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Inside Sales Representative - Fleet Compliance Solutions

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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 systems that support not only fleets but the broader economy. It all starts with enabling commercial vehicles to keep rolling with 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 are implemented in real-time, on highways and interstates across the nation, helping fleets go farther, faster. This work challenges and rewards, presenting complex problems that need ambitious answers. We hire bold thinkers with a heart for impact, a passion for progress, and the optimism to shape the future of transportation.

About the Role

We are seeking a results-driven Inside Sales Representative – SMB Fleet Compliance Software to join our growing sales team. This role focuses on selling PrePass software solutions to small and mid-sized fleets through a combination of outbound prospecting and inbound lead management.

You will own the full sales cycle—from identifying and qualifying opportunities to delivering product demonstrations and closing new business. This is a quota-carrying role ideal for a motivated sales professional with 3–5 years of experience in SaaS and fleet-related sales who thrives in a fast-paced, high-growth environment.

Essential Responsibilities

Sales Execution & Pipeline Development

  • Prospect and engage SMB fleet customers through outbound calls, email, and digital channels.
  • Manage inbound leads, qualify opportunities, and convert prospects into customers.
  • Own the full sales cycle, including discovery, product demonstrations, proposal development, and closing.
  • Consistently meet or exceed monthly and quarterly sales quotas.

Customer Engagement & Value Selling

  • Build strong relationships with prospective customers and understand their operational needs.
  • Clearly articulate the value of PrePass software solutions, including safety, compliance, and efficiency benefits.
  • Address objections and guide prospects through the decision-making process.

CRM Management & Reporting

  • Maintain accurate and up-to-date records of all sales activities in CRM systems.
  • Track pipeline, forecast performance, and report on sales progress.
  • Ensure timely follow-up and disciplined pipeline management.

Collaboration & Continuous Improvement

  • Partner with marketing, product, and sales leadership to refine messaging and improve conversion rates.
  • Participate in training and ongoing development to deepen product knowledge and sales effectiveness.
  • Contribute to a high-performance, team-oriented sales culture.

Requirements

Qualifications

  • 3–5 years of experience in inside sales, preferably in transportation/fleet software solutions.
  • Proven track record of meeting or exceeding sales quotas.
  • Experience managing a full sales cycle, from prospecting to close.
  • Strong communication, presentation, and objection-handling skills.
  • Ability to quickly learn and effectively communicate technical product offerings.
  • Experience with CRM systems (e.g., Salesforce) and sales engagement tools.
  • Self-motivated with a high level of accountability and drive.
  • Bachelor’s degree preferred but not required.

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.
  • 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.

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.

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What this application asks

workable

First name, Last name, Email, Phone, Address, Resume, How many years of relevant experience do you have?, What is the highest level of education that you have completed?, Cover letter, Are you authorized to work in the United States?, Will you now or in the future require sponsorship for employment visa status?, We are an Equal Opportunity Employer and are committed to excellence through diversity. By affixing your name and submitting your resume or completing this application, you certify that the information you have provided is true and complete to the best of your knowledge. If this application leads to employment, you understand that false or misleading information in your application or interview may result in your employment being terminated.

  • Do you have experience selling transportation, fleet management, or logistics software (SaaS) solutions? written answer
  • Could you share a bit about your experience in inside sales, including how many years you've worked in this area and the types of products or services you've sold? written answer
  • What are your salary expectations (OTE)?
  • Can you describe a time when you met or exceeded your sales targets? What strategies or approaches helped you achieve those results? written answer
  • Were you referred by a PrePass employee? If so, please provide the first and last name of the employee. written answer
  • What has been your experience managing the entire sales cycle, from initial prospecting through closing the deal? Could you walk us through your typical process? written answer

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