Mid-Market Account Executive

Job Description

About PrePass

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.

Essential Responsibilities

Revenue Growth & Pipeline Development

• 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

Sales Execution & Deal Management

• 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

Customer Engagement & Consultative Selling

• 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

Cross-Functional Collaboration

• 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

What Success Looks Like

• 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

Requirements

Qualifications

• 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

Benefits

How We Will Take Care of You

• 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.

Join Us

At PrePass, our mission drives us.

We invest in relationships. We challenge ourselves to innovate and improve. We win together. Simply put, we live our Core Values.

Ready to help move the transportation industry forward? Join us and let’s drive progress—together.