Digital Transformation is ‘Genuinely Hard’: Teachers Mutual Bank’s Dan Chesterman

If there’s one big lesson Dan Chesterman learnt during his 7-year stint in senior technology roles at the Australian Securities Exchange (ASX), it’s that digital transformation is “genuinely hard.”

“As the stats will tell you, many digital transformations, particularly multi-year significant ecosystem change [can] take multiple efforts,” he tells ADAPT.

Chesterman was technology chief at the ASX in 2022, during an overhaul of its ageing platforms alongside a program to replace its legacy CHESS system with blockchain-based distributed ledger technology. The CHESS project was discontinued later that year after an independent review found it didn’t meet market and legal requirements.

“A key learning I have, not from just that project, but more broadly, is that when you are trying to do significant technology change, particularly over multiple years, you do need to be very mindful of maintaining a degree of flexibility because the environment changes around you.”

Chesterman says AI…