Welcome to The Journey Podcast, where we talk freight, sales, tech, the market and everything in between. Hosted by Will Jenkins, CEO and Founder of Journey, this show pulls from years of building & scaling freight brokerages along with the work our team does with hundreds of clients. We break down how brokers grow, how teams sell, how leaders hire, and what it takes to perform at a high-level in this industry.

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Podcast Overview
Welcome to The Journey Podcast, where we talk freight, sales, tech, the market and everything in between. Hosted by Will Jenkins, CEO and Founder of Journey, this show pulls from years of building & scaling freight brokerages along with the work our team does with hundreds of clients. We break down how brokers grow, how teams sell, how leaders hire, and what it takes to perform at a high-level in this industry.
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Publishing Since
4/18/2024
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Recent Episodes

May 14, 2026
Kevin McMaster, Flock Freight on Shared Truckload, Shipper Success, and the Tech Behind the Model
If you've ever wondered how technology is actually transforming freight beyond buzzwords and hype, this episode will show you what's possible. Kevin McMaster, SVP of Sales and Operations at Flock Freight, didn't just talk about innovation, he built it. Flock Freight's shared truckload model combines multiple LTL shipments into full truckloads using AI-powered optimization. The result? Lower costs for shippers, better rates for carriers, and freight that moves without touching a dock.

April 30, 2026
How Axle Logistics Uses AI to Upskill Reps Faster
If you've ever watched new sales reps struggle for months before landing their first customer, this episode will change how you think about training. Ali Fraley and Haley Williams from Axle Logistics didn't just adopt AI for training, they proved it works. Their January class of 17 reps completed over 1,400 AI practice calls before touching a real prospect. The results? Five weeks later: 27 new customers, $139,000+ in revenue, and 14 out of 17 reps had already landed business.

April 23, 2026
Todd Waldron, Brokerage, Trucking, and Tech All in One Career
If you've ever wondered how someone goes from brokering freight to leading tech innovation at one of the industry's biggest platforms, this episode will change how you think about career growth in transportation. Todd Waldron didn't just work in logistics—he mastered every level of it. From the high-energy cubicles at CH Robinson, to opening JB Hunt's Minnesota brokerage branch, to transforming a 40-year-old trucking company, to now shaping carrier experience at TruckStop—Todd's 17-year journey proves that great leaders are built through relentless learning and adaptation.
94 total episodes available
Recent guests on Sales Bites
Guests from recent episodes — sign up to see every guest that has ever appeared on this show.
Will Jenkins
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Justin Turner
Guest
Tyler Harper
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Daniel Solida
Guest
Matt Fain
Guest
Cameron Robertson
Guest
Robert Bain
Guest
Megan Masud
Guest
Sarah Hanna
Guest
Krystian Gebis
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Michael Sternberg
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Kyle Richards
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Frequently asked questions
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- What is Sales Bites?
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This podcast updates daily.
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This podcast is available on 6 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
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Yes, this podcast regularly features guests.
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