Quit Punting on Fourth Down: Jon Gary Herrera on Taking the Risks Public Leaders Are Trained to Avoid

Season #6

Episode 51: Quit Punting on Fourth Down: Jon Gary Herrera on Taking the Risks Public Leaders Are Trained to Avoid 

“We’ve all got to be willing not to punt on fourth down when it’s necessary, and be willing to take the criticism if it doesn’t work. You’ve got to have some thick skin and know it’s not personal, but believe in what you’re doing.” ~Jon Gary Herrera 

Most public-sector leaders operate as if their customers have no alternative. Jon Gary Herrera runs VIA Metropolitan Transit as if every rider could leave tomorrow, because they can. That single shift in posture, borrowed from 18 years inside a Fortune 50 company, explains how VIA grew from fewer than 800 operators to more than 1,000, delivered the largest service change in its history, added two million trips in a year, and earned the top national ranking for customer experience three years running. In this conversation, Herrera explains how transparency and collective decision-making became the operating system for his senior team, how that same discipline produced a rare moment of full alignment with the union, and why he tells leaders to stop punting on fourth down. 

Key takeaways: 

  1. Public agencies have competitors (rideshares, private cars, bikes, walking). Know who they are so you can be the service of choose. 
  2. Tell your senior team everything you know before a big decision. Transparency is the engine of trust. 
  3. That your union the way you treat your leadership team. 
  4. Let your leaders run their departments. Your job is to keep everyone aligned, not make every decision. 
  5. Use a measured approach to AI. Decide what the technology will improve for customers and operations before you commit to it. 

 

About Jon Gary Herrera 

 

As the first Latino to lead VIA in the agency’s nearly 50-year history, President & CEO Jon Gary Herrera is guiding one of the most transformative periods in public transportation for San Antonio and Bexar County. Since joining VIA in 2017, he has helped advance major initiatives that are expanding mobility, strengthening community partnerships and preparing the region for future growth. His leadership and service have earned him numerous recognitions, including being named a 2025 South Texas Power Player and a 2025 Texas 100 honoree by The Business Journals. And while his title may be President & CEO, those who know him know his favorite role is being a connector, bringing people, ideas and opportunities together. 

 

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