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:

This conversation will give you the blueprint.

Todd shares honest insights about:

TAKEAWAYS:

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.

⭐ LOVE THE JOURNEY PODCAST? Help us grow! ⭐

→ Leave a 5-star review on Apple Podcasts or Spotify

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→ Share this episode with someone in freight or logistics

Your support helps others in the industry find these conversations!

CHAPTERS:

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
• Instagram
• Twitter
• 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.

If you've ever wondered how traditional industries can transform into AI-powered innovation engines, this episode will change how you think about entrepreneurship. 

Hunter Bell didn't just grow up in the transportation and logistics world, he revolutionized it. 

From watching his family run trucking operations to building MySavant.AI, an AI-powered nearshoring platform, Hunter's journey proves that the biggest opportunities often hide in plain sight within the industries we know best. 

If you've ever thought: 

This conversation will give you a roadmap. 

Hunter shares raw, honest insights about: 

TAKEAWAYS:

⭐ LOVE THE JOURNEY PODCAST? HELP US GROW! ⭐ 

Your support helps others in the industry find these conversations! 

CHAPTERS: 

EPISODE RESOURCES: 

Think and Grow Rich by Napoleon Hill https://www.amazon.com/Think-Grow-Rich-Napoleon-Hill/dp/1934451509 

The Strangest Secret by Earl Nightingale https://www.youtube.com/watch?v=7X7X7X7X7X 

MySavant AI Platform https://mysavant.ai 

CONNECT WITH HUNTER BELL: 

LinkedIn: https://www.linkedin.com/in/hunter-bell-0299b4167/ 

Website: https://mysavant.ai 

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
• Instagram
• Twitter
• 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.

SUMMARY:

In this episode of the Journey Podcast, Will Jenkins and Justin Turner discuss the critical importance of customer and account segmentation in sales strategy. They explore how different customer segments behave based on size and technical requirements, emphasizing the need for a tailored approach to sales and marketing. The conversation delves into actionable insights for sales leaders, focusing on optimizing for quick wins and aligning brand messaging with target audiences.

TAKEAWAYS:

CHAPTERS:

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
• Instagram
• Twitter
• 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.

SUMMARY:

What does Black History Month mean inside corporate America?

In this episode of The Journey Podcast, Will Jenkins and Justin Turner share personal stories about growing up in the South, navigating executive leadership roles, and building careers in the logistics industry as Black professionals.

They discuss:

• The importance of representation in corporate leadership

This is a conversation about progress, responsibility, and building real pathways for the next generation.

If you care about leadership, representation, mentorship, diversity in logistics, or corporate culture, this episode is for you.

TAKEAWAYS: 

CHAPTERS: 

00:00 Introduction | Leadership in Logistics 

00:31 Black History Month Reflection

01:55 Growing Up in the South 

04:30 Representation in Executive Roles 

06:01 Breaking Stereotypes in Corporate America 

09:06 Navigating Logistics as Black Professionals

12:27 Family Values & Leadership Foundations 

19:29 Understanding the Corporate Game 

23:03 Diversity Challenges in the Freight Industry 

28:28 Mentorship & Creating Opportunity

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
• Instagram
• Twitter
• 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.

SUMMARY:

In this episode of the Journey podcast, Will Jenkins sits down with Justin Turner to unpack how modern revenue teams must operate in today’s market. They break down why precision now matters more than volume, how ideal customer profiles drive faster sales cycles, and why smaller teams are being held to higher revenue expectations than ever before.

The conversation covers top-of-funnel strategy, the role of intent data in warming outreach, and how revenue operations create visibility across the entire sales process. This episode is built for founders, CROs, sales managers, and revenue leaders who want cleaner pipelines, tighter focus, and more predictable outcomes.

TAKEAWAYS:

• Why revenue teams are operating in a completely different environment than just a few years ago
• How smaller sales teams are expected to hit the same or higher revenue goals
• Why top-of-funnel discipline matters more than headcount
• How to clearly define and operationalize your ideal customer profile
• How historical data reveals which customer segments actually drive revenue
• Why warm leads outperform high-volume cold outreach
• How intent data shortens sales cycles and improves conversion rates
• Where revenue operations fits into forecasting and execution
• Why sales leaders should actively audit leads and accounts
• How strong brand equity and repeatable processes support long-term sales success

CHAPTERS:

• 00:00 Introduction and context
• 01:02 How revenue functions have changed
• 02:53 Why top-of-funnel focus still drives results
• 05:21 Defining and validating your ideal customer profile
• 09:28 Using data to identify strong customer segments
• 10:49 Warm leads versus cold volume
• 12:29 Using intent signals to shorten sales cycles
• 14:16 Lead quality, accounts, and buying roles
• 17:24 Revenue operations, forecasting, and execution

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
• Instagram
• Twitter
• 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.

SUMMARY:

In this episode, host Will Jenkins sits down with Tyler Harper, Co-Founder and Chief Revenue Officer of Pinnacle Logistics Group, to break down a modern approach to LTL shipping, carrier relationships, and building a freight brokerage in a competitive market. Tyler shares how Pinnacle Logistics Group was built from the ground up, lessons from the first year in business, and why trust, consistency, and clear market positioning matter in freight entrepreneurship. The conversation covers LTL freight strategy, complex shipments, carrier sales, marketing fundamentals, and how Pinnacle delivers enterprise-level logistics solutions to mid-market shippers. This episode is packed with real-world insights for freight brokers, logistics professionals, sales leaders, and anyone interested in entrepreneurship within transportation and supply chain. 

TAKEAWAYS: 

• Tyler Harper brings a multi-disciplinary mindset to freight leadership 
• Trust with carriers is foundational to long-term brokerage success 
• Pinnacle Logistics Group specializes in complex freight, including furniture and LTL shipments 
• The first year of entrepreneurship brings both pressure and momentum 
• Pinnacle expanded from multi-stop consolidation into cross-border logistics 
• Strong market positioning helps mid-market shippers access enterprise-grade solutions 
• Consistency matters more than short-term wins in business growth 
• Team structure and shared ownership drive internal performance 
• Marketing works best when the ideal customer profile is clearly defined 
• A recent rebrand helped Pinnacle sharpen its message and presence 

CHAPTERS: 

00:00 – Introduction 

02:59 – Tyler Harper’s Background and Entry Into Freight 

06:01 – Building Pinnacle Logistics Group 

09:02 – First-Year Challenges and Early Wins 

12:06 – LTL and Complex Freight Services 

14:57 – Market Positioning and Differentiation 

18:12 – Managing Market Volatility 

21:06 – Advice for Freight Entrepreneurs 

24:03 – Team Structure and Leadership 

27:14 – Marketing Strategy in Logistics 

29:48 – What’s Next for Pinnacle Logistics Group 

WHERE TO LISTEN: 

🎥 Watch on YouTube 

🎧 Listen on Spotify 

🎙️ Listen on Apple Podcasts 

Download, subscribe, and leave a review to support the show!

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
• Instagram
• Twitter
• 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.

SUMMARY: 

In this episode of the Journey Podcast, Will Jenkins sits down with Robert Bain to talk through what actually drives success in Freight Tech sales. They break down why deep product knowledge matters, how to sell technology without overselling, and why live demos outperform polished recordings every time. The conversation covers diagnosing real customer pain points, understanding the full business lifecycle of a freight brokerage, and knowing when to walk away from the wrong deal. If you sell FreightTech, logistics software, or consulting solutions, this episode offers practical sales strategies rooted in honesty, preparation, and real-world freight experience. 

TAKEAWAYS: 

• Your solution is not a silver bullet 
• Know exactly what your product does and what it does not 
• Live demos build more trust than recorded demos 
• Ask better questions to diagnose real customer pain 
• Understand the full business lifecycle of your buyer 
• Honesty closes more deals than hype 
• Saying no often leads to better long-term sales 
• Strong sellers are meticulous about preparation 
• Deep customer understanding drives better outcomes 
• FreightTech works best when paired with freight expertise 

CHAPTERS: 

• 00:00 FreightTech Sales and Why Product Knowledge Matters 
• 02:36 Understanding FreightTech Solutions and Buyer Fit 
• 06:47 Communication Strategies That Win FreightTech Deals 
• 10:25 Why Craft and Preparation Separate Top Sellers 
• 14:55 Final Takeaways for Selling FreightTech Successfully

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
• Instagram
• Twitter
• 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.

SUMMARY:

In this episode of the Journey Podcast, host Will Jenkins sits down with Daniel Solida to break down value-based selling in the freight and logistics industry. Daniel shares his path from interning at Coyote Logistics to closing deals at MoLo and now working at Journey. The conversation focuses on how strong sales reps win by identifying a buyer’s core needs, listening closely, and aligning their approach to outcomes that actually matter to the customer. This episode gets practical fast, covering how to ask better questions, when to pause during sales calls, and how genuine rapport drives better results. For freight brokers, logistics sales reps, and anyone sharpening their sales skills, this episode offers clear takeaways you can apply right away. 

TAKEAWAYS: 

• Identify and align with the buyer’s core needs 
• Shift from features to outcomes 
• Ask sharper questions on sales calls 
• Silence leads to better answers 
• Trust drives buying decisions 

CHAPTERS: 

• 00:00 Intro 
• 00:31 Daniel Solida’s sales path 
• 05:01 What value-based selling means 
• 08:06 Active listening on sales calls 
• 12:09 Building real rapport 
• 14:11 Final takeaways

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
• Instagram
• Twitter
• 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.

SUMMARY: 

In this episode of The Journey Podcast, host Will Jenkins sits down with Matt Fain, CEO and founder of Pop Capacity, to talk warehousing, logistics technology, and where the supply chain is headed next. Matt shares how his background in electrical distribution led him into logistics and why he saw a clear gap in how companies source warehouse space. That insight became Pop Capacity, a platform built to simplify warehouse procurement through technology. The conversation covers real startup lessons, early execution decisions, customer experience, and how shifts in freight and trucking directly impact the warehousing market. Matt also breaks down how logistics companies are adapting by expanding services and paying closer attention to buyer behavior. This episode is packed with insights for logistics operators, founders, sales teams, and anyone focused on warehousing, supply chain technology, freight, and market trends. 

TAKEAWAYS: 

• Matt Fain transitioned from electrical distribution into logistics 
• A clear gap existed in how companies sourced warehouse capacity 
• Pop Capacity introduced a tech-driven approach to warehouse procurement 
• The first year of a startup shapes execution and learning 
• Customer experience drives better logistics outcomes 
• Warehousing demand is closely tied to trucking and freight cycles 
• Logistics providers are expanding services to stay competitive 
• Listening to buyers improves product decisions 
• Technology reduces friction in warehouse sourcing 
• Early funding choices influence long-term growth 

CHAPTERS: 

• 00:00 – Introduction 
• 02:05 – Matt Fain’s Background and Early Career 
• 05:57 – The Pivot to Pop Capacity 
• 10:03 – Building the Product and Early Challenges 
• 13:50 – Customer Experience and Market Signals 
• 20:05 – The Warehousing Market and Freight Impact 
• 24:08 – Expanding Services in Logistics 
• 28:00 – Target Audience and Inbound Demand 
• 32:08 – Positioning in the Market 
• 36:05 – What’s Next for Pop Capacity 

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
• Instagram
• Twitter
• 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.

SUMMARY:

In this episode of The Journey Podcast, host Will Jenkins speaks with Cameron Robertson, CEO of 3PL Systems, about his journey from a tech support role to leading a freight technology company. Cameron shares insights into his early life, career decisions, and the importance of curiosity and mentorship in professional growth. He discusses the challenges of rebuilding BrokerWare, navigating the COVID-19 pandemic as a new CEO, and the current trends in freight technology, particularly the role of AI. Cameron also highlights the upcoming projects at 3PL Systems and the company's commitment to innovation and customer satisfaction. 

TAKEAWAYS: 

• Cameron grew up in Southern California and had a passion for technology from a young age. 
• He initially planned to join the Coast Guard but shifted to a career in IT after meeting his wife. 
• Cameron joined 3PL Systems in 2011 and quickly took on various roles, showcasing his adaptability and eagerness to learn. 
• His first role was in technical support, where he learned about the freight industry by engaging directly with clients. 
• Cameron emphasized the importance of curiosity and mentorship in his career development. 
• He became CTO in 2015 and led the effort to rebuild BrokerWare from the ground up, focusing on scalability and efficiency. 
• Cameron became CEO in January 2020, just before the COVID-19 pandemic, which posed significant challenges for the business. 
• He values company culture and ensures that every employee has a voice, contributing to high employee retention. 
• Cameron believes that while AI is important, not everything should be automated, and companies need to focus on building strong foundational products. 
• 3PL Systems is launching new projects, including Freight Fusion and Shepherd AI, to enhance their offerings. 

CHAPTERS: 

• 00:00 Introduction to the Journey Podcast 
• 02:04 Cameron's Early Life and Education 
• 06:12 Career Beginnings at 3PL Systems 
• 14:33 Career Progression and Growth at 3PL Systems 
• 22:13 Transition to CTO and Rebuilding BrokerWare 
• 31:07 Becoming CEO and Navigating COVID-19 
• 37:03 Current Trends in Freight Tech and AI 
• 39:55 Future Projects and Innovations at 3PL Systems

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
• Instagram
• Twitter
• 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.