Peer Power: Why Tech Leaders Need Each Other with Scott Smeester
From All Things Parking with Dani and John by John D. Conway, Dani Crain
June 5, 2025 · 1h 30m · Season 2 · Episode 21
About this episode
Scott Smeester joins Dani and John to discuss the importance of peer support among tech leaders and share insights from his entrepreneurial journey.
In this episode, John and Dani welcome tech leader and entrepreneur Scott Smeester to explore the importance of trusted insight and peer support among chief information officers (CIOs) and chief technology officers (CTOs). Scott shares how his mastermind group helps tech executives move beyond isolation and grow as strategic business leaders. From startup failures to leadership insights, this is a candid, funny, and illuminating conversation that bridges tech and parking in unexpected ways. Today’s guest is Scott Smeester, the CEO of CIO Mastermind and a self-described “geek with executive tendencies.” Join Scott and your hosts Dani Crain and John D. Conway as they get into: (8:03) Breaking Down CIOs and CTOs * The roles of CIOs and CTOs and their differences in leadership scope. * Why many CIOs struggle with communication and executive alignment. (33:49) Tech Trends & Industry Crossover * How AI, edge computing, and digital customer experiences are impacting various industries. * Why collaboration across industries is a key opportunity. (42:50) Scott’s Entrepreneurial Backstory * Scott recounts the rise and fall of Talus, his startup that nearly made it to Wall Street…
People in this episode
Hosts: Dani Crain, John D. Conway
Guest: Scott Smeester
Topics covered
- peer support
- CIOs and CTOs
- tech leadership
- entrepreneurship
- industry collaboration
- AI and technology trends
Keywords
- CIO
- CTO
- mastermind group
- tech trends
- entrepreneurial insights
- leadership
- AI
- communication
Sponsors
Laney Solutions, SpotHero, Parking Revenue Recovery Services (PRRS)
Mentioned in this episode
Organizations: CIO Mastermind
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