired outcomes. I then tailor the demo around the most relevant use cases, quantify the business impact where possible, and confirm next steps with clear mutual commitments.
I map the buying committee early and identify the economic buyer, champion, technical evaluators, and potential blockers. I adapt the value message for each stakeholder, maintain a mutual action plan, and use regular communication to keep the process aligned and moving forward.
I treat objections as opportunities to clarify needs and risk. I acknowledge the concern, ask focused questions to understand its source, provide evidence or a relevant customer example, and confirm whether the response resolves the issue before moving to the next step.
I manage my time using a structured weekly plan that protects high-value selling activities such as prospecting, follow-up, discovery, and proposal advancement. I review pipeline health and activity metrics regularly, prioritize opportunities by fit and stage, and adjust quickly when conversion data indicates a bottleneck.
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 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 (205) 718-7500.
Annual salary information is not provided for this position. Explore salary ranges for similar roles in our Salary Directory ›
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