INVITE-ONLY INSURANCE EXECUTIVE ROUNDTABLE
AI in Insurance: Avoiding Common Pitfalls to DeliverEnd-to-End Effectiveness
A private roundtable for insurance leaders responsible for AI, data, digital transformation and technology strategy.
📅 Tuesday, August 20th, 2026
⏰ 12:00 PM – 2:00 PM
📍 Bentley Restaurant, 27 O'Connell Street, Sydney
Most insurers have already invested in AI. The challenge now isn't adoption, it's delivering measurable value at enterprise scale.
A proof of concept can look impressive and still fail in production. Governance gaps only emerge when decisions need to be explained. Integration that looks straightforward becomes a long-term constraint. Costs that seemed insignificant during a pilot can escalate rapidly at scale.
The question is no longer whether to invest in AI. It's whether the technology you're investing in today will still be delivering value five years from now.
Participation is limited to a small group of senior insurance executives to encourage open discussion and the sharing of practical experiences under Chatham House Rules..
Why This Matters Now
AI adoption in insurance has moved well beyond the pilot stage. The challenge now is ensuring today's investment becomes tomorrow's competitive advantage, rather than tomorrow's legacy problem.
What leaders are contending with right now:
AI costs often remain invisible until solutions move from pilot to enterprise scale.
Explainability and governance become critical when decisions need to be defended months or years later.
Legacy integration patterns weren't designed for agentic AI, increasing future re-platforming risk.
Many AI investments improve visibility but fail to automate meaningful work across the insurance value chain.
Governance, architecture and integration are no longer technical considerations. They are strategic decisions that determine whether AI compounds in value or compounds in complexity.
This roundtable is designed to help leaders benchmark their own AI strategy against the practical experiences of peers navigating many of the same investment decisions.
What This Discussion Will Cover
The discussion will centre around three core areas:
Production-Readiness vs. Proof of Concept
What separates AI that holds up at scale from AI that only impressed in a demo. Identifying the warning signs before the contract is signed, not after..
Governance and Cost Control
Where token costs and decision governance quietly become a board-level issue. Building the audit trail and explainability an insurance decision needs to survive regulatory scrutiny, years after it was made.
Integration and Architecture
Where AI investment becomes stranded investment. What it takes to ensure AI connects to the rest of the stack and drives action, rather than sitting as another system that only displays information.
What You Will Take Away
You’ll leave with:
A sharper lens for evaluating AI platforms
How to tell production-ready architecture apart from a generic AI tool with an insurance label, before you commit budget.
A practical view of where governance gaps actually bite
Audit trails, explainability, and drift detection, and what "good" looks like for products with decades-long risk horizons
Peer benchmarks and real-world examples
How other Australian insurers are managing AI cost, governance, and integration as they move from pilot to portfolio
A clear set of questions to take back to your technology roadmap
What to ask your current and prospective vendors next, and what a credible investment case actually looks like
Who Will Be In The Room
The value of this discussion won't come from a single viewpoint. It will come from bringing together insurers at different stages of their AI journey to openly discuss what's working, what's proving difficult, and where the next wave of investment is heading.
A curated group of senior leaders from Australian insurance organisations, including:
C-Suite executives from technology, strategy, data and customer programs
General Managers/ Heads of AI, Data and Analytics, Strategy, Digital Transformation, Customer, and Technology
Executive Managers and Senior Managers overseeing AI, data, and technology investment decisions
Participants are selected to ensure a high-calibre, peer-level discussion under Chatham House Rules.
The Programme
12:00 PM – Arrivals and networking
12:15 PM – Welcome and Introduction
12:20 PM – Scene-setter: What separates successful AI programmes from expensive experiments?
12:35 PM – Lunch service and discussion commence
1:50 PM – Closing reflections and key takeaways
2:00 PM – Close, though attendees are welcome to stay for informal discussion
Participation is limited to a select group of senior leaders to ensure a high-quality, peer-level discussion
Reserve Your Seat
Participation is limited to a select group of senior leaders to ensure a high-quality, peer-level discussion.
If you're responsible for AI strategy, data, digital transformation or technology investment within an insurance organisation, this discussion will be highly relevant.
Please complete the form below to request your invitation.
If confirmed, you'll receive a calendar invitation and full session details.
To maintain the integrity of the discussion, we ask that confirmed participants make every effort to attend or provide advance notice should their availability change.
📅 Date: Tuesday, August 20th 2026
📍 Location: Bentley Restaurant, 27 O'Connell Street, Sydney
⏰ Time: 12:00 PM – 2:00 PM