George Adair of Goodwill of Colorado on Technology's Role in M&A, AI and Digital Transformation, and AI and Cybersecurity - Spotlight Interview

 George Adair of Goodwill of Colorado on Technology’s Role in M&A, AI and Digital Transformation, and AI and Cybersecurity - Spotlight Interview 

In this Technology Executives Club® Spotlight Interview, Alex Jarett sits down with George Adair, a senior technology leader at Goodwill of Colorado, to discuss mergers and acquisitions, digital transformation, AI, customer experience, and cybersecurity.

George has worked across a variety of technology environments, with digital transformation as a core focus throughout his career. Today at Goodwill of Colorado, he is helping the organization use technology, data, and AI to improve how the business operates and how customers experience its retail stores.

M&A Requires a Technology Roadmap
Mergers and acquisitions create a unique challenge for technology leaders because acquired organizations rarely begin in the same place. George explains that leaders need to understand how quickly an organization can realistically move, create the right technology roadmap, and connect those plans to the needs of the business.

He saw that firsthand at CCRM Fertility, where the organization had acquired more than 15 clinics across the United States. Those clinics had largely been operating independently, and individual locations began experiencing different technology problems without a unified approach.

George’s role was not simply to introduce a standard technology plan. He worked directly with the clinics, addressed immediate needs, created early wins, and built trust before moving them toward a broader technology strategy. He spent more than a year traveling from clinic to clinic, meeting with people, assessing what each location needed, and helping connect those needs to the larger direction of the organization.

Change Management Is Part of the Roadmap
The CCRM experience also reinforced the importance of the people side of transformation. Some acquired organizations were newer and more open to change, while others were more established and comfortable with the way they had been operating.

George says technology leaders may see a clear list of platforms, systems, and controls that should be implemented, but that does not mean every part of the organization is ready to move at the same pace. His approach was to understand where each group was in its journey and adjust the roadmap accordingly rather than force every acquired organization through the same process at the same time.

Digital Transformation Is Increasingly About AI
AI is now becoming a major part of the digital transformation work George is helping lead at Goodwill of Colorado. Rather than treating AI as a single technology purchase, the organization is actively experimenting with different tools and looking for practical business applications.

Goodwill is testing several major AI platforms through proof-of-concept initiatives. Employees from different business functions are taking portions of their existing work and asking how those processes could be improved, optimized, or made more efficient with AI. George works with those teams to develop efficiency-focused business cases and evaluate what the tools can actually do in practice.

At the time of the interview, Goodwill was several months into a number of those initiatives. The goal is not simply to experiment with AI, but to understand where different tools can create practical value before making broader decisions.

CEO Support Helps Move AI Forward
George points to executive sponsorship as one of the most important parts of the AI initiative. Goodwill’s CEO is actively supporting the work and helping identify areas where AI may create business value.

That gives the technology team a clearer connection to real business needs. Instead of IT trying to generate interest in AI from the outside, senior leadership is helping identify where the organization wants to improve and where AI may be worth exploring.

Using Technology to Improve the Retail Experience
Another major area of George’s work at Goodwill is the retail environment itself. Retail conditions can change quickly, and customer behavior, seasonal demand, local events, and broader economic factors can all influence what people may be interested in when they enter a store.

Goodwill is using technology and data to help retail managers respond more effectively. George explains that the organization is looking not only at what merchandise is available on the retail floor, but also at how it is positioned and moved so customers see the right products at the right time.

He gives a simple example involving the Denver Broncos. If the team played on Monday Night Football, managers may want Broncos merchandise presented more prominently the following day. Technology can help connect those external signals with what is happening inside the store, while AI can help turn that information into actionable insight for day-to-day merchandising decisions.

AI Is Also Changing Cybersecurity
The same AI technologies creating new opportunities are also creating new cybersecurity challenges. George points to social engineering as one area becoming increasingly difficult because employees may have a harder time determining whether a communication is coming from a real person or whether AI is being used to imitate or manipulate someone.

Those threats are also moving beyond traditional email phishing. Organizations therefore need to detect suspicious activity quickly, alert employees, and respond rapidly when something does not look right.

Using AI to Fight Against AI
George also emphasizes that cybersecurity awareness cannot remain limited to the IT department. Frontline business leaders and employees across the organization need to understand the risks because anyone can become a target of increasingly sophisticated social engineering.

At the same time, technology teams are evaluating tools that can help identify suspicious behavior and respond more quickly. George summarizes the changing environment simply: organizations are increasingly “using AI to be able to fight against AI.”

Technology Leadership Across a Changing Enterprise
George’s experience reflects how broad the technology leadership role has become. A technology leader may be helping integrate acquired companies and build the roadmap for change while also driving digital transformation, evaluating AI through proofs of concept, helping improve the customer experience, and protecting the organization from a rapidly changing cybersecurity environment.

Across each of those areas, the technology has to connect back to the business. That means understanding the people affected by change, identifying practical use cases, building the right business cases, and using technology to help the organization operate more effectively.

➡️ Watch the full Spotlight Interview with George Adair to hear his perspective on mergers and acquisitions, technology roadmaps and change management, digital transformation and AI, Goodwill of Colorado’s AI proof-of-concept initiatives, using data and AI to improve the retail customer experience, and the growing cybersecurity challenges created by AI.

*️⃣ Guest: George Adair, Senior Technology Leader, Goodwill of Colorado
*️⃣ Host: ALEX JARETT, Founder, Technology Executives Club®