In the hyper-competitive world of freight brokerage, where talent is one of the few differentiators, no one understands the stakes better than Will Jenkins. The co-founder of MoLo Solutions — the Chicago-based brokerage that rocketed from zero to over $600 million in revenue before its 2021 acquisition by ArcBest — has turned his attention to solving one of the industry’s most persistent pain points: finding, developing and retaining top performers.
In November 2023, Jenkins launched Journey, a bootstrapped “full-cycle brokerage support organization” that provides recruiting, consulting and training services exclusively to freight brokerages. Approaching its two-year anniversary, Journey has already established itself as a go-to partner for some of the largest players in the space, working with eight of the top 100 brokerages and a handful of the top 25.
Learning how to grow a brokerage
Jenkins’ freight journey began modestly in January 2014 when he joined Coyote Logistics as a carrier sales rep with zero industry knowledge. A former Illinois Wesleyan football player who once sold Cutco knives and ran a college office for the brand, Jenkins quickly grasped the grind required in brokerage sales. By 2015, longtime colleague (and now Journey partner) Justin Turner tapped him to move into customer sales, a pivot Jenkins calls “life-changing.”
He rose to customer sales manager, training a team of nine green reps on everything from cold calling to RFPs and in-person shipper visits. In 2017, Jenkins left Coyote to help launch MoLo Solutions alongside Andrew Silver, Matt Vogrich and Stephan Mathis. What followed was explosive growth: MoLo trained its first 200 hires, scaled operations from scratch and hit $276 million in revenue by 2020. Jenkins eventually took over the customer sales group, building proprietary training programs that became a cornerstone of the company’s culture.
The 2021 sale to ArcBest — reportedly valued at $235 million — capped an extraordinary run. MoLo posted $1.25 billion in revenue in 2022 under ArcBest ownership. Jenkins stayed on for 18 months post-acquisition before stepping away in May 2023, “feeling really good about what we had accomplished.”
Rather than retire on the proceeds or jump back into another brokerage, Jenkins spotted a broader opportunity. “A lot of it has to do with our team’s understanding of how to successfully build and scale a large freight brokerage,” he explained. Journey was born to package that hard-won expertise for the rest of the industry.
The company takes a deliberate, diagnostic approach with clients. Jenkins recounts one early engagement with a $150 million Chicago brokerage seeking a VP of sales. After digging in, Journey determined the owner actually needed a player-coach director who could personally build a book of business rather than manage a non-existent enterprise sales team. “We ask better questions about the deliverables,” Jenkins said. Sometimes consulting or structural work must precede recruiting, he said, reminding clients to “slow down to speed up” for sustainable results.
Training has emerged as one of Journey’s most dynamic offerings. More than 750 professionals have completed its self-paced online courses, while in-person and virtual bootcamps — including three-day hands-on sales sessions — teach reps how to construct a book of business from the ground up.
The key component is an AI-powered sales training platform developed with Hyperbound, in which Jenkins is an investor and Journey serves as the exclusive transportation vertical partner. Sales reps role-play against AI shippers that sound authentically like real buyers on cold calls or quarterly business reviews. Managers can listen in live, deliver instant feedback and track scores, all in a zero-risk environment. The tool is already live at eight top-100 brokerages.
Journey remains lean and organic in its growth: a six-person team, zero paid marketing and fully self-funded. Key players include partner Justin Turner (joined February 2025 and former Coyote/Flock Freight executive), day-one member Erin Sweeney (marketing and messaging), Maya Quijada (business operations), 14-year veteran Dan Solida (customer success) and Jenkins’ mom handling full-time operations.
“Talent is the tip of the spear,” Jenkins emphasized. “We’re assembling what we are confident are the freight brokerage professionals who understand how this game is played.”
As the industry wrestles with talent shortages and ever-thinner margins, Journey’s mission is straightforward: help brokerages recruit smarter, structure better and train relentlessly. For Jenkins, it’s the logical next chapter after building one of the fastest-growing brokerages in history. Now he’s helping everyone else do the same.
