The CIO Playbook: Brian Glass on Failing Forward & Building Resilient IT Teams

🔊 In this episode of Heartbeat: Tactical Insights for CIOs, we sit down with Brian Glass, CIO of Transcend Company, to explore his journey from tech enthusiast to executive leadership at giants like GM, Volkswagen, and Ally Financial.

Brian unpacks what it really takes to lead IT in complex industries like healthcare—from building resilient teams and navigating AI disruption to fostering a culture where innovation and "failing forward" are encouraged.

We cover: ✅ Servant leadership in action
✅ Managing tech teams through constant change
✅ Aligning IT strategy with business outcomes
✅ Building a culture of accountability and innovation
✅ The real-world impact of AI in the enterprise

This episode is packed with lessons from the frontlines for CIOs ready to level up their leadership and transform their organizations.

Don’t miss Brian’s take on the future of IT leadership and why a broad, adaptable skillset is more important than ever.

**🎧 Whether you're rethinking your CRM stack or exploring AI in Salesforce, this is a must-watch for modern tech leaders.**

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00:00 Introduction to Brian Glass, CIO of Transcend
00:43 Brian's Journey to Becoming a CIO
03:45 The Importance of a Broad Skill Set in IT Leadership
05:09 Lessons from Failure: The Smart Auction Project
09:05 Empowering Teams and Fostering a Culture of Innovation
15:38 Balancing Innovation with Regulation in Healthcare IT
18:26 The Role of AI in Modern Healthcare
23:44 Guiding Principles for CIOs
24:29 Servant Leadership in IT
25:11 Building Team Connections
25:40 Remote Work Challenges
27:54 Hiring for Cultural Fit
30:58 Adapting to Modular IT Systems
37:58 Scaling from Startup to Mid-Size
41:31 Advice for Aspiring IT Leaders
43:27 Personal Passions and Leadership Philosophy
45:45 Final Thoughts and Gratitude