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What if you could gain insight from a man who started as a sales guy and climbed the ladder all the way to CEO of a publicly traded brokerage? Our guest this week, Drew Wilkerson, takes us on a thrilling journey of his career, and if you're a fan of incredible success stories, you're in for a treat. From his humble beginnings at CH Robinson in 2006, Drew shares how he harnessed the power of relationships and excellent customer service to rise through the ranks to where he is today - at the helm of RXO.
This episode could serve as a masterclass on leadership, as Drew walks us through how he went from being an individual contributor to eventually overseeing 7,500 people today. He talks about the importance of transparency, alignment of employees through a powerful mission and pointed surveys, an open-door policy, and more. It's no surprise Brad Jacobs saw the potential and chose to mentor him, which made him an excellent fit to lead RXO as it was spun-off from XPO as the new asset-light transportation business.
We hit on additional specific topics including managing through COVID, making and communicating difficult decisions around in-office versus remote work policies, dealing with investors in the public eye, and much more.
Enjoy this episode of The Freight Pod.
Follow The Freight Pod and host Andrew Silver on LinkedIn.
*** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more.
A special thanks to our additional sponsors:
By Andrew Silver4.8
6969 ratings
What if you could gain insight from a man who started as a sales guy and climbed the ladder all the way to CEO of a publicly traded brokerage? Our guest this week, Drew Wilkerson, takes us on a thrilling journey of his career, and if you're a fan of incredible success stories, you're in for a treat. From his humble beginnings at CH Robinson in 2006, Drew shares how he harnessed the power of relationships and excellent customer service to rise through the ranks to where he is today - at the helm of RXO.
This episode could serve as a masterclass on leadership, as Drew walks us through how he went from being an individual contributor to eventually overseeing 7,500 people today. He talks about the importance of transparency, alignment of employees through a powerful mission and pointed surveys, an open-door policy, and more. It's no surprise Brad Jacobs saw the potential and chose to mentor him, which made him an excellent fit to lead RXO as it was spun-off from XPO as the new asset-light transportation business.
We hit on additional specific topics including managing through COVID, making and communicating difficult decisions around in-office versus remote work policies, dealing with investors in the public eye, and much more.
Enjoy this episode of The Freight Pod.
Follow The Freight Pod and host Andrew Silver on LinkedIn.
*** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more.
A special thanks to our additional sponsors:

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