Specialist, Sales Training & 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

The Specialist, Sales Training & Enablement plays a key role in designing, developing, and delivering advanced sales training programs that strengthen sales capability across inside, middle market, and enterprise teams within the transportation and trucking industry. This position drives performance improvement by enhancing product knowledge, refining sales methodologies, and ensuring consistent, high-quality execution across channels.

In collaboration with Sales Leadership and Revenue Operations, the Specialist aligns learning initiatives with business objectives, market strategy, and customer success goals, while supporting the ongoing improvement of sales enablement processes and curriculum. Training is the primary focus; enablement is a secondary priority centered on maintaining and improving core enablement assets (playbooks, talk tracks, job aids) and reinforcing process and tool adoption through training. This is an on-site or hybrid role based in our downtown Phoenix office.

Essential Responsibilities

Leadership & Strategy

• Lead the design and implementation of sales training strategies that drive revenue growth across multiple business segments (inside sales, middle market, enterprise, and partner channels)

• Partner with sales and operations leadership to align training programs with organizational goals, performance metrics, and emerging market trends

• Serve as a subject matter expert in sales enablement within the transportation and logistics sector, advising on best practices and innovations

• Facilitate "train-the-trainer" sessions to ensure consistent and scalable delivery across all revenue teams and vendor partners

Training Development & Facilitation

• Design, customize, and deliver advanced sales training programs covering onboarding, consultative selling, strategic account management, and enterprise deal negotiation

• Facilitate dynamic and interactive training sessions, both in-person and virtually, for sales professionals and leaders across the organization

• Develop and manage certification programs and structured learning paths tailored to specific sales roles and customer segments

• Incorporate real-world transportation and trucking scenarios into training to ensure relevance and practical application

Sales Coaching & Performance Optimization

• Collaborate with sales leaders to identify performance gaps and execute targeted coaching strategies

• Conduct onsite and virtual observations to assess sales execution, deliver actionable feedback, and reinforce learning outcomes

• Analyze performance data and CRM insights to evaluate training effectiveness and continuously optimize content and approach

Enablement Support (Secondary Priority)

• Create and maintain sales enablement materials that reinforce training (playbooks, talk tracks, job aids, checklists, and onboarding resources)

• Partner with Sales Leadership and Revenue Operations to ensure training content aligns to the sales process, CRM workflows, and evolving rep expectations

• Help operationalize reinforcement (e.g., refreshers, certifications, and manager coaching guides) to ensure training translates into consistent field execution

• Maintain content hygiene: keep materials current as offerings, tools, and messaging evolve in partnership with Product/Marketing

Cross-Functional Collaboration

• Partner with Product, Marketing, and Operations teams to ensure training materials accurately reflect current offerings, technologies, and competitive advantages

• Collaborate with HR and Learning & Development to maintain alignment with corporate learning standards and compliance policies

• Champion adoption of sales technologies, CRM processes, and enablement tools by embedding them into training, certifications, and reinforcement

Requirements:
Required Qualifications:

• Bachelor's degree in Business, Communications, Education, or a related field (or equivalent experience)

• 5-8 years of experience in sales training, enablement, or sales leadership within transportation, trucking, logistics, or supply chain industries

• Proven success designing and delivering comprehensive sales training programs across multiple sales segments

• Strong knowledge of B2B sales strategies, including inside sales, fleet services, brokerage, and enterprise logistics

• Exceptional facilitation, presentation, and coaching skills across varied audiences

• Experience creating and maintaining sales enablement assets (e.g., playbooks, talk tracks, job aids, and learning resources) that reinforce training and improve field execution.

• Proficiency with CRM platforms (e.g., Microsoft Dynamics), LMS systems, and enablement tools (e.g., Five9, Seamless.AI, Outreach), including using these tools to support adoption and reinforcement.

Preferred Qualifications:

• Professional certification in sales methodologies (Challenger, SPIN, Sandler, MEDDIC, or similar)

• Experience leading or mentoring other trainers or enablement professionals

• Background in instructional design, adult learning theory, or e-learning development

• Ability to use performance data and CRM insights to identify additional enablement needs, measure training/enablement impact, and iterate content accordingly.

• Strong analytical and strategic planning abilities, with a data-driven approach to sales enablement

Desired Characteristics

• Strategic thinker with strong leadership and team development skills

• Deep understanding of transportation and logistics sales cycles

• Consultative and analytical mindset with strong communication and influence capabilities

• Innovative approach to learning design and delivery

• Proactive, data-informed decision-making style that drives continuous improvement

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.