
Tech Budget 2027: What AI Bets to Fund + IT/Security to Protect
We focused on technology budget planning for 2027, particularly AI funding strategies. Host Isaac Sacolick led a discussion with panelists on prioritizing AI initiatives, emphasizing strategic clarity...
21 Sep 1h 1min

The Hidden Cost of Confident AI: Semantics, Guardrails, and the Context Layer
The discussion led by Isaac Sacolick focused on AI challenges, particularly the "hallucination tax," emphasized by Felix Van de Maele, CEO of Collibra. Contributors highlighted the importance of gover...
14 Sep 1h

SaaS, Cloud, and AI Contracts: Where Technology Leaders Lose Leverage
The 186th episode of Coffee with Digital Trailblazers focused on negotiation tactics for SaaS contracts. Key topics included competitive bidding, avoiding auto-renewals, and ensuring data ownership. M...
31 Aug 1h 2min

Shadow AI at Work: Real Risks, Practical Guardrails, Hidden Innovation
The real risks and practical guardrails around shadow AI, which goes beyond traditional shadow IT with new risks including data leakage, agentic AI poor decisions, and potential legal compliance issue...
24 Aug 1h 1min

Networking in the AI Era: A Guide for Digital Transformation Leaders
An expert advisory panel discussed networking in the AI era, emphasized the importance of authenticity, curiosity, and relationship-building. Panelists explored strategies for meaningful connections a...
11 Aug 1h 1min

Evaluating Technologies in the AI Era: Value, Risk, Ecosystem Evaluation
This week's "Coffee with Digital Trailblazers" episode featured industry analyst Maribel Lopez discussing the evaluation of AI technologies. Key topics included the significance of aligning AI selecti...
31 Jul 1h 2min

Does IT Leadership in the AI Era Require an IT Background Anymore?
The 180th episode of Coffee with Digital Trailblazers explored whether IT leadership in the AI era necessitates an IT background. Host Isaac Sacolick and guests discussed the importance of IT knowledg...
17 Jul 59min




















