Manager of Customer Training and Enablement

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’re seeking a Manager of Customer Training and Enablement to build and scale our customer education function. This role is responsible for designing and delivering a comprehensive, customer‑facing training ecosystem that enables faster onboarding, stronger product adoption, and long‑term customer success.

This individual will own the strategy and execution of customer education initiatives, including a customer LMS, training content, webinars, and help center resources. They will partner closely with Product, Customer Success, Support, and Marketing to ensure customers have the knowledge and tools needed to succeed, while also leading and developing a Customer Training Specialist. This is a hybrid position based out of our [Phoenix, AZ] office

Essential Responsibilities

Customer Training Strategy & Program Ownership

• Define and execute a scalable customer education strategy aligned to customer lifecycle stages.
• Establish clear learning objectives, success metrics, and feedback loops to continuously improve training effectiveness.
• Ensure training programs support customer adoption, retention, and reduced support dependency.

Learning Management System (LMS) Development

• Partner with HR to implement new customer‑facing LMS platform.
• Own and manage the customer‑facing LMS to house all training content and learning paths.
• Design structured learning journeys tailored to different customer segments and use cases.
• Maintain governance, organization, and ongoing optimization of LMS content.

Training Content & Help Center Development

• Lead and partner with Marketing on the creation and ongoing evolution of customer training materials, including videos, guides, documentation, and self‑service resources.
• Own the curation and maintenance of a customer help center that is intuitive, searchable, and aligned with product capabilities.
• Partner with internal teams to keep content current as products and features evolve.

Webinars & Live Enablement

• Plan and host recurring customer training webinars and one‑to‑many enablement sessions.
• Develop presentation materials, agendas, and training flows to support onboarding and ongoing education.
• Support internal presenters and subject matter experts as needed.

People Leadership

• Manage and develop a Customer Training Specialist, providing direction, coaching, and performance feedback.
• Define clear roles, workflows, and quality standards for training delivery.
• Support team growth as customer education needs scale.

Cross‑Functional Collaboration

• Collaborate with Customer Success and Implementation teams to integrate training into onboarding and post‑launch workflows.
• Partner with Support to identify knowledge gaps and reduce recurring customer issues through proactive education.
• Work with Product and Marketing to align training content with releases, messaging, and customer needs.

Requirements

Qualifications

• Bachelor’s degree or equivalent experience.
• 5+ years of experience in customer education, enablement, training, or related roles within a SaaS or technology environment.
• Experience building or administering customer‑facing LMS platforms.
• Strong instructional design, content creation, and presentation skills.
• Proven ability to manage multiple initiatives and prioritize effectively.
• Excellent written and verbal communication skills.

Bonus Points For (Optional)

• Experience supporting customer education across SMB, mid‑market, and enterprise segments.
• Familiarity with AI video creation tools, knowledge base platforms, or webinar technologies.
• Background in customer success, onboarding, or implementation functions.
• Experience defining and tracking adoption or enablement metrics.

Desired Characteristics

• Strategic and systems‑oriented thinker who can build from the ground up.
• Customer‑centric mindset with a passion for education and enablement.
• Comfortable operating in ambiguity and driving structure where needed.
• Strong collaborator who can influence across teams.
• High ownership, accountability, and bias toward action.

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.