Sales Manager - Transportation Compliance Solutions
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
PrePass is seeking a Sales Manager with experience in transportation, fleet technology, or regulatory compliance solutions to lead our Compliance Services Sales organization. This role will drive growth across our FMCSA and DOT compliance management solutions, serving trucking fleets and transportation companies across North America.
This leader will be responsible for developing and scaling a high-performing sales team, executing go-to-market strategies, and driving revenue growth across both compliance services and software offerings. The ideal candidate brings a strong understanding of fleet operations, driver compliance, and transportation regulations, along with a proven ability to lead sales teams in a SaaS or services environment.
Essential Responsibilities
Team Leadership & Sales Development
- Lead, coach, and develop new and tenured Services Sales Representatives.
- Manage onboarding, training, and continuous skill development to elevate sales effectiveness.
- Establish clear performance expectations, KPIs, and accountability standards.
- Conduct regular performance reviews, pipeline coaching, and call evaluations.
- Build a culture of ownership, urgency, and continuous improvement.
Services Sales Management & Software Sales Support
- Own and manage the Services Sales pipeline to drive consistent revenue growth.
- Support the growth of Software Sales through alignment, cross-training, and strategic coordination.
- Ensure alignment between services offerings and compliance software management solutions.
- Identify expansion opportunities within the existing PrePass client portfolio.
Go-to-Market Strategy & New Business Development
- Develop and implement an efficient GTM strategy to secure new business.
- Refine targeting, segmentation, and outreach strategies to improve conversion rates.
- Partner with Marketing to align campaigns and lead-generation efforts.
- Monitor competitive landscape and adjust strategy to maintain market advantage.
Reporting, Analysis & Operational Excellence
- Analyze sales metrics, pipeline health, and conversion data to inform decision-making.
- Manage forecasting and reporting to ensure accurate revenue projections.
- Improve sales processes and workflows to increase efficiency and scalability.
- Ensure adherence to FMCSA and DOT compliance standards within sales messaging and positioning.
Requirements
Qualifications
- Bachelor’s degree in Business, Marketing, or related field (or equivalent experience)
- 5+ years of experience in SaaS and/or services sales
- 2+ years of experience leading and developing sales teams
- Proven success building and executing go-to-market strategies
- Demonstrated ability to secure new business and drive revenue growth
- Strong understanding of FMCSA, DOT, and transportation compliance requirements
- Experience selling into trucking fleets, carriers, or transportation/logistics companies
- Proficiency with CRM systems and sales performance tools
- Strong leadership, coaching, and analytical skills
Preferred Experience
- Experience in transportation, fleet technology, or compliance solutions
- Background selling compliance services, safety solutions, or compliance software
- Familiarity with ELD, TMS, fleet management, or driver compliance platforms
- Experience working with driver qualification, Hours of Service (HOS), or CSA regulations
Desired Characteristics
- Strategic thinker with a proactive, solution-oriented mindset
- Strong coach and team builder with a passion for developing talent
- Comfortable operating in a fast-paced, evolving environment
- Excellent communication and influencing skills
- High level of ownership and accountability
- Ability to generate excitement around new transportation and compliance solutions
- Strong business acumen with a customer-first mindset
Why This Role
This is an opportunity to lead and scale a critical growth area within PrePass, helping shape how trucking fleets manage safety and compliance in an increasingly complex regulatory environment.
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.