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Rental Roundtable #59: What Rental Can Learn from Freight’s AI Shift

41 Min
July 9, 2025
Episode #59

Episode Overview

Jesse Buckingham, founder of Vooma and former CEO of Record360, shares how AI is transforming freight and what it means for the rental industry. He walks through a live demo of an AI voice agent booking freight calls without human involvement, explains freight’s head start on automation, and explores how similar technology could reshape invoicing, dispatch, and service in equipment rental.

Timestamps:

  • 00:57 – Jesse’s career path from Record360 CEO to Quipli advisor and founder of Vooma
  • 04:34 – Defining an AI agent and how it executes tasks like booking equipment
  • 07:11 – The “before and after” impact of AI on freight brokerage operations
  • 10:12 – Live demo of Vooma’s AI voice agent answering a call and booking freight
  • 13:34 – Best practices for transparency when customers interact with AI vs humans
  • 19:44 – How AI could transform rental by automating invoicing, billing, and customer service
  • 23:50 – Spotting the AI opportunity in 2022 before ChatGPT went public
  • 28:22 – Predictions for AI in 2028, including the path toward artificial general intelligence
  • 30:42 – Balancing AI’s risks and benefits and lessons from past technology shifts
  • 37:17 – How AI will push software from reducing clicks to eliminating them entirely

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About the Speakers

Jesse Buckingham

Jesse Buckingham

Jesse Buckingham is the founder of Vooma, an AI agent for freight brokers and carriers that automates workflows across email, text, and voice. Previously, he was CEO of a logistics software company that scaled from $2M to $20M+ ARR, a strategy consultant with Bain & Company, and earned his MBA from Stanford GSB.

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