Will Jenkins
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.
Author
Will Jenkins
Category
Podcast website
Latest episode
Jul 9, 2026
Where to listen?
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Episodes
Kyle Richards, Selling At A Start-Up 28.08.2025 19:15
SUMMARY: In this episode of Sales Bites, host Will Jenkins sits down with Kyle Richards, VP of Sales at CloneOps, to talk about what it takes to build sales from the ground up at a startup. Kyle shares his journey in sales, how sales strategies shift in fast-moving startup culture compared to larger organizations, and why adaptability and teamwork matter most when everything is being built from s...
Gabe Ribeiro, Pivoting with Go-To-Market Trends 21.08.2025 16:19
SUMMARY: In this episode of Sales Bites, host Will Jenkins sits down with Gabe Ribeiro, Senior Director of Partnerships & Marketing at Hey Bubba, to talk about how sales leaders can pivot with today’s go-to-market trends. They cover the shift from the traditional sales funnel to the flywheel model, the rise of partnership and relationship selling, and the role of change management in staying comp...
Michael Sternberg, Cold Calling 14.08.2025 16:51
SUMMARY: In this episode of Sales Bites, host Will Jenkins speaks with Michael Sternberg, Director of Sales at 3PL Systems, about the intricacies of cold calling in sales. They discuss the purpose of cold calling, strategies for effective outreach, overcoming fear, the importance of research and preparation, and the necessity of time management in maintaining a successful cold calling routine. Mic...
Kyle Richards, Selling to Execs 07.08.2025 21:32
SUMMARY: In this episode of Sales Bites, host Will Jenkins sits down with Kyle Richards, VP of Sales at CloneOps, to talk about what it really takes to sell to executives. From understanding the buying committee to mastering relationship building, Kyle shares how patience, transparency, and the right sales strategies can set reps apart. Whether you’re managing long sales cycles or trying to build...
Vincent Lamia, Networking & Conferences 31.07.2025 17:47
SUMMARY: In this episode of Sales Bites, host Will Jenkins sits down with Vincent Lamia, President of Business Development at Pinnacle Logistics, to explore smart sales strategies and networking tips for conferences. From building authentic relationships to navigating rejection, Vincent shares actionable insights on how to turn conversations into long-term business opportunities. Whether you're in...
Gabe Ribeiro, We're Talking About Practice 17.07.2025 16:22
SUMMARY: In this episode of Sales Bites, we’re joined by Gabe Ribeiro, Senior Director of Partnerships & Marketing at Hey Bubba, to talk about something that’s too often overlooked: practice. We cover why role playing, active listening, and creating a culture of continuous sales training are must-haves, not nice-to-haves. Gabe shares how his background in freight tech and marketing has shaped his...
Jordan Reber, Organization Skills & Discipline 10.07.2025 15:44
SUMMARY: In this episode of Sales Bites, host Will Jenkins speaks with Jordan Reber about the critical importance of organizational skills and discipline in sales. They discuss how being organized can enhance efficiency, the significance of preparation, and the role of discipline in achieving sales success. Jordan shares strategies for individual contributors and sales leaders to maintain organiza...
Vincent Lamia, Selling Within Your Niche 03.07.2025 15:41
SUMMARY: In this episode of Sales Bites, host Will Jenkins speaks with Vincent Lamia, President of Business Development at Pinnacle Logistics. They discuss the significance of niche selling in the logistics industry, emphasizing the importance of understanding the specific needs and pain points of clients within a niche. Vincent shares his experiences and insights on building credibility, the adva...
Justin Reber, What Sets You Apart From Others 26.06.2025 15:16
SUMMARY: In Episode 37 of Sales Bites, host Will Jenkins talks with Jordan Reber, Executive Vice President at ARL Network, about what sets top freight brokers apart. They dig into how to differentiate in a crowded logistics market, adapt your sales pitch to different audiences, and train new reps the right way. Jordan shares hard-won lessons on building lasting relationships, maintaining a strong...
Vincent Lamia, Building Warm Lead Funnels 12.06.2025 16:30
SUMMARY: In this episode of Sales Bites, host Will Jenkins interviews Vincent Lamia, President of Business Development at Pinnacle Logistics. They discuss Vincent's journey in sales, focusing on the importance of building warm lead funnels through a referral program. Vincent shares his strategies for generating inbound leads, managing relationships with referral reps, and optimizing daily operati...
Jordan Reber, Building Relationships 05.06.2025 15:32
SUMMARY: In this episode, Will Jenkins and Jordan Reber break down what it really takes to build long-term success in freight sales. From mastering the art of relationship-building to staying curious and patient, they share strategies that go far beyond scripts. Jordan taps into his decades of experience to explain how value-first selling, industry expertise, and genuine networking can open doors...
Lars Ward, AI Impact 29.05.2025 14:32
SUMMARY: Will Jenkins sits down with Lars Ward, VP of Automation Solutions at Transflo, to cut through the AI noise. They talk about what’s actually working today, where automation is driving real results, and why it’s time to stop chasing buzzwords and start solving real problems. Lars brings hard-won insights from across the logistics world, and makes the case for smarter, simpler tech that work...
Mike Beckwith, Setting the Tone for the Day 15.05.2025 21:46
SUMMARY: In this episode of Sales Bites, Will Jenkins sits down with Mike Beckwith, VP of Brokerage at FreightPlus, to talk mindset, prep, and why authenticity still wins in sales. Mike shares how he stumbled into logistics and built a career by focusing on real relationships, asking smarter questions, and showing up with confidence and clarity. Whether you’re just starting out or sharpening your...
Justin Turner, Good leads vs. Bad Leads 08.05.2025 17:02
SUMMARY: In this episode of Sales Bites , Will Jenkins sits down with Justin Turner, Managing Partner at Journey, to unpack the sales strategies that separate high-performing reps from the rest. They explore how to qualify leads effectively, the role of buyer personas in B2B sales, and the importance of collaboration between sales and operations. Justin also shares how to evaluate customer potenti...
Madison Santo, EQ & Sales Skills 01.05.2025 19:00
SUMMARY: In this episode of Sales Bites, host Will Jenkins speaks with Madison Santo about the importance of emotional intelligence in sales, the journey of her career in the logistics industry, and the significance of transparency and honesty in the sales process. They discuss how to navigate career transitions, the importance of understanding your buyer, and key takeaways for sales professional...
Lars Ward, Gap On Ops and Sales 17.04.2025 17:01
SUMMARY: In this episode of Sales Bites, host Will Jenkins speaks with Lars Ward, VP of Automation Solutions at Transflo, about the critical relationship between sales and operations in the freight industry. They discuss the importance of understanding operations for sales success, the need for empathy and collaboration between teams, and how fostering a culture of accountability can lead to busin...
Mike Beckwith, Sell Solutions Not Service 10.04.2025 20:11
SUMMARY: In this episode of Sales Bites, host Will Jenkins speaks with Mike Beckwith, VP of Brokerage at Freight Plus, about the evolution of sales strategies in the freight industry. They discuss the importance of transitioning from traditional pitching to a more consultative approach, emphasizing authenticity, relationship building, and the art of asking the right questions. Mike shares insights...
Justin Turner, Sales Day to Day 03.04.2025 16:37
SUMMARY: In this episode of Sales Bites, host Will Jenkins and guest and Managing Partner of Journey, Justin Turner, discuss the essential elements of successful sales strategies. They emphasize the importance of preparation, effective cold calling techniques, and the need for sales reps to understand their customers deeply. The conversation also covers the significance of planning one's day effec...
Will Hopkins, Selling Open Deck Freight 20.03.2025 14:08
SUMMARY: In this episode of Sales Bites, host Will Jenkins interviews Will Hopkins, Founder of Black Box Logistics, discussing the intricacies of open deck freight sales. They explore the importance of understanding accessorials, dimensions, and the vocabulary specific to open deck freight. Hopkins shares insights on creative approaches to sales, the significance of vetting carrier partners, and r...
Lars Ward, Freight Sales in 2025 13.03.2025 19:05
SUMMARY: In this episode of Sales Bites, host Will Jenkins speaks with Lars Ward, VP of Automation Solutions at Transflo, about the evolving landscape of freight sales in 2025. They discuss the importance of understanding shipper needs, market dynamics, and the necessity of building long-term relationships in sales. Lars shares insights on how to tailor value propositions to different shippers and...
Madison Santo, Striving to be an Independent Seller 20.02.2025 14:54
SUMMARY: In this episode of Sales Bites, host Will Jenkins speaks with Madison Santo, Growth at AVRL, about the journey to becoming an independent seller in the logistics industry. They discuss the importance of mindset, the need for industry and product knowledge, and the significance of taking action and continuous learning in sales. Madison emphasizes that sales is akin to entrepreneurship, whe...
Mike Beckwith, Know the Industry Inside-Out 13.02.2025 17:19
SUMMARY: In this episode of Sales Bites, host Will Jenkins speaks with Mike Beckwith, VP of Brokerage at FreightPlus, about his unconventional journey into the logistics industry, the importance of becoming a student of the industry, and how to effectively lead and teach others in the field. They discuss the significance of understanding market dynamics, leveraging data, and fostering a genuine in...
Madison Santo, Effective Cold Calling 30.01.2025 19:08
SUMMARY: In this episode of Sales Bites, host Will Jenkins speaks with Madison Santo, Growth at AVRL, about effective cold calling strategies. They discuss the importance of consistency, the need to sound casual rather than salesy, and techniques for grabbing attention in the first few seconds of a call. Madison emphasizes the significance of handling objections directly and the necessity of qual...
Dushawn Falls, Building Sales Funnels 23.01.2025 16:22
SUMMARY: In this conversation, Will Jenkins and Dushawn Falls, CEO of Tenacity Express, discuss the intricacies of building effective sales funnels, the importance of qualifying opportunities, nurturing customer relationships, and understanding key sales metrics. Dushawn shares his insights on how to effectively engage with prospects, the significance of personalizing communication, and the metric...
Will Hopkins, Getting Creative With Outreach 16.01.2025 13:42
SUMMARY: In this episode of Sales Bites sponsored by Revenova, host Will Jenkins engages with Will Hopkins, Founder of BlackBox Logistics, to explore creative outreach strategies in sales. They discuss the importance of building genuine relationships, the effectiveness of humor and authenticity in outreach, and practical tips for overcoming apprehension in sales roles. The conversation emphasizes...
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