What’s Your Plan for the Legacy System No One Wants to Touch?
How technology leaders are modernising long-serving systems without a full rebuild, before they become a risk only a few people can resolve.
Join an exclusive group of Technology Leaders from some of Australia's leading organisations for this invite-only roundtable discussion.
- Wednesday, 23 September, 2026
- 12:00 pm - 2:00 pm
- Ananas Bar & Brasserie, The Rocks
Almost every company has one: a system built years ago, deeply connected to daily operations and fully understood by only a small number of people. Replacing it has often been scoped, costed and deferred because the expense, disruption and delivery risk can be difficult to justify.
Insurers are asking more detailed questions about unsupported software and ageing technology at renewal. Customers expect capabilities that older platforms were never designed to support. At the same time, the people who understand these systems are retired or may leave before the systems themselves are replaced.
The key question is whether the business can securely upgrade these systems efficiently with minimal disruption, and whether AI has materially changed what technology teams can achieve with the resources available to them.
We’ll discuss:
- Where legacy systems create the greatest operational cost today, from maintenance burden and key-person dependency to integrations sustained by workarounds.
- How technology teams are using AI to understand, document and modernise established codebases without committing to a full rebuild.
- What leaders need to put in place to reduce single-person risk, improve documentation and prioritise modernisation efforts.
Join your peers to compare which systems organisations are addressing first, what approaches are delivering results, and what needs to change before a resignation, insurance renewal or customer requirement forces action.
This event includes hosted dining (estimated value $130.00 AUD per person). We are pleased to accept payment for all or a portion of this event as permitted or required under your ethics laws and policies and can provide additional information or documentation upon request.
Agenda.
12:00pm - Arrival, Refreshments & Networking
12:15pm - Welcome & Introduction
12:20pm - Discussion Topic 1:
Where are legacy systems creating the greatest operational, commercial and technology risks today, and how are leaders prioritising which systems to address first?
12:40pm - Discussion Topic 2:
How are mid-sized development teams using AI to better understand, document and modernise legacy codebases without taking on the cost and risk of a full-scale rebuild?
1:00pm - Discussion Topic 3:
What capabilities and safeguards do technology leaders need to reduce key-person dependency, preserve critical system knowledge and ensure legacy platforms can continue to evolve safely?
1:20pm - Discussion Wrap Up & Conclusion
1:30pm - Networking
2:00pm - Official Event Closed
Guests welcome to stay at leisure.
Speakers.
Santhan Naidoo
Managing Director
Venue.
Ananas Bar & Brasserie, The Rocks
Ananas Bar & Brasserie is a stylish French-inspired restaurant and bar in Sydney, offering an elegant setting for corporate dinners, networking events, private functions, and social celebrations. Located in the city’s CBD, the venue combines contemporary interiors with classic brasserie influences, serving French and Mediterranean-inspired cuisine alongside cocktails and an extensive wine selection for a refined dining experience.
Address:
18a Argyle Street, The Rocks, New South Wales, 2000, Australia
Hosts.
