About this role.
Fleetio is seeking a full-time SMB Account Executive to sell fleet-management SaaS to small and medium-sized businesses. The role owns customer engagement from prospecting and qualification through web demos, pricing negotiation, and closing. It combines inbound lead management with strategic outbound pipeline generation and requires strong presentation, communication, and sales discipline. Candidates need at least two years of SaaS sales experience, while prior closing experience is preferred. The position is remote anywhere in the United States or may be based at the Birmingham, Alabama headquarters.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
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 SMB Account Executive role at Fleetio. My SaaS sales experience has prepared me to build pipeline through thoughtful outbound outreach, run consultative discovery, deliver compelling demos, and guide prospects through negotiation and close.
I am motivated by high-accountability environments and would bring disciplined follow-up, strong business communication, and a customer-focused approach to helping fleet-operating organizations realize value from Fleetio.
I would welcome the opportunity to contribute to Fleetio’s growth and collaborate with a high-performing remote sales team. Thank you for your consideration.
Sample interview questions
I would begin by researching the prospect’s fleet size, operating model, and likely workflow challenges. In discovery, I would ask open-ended questions about maintenance, compliance, asset utilization, and current systems, then connect Fleetio capabilities to the highest-priority business outcomes before proposing a focused next step.
I use a structured prospecting cadence that combines targeted email, phone, social touches, and relevant follow-up. I prioritize accounts using fit and intent signals, personalize the first outreach around a likely operational challenge, and track activity and conversion metrics so I can improve the sequence over time.
I prepare by confirming decision criteria, stakeholders, timeline, current process, and the cost of inaction throughout the sales cycle. If pricing becomes an issue, I return to the agreed value, address the underlying concern directly, and seek a mutually clear path to close rather than discounting prematurely.
I would tailor the demo to the prospect’s stated goals rather than provide a generic product tour. I would show the relevant workflows, confirm understanding after each key section, and end by connecting the solution to measurable operational and business value along with a specific next step.
I manage my week around pipeline health, opportunity stage, next steps, and the activities most likely to create qualified conversations. I keep CRM records current, set follow-up commitments immediately, and reserve dedicated blocks for prospecting so urgent deal work does not eliminate future-pipeline generation.
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 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 (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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