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PODCAST

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.

business careers

All Episodes

00:54:17

Sebastian Pedraza, Entrepreneurship, Ambition, &...

The Journey Podcast ·

2025/12/03

SUMMARY: Sebastian Pedraza, Co-Founder and Chief Revenue officer of Oko, takes us on a journey through his career journey. From his formative years in Colombia, where his fascination with math & science took root, to his collegiate days balancing football & school, Sebastian shares how these experiences instilled in him crucial skills like discipline and time management. Sebastian recounts his early career days through internships and sales roles, culminating in a pivotal position in chemical

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00:35:29

Joy Stephens, Finding Your Authentic Path to Success

The Journey Podcast ·

2025/12/03

SUMMARY:Joy Stephens, Chief Consultant at New Heights Academic and Leadership Consulting, shares her career journey and the pivotal moments that led her to her current role. She discusses her early aspirations to be an actress, her background in engineering, and her transition into sales and leadership consulting. Joy emphasizes the importance of knowing oneself and being authentic in order to build trust and successful relationships. She also mentions upcoming events and her YouTube channel, 'A

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00:40:40

The Women of Journey, Women's History Month Edition

The Journey Podcast ·

2025/12/03

SUMMARY:Erin Sweeney, Maya Quijada, Nicki Childers and Morgan MacDermaid discuss their career journeys as women in & out of the transportation industry in honor of Women's History Month. They share their experiences of being the only woman in the room, facing stereotypes and objectification, and the challenges of being a woman in a male-dominated industry. They also talk about the importance of female leaders who have supported and empowered them, the need for transparency and allyship, and the

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00:36:21

Liz Wayne, Building a Successful Brokerage with...

The Journey Podcast ·

2025/12/03

SUMMARY:In this episode, Will Jenkins interviews Liz Wayne, Founder & CEO of Able Transport Solutions. Liz shares her career journey in the logistics industry, starting from her early days as a receptionist at a trucking company to eventually starting her own brokerage. She discusses the challenges and successes she faced along the way, including building a sales team and navigating organizational changes. Liz also highlights her involvement in the Women in Logistics Committee and upcoming events in

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00:44:04

Germaine Harris & Walter Hughes, Black History Month...

The Journey Podcast ·

2025/12/03

TAKEAWAYS:Representation on social media is important for black professionals to celebrate their success and inspire others.Sponsorship is crucial for black professionals to advance in their careers and gain access to opportunities.Sharing knowledge and helping others is a powerful way to create change and support the success of black individuals.Education and self-advocacy are key for young black professionals to thrive in their careers. CHAPTERS:00:00 Introduction and Career Backgrounds03:06

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00:49:48

Adrian Dodds, A Career In Sales & Transportation

The Journey Podcast ·

2025/12/03

SUMMARY:On this episode, Adrian Dodds shares his career journey in the supply chain industry. He discusses leaving Coyote for a new opportunity and the lessons he learned. Adrian emphasizes the importance of culture and leadership access, highlighting the value of working at Arrive Logistics. He also talks about his approach to sales and sales management, focusing on building confidence and making customers look good. Adrian shares his experience working at Amazon Freight and navigating a large

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00:39:20

Kevin Miles, Tackling The Complex Pricing Problem

The Journey Podcast ·

2025/12/03

SUMMARY:Kevin Miles, co-founder and CEO of Eureka BI, shares his journey in the logistics industry and the development of his company. He discusses his background, education, and early experiences working at UPS and a retail grocery chain. Kevin explains the pain points in the bidding process for brokers and how Eureka BI aims to solve them. He highlights the importance of customer feedback and collaboration in product development. Kevin also emphasizes the significance of sales skills and personal

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00:17:28

Dan Solida, Building Trust & Rapport

The Journey Podcast ·

2025/11/20

SUMMARY: In this Sales Bites episode, Will Jenkins sits down with Dan Solida to talk about what really builds strong customer relationships. It is not scripts or canned lines. It is trust. It is rapport. It is the ability to connect with someone on a real level. Dan explains why personal connection is the foundation of every long-term business relationship. He shares the customers he still talks to years later and how simple conversations about life, sports, and everyday things created trust that

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00:17:42

Robert Bain, Partnerships

The Journey Podcast ·

2025/11/13

SUMMARY:In this episode of Sales Bites, host Will Jenkins and guest Robert Bain discuss the critical role of partnerships in the logistics industry. They explore how effective partnerships can reduce customer acquisition costs, build trust, and enhance service delivery. The conversation emphasizes the importance of vetting potential partners and developing relationships that can lead to mutual success. They also introduce the 'Crawl, Walk, Run' approach to building partnerships, highlighting that

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00:19:52

Krystian Gebis, Mental Alignment

The Journey Podcast ·

2025/10/30

SUMMARY: In this episode of Sales Bites, host Will Jenkins sits down with Krystian Gebis to talk about mental alignment in sales and why mindset matters just as much as skill. They unpack how to stay consistent through rejection, build genuine customer relationships, and separate personal goals from customer needs. The conversation dives into the power of persistence in follow-ups, qualifying opportunities effectively, and creating long-term trust instead of chasing short-term wins. If you’ve ever

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00:17:28

Daniel Solida, Professional Persistence

The Journey Podcast ·

2025/10/23

SUMMARY:In this episode of Sales Bites, host Will Jenkins sits down with Daniel Solida to unpack what professional persistencereally looks like in sales.They discuss why many reps give up too soon, how to stay consistent with outreach strategies, and the mindset needed to build long-term success in a sales organization. Daniel shares lessons from his own experience managing teams and improving customer engagement, including how to write relevant emails, stay organized, and follow up with purpose.If

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00:14:31

Michael Sternberg, Referrals

The Journey Podcast ·

2025/10/09

SUMMARY:In this episode of Sales Bites, host Will Jenkins sits down with Michael Sternberg, Director of Sales at 3PL Systems, to unpack the power of referrals in driving real sales growth. They explore how trust and consistency turn customers into your strongest advocates, why incentives matter, and how to earn the right to ask for referrals. Michael shares proven referral strategies from his experience in sales and logistics, highlighting why your most loyal customers often make the best

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00:17:46

Krystian Gebis, The Art of Email Communication

The Journey Podcast ·

2025/10/02

SUMMARY:In this episode of Sales Bites, host Will Jenkins sits down with Krystian Gebis, Co-Founder of FreightCaviar and CEO of ShipperCRM, to unpack the art of writing sales emails that actually get responses. They discuss why most emails go unread, how brevity and personalization change the game, and why authenticity always beats fluff. Krystian shares tactics on crafting short, impactful outreach, the role of open-ended questions, and how to use social proof to build credibility. This episode is

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00:18:49

Kyle Richards, Difference Between Brokerage & Freight...

The Journey Podcast ·

2025/09/25

SUMMARY:In this episode of Sales Bites, host Will Jenkins sits down with Kyle Richards, VP of Sales at CloneOps, to talk about what drives success in freight tech sales. From moving out of brokerage and into tech, to navigating enterprise buying groups, Kyle shares firsthand insights on the sales process, adoption, and relationship building.They also break down how AI in logistics is shaping the future of sales, why implementation and adoption make or break deals, and what sales leaders should focus

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00:17:29

Gabe Riberio, Building Real Relationships In A World...

The Journey Podcast ·

2025/09/18

SUMMARY:In this episode of Sales Bites, host Will Jenkins sits down with Gabe Ribeiro to discuss why authentic relationships remain the foundation of successful sales, even in an age dominated by AI and automation. They share proven sales strategies that combine technology with genuine human interaction, focusing on active listening, authenticity, and personal development. From subtle relationship cues to avoiding shortcuts that feel inauthentic, this conversation explores how sales professionals

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00:15:54

Michael Sternberg, Pipeline Management

The Journey Podcast ·

2025/09/11

SUMMARY:In this episode of Sales Bites, host Will Jenkins and guest Michael Sternberg discuss the intricacies of pipeline management in sales. They explore the importance of understanding where prospects are in the sales funnel, the need for creating value, and the significance of building relationships. The conversation delves into strategies for moving prospects through the funnel, the role of internal events in driving sales, and the importance of effective communication throughout the sales

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00:19:15

Kyle Richards, Selling At A Start-Up

The Journey Podcast ·

2025/08/28

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 scratch. They break down how sales pitches evolve alongside the product and market, what to focus on to

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00:16:19

Gabe Ribeiro, Pivoting with Go-To-Market Trends

The Journey Podcast ·

2025/08/21

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 competitive.The conversation digs into why buyers are more educated than ever, how to leverage data for

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00:16:51

Michael Sternberg, Cold Calling

The Journey Podcast ·

2025/08/14

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. Michael emphasizes that cold calling is not just about making sales but about learning and understanding

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00:21:32

Kyle Richards, Selling to Execs

The Journey Podcast ·

2025/08/07

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 trust with C-suite buyers, this conversation is packed with real-world insight on how to improve your

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61 results

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