Share this job SVGs not supported by this browser. 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 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 Sales Trainer 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 all channels. In collaboration with Sales Leadership and Revenue Operations, the Sales Trainer aligns learning initiatives with business objectives, market strategy, and customer success goals. The role also contributes to the continuous enhancement of sales enablement processes and curriculum. 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. 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. Promote adoption of new sales technologies, CRM processes, and enablement tools to improve efficiency and consistency. Requirements Required: 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. Proficiency with CRM systems (e.g., Microsoft Dynamics), LMS platforms, and enablement tools (e.g., Five9, seamless.ai, Outreach). Preferred: 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. 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. 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. Apply for this job