How intelligent systems are evolving: Rob Green, CDO at Insight Enterprises

In this wide-ranging conversation, we sat down with Rob Green, Chief Digital Officer, Insight Enterprises to explore the rapid evolution of intelligent systems, the shift toward agentic AI, and the profound implications these advancements hold for enterprises. The discussion delves into the breakthroughs driving next-generation automation, the strategic choices shaping product innovation, and the responsibility leaders carry as AI becomes deeply embedded in everyday workflows. This interview offers a clear, grounded view of where the field is headed—and what it will take to get there.

A CDO's point of view

My role at Insight shapes how I think about security, AI, and IT investments. I also view my organization as “client zero” for Insight, meaning everything we do internally serves as a model for what we would implement for clients. I am Insight’s Chief Digital Officer, responsible for our client-facing digital platforms and our internal systems.

I joined Insight four years ago after a decade at Amazon. Initially, I focused on the digital experience for clients, and during the first few years, we invested heavily in improving that experience. We operate a large e-commerce engine, a cloud platform, and a managed services business supported by a digital platform.

Over the last two years, I have worked closely with our internal IT team. We merged our digital and IT teams into a single organization given the deep dependencies between internal and external platforms. We are now concentrating on modernizing core internal systems. When I think about priorities and investments in security, I consider both Insight’s needs and how we can serve as a reference for our services and sales organizations, because many of the challenges we face are the same ones our clients encounter.

Although I view my team as client zero, we are also a literal client of Insight. Our managed SOC is supported by Insight, and we leverage talent in India as additional development capacity. My dedicated development team works with our services organization when additional capacity is required. This interconnected relationship informs how I think about priorities, which mirror those of our clients.

Given that you met Joyce earlier, I assume you have general context on Insight and our strategy.

Operational Challenges & Cybersecurity Priorities

Insight has multiple verticals, platforms, and solutions. With such a large surface area, cybersecurity risks also increase. What operational challenges do you face as CDO when it comes to securing the organization?

Our primary focus is securing the digital perimeter. We have an e-commerce platform, a cloud platform, and a managed services platform. These platforms serve as entry points for clients but also represent potential attack vectors. Securing the perimeter is the top cybersecurity priority.

Over the last two years, we have invested significantly in identity and access management. We are also leveraging AI tools for large-scale threat detection. If we keep external threats out, internal controls become easier to manage, though we remain vigilant internally as well.

Another key area is security-by-design. Every new application or agent we develop embeds security as a foundational requirement. Finally, we rely on internal capabilities and partner technologies, such as Microsoft and Palo Alto Networks, to deploy agentic threat detection and other advanced security measures at scale.

Security Framework & Zero Trust

How does your security framework look? Have you adopted a zero-trust environment?

Yes, we operate on a zero-trust model and corresponding policies. An additional advantage of being a major Microsoft partner is that we received early access to ChatGPT, which we deployed internally as “InsightGPT.” We launched it early to develop AI capabilities within our services, solutions, and IT teams.

We recognised the need for clear guidelines around AI usage and deployment. Our AI usage policies, first introduced two years ago, ensure employees understand how to implement and experiment with AI responsibly. These policies are continuously updated, our most recent revision was released three weeks ago. Regulatory and compliance requirements vary by region, and our policies are adapted accordingly.

AI as Both Protector and Threat

AI enhances security but also enables cybercriminals. How do you advise clients to defend against AI-enabled threats?

Our guidance mirrors our internal approach. Securing the digital perimeter remains the most critical priority. We advise clients on implementing tools, platforms, and procedures that prevent unauthorised access. Given our extensive partnerships across the cybersecurity landscape, we also help clients adopt best-in-class capabilities introduced by our partners.

Return on Investment (ROI) from AI

AI adoption is costly. How is AI delivering tangible ROI for your organisation?

First, we ensure awareness and education across the organization. Not everyone needs to be an AI developer, but we want employees to be fluent with AI tools and understand how to use them productively. We recently launched the AI Flight Academy, which includes five proficiency levels. A large portion of employees is expected to reach advanced levels.

Our mission has evolved, we aim to be a leading AI-first solutions integrator. To support this, my team is building platforms that enable agentic capabilities across shared functions such as finance, HR, IT, warehouse operations, and marketing.

InsightGPT has become our internal deployment platform for agents. It has also evolved into a multi-model platform, providing access to AWS Bedrock, Llama, Claude, Gemini, and others. Employees can choose the optimal model for the task. Beyond this, we are ensuring widespread certifications in tools like GitHub Copilot, Microsoft 365 Copilot, Fabric, and Databricks. By year-end, we expect 100% coverage for the services group.

Upskilling the Partner Ecosystem

Insight has a large ecosystem of employees and partners. How do you upskill them?

We have approximately 14,000 employees globally, all of whom have access to the AI Flight Academy. Within our partner ecosystem, Microsoft, Google, AWS, Cisco, and others, we leverage the AI capabilities they introduce and guide clients on how to implement them. For example, Microsoft’s Copilot Studio is a powerful agentic development platform that we use internally and recommend to clients.

Impact of Agentic AI on B2B Client Relationships

How will agentic AI transform the relationship between B2B clients and technology providers?

A concrete example is our client-specific catalogs on Insight.com. Historically, these catalogs required significant manual configuration based on client preferences. We are now introducing agentic capabilities that automate and streamline procurement workflows. This will significantly improve the digital interaction between Insight, its partners, and clients.

More broadly, as agentic capabilities proliferate, our solutions architects must stay aligned with innovations from partners to guide clients effectively. We are also developing new capabilities to help clients prioritize AI use cases, details on this will be shared in the coming months.

India’s Role in Insight’s Global Strategy

How do you position India in your global growth strategy?

India is central to our talent strategy. I have visited many times over the past 20 years and am consistently impressed by the depth of talent here. One of the largest teams in my organization operates across 10 cities in India, reflecting the broad availability of high-quality talent nationwide.

India will remain a key investment geography for Insight. The development teams here are heavily engaged in AI. A new agentic capability launching on Insight.com in three weeks was predominantly built by our India teams, with over 60% of its code generated using AI tools.

Regulatory Alignment Across Geographies

How do you manage varying regulatory frameworks like GDPR and India’s DPDP Act?

Staying aligned with regulatory requirements across geographies is a continuous challenge. We work closely with our compliance team to ensure our policies are adaptable. Our recent AI usage policy refresh reflects the latest global developments.

There are common themes across major jurisdictions, the EU AI guidelines, California’s upcoming regulations, Colorado’s policies, and India’s DPDP Act. We create general policies that can be customized for local requirements.

Can you give one or two examples of regulatory hurdles you face?

A specific example is the stringent data residency and usage requirements for UK public sector data. We must maintain dedicated infrastructure and policies to meet those requirements. All UK public-sector data remains within UK borders. Continental Europe has similar requirements under GDPR, though the UK’s rules are more prescriptive.