Mid-Market Account Executive

PrePass

About The Position

PrePass® is North America's most trusted weigh station bypass and toll management platform. We’re transforming how the transportation industry operates—creating solutions that keep trucks moving safely, efficiently, and compliantly. This means making bold decisions and building scalable systems that support not only fleets but the broader economy. It all starts with enabling commercial vehicles to keep rolling through seamless toll management, weigh station bypass, and safety solutions. It’s what we do best, and we do it to meet the demands of the road every day. That’s why people join us: our solutions operate in real time on highways and interstates across the nation, helping fleets go farther, faster. This work is high-impact and complex, requiring thoughtful leadership, strong execution, and a deep understanding of customer and business needs. We hire bold thinkers with a heart for impact, a passion for progress, and the optimism to shape the future of transportation. Position Summary As a Mid Market Account Executive, you will own the full sales cycle for fleets operating between 200 and 1,000 vehicles. You will serve as a consultative partner to mid-sized for-hire and private carriers, demonstrating how PrePass’s weigh station bypass, toll management, and safety solutions reduce operational costs and improve fleet efficiency. This role requires strong discovery skills, multi-stakeholder relationship management, and a proven ability to close new business in competitive mid-market segments.

Requirements

5–8 years of B2B sales experience selling into mid-market accounts, preferably within transportation, logistics, fleet technology, or adjacent industries
Demonstrated success managing full-cycle sales processes and closing multi-year commercial agreements
Experience selling to operational, safety, and finance stakeholders within fleet-based organizations
Strong ability to manage multiple stakeholders, build consensus, and position solutions aligned to customer business goals
Self-driven, goal-oriented mindset with the discipline to balance strategic account planning and daily pipeline activity
Excellent communication, presentation, and negotiation skills across frontline and executive audiences
Passion for contributing to a high-performance sales culture and helping shape the future of the Mid Market sales function at PrePass

Responsibilities

Drive net-new revenue by sourcing, qualifying, and closing mid-market fleet customers
Partner with marketing to convert inbound demand and execute targeted outbound efforts across the 200–1,000 vehicle fleet segment
Consistently prospect, secure meetings, and advance opportunities through the sales pipeline
Own the full sales cycle, including discovery, product demonstrations, business case development, pricing, and contract execution
Lead contract negotiations that balance customer value with strong commercial outcomes for PrePass
Maintain accurate forecasting and pipeline hygiene using PrePass sales technologies and processes
Navigate complex fleet organizational structures and engage stakeholders across safety, operations, maintenance, finance, and executive leadership
Deliver consultative value by understanding fleet workflows and aligning PrePass solutions to operational and financial objectives
Serve as a knowledgeable advisor on bypass, tolling, and compliance trends impacting mid-market fleets
Leverage internal resources including solutions consulting, marketing, analytics, and revenue operations to accelerate deal cycles
Collaborate cross-functionally to support customer success and inform go-to-market improvements
Develop a deep understanding of how PrePass solutions improve fleet efficiency, safety performance, and cost savings
Build credibility as a trusted advisor to mid-market fleets through expertise in operations, compliance requirements, toll program dynamics, and technology adoption
Consistently generate pipeline, secure meetings with decision-makers, and deliver effective product demonstrations
Thrive in a fast-paced, growth-oriented environment and contribute to the development of repeatable Mid Market AE playbooks and best practices

Benefits

Robust benefit package that includes medical, dental, and vision that start on date of hire.
Paid Time Off, to include vacation, sick, holidays, and floating holidays.
Paid parental leave.
401(k) plan with employer match.
Company-funded “lifestyle account” upon date of hire for you to apply toward your physical and mental well-being (i.e., ski passes, retreats, gym memberships).
Tuition Reimbursement Program.
Voluntary benefits, to include, but not limited to Legal and Pet Discounts.
Employee Assistance Program (available at no cost to you).
Company-sponsored and funded “Culture Team” that focuses on the Physical, Mental, and Professional well-being of employees.
Community Give-Back initiatives.
Culture that focuses on employee development initiatives.
Company-wide bonus and commission plans.