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.

If you’ve ever thought:

• “How do I move from operations to leadership?”
• “Can I build tech without being a tech person?”
• “How do I create culture when everyone’s remote?”
• “What does real leadership actually look like?”
• “How do I prioritize when everything feels urgent?”

This conversation will give you the blueprint.

Todd shares honest insights about:

• Why “motion creates emotion” and how to create energy in any team
• How trust is built or destroyed in every single interaction
• The difference between managing people and leading them
• Why asking questions beats making assumptions every time
• What it really takes to transform a decades-old company culture

TAKEAWAYS:

• Why the energy at CH Robinson shaped Todd’s entire leadership philosophy
• The sales manager conversation that forever changed how Todd prioritizes time
• What Todd learned opening JB Hunt’s Minnesota brokerage branch from scratch
• Inside look at building JB Hunt 360 marketplace and the tech lessons learned
• How Todd transformed Q Carriers’ culture in a 40-year-old trucking company
• The moment Todd realized great culture starts with how leaders actually listen
• What carriers really want from load boards (it’s not what brokers think)
• Why TruckStop built a Carrier Advisory Board and how it changes product development
• The fraud problem hitting the industry and how technology is solving it
• Where AI actually helps carriers vs. where it creates more problems
• How authority age filters help new carriers cut through the noise
• Why “boost loads” might finally solve the duplicate load nightmare
• Todd’s time management system that reduced chaos and increased productivity
• The leadership frameworks from “Good to Great” and “Five Dysfunctions” that actually work in freight

Whether you’re in brokerage, running trucks, building tech, leading a team, or just trying to level up your career, this episode is packed with hard-earned wisdom.

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CHAPTERS:

• 0:00 Introduction: Meet Todd Waldron
• 1:32 Career Journey: From CH Robinson to VP at TruckStop
• 3:21 Early Brokerage Lessons: Energy, Prioritization & Sales
• 5:58 Leadership Philosophy: Trust in Every Interaction
• 12:35 JB Hunt Experience: Building Tech & Opening Minnesota Branch
• 17:43 Leading Q Carriers: Cultural Transformation of a 40-Year Company
• 22:08 The Culture Shift: Employee Engagement & Retention
• 23:32 TruckStop Innovation: Building Products Carriers Want
• 25:38 Understanding Carrier Needs: The Advisory Board Approach
• 28:37 Tech Integration Lessons: What Worked at JB Hunt
• 30:27 Market Insights: Cycles, Trends & What’s Coming Next
• 34:04 Technology Adoption: Getting Carriers to Actually Use It
• 37:51 What’s Next at TruckStop: Authority Filters, Deduplication & AI
• 39:42 Book Recommendations: Leadership & Time Management

RESOURCES:

Good to Great by Jim Collins

https://www.amazon.com/dp/0066620996

Do More Better by Tim Chalies

https://www.amazon.com/dp/1950523774

Five Dysfunctions of a Team by Patrick Lencioni

https://www.amazon.com/Five-Dysfunctions-Team-Leadership-Fable/dp/0787960756

TruckStop Platform

https://truckstop.com

JB Hunt 360 Marketplace

https://www.jbhunt.com/360/

Q Carriers

https://qcarriers.com

CONNECT WITH TODD WALDRON:

LinkedIn: https://www.linkedin.com/in/todd-w-21897b19/

Website: https://truckstop.com

FOLLOW JOURNEY:

Instagram: @journeydelivers

Twitter/X: @journeydelivers

TikTok: @journeydelivers

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

• LinkedIn
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• Facebook
• TikTok
• YouTube

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.