Will Jenkins

The Journey Podcast

Business EN ↓ 95 episodes

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

Business

Latest episode

Jul 9, 2026

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Episodes

Special Edition: Journey Turns 1 03.12.2025

SUMMARY: Will Jenkins and Erin Sweeney reflect on the first year of Journey, discussing their personal and professional journeys that led to the founding of the company. They explore the importance of mentorship, the evolution of their brand, the significance of training, and the key hires that have shaped their team. The conversation highlights their commitment to authenticity, diversity, and del...

Journey & Shipper CRM, Elevating Freight Sales with Tech 03.12.2025

SUMMARY:  In this special edition of Choppin' It Up, Will Jenkins interviews Krystian Gebis, CEO & Co-Founder of Shipper CRM and Co-Founder of FreightCaviar. They discuss Krystian's Journey from computer engineering to building self-driving trucks and eventually creating Shipper CRM. The conversation covers the evolution of Shipper CRM, its current state, and future aspirations, including the impo...

Chadd Olesen, The Power of Automation: AVRL’s Impact on Logistics 03.12.2025

SUMMARY:  In this episode of Choppin' It Up, Will Jenkins interviews Chadd Olesen, CEO of AVRL, discussing his journey from a small-town upbringing to launching a successful voice technology company. Chadd shares insights on work ethic, the evolution of AVRL, and the importance of customer relationships and implementation in the tech industry. He emphasizes the need for innovation and collaboratio...

Michael Horvath, Building Revenova: A Cloud-Based TMS 03.12.2025

SUMMARY: In this episode of Choppin' It Up, host Will Jenkins interviews Michael Horvath, Co-Founder and COO of Revenova. Mike shares his journey from a musician to a successful entrepreneur in the tech industry, detailing his experiences in various roles, the founding of Forseva, and the subsequent creation of Revenova. The conversation explores themes of innovation, collaboration, and the import...

Amado Cruz, National Truck Driver Appreciation Week Edition 03.12.2025

SUMMARY: In this episode of Chopping It Up, host Will Jenkins interviews Amado Cruz, CEO and Founder of Limitless Carriers. Amado shares his journey from being a truck driver to becoming a successful trucking company owner. He discusses the importance of understanding the trucking industry, the challenges faced by drivers, and the strategies he employed to grow his business. Amado emphasizes the s...

Steve Zambo, Growing Up In Freight 03.12.2025

SUMMARY: Steve Zambo, CEO and founder of AGL, shares his background and journey in the freight industry. He grew up in a logistics household and interned at a freight forwarding company before exploring other industries like marketing and telecom. Eventually, he decided to start his own company and moved to Los Angeles to open a branch for an IT recruiting organization. During this time, he learne...

Kristy Knichel, Building Confidence as a CEO 03.12.2025

SUMMARY: In this episode of Choppin' It Up, Will Jenkins interviews Kristy Knichel, President and CEO of Knichel Logistics. Kristy shares her career journey and the growth of her company from a two million dollar business to a hundred million dollar company. She discusses the importance of having a niche and being really good at a few modes and commodities. Kristy also emphasizes the significance...

Kary Jablonski, Lessons Learned as a Leader 03.12.2025

SUMMARY:  Kary Jablonski, CEO of Trucker Tools, shares her background and career journey in this conversation. She discusses her experience as a certified archery instructor, growing up in Boston with two brothers, and the impact of attending an all-girls summer camp. Kary talks about her college years at Georgetown, where she studied economics and government, and her time working at Deloitte as a...

Morgan MacDermaid, Life On Your Own Terms 03.12.2025

SUMMARY:  Will Jenkins interviews Morgan MacDermaid, previously Sr. Recruiting Advisor at Journey. Morgan shares her career journey, which includes working at Disney World, backpacking around the world, and working odd jobs in different countries. She eventually found her way into the transportation industry and became a successful recruiter. Morgan discusses the importance of taking risks, learni...

Sebastian Pedraza, Entrepreneurship, Ambition, & Automation 03.12.2025

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 e...

Joy Stephens, Finding Your Authentic Path to Success 03.12.2025

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 bu...

The Women of Journey, Women's History Month Edition 03.12.2025

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 f...

Liz Wayne, Building a Successful Brokerage with Resilience & Adaptability 03.12.2025

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 organizationa...

Germaine Harris & Walter Hughes, Black History Month Edition 03.12.2025

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 b...

Adrian Dodds, A Career In Sales & Transportation 03.12.2025

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 makin...

Kevin Miles, Tackling The Complex Pricing Problem 03.12.2025

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 c...

Dan Solida, Building Trust & Rapport 20.11.2025

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...

Robert Bain, Partnerships 13.11.2025

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 su...

Krystian Gebis, Mental Alignment 30.10.2025

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 op...

Daniel Solida, Professional Persistence 23.10.2025

SUMMARY: In this episode of Sales Bites, host Will Jenkins sits down with Daniel Solida to unpack what professional persistence really 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...

Michael Sternberg, Referrals 09.10.2025

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 exp...

Krystian Gebis, The Art of Email Communication 02.10.2025

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 outre...

Kyle Richards, Difference Between Brokerage & Freight Tech Sales 25.09.2025

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 th...

Gabe Riberio, Building Real Relationships In A World Filled with AI 18.09.2025

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 relationshi...

Michael Sternberg, Pipeline Management 11.09.2025

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...

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