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June 18, 2025 41 mins

This week on the Oakley Podcast, host Jeremy Kellett chats with Jason Webb & Bradley Simpson, Operations Managers at Oakley Trucking. During the conversation, the group provides an insider's view of managing bulk freight across pneumatic and end dump divisions. They discuss the challenges of coordinating over 900 owner operators, emphasizing the critical importance of communication, customer service, and building strong relationships. With over 1,000 customers and opportunities for growth, the podcast highlights how Oakley's success stems from reliable drivers, strategic operations, and a commitment to solving problems quickly. The conversation also reveals the complex world of trucking, where technology, customer expectations, and operational efficiency intersect to create a thriving business. Don’t miss this episode!

Key topics in today’s conversation include:

  • Previewing Today’s Episode (0:12)
  • Role of Operations Managers and Dispatchers (4:04)
  • Current State of Freight: End Dumps and Pneumatics (7:14)
  • Challenges: Capacity and Missed Opportunities (10:00)
  • Customer Base and Untapped Potential (12:54)
  • Communication: The Key Challenge (15:06)
  • Booking Loads: Then vs. Now (17:23)
  • Building Customer Relationships (20:13)
  • Oakley’s Competitive Edge (22:12)
  • Customer Feedback and Owner-Operator Excellence (25:09)
  • Importance of Customer Service and Owner-Operator Standards (30:04)
  • Behind-the-Scenes Operations and Trust (33:33)
  • Looking to the Future (37:18)
  • Final Thoughts and Takeaways (39:23)

Oakley Trucking is a family-owned and operated trucking company headquartered in North Little Rock, Arkansas. For more information, check out our show website: podcast.bruceoakley.com.

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