Sales Bites
Sales Bites
Podcast Description
Welcome to "Sales Bites" by Journey! Join our host, Journey's CEO & Founder, Will Jenkins, to learn everything you need to know to be a killer at sales.
We're bringing you biweekly bite-sized content so that you can easily stay on top of your A game. Tune in for direct, actionable tips, and best practices based on what he’s learned from experts inside and outside the world of sales.
Will covers topics from freight & supply chain to entrepreneurship, sales & marketing. Get ready to level up!
Podcast Insights
Content Themes
The podcast covers a broad range of sales-related topics including effective outreach, building relationships, emotional intelligence, and persistence in sales. For instance, recent episodes discuss the significance of cold calling, video outreach strategies, and the importance of team selling, providing concrete examples and actionable takeaways for listeners.

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.
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
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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