["Full-Time"]
Remote
SaaS
jobicy
About this role
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
Selling Motion
Sales Cycle
Mid-Market
1–6 month cycles, moderate deal complexity
Prospecting
Hybrid
Mix of inbound leads and outbound prospecting
Buyer Persona
C-Suite
Selling to executive decision-makers
Requirements at a Glance
Typical Day — Account Executive
Estimates based on role type and selling motion — actual may vary by company.
Role Signals
Green Flags
Location flexibility
SaaS — Interview Intel
Typical Sales Cycle
30–90 days (SMB) · 3–9 months (Mid-Market) · 6–18 months (Enterprise)
Common Buyer Objections
- "We're locked into a contract with [competitor]"
- "We built something in-house already"
- "We don't have budget until next quarter"
- "Our team won't adopt another tool"
Key Industry Metrics
Hot Topics to Reference
- • AI-native product disruption
- • PLG vs sales-led motion debate
- • Vertical SaaS consolidation
- • Usage-based pricing models
Use these insights to speak the buyer's language in interviews.
Tags
Walk me through your discovery process.
Template questionHow do you handle a prospect who goes silent mid-deal?
Template questionTell me about your largest closed deal and the sales cycle.
Template questionHow do you build business cases for stakeholders?
Template questionDescribe a deal you lost and what you learned.
Template questionThis Account Executive position at Fleetio involves managing the full sales cycle from prospecting through close.
SaaS sales roles typically involve consultative selling with longer deal cycles.
This remote-friendly role provides geographic flexibility while maintaining access to a SaaS market.
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