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AI+ITOPS Podcast - Episode 9: Sean McDermott, President and CEO, Windward Consulting Group

In Episode 9, Sean McDermott, President, CEO and Founder of Windward Consulting Group, joins the AI+ITOPS Podcast to discuss how the pandemic has impacted IT and is driving the need for AIOps.


Sean McDermott on the podcast: "AIOps is really about the processing of vast amounts of data and the ability to move into a more analytical, prescriptive and automated methodology."

For your convenience, Episode 9 is available in a shorter "express version" and a longer full interview.

You can go to the AI+ITOPS Podcast page or simply listen to or download your choice of podcast below.

If you prefer to listen via a podcast service, the AI+ITOPS Podcast is currently available on RSS Feed, Apple Podcasts, Google Podcasts, Spotify and more. Go to the AI+ITOPS Podcast page for a full list of podcast services.

Episode 9 - Express Version (21:16)

Click here for a direct MP3 download of Episode 9 - Express Version

Episode 9 - Full Interview (37:56)

Click here for a direct MP3 download of Episode 9 - Full Interview

Hot Topics

The Latest

Many organizations describe AI as strategic, but they do not manage it strategically. When AI plans are disconnected from strategy, detached from organizational learning, and protected from serious assumptions testing, the problem is no longer technical immaturity; it is a failure of management discipline ... Executives too often tell organizations to "use AI" before they define what AI is supposed to change. The problem deepens in organizations where strategy isn't well articulated in the first place ...

Across the enterprise technology landscape, a quiet crisis is playing out. Organizations have run hundreds, sometimes thousands, of generative AI pilots. Leadership has celebrated the proof of concept (POCs) ... Industry experience points to a sobering reality: only 5-10% of AI POCs that progress to the pilot stage successfully reach scaled production. The remaining 90% fail because the enterprise environment around them was never ready to absorb them, not the AI models ...

Today's modern systems are not what they once were. Organizations now rely on distributed systems, event-driven workflows, hybrid and multi-cloud environments and continuous delivery pipelines. While each adds flexibility, it also introduces new, often invisible failures. Development speed is no longer the primary bottleneck of innovation. Reliability is ...

Seeing is believing, or in this case, seeing is understanding, according to New Relic's 2025 Observability Forecast for Retail and eCommerce report. Retailers who want to provide exceptional customer experiences while improving IT operations efficiency are leaning on observability ... Here are five key takeaways from the report ...

Technology leaders across the federal landscape are facing, and will continue to face, an uphill battle when it comes to fortifying their digital environments against hostile and persistent threat actors. On one hand, they are being asked to push digital transformation ... On the other hand, they are facing the fiscal uncertainty of continuing resolutions (CR) and government shutdowns looming near and far. In the face of these challenges, CIOs, CTOs, and CISOs must figure out how to modernize legacy systems and infrastructure while doing more with less and still defending against external and internal threats ...

Reliability is no longer proven by uptime alone, according to the The SRE Report 2026 from LogicMonitor. In the AI era, it is experienced through speed, consistency, and user trust, and increasingly judged by business impact. As digital services grow more complex and AI systems move into production, traditional monitoring approaches are struggling to keep pace, increasing the need for AI-first observability that spans applications, infrastructure, and the Internet ...

If AI is the engine of a modern organization, then data engineering is the road system beneath it. You can build the most powerful engine in the world, but without paved roads, traffic signals, and bridges that can support its weight, it will stall. In many enterprises, the engine is ready. The roads are not ...

In the world of digital-first business, there is no tolerance for service outages. Businesses know that outages are the quickest way to lose money and customers. For smaller organizations, unplanned downtime could even force the business to close ... A new study from PagerDuty, The State of AI-First Operations, reveals that companies actively incorporating AI into operations now view operational resilience as a growth driver rather than a cost center. But how are they achieving it? ...

In live financial environments, capital markets software cannot pause for rebuilds. New capabilities are introduced as stacked technology layers to meet evolving demands while systems remain active, data keeps moving, and controls stay intact. AI is no exception, and its opportunities are significant: accelerated decision cycles, compressed manual workflows, and more effective operations across complex environments. The constraint isn't the models themselves, but the architectural environments they enter ...

Like most digital transformation shifts, organizations often prioritize productivity and leave security and observability to keep pace. This usually translates to both the mass implementation of new technology and fragmented monitoring and observability (M&O) tooling. In the era of AI and varied cloud architecture, a disparate observability function can be dangerous. IT teams will lack a complete picture of their IT environment, making it harder to diagnose issues while slowing down mean time to resolve (MTTR). In fact, according to recent data from the SolarWinds State of Monitoring & Observability Report, 77% of IT personnel said the lack of visibility across their on-prem and cloud architecture was an issue ...

AI+ITOPS Podcast - Episode 9: Sean McDermott, President and CEO, Windward Consulting Group

In Episode 9, Sean McDermott, President, CEO and Founder of Windward Consulting Group, joins the AI+ITOPS Podcast to discuss how the pandemic has impacted IT and is driving the need for AIOps.


Sean McDermott on the podcast: "AIOps is really about the processing of vast amounts of data and the ability to move into a more analytical, prescriptive and automated methodology."

For your convenience, Episode 9 is available in a shorter "express version" and a longer full interview.

You can go to the AI+ITOPS Podcast page or simply listen to or download your choice of podcast below.

If you prefer to listen via a podcast service, the AI+ITOPS Podcast is currently available on RSS Feed, Apple Podcasts, Google Podcasts, Spotify and more. Go to the AI+ITOPS Podcast page for a full list of podcast services.

Episode 9 - Express Version (21:16)

Click here for a direct MP3 download of Episode 9 - Express Version

Episode 9 - Full Interview (37:56)

Click here for a direct MP3 download of Episode 9 - Full Interview

Hot Topics

The Latest

Many organizations describe AI as strategic, but they do not manage it strategically. When AI plans are disconnected from strategy, detached from organizational learning, and protected from serious assumptions testing, the problem is no longer technical immaturity; it is a failure of management discipline ... Executives too often tell organizations to "use AI" before they define what AI is supposed to change. The problem deepens in organizations where strategy isn't well articulated in the first place ...

Across the enterprise technology landscape, a quiet crisis is playing out. Organizations have run hundreds, sometimes thousands, of generative AI pilots. Leadership has celebrated the proof of concept (POCs) ... Industry experience points to a sobering reality: only 5-10% of AI POCs that progress to the pilot stage successfully reach scaled production. The remaining 90% fail because the enterprise environment around them was never ready to absorb them, not the AI models ...

Today's modern systems are not what they once were. Organizations now rely on distributed systems, event-driven workflows, hybrid and multi-cloud environments and continuous delivery pipelines. While each adds flexibility, it also introduces new, often invisible failures. Development speed is no longer the primary bottleneck of innovation. Reliability is ...

Seeing is believing, or in this case, seeing is understanding, according to New Relic's 2025 Observability Forecast for Retail and eCommerce report. Retailers who want to provide exceptional customer experiences while improving IT operations efficiency are leaning on observability ... Here are five key takeaways from the report ...

Technology leaders across the federal landscape are facing, and will continue to face, an uphill battle when it comes to fortifying their digital environments against hostile and persistent threat actors. On one hand, they are being asked to push digital transformation ... On the other hand, they are facing the fiscal uncertainty of continuing resolutions (CR) and government shutdowns looming near and far. In the face of these challenges, CIOs, CTOs, and CISOs must figure out how to modernize legacy systems and infrastructure while doing more with less and still defending against external and internal threats ...

Reliability is no longer proven by uptime alone, according to the The SRE Report 2026 from LogicMonitor. In the AI era, it is experienced through speed, consistency, and user trust, and increasingly judged by business impact. As digital services grow more complex and AI systems move into production, traditional monitoring approaches are struggling to keep pace, increasing the need for AI-first observability that spans applications, infrastructure, and the Internet ...

If AI is the engine of a modern organization, then data engineering is the road system beneath it. You can build the most powerful engine in the world, but without paved roads, traffic signals, and bridges that can support its weight, it will stall. In many enterprises, the engine is ready. The roads are not ...

In the world of digital-first business, there is no tolerance for service outages. Businesses know that outages are the quickest way to lose money and customers. For smaller organizations, unplanned downtime could even force the business to close ... A new study from PagerDuty, The State of AI-First Operations, reveals that companies actively incorporating AI into operations now view operational resilience as a growth driver rather than a cost center. But how are they achieving it? ...

In live financial environments, capital markets software cannot pause for rebuilds. New capabilities are introduced as stacked technology layers to meet evolving demands while systems remain active, data keeps moving, and controls stay intact. AI is no exception, and its opportunities are significant: accelerated decision cycles, compressed manual workflows, and more effective operations across complex environments. The constraint isn't the models themselves, but the architectural environments they enter ...

Like most digital transformation shifts, organizations often prioritize productivity and leave security and observability to keep pace. This usually translates to both the mass implementation of new technology and fragmented monitoring and observability (M&O) tooling. In the era of AI and varied cloud architecture, a disparate observability function can be dangerous. IT teams will lack a complete picture of their IT environment, making it harder to diagnose issues while slowing down mean time to resolve (MTTR). In fact, according to recent data from the SolarWinds State of Monitoring & Observability Report, 77% of IT personnel said the lack of visibility across their on-prem and cloud architecture was an issue ...