Job Overview
Location
Remote
Job Type
Full-time
Category
Sales
Date Posted
April 14, 2026
Full Job Description
đź“‹ Description
- • As a Mid-Market Account Executive at Fleetio, you will drive new business growth by selling a leading fleet management software platform to medium and large organizations, directly contributing to the company’s ARR expansion and market leadership in transportation technology.
- • Day to day, you will manage a mix of inbound and outbound leads, conduct consultative sales conversations, deliver web-based demos and presentations, negotiate pricing, close deals, and maintain consistent follow-up via phone and email while collaborating with cross-functional teams to convert prospects into long-term customers.
- • Fleetio is a profitable, fast-growing SaaS company that raised $450M in Series D funding in March 2025, serves thousands of organizations globally, and is a founding member of the Rails Foundation, offering a mission-driven, innovative culture rooted in solving real-world fleet operations challenges.
- • In this role, you will deepen your expertise in SaaS sales, master consultative selling techniques, develop advanced negotiation and presentation skills, and build a track record of high-impact customer acquisition—positioning yourself for accelerated career growth and top-tier earnings in a high-performance sales organization.
🎯 Requirements
- • 3+ years of SaaS sales experience
- • Experience owning customer engagements end-to-end, from prospecting and qualification to close
- • Strong verbal and written communication skills
- • Excellent presentation and negotiation skills
- • Ability to remain focused and disciplined with your time
- • Driven by results with 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
Skills & Technologies
Rails
Mid-level
Remote
About RareStep, Inc.
RareStep, Inc. provides fleet management software for commercial vehicle operators. The cloud platform tracks maintenance, fuel, inspections, parts, work orders, and driver assignments across trucks, vans and equipment. Customers use mobile apps and telematics integrations to monitor utilization, schedule services, control costs and ensure compliance. Founded in 2012 in Birmingham, Alabama, the company serves thousands of fleets worldwide.
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