July 09, 2026

Kevin Miles, The RFP Game Is Changing

24 minutes

SUMMARY:

Kevin Miles, CEO of Eureeka BI, returns to The Journey Podcast to talk with Will Jenkins about the current freight market, where brokerages are feeling pressure, and how leaders should be thinking about growth right now. Kevin brings more than 20 years of supply chain experience, including time on the shipper side managing RFPs. In this conversation, he breaks down how policy changes, rising costs, technology, and AI are all hitting brokers at the same time. Will and Kevin also get into one of the biggest questions facing freight leaders today: when the market starts to move, how do you grow without spending too fast, hiring too late, or buying technology that does not solve the actual problem? This episode covers smarter RFP strategy, freight pricing, AI adoption, TMS mistakes, hiring trends, and how brokers can position themselves for the next cycle with more discipline.

TOPICS:

The current freight market and what brokers are watching

How policy changes may affect rates and capacity

Why shippers are increasing RFP cadence

How brokers can approach net-new RFP opportunities

Common mistakes in TMS and technology buying

The difference between a prototype and a working product

Where AI can help and where leaders need to be careful

Why some brokerages are hiring too reactively

How to prepare before the market fully turns

What Eureka BI is building next

TAKEAWAYS:

Brokers need to understand the business problem before adding new technology.

AI can help teams move faster, but it has to be tied to a real strategy.

A great demo does not always mean the product is ready to use.

RFPs are becoming more frequent, which creates more work for brokers and shippers.

The best RFP strategy starts with knowing where your network is already strong.

Higher revenue does not always mean true growth if load count and customer count are not expanding.

Brokerages should stay disciplined with spending, hiring, and tech adoption as the market shifts.

The teams that invested early in people, systems, and infrastructure are better positioned now.

CHAPTERS:

00:00 Introduction to The Journey Podcast

01:00 Kevin Miles returns as the first-ever Journey Podcast guest

01:18 Kevin’s background and the start of Eureka BI

03:40 Freight market pressure, policy changes, and technology shifts

05:01 Where technology implementation breaks down

07:54 AI adoption, demos, prototypes, and real-world use

11:23 Building, testing, and improving technology faster

12:06 Policy changes and the impact on capacity

13:03 Insurance costs, rate pressure, and RFP changes

15:07 Healthy growth versus market-driven revenue gains

18:05 Spending discipline during a market shift

19:02 Hiring trends across freight brokerages

21:23 How brokers should approach new RFP opportunities

23:35 What is next for Eureka BI

24:18 Closing thoughts

RESOURCES:

Eureka BI: https://www.eureekabi.com/

Kevin Miles on LinkedIn: https://www.linkedin.com/in/kwmiles/?isSelfProfile=false

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

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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.

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By Will Jenkins