The Journey Podcast

Will Jenkins
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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.

  1. 1d ago

    Kelly Usher, Why Agency Recruiting Is Sales Through and Through

    Kelly Usher didn’t start out planning to work in recruiting. Her path took her from dance and entrepreneurship into logistics, internal talent acquisition and, eventually, third-party recruiting with the Journey Recruiting team. In this episode, Kelly talks about what changes when you move from recruiting inside one company to representing multiple clients and candidates. She shares why agency recruiting is sales through and through, how she earns trust with different decision-makers, and why some of the skills that worked internally had to be relearned in a third-party setting. Kelly and Will also get into candidate coaching, client communication, managing expectations and knowing where to spend your time when every search is moving at a different pace. If you work in recruiting, lead a team or are hiring in freight, this conversation gives you a look at what strong recruiting work requires on both sides of the table.   TAKEAWAYS: Internal recruiting vs. third-party recruiting Getting to know each hiring decision-maker Building trust with candidates and clients Why recruiting is a sales job Coaching candidates through the hiring process Managing client expectations Knowing when to push and when to give a search time Working efficiently across multiple searches Kelly’s experience with the Journey Recruiting team   CHAPTERS: 00:00 Meet Kelly Usher01:04 From dance and entrepreneurship to logistics02:27 Finding recruiting03:47 Internal vs. agency recruiting05:39 What Kelly had to unlearn07:29 Earning trust with clients and candidates09:32 Communication and hiring decisions12:38 Coaching candidates and clients15:30 Managing time across searches19:42 Building trust in freight22:02 Kelly’s experience with the Journey Recruiting team23:34 Closing Connect with Kelly: LinkedIn: https://www.linkedin.com/in/kelly-usher/Kelly@journeydelivers.com Work with the Journey Recruiting team: journeydelivers.com EPISODE CREDITS: Host, Will Jenkins Creative Director, Erin Sweeney Edited and mixed by Keenan McCarthy Music licensed through Envato LINKS: Be sure to follow and tag @JourneyDelivers on LinkedInInstagramTwitterFacebookTikTokYouTube ABOUT THE JOURNEY PODCAST: 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.

  2. Aug 13

    Celebrating 100 Episodes of The Journey Podcast

    100 episodes. A lot of freight conversations. Even more lessons along the way.  For our 100th episode, Will Jenkins goes back through some of his favorite conversations from The Journey Podcast, from the early days of Choppin’ It Up and Sales Bites to the show it is today. Featuring Kevin Miles, Abby Hafenbredl, Kary Jablonski, Ben Bar-Lev, Chadd Olesen, Will Hopkins, Kevin McMaster, and Madison Santo, this episode brings back lessons on freight pricing, sales, leadership, prospecting, automation, cold calling, and building a business for the long game.  Most importantly, it’s a thank you to every guest, listener, and member of the team who helped get us to 100.  TAKEAWAYS: Kevin Miles on using freight bid data to make smarter pricing decisions  Abby Hafenbredl on getting more out of freight conferences through preparation Kary Jablonski on building trust by listening before leading Ben Bar-Lev on finding better freight leads through genuine interests and personal connection Chadd Olesen on why strategy and adoption have to come before automation Will Hopkins on bringing personality and creativity into shipper outreach Kevin McMaster on confidence, taking chances, and playing the long game in freight Madison Santo on getting to the financial impact quickly during a cold call    TIMESTAMPS: 00:19 Celebrating 100 episodes of The Journey Podcast  01:15 Kevin Miles: Freight pricing and getting more from bid data  02:35 Looking back at Episode 1 and Kevin’s return in Episode 95  03:14 Abby Hafenbredl: Preparing for freight conferences  05:10 Kary Jablonski: Listening, trust, and leadership  07:38 Ben Bar-Lev: Finding fresh freight leads  10:18 Chadd Olesen: Strategy before automation  13:30 Will Hopkins: Getting creative with shipper outreach  15:26 Kevin McMaster: Confidence and the long game in freight  17:11 Madison Santo: Getting to the money on cold calls  19:16 What 100 episodes have meant to Will and the team  20:57 Here’s to the next 100    ABOUT THE JOURNEY PODCAST: The Journey Podcast brings together freight leaders, founders, operators, sales professionals, and technology leaders for conversations about freight, sales, tech, the market, and everything in between. Subscribe wherever you listen to podcasts and join us for the next 100.    Start your Journey: www.journeydelivers.com EPISODE CREDITS: Host, Will Jenkins Creative Director, Erin Sweeney Edited and mixed by Keenan McCarthy Music licensed through Envato LINKS: Be sure to follow and tag @JourneyDelivers on LinkedInInstagramTwitterFacebookTikTokYouTube ABOUT THE JOURNEY PODCAST: 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.

  3. Aug 6

    Shannon Breen, How FreightVana Climbed Into the Top 100 in a Down Market

    What happens when you remove commissions from freight brokerage? Shannon Breen, Founder and CEO of FreightVana, joins Will Jenkins to explain how the company grew into a top 100 brokerage with a non-commissioned operating model and an equipment-backed power-only network. Shannon shares how FreightVana built shipper trust, grew through a prolonged freight downturn, and created a power-only network that connects more than 50 shippers each week.   TAKEAWAYS: Why FreightVana built its brokerage without commissions What separates a true power-only network from leased trailers How FreightVana grew during a difficult freight market What new freight companies need to do differently   CHAPTERS: 00:00 Meet Shannon Breen02:43 Building FreightVana Differently08:28 Growing Through the Freight Downturn14:20 Why FreightVana Removed Commissions21:16 Finding the Right Shipper Fit27:09 Building a True Power-Only Network30:43 Questions Shippers Should Ask32:35 Starting a Freight Company Today   Listen to the full episode to hear how FreightVana built a different kind of freight brokerage. Subscribe to The Journey Podcast for weekly conversations on freight, sales, technology, and building stronger companies. EPISODE CREDITS: Host, Will Jenkins Creative Director, Erin Sweeney Edited and mixed by Keenan McCarthy Music licensed through Envato LINKS: Be sure to follow and tag @JourneyDelivers on LinkedInInstagramTwitterFacebookTikTokYouTube ABOUT THE JOURNEY PODCAST: 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.

  4. Jul 30

    Travis Dodge, How Wheelhouse Wins Business the Big Brokerages Miss

    Travis Dodge, Founder of Wheelhouse Logistics, joins Will Jenkins to share how he went from a commission-only freight agent to building a brokerage of his own. Travis explains why consistent prospecting remains the foundation of freight sales and why founders cannot step away from selling too early. He also shares how Wheelhouse found an opening in dry partial truckload and temperature-controlled LTL, two areas many larger brokerages overlook or avoid. The conversation gets into why specialization helps smaller brokerages compete, how operating experience builds trust with shippers, and why strong carrier partners can become a real sales advantage. Travis also shares how Wheelhouse uses LinkedIn to build familiarity, recruit proven people, and earn a seat at the table. Will and Travis close with a conversation about honesty, reputation, and why doing right by people matters in an industry where everyone seems to know everyone.    TAKEAWAYS:  Consistent prospecting remains the foundation of freight sales.  Commission-only sales taught Travis personal accountability and how to bet on himself.  Smaller brokerages can compete by owning freight modes larger companies often overlook.  Dry partial truckload and temperature-controlled LTL became clear points of difference for Wheelhouse.  Deep operating knowledge helps sellers speak with more confidence and earn trust faster.  Founders should stay close to sales while the company is still building.  Strong carrier partners help brokerages win, retain, and grow customer accounts.  A broader customer base reduces the risk of depending too heavily on one shipper.  LinkedIn can build familiarity and credibility before the first conversation.  Honesty, kindness, and doing business the right way carry real value in freight.    CHAPTERS  00:00 Introduction  02:59 From sales jobs to freight brokerage  05:29 Betting on yourself in commission-only sales  10:58 Why consistent prospecting still wins  13:38 Building a freight agency and launching Wheelhouse  17:06 Finding an opening in partial truckload and refrigerated LTL  21:33 How specialization changes the sales conversation  27:21 Why founders still need to sell  30:24 Choosing the right customers and reducing account risk  36:41 Why carrier partners are central to growth  41:33 Building credibility and recruiting through LinkedIn  47:19 Authenticity, reputation, and doing business the right way    Listen to How Wheelhouse Wins Business the Big Brokerages Miss on Apple Podcasts, Spotify, and YouTube.  EPISODE CREDITS: Host, Will Jenkins Creative Director, Erin Sweeney Edited and mixed by Keenan McCarthy Music licensed through Envato LINKS: Be sure to follow and tag @JourneyDelivers on LinkedInInstagramTwitterFacebookTikTokYouTube ABOUT THE JOURNEY PODCAST: 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.

  5. Jul 23

    Kevin Coomes, How Chain Built Freight Tech Brokers Depend On

    SUMMARY:  Kevin Coomes, CRO at Chain, joins Will Jenkins to talk about where the freight market is headed and how brokers should be thinking about automation as capacity tightens. Kevin breaks down how Chain is helping brokerages reduce manual work across tracking, exception management, and booking. He also shares what the company has learned from working across more than 3 million loads. Will and Kevin get into what freight tech companies need to prove in a down market, how the sales message changes when volume returns, and why brokers should be getting more from the people, carriers, and systems they already have. This episode is for freight leaders thinking about where to spend, where to automate, and how to grow without adding headcount too quickly.    TAKEAWAYS:  Kevin Coomes’ path from freight in China to leadership roles across freight tech  What tightening capacity could mean for brokers  Why adding headcount is no longer the default answer  Getting more from the carriers already inside your network  How freight tech sales change across market cycles  Why products need to prove clear ROI in a down market  How Chain automates tracking, exception management, and booking  What Chain has learned from working across more than 3 million loads  Why Chain focused on tracking before expanding into booking  Using carrier data to make better booking decisions  Why freight experience matters inside product and leadership teams  Building technology brokers would feel immediately if it disappeared    CHAPTERS:  00:00 Meet Kevin Coomes, CRO at Chain  01:33 Kevin’s path into freight technology  05:33 Working in China and speaking Mandarin  06:22 What is changing in the freight market  09:16 Selling through different market cycles  13:17 How Chain got started  16:31 Automating freight tracking at scale  18:50 Moving from tracking into booking  20:40 Why freight experience matters in product development  22:01 Proving ROI in a down market  26:34 Helping brokers grow without adding headcount  32:28 Carrier data and what comes next 37:40 Closing thoughts    START YOUR JOURNEY:  http://www.journeydelivers.com  KEYWORDS: freight tech, freight automation, freight brokerage, freight market, Chain, Kevin Coomes, freight tracking, freight booking, carrier management, freight sales, logistics technology, capacity planning, freight operations, carrier networks, brokerage automation, freight market cycles, product-market fit, logistics software, transportation technology    RESOURCES:  Chain: https://trychain.com/  Kevin Coomes on LinkedIn:https://www.linkedin.com/in/kevin-c-46a8a129/ EPISODE CREDITS: Host, Will Jenkins Creative Director, Erin Sweeney Edited and mixed by Keenan McCarthy Music licensed through Envato LINKS: Be sure to follow and tag @JourneyDelivers on LinkedInInstagramTwitterFacebookTikTokYouTube ABOUT THE JOURNEY PODCAST: 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.

  6. Jul 16

    Tom Curee, Ask Better Questions. Win More Business.

    SUMMARY:  What separates a trusted freight sales professional from someone simply chasing the next deal? Tom Curee, President of Qued, joins Will Jenkins to share lessons from 20 years in freight brokerage, transportation, and freight technology sales. Tom began his freight experience at TQL when he was 19, scheduling appointments and working directly with carriers.  Today, he is helping Qued solve that same appointment scheduling problem at scale. Tom explains why sales starts with knowing whether you can genuinely help the buyer. He shares why freight sales teams should stop forcing square pegs into round holes, focus on the problems they understand best, and become specialists rather than trying to sell every possible service. The conversation also covers the role of end-user buy-in when selling freight technology.  Tom explains why executive approval may get a contract signed, but trust from schedulers and operations teams is what keeps customers engaged. Will and Tom also discuss asking stronger discovery questions, solving problems for the customer’s customer, reading the room during a sales call, and staying true to your own personality rather than copying someone else’s sales style. For freight brokers, logistics sales teams, freight technology companies, and transportation leaders, this episode offers a practical look at building trust, earning referrals, and creating lasting customer value.    TAKEAWAYS:  Tom Curee’s 20 years in freight and his start at TQL  Selling to shippers, carriers, drivers, brokers, and executives  Knowing when a prospect is not the right fit  Why Qued focuses only on freight appointment scheduling  Becoming a specialist instead of trying to solve every problem  Understanding the buyer’s goals and performance measures  Getting schedulers and operations teams involved early  Why executive approval does not guarantee adoption  Building trust with the people using the technology every day  How appointments affect margins, driver satisfaction, and shipper revenue  Solving problems for your customer’s customer  Asking better sales discovery questions  Why honesty can lead to referrals even when no sale occurs  Finding a sales style that fits who you are  Reading the room and adjusting the sales conversation  Pull Quotes  CHAPTERS:  00:00 Meet Tom Curee, President of Qued  02:59 Starting in freight at TQL at 19  05:02 Selling by serving a real customer need  07:10 Understanding buyer goals and performance measures  08:59 Knowing when not to make the sale  09:53 Why Qued stays focused on appointment scheduling  12:04 Specialists vs. companies that promise everything  14:19 Understanding the problem before pitching the solution  15:59 Winning trust from schedulers and end users  17:32 Executive approval vs. team adoption  18:14 Sales makes promises. Operations keeps them.  20:43 How appointments affect freight margins  23:04 Solving problems for your customer’s customer  24:05 Asking stronger discovery questions  26:56 Selling something you truly care about  27:24 Finding your own sales style  29:45 Why honesty earns referrals  32:26 Knowing who you are as a salesperson  34:27 Reading the room and adapting the call  36:02 Closing thoughts    START YOUR JOURNEY: www.journeydelivers.com    KEYWORDS: recruiting, consulting, training, freight sales, freight technology sales, freight brokerage sales, logistics sales, Qued, Tom Curee, freight appointment scheduling, transportation sales strategy, freight broker training, logistics customer service, freight technology implementation, customer discovery questions, sales trust, freight operations, shipper needs, carrier sales, end-user adoption, logistics software sales EPISODE CREDITS: Host, Will Jenkins Creative Director, Erin Sweeney Edited and mixed by Keenan McCarthy Music licensed through Envato LINKS: Be sure to follow and tag @JourneyDelivers on LinkedInInstagramTwitterFacebookTikTokYouTube ABOUT THE JOURNEY PODCAST: 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.

  7. Jul 9

    Kevin Miles, The RFP Game Is Changing

    SUMMARY:  Kevin Miles, CEO of Eureeka BI, returns to The Journey Podcast to talk with Will Jenkins about the current freight market, where brokerages are feeling pressure, and how leaders should be thinking about growth right now. Kevin brings more than 20 years of supply chain experience, including time on the shipper side managing RFPs. In this conversation, he breaks down how policy changes, rising costs, technology, and AI are all hitting brokers at the same time. Will and Kevin also get into one of the biggest questions facing freight leaders today: when the market starts to move, how do you grow without spending too fast, hiring too late, or buying technology that does not solve the actual problem? This episode covers smarter RFP strategy, freight pricing, AI adoption, TMS mistakes, hiring trends, and how brokers can position themselves for the next cycle with more discipline.  TOPICS:  The current freight market and what brokers are watching How policy changes may affect rates and capacity Why shippers are increasing RFP cadence How brokers can approach net-new RFP opportunities Common mistakes in TMS and technology buying The difference between a prototype and a working product Where AI can help and where leaders need to be careful Why some brokerages are hiring too reactively How to prepare before the market fully turns What Eureka BI is building next    TAKEAWAYS: Brokers need to understand the business problem before adding new technology. AI can help teams move faster, but it has to be tied to a real strategy. A great demo does not always mean the product is ready to use. RFPs are becoming more frequent, which creates more work for brokers and shippers. The best RFP strategy starts with knowing where your network is already strong. Higher revenue does not always mean true growth if load count and customer count are not expanding. Brokerages should stay disciplined with spending, hiring, and tech adoption as the market shifts.  The teams that invested early in people, systems, and infrastructure are better positioned now.    CHAPTERS:  00:00 Introduction to The Journey Podcast  01:00 Kevin Miles returns as the first-ever Journey Podcast guest  01:18 Kevin’s background and the start of Eureka BI  03:40 Freight market pressure, policy changes, and technology shifts  05:01 Where technology implementation breaks down  07:54 AI adoption, demos, prototypes, and real-world use  11:23 Building, testing, and improving technology faster  12:06 Policy changes and the impact on capacity  13:03 Insurance costs, rate pressure, and RFP changes  15:07 Healthy growth versus market-driven revenue gains  18:05 Spending discipline during a market shift  19:02 Hiring trends across freight brokerages  21:23 How brokers should approach new RFP opportunities  23:35 What is next for Eureka BI  24:18 Closing thoughts    RESOURCES:  Eureka BI: https://www.eureekabi.com/  Kevin Miles on LinkedIn: https://www.linkedin.com/in/kwmiles/?isSelfProfile=false EPISODE CREDITS: Host, Will Jenkins Creative Director, Erin Sweeney Edited and mixed by Keenan McCarthy Music licensed through Envato LINKS: Be sure to follow and tag @JourneyDelivers on LinkedInInstagramTwitterFacebookTikTokYouTube ABOUT THE JOURNEY PODCAST: 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.

  8. May 14

    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. If you've ever thought: "How do we differentiate in a commoditized brokerage market?" "Can technology actually solve freight problems or is it just marketing?" "What does real innovation look like in logistics?" "How do I build a team that embraces change instead of resisting it?" This conversation will give you the roadmap. Kevin shares insights on building technology that actually works, selling differentiation in a skeptical market, and leading teams through constant evolution.   TAKEAWAYS: How shared truckload actually works and why it's more than just pooling freight The routing technology and AI that powers Flock's optimization engine Why market timing matters when introducing disruptive models Taking a consultative approach with shippers instead of pitching features How data and flexibility drive operational excellence Why Flock focuses exclusively on shared truckload instead of expanding services Building trust when your business model is unfamiliar to customers Real differentiation vs. claiming you're different in brokerage Customer retention strategies when you solve actual problems How to prepare shippers for the shared truckload transition Building teams that are energized by change instead of exhausted by it The future outlook for shared truckload and freight optimization Why delivering on promises matters more than perfect marketing Whether you're in brokerage, building freight tech, leading sales teams, or exploring new business models, this episode delivers insights from someone actually doing it.   CHAPTERS: 0:00 Introduction: Flock Freight and Shared Truckload 2:57 The Technology Behind Shared Truckload Routing 5:57 Market Timing and Why Now for Shared Truckload 9:09 Consultative Selling in Freight Innovation 11:58 Data, Flexibility, and Operational Excellence 14:51 Why Flock Only Does Shared Truckload 17:57 Building Trust and Delivering on Promises 20:59 Real Differentiation in Brokerage 23:59 Customer Retention Through Value Creation 27:03 Preparing Shippers for Shared Truckload 30:14 Future Outlook for Flock Freight   RESOURCES: Flock Freight: https://flockfreight.com   CONNECT WITH KEVIN MCMASTER: LinkedIn: https://www.linkedin.com/in/kevin-mcmaster-25a7237/   FOLLOW JOURNEY: Instagram: @journeydelivers Twitter/X: @journeydelivers TikTok: @journeydelivers   ⭐ LOVE THE JOURNEY PODCAST? Help us grow! ⭐  → Leave a 5-star review on Apple Podcasts or Spotify  → Subscribe so you never miss an episode  → Share this episode with someone in freight or logistics   LISTEN & SUBSCRIBE: 🎧 Apple Podcasts: https://buff.ly/d9QupIc 🎧 Spotify: https://buff.ly/rm6ZRT0 🎥 YouTube: https://buff.ly/Vf0w739   ABOUT THE JOURNEY PODCAST 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. EPISODE CREDITS: Host, Will Jenkins Creative Director, Erin Sweeney Edited and mixed by Keenan McCarthy Music licensed through Envato LINKS: Be sure to follow and tag @JourneyDelivers on LinkedInInstagramTwitterFacebookTikTokYouTube ABOUT THE JOURNEY PODCAST: 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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About

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.

Information

  • Creator
    Will Jenkins
  • Years Active
    2024 - 2026
  • Episodes
    101
  • Rating
    Explicit
  • Copyright
    © Journey Solutions Group, LLC
  • Show Website
    The Journey Podcast

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