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The Journey Podcast covers freight brokerage sales, recruiting, market conditions, and the technology brokers are using to compete right now. Hosted by Will Jenkins — who's spent years building and scaling freight brokerages — every episode draws from Journey's hands-on work with hundreds of freight companies. The context is always freight-specific. If you run a brokerage, sell freight, or hire for one, this is the show.

Freight Brokerage Sales, Recruiting & Market Insights
From People Who've Actually Done It

Journey Podcasts Episodes

Episode
75
Michael Sternberg, Referrals
Michael Sternberg of 3PL Systems explains how to build a freight referral engine — why trust and consistency are the prerequisites, how to structure incentives, and when you've actually earned the right to ask a customer to refer you.
Episode
74
Krystian Gebis, The Art of Email Communication
Krystian Gebis, CEO of ShipperCRM and co-founder of FreightCaviar, unpacks what makes freight sales emails actually get responses — brevity, personalization, and the authenticity that separates email that earns attention from email that fills inboxes.
Episode
73
Kyle Richards, Difference Between Brokerage and Freight Tech Sales
Kyle Richards of CloneOps breaks down what makes freight tech sales fundamentally different from brokerage sales — from navigating enterprise buying groups to understanding how AI in logistics is reshaping what buyers evaluate and expect.
Episode
72
Gabe Riberio, Building Real Relationships In A World Filled with AI
Gabe Ribeiro explains why authentic human relationships remain the foundation of freight sales even as AI and automation reshape outreach — and how to combine technology with genuine connection to build something AI can't replicate.
Episode
71
Michael Sternberg, Pipeline Management
Michael Sternberg, Director of Sales at 3PL Systems, breaks down freight sales pipeline management — how to understand where prospects actually are, create value at each stage, and use internal events and communication to keep deals moving.
Episode
70
Megan Masud & Sarah Hanna, Mental Health and Compliance
Megan Masud and Sarah Hanna, co-founders of Competum Collective, share how their company is tackling mental health support, compliance education, and affordable healthcare for truck drivers — the people whose wellbeing the freight industry depends on.
Episode
69
Kyle Richards, Selling At A Start-Up
Kyle Richards, VP of Sales at CloneOps, shares what freight tech startup sales requires that established-company sales doesn't — the adaptability, the collaboration, and the willingness to build process while simultaneously executing against it.
Episode
68
Gabe Ribeiro, Pivoting with Go-To-Market Trends
Gabe Ribeiro of Hey Bubba shares how freight sales leaders can adapt their go-to-market approach to current trends — the shift from funnel to flywheel thinking, the rise of partnership selling, and what change management looks like inside a freight sales organization.
Episode
67
Michael Sternberg, Cold Calling
Michael Sternberg, Director of Sales at 3PL Systems, breaks down what effective freight cold calling actually requires — research before the dial, the right opening structure, time management for sustainable activity, and treating calls as learning opportunities, not just sales attempts.
Episode
66
Kyle Richards, Selling to Execs
Kyle Richards, VP of Sales at CloneOps, breaks down what it takes to sell to freight executives — how to navigate buying committees, manage long sales cycles, and build the C-suite trust that closes deals at the highest level.
Episode
65
Vincent Lamia, Networking & Conferences
Vincent Lamia of Pinnacle Logistics shares a practical approach to networking at freight conferences — how to prepare, how to turn conversations into long-term business opportunities, and why the reps who show up with a plan consistently outperform those who just show up.
Episode
64
CJ Johnson, No Shortcuts in This Game
CJ Johnson, founder of BWS Logistics, shares what building a 3PL from scratch actually taught him — that entrepreneurial grit, sales fundamentals, and the willingness to handle complex freight without shortcuts is what builds something real.
Episode
63
Gabe Ribeiro, We're Talking About Practice
Gabe Ribeiro of Hey Bubba makes the case for deliberate practice in freight sales — why role-playing, active listening, and continuous coaching aren't nice-to-haves but the actual mechanism for developing reps who perform under pressure.
Episode
62
Jordan Reber, Organization Skills & Discipline
Jordan Reber of ARL Network explains why organizational skills and daily discipline are the underrated foundation of freight sales performance — and how both individual reps and sales leaders can build the habits that sustain results over time.
Episode
61
Vincent Lamia, Selling Within Your Niche
Vincent Lamia of Pinnacle Logistics explains why freight brokers who specialize in a niche build more credibility, close more deals, and retain accounts longer than those who try to serve every type of freight.
Episode
60
Jordan Reber, What Sets You Apart From Others
Jordan Reber of ARL Network breaks down what actually differentiates top freight brokers — how to adapt your sales pitch across audiences, train new reps the right way, and build a reputation for integrity that outlasts any market cycle.
Episode
59
Elizabeth Moscoso, A Second-Gen Freight Story
Elizabeth Moscoso, President of Moscoso Express, shares what it means to lead a second-generation trucking company specializing in air freight — and the leadership, technology, and retention challenges that come with building on what your family started.
Episode
58
Vincent Lamia, Building Warm Lead Funnels
Vincent Lamia of Pinnacle Logistics shares how to build warm lead funnels in freight sales through structured referral programs — replacing cold call dependency with inbound leads generated by relationships that compound over time.
[Podcast]

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