Building an Effective CIO Strategy for AI Success: Lessons from Hiscox’s Microsoft Copilot Rollout

Interview: Developing a CIO Strategy for Artificial Intelligence

Chris Loake joined Hiscox as group CIO in late 2023, stepping into an insurance firm already experimenting with AI through Microsoft Copilot (M365 Copilot). A longstanding Microsoft partner, Hiscox saw the rise of generative AI as an opportunity to explore new capabilities, even if the exact benefits were unclear at the start. They began by offering limited Copilot licenses to employees who applied, encouraging engagement from those who believed the tool would help them.

How AI is Shaping IT Leadership

Loake compares AI’s current impact to the internet’s early days in the late 1990s. Back then, companies scrambled to develop internet strategies, many of which lacked substance. Today, having an AI strategy is similarly essential—but it must serve as a clear guide, not just a checkbox. For Hiscox, AI is a foundational technology that will influence many aspects of the business.

The firm embraces a multi-provider approach, integrating different AI tools and models across departments as needs evolve. Flexibility is key. The company designs its operating model, architecture, and teams to pivot quickly when new AI capabilities emerge. Loake stresses making informed bets while remaining agile.

One challenge with off-the-shelf AI systems is their commoditized nature—every business has access to the same features, which makes differentiation tricky. Loake uses email as an analogy: while email is ubiquitous, how and where you use it to enhance the customer experience matters. For Hiscox, the claims process is a critical moment where empathy is vital. AI supports this differently than in insurers focused on high volume and low cost, tailoring solutions to their unique value propositions.

Insights from the Microsoft Copilot Pilot

During a six-month pilot involving 300 users, distinct user profiles emerged. Some users actively sought solutions and quickly adapted when initial attempts failed. These frequent users gained the most value. Others, curious about the technology, became internal AI champions, sharing insights and encouraging adoption through a dedicated Microsoft Teams channel.

The tool proved especially useful for roles requiring document creation from scratch or consolidation of large information sets. It also helped employees who attend many meetings by generating summaries and action points, reducing the need to attend every meeting.

Conversely, roles with fewer meetings or less need for document preparation found less benefit. Some users felt the tool didn’t fit their workflows and chose not to continue using it.

Quantitatively, the pilot found:

• 15% of users saved around one hour per day
• 20% saved about 30 minutes daily
• 20% saved 10-15 minutes
• 25% saved only a few minutes

Seeing significant time savings among a portion of users encouraged Hiscox to expand the rollout to 1,000 licenses. The application process remained to ensure commitment. Over time, the AI champions took on more formal roles, leading adoption programs and workshops, especially in claims processing.

Today, M365 Copilot is available to over 3,000 employees across 14 countries. Loake emphasizes that while usage varies, democratising AI tools helps employees feel included and equipped with modern capabilities. Executives also gain visibility into how AI is changing workflows.

Crafting a Practical CIO AI Strategy

Loake advises CIOs to focus on a limited number of high-impact AI use cases rather than spreading efforts too thin. Managing hundreds of proofs of concept that never reach production is inefficient. Instead, zero in on around five meaningful applications, rigorously test them, and scale successful pilots.

This focused approach keeps IT and business aligned as AI models mature and stabilise. When new capabilities become available, companies can deploy them quickly on a flexible platform designed to adapt.

For IT leaders and managers aiming to develop or refine their AI strategy, the key takeaways are:

• Start small but think big—test concrete use cases thoroughly
• Encourage user buy-in by giving access to those eager to experiment
• Build internal champions to support adoption and share learnings
• Design flexible architectures and teams ready to pivot
• Recognize that AI tools won’t be equally valuable to every role

AI integration is a marathon, not a sprint. A clear strategy combined with hands-on learning and adaptability will help organisations capture the most value.

For practical AI courses and training to support your AI initiatives, consider exploring resources at Complete AI Training.