In this episode of Freight Nation: A Trucking Podcast, host Brent Hutto is joined by Will Jenkins, Founder & CEO of Journey and Investor & Partner at Shipper CRM.

Join them as they explore:

Will Jenkins is the Founder & CEO of Journey, a leading recruiting, consulting, and training firm in the transportation industry. His fifteen years experience includes founding and scaling MOLO to a successful exit to ArcBest, demonstrating his expertise in building and growing freight brokerages. With a background spanning from carrier sales to executive leadership, Will brings a comprehensive understanding of the trucking industry's talent needs and operational challenges.

[05:25 - 08:10] Will reveals his unexpected entry into sales through Cutco, where he achieved remarkable success by selling $10,000 worth of products in his first ten days, laying the foundation for his future career in freight brokerage and demonstrating his natural aptitude for building client relationships.

[10:30 - 13:50] Transitioning into the freight industry, Will recounts his first role at Coyote Logistics and his rapid rise within the company. He highlights the energy of Coyote’s collaborative culture and how it shaped his understanding of freight brokerage. Will discusses how he embraced the steep learning curve, leveraging his sales background and the mentorship of industry veterans to excel in carrier sales. The dynamic environment and strong training foundation helped him develop the expertise that would later serve him as an entrepreneur. This period laid the groundwork for his journey to leadership in the freight sector.

[16:15 - 20:05] Will explains the inspiration behind co-founding MoLo Solutions and the guiding principles that fueled its rapid growth. He highlights the importance of treating drivers, shippers, and employees with respect, emphasizing service excellence as MoLo’s competitive edge. Will also touches on the challenges of scaling a company in a fast-paced industry and the importance of assembling a capable and empowered team. By prioritizing relationships and core values, MoLo grew to over 900 employees and $1 billion in revenue before its acquisition. Will’s reflections underscore the impact of building a company culture that aligns with both customer and employee needs.

[34:15 - 38:50] Now leading Journey, Will discusses the freight talent gap and the critical role of training in closing it. He highlights the challenges companies face in recruiting top talent, particularly for revenue-generating roles like sales. Will explains that strong onboarding and training programs are not just a competitive advantage—they’re essential for operational success in the industry. Drawing from his experiences at MoLo and Journey, he shares insights on how companies can attract and retain high-performing employees while improving overall efficiency. His perspective reinforces the need for long-term investments in people as the foundation for business growth.

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