Our annual Agent Roundtable is unlike any other professional development opportunity in the freight world! And our 2025 Roundtable was no exception. This September, we rolled out the red carpet (well, actually the rooftop bar) for our freight agents at the stunning Crossroads Hotel in Kansas City. Because when you’re serious about putting agents first, you show up with more than just a conference room and stale donuts.
While other companies might talk a big game about supporting their people, we actually put our money where our mouth is. Year after year, our Agent Roundtable delivers the kind of insights, strategies and connections that transform good freight agents into great ones.
All our agents receive year-round professional development and back office support, 365 days a year. But the annual Roundtable is designed for our most ambitious agents who are ready to take their business to record-breaking levels. Whether you’re grinding to build your book or you’re running a multi-million-dollar agency, this event meets you where you are and pushes you toward where you want to be.
Learn more about the Roundtable, and what makes this professional development event unlike anything else in the freight world.
Kicking Off with Kansas City Hospitality
One of the best parts of the Roundtable? The connections. Nothing beats being in a room full of people who just get it. The grind. The wins. The challenges. That’s why we always kick things off with a chance to connect. This year, we gathered at The Percheron, the hotel’s incredible rooftop bar. With the city skyline stretching out before us, agents from all over the country settled in with drinks in hand, ready to swap stories and catch up.
New faces met veteran agents, questions were asked, laughs were shared, and the foundation for a powerful weekend was laid. As Tallgrass President Sean Richardson reminded agents, “Not everyone can do freight. But you guys are putting in the work and deserve to be rewarded.” And that really captures what Tallgrass is all about.
Planning for Your Financial Future
On Saturday morning, we were joined by our friends at Renaissance Financial for a deep dive into financial planning as a freight agent. Because as businesses grow and paychecks get bigger, knowing how to manage all those extra zeros is everything. The Renaissance team walked agents through a number of topics spanning estate planning, life insurance, and the different types of retirement accounts available to independent contractors. If there was one takeaway agents heard again and again, it was this: separate your business and personal accounts, and don’t wait to get started. The sooner you establish smart money habits, the better off you’ll be down the road.
Building Your Brand
Next up was our marketing partner, The Connection Shop. Their presentation, “The Future is Branded,” gave agents the playbook for how to stand out in a crowded freight market and actually turn that visibility into revenue. Agents walked through seven steps to build a branding strategy that works. We’re talking about intentional marketing that attracts the right customers, not just posting for the sake of posting. Agents also learned how to dig into the data to see what’s working, refine what’s not and chase real growth and quality leads.
Learning from the Best: Agent Panel Discussion
The highlight of any Roundtable is always the agent panel, and this year absolutely delivered. For four hours, some of our most successful freight brokers sat down to share their stories, strategies, and the lessons they’ve learned along the way.
They got into the nitty-gritty of CRM tips and tricks, talked through high-level business strategies and covered everything in between. They emphasized how hiring a team can be a total game-changer because it transforms your capacity, opens up new opportunities, and lets you scale in ways you just can’t when you’re a solo operation.
Our veteran agents also talked about the importance of planning ahead for seasonal changes before they hit, so you’re never caught off guard when the market shifts. They shared strategies for building carrier lanes that keep working for you long-term, and creating systems that run smoothly even when you’re not directly involved.
And with freight fraud on the rise, the panel dedicated some serious time to how best to protect yourself and your business from scams and theft. These threats are out there right now, and they can seriously damage your business if you’re not prepared.
Wrapping Up the Weekend
After the panel wrapped, agents had the rest of the afternoon to explore Kansas City. They grabbed lunch at local spots, wandered the city, and soaked in everything KC has to offer. That evening, everyone came back together for dinner. It was the perfect way to close out the weekend, reflecting on everything they’ve learned and ways to put it all into action.
Throughout the weekend, it was clear what sets Tallgrass apart from other freight brokerages. Agent Trent F. summed it up perfectly: “I can call up Sean on the weekend, and he’ll help me out. It’s the culture — it’s unlike anywhere else.” That kind of accessibility and genuine support from leadership? You just don’t find that everywhere. When asked what keeps her at Tallgrass, agent Chelsea M. didn’t even have to think about it, sharing, “The culture. The commission split. The rewards. Not a lot of companies out there pour back into their agents like Tallgrass does.”
The sense of community at these Roundtable events is something you have to experience to fully understand. Watching agents lift each other up, share what’s working (or what’s not), and build genuine friendship is what makes this event one of a kind. It’s proof that when you invest in your people, everyone wins.
We’ll See You at the Next One
That’s a wrap on another amazing Roundtable! We’re already looking forward to the next one. If you want to be part of a company that genuinely invests in your growth and success, there’s no better time than right now. Join the Tallgrass team and make sure you’re in the room for our next Agent Roundtable.