What happens when you try to monitor something fundamentally unpredictable? In this featured guest episode, Wayne Segar from Dynatrace joins Corey Quinn to tackle the messy reality of observing AI workloads in enterprise environments. They explore why traditional monitoring breaks down with non-deterministic AI systems, how AI Centers of Excellence are helping overcome compliance roadblocks, and why “human in the loop” beats full automation in most real-world scenarios.

From Cursor’s AI-driven customer service fail to why enterprises are consolidating from 15+ observability vendors, this conversation dives into the gap between AI hype and operational reality, and why the companies not shouting the loudest about AI might be the ones actually using it best.

Show Highlights

(00:00) - Cold Open
(00:48) – Introductions and what Dynatrace actually does

(03:28) – Who Dynatrace serves

(04:55) – Why AI isn't prominently featured on Dynatrace's homepage

(05:41) – How Dynatrace built AI into its platform 10 years ago

(07:32) – Observability for GenAI workloads and their complexity

(08:00) – Why AI workloads are "non-deterministic" and what that means for monitoring

(12:00) – When AI goes wrong

(13:35) – “Human in the loop”: Why the smartest companies keep people in control

(16:00) – How AI Centers of Excellence are solving the compliance bottleneck

(18:00) – Are enterprises too paranoid about their data?

(21:00) – Why startups can innovate faster than enterprises

(26:00) – The "multi-function printer problem" plaguing observability platforms

(29:00) – Why you rarely hear customers complain about Dynatrace

(31:28) – Free trials and playground environments

About Wayne Segar

Wayne Segar is Director of Global Field CTOs at Dynatrace and part of the Global Center of Excellence where he focuses on cutting-edge cloud technologies and enabling the adoption of Dynatrace at large enterprise customers. Prior to joining Dynatrace, Wayne was a Dynatrace customer where he was responsible for performance and customer experience at a large financial institution.

Links

Dynatrace website: https://dynatrace.com

Dynatrace free trial: https://dynatrace.com/trial

Dynatrace AI observability: https://dynatrace.com/platform/artificial-intelligence/

Wayne Segar on LinkedIn: https://www.linkedin.com/in/wayne-segar/

Sponsor

Dynatrace: http://www.dynatrace.com

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