Paul and Jenny O’Brien on holidays in Europe / Spring in the O’Brien family’s high-maintenance garden

Twilight seminars loom large for AILA luminary

By Resolve Editor Kate Tilley

The AILA NSW Branch’s twilight seminars have a persistent presence in Paul O’Brien’s professional life.

In the late 1990s, the commercial and insurance litigator who co-founded boutique insurance law firm YPOL, was asked to present at a twilight seminar on reinsurance law.

That introduction to AILA led to an invite to become a member and then to join the NSW committee and, 25 years later, he’s still there. He also chairs the organising committee for the twilight seminar series.

Paul was NSW Branch president and an AILA board member for two years and last year was honoured with AILA life membership.

He has dedicated so much time to AILA because he understands the organisation’s value, saying it’s been “a privilege and a pleasure” to work with his fellow committee members. While some are lawyers who are technically competitors, “we work together in a very collegial way”.

AILA ‘does it best’

Paul says AILA is Australia’s pre-eminent provider of insurance law education while concurrently enabling social networking opportunities that bring together all elements of the industry, from insurers to insurance lawyers and other industry service providers, like brokers and loss adjusters.

Commercial seminar organisers have told him it’s hard to compete in insurance law education “because AILA does it best”.

Paul’s career began at Minter Ellison and on day one he went into commercial litigation. Moving to Phillips Fox (now DLA Piper) in the early 1990s was an opportunity to work with AILA co-founder Michael Gill, and that launched his stellar career in insurance law.

Paul enjoys the broad spectrum that encompasses insurance law. He focuses particularly on D&O, financial lines and professional indemnity. “I like the intellectual challenge and diversity of the work,” he told Resolve.

Paul’s involved with many high-profile, newsworthy financial lines claims and finds them “intrinsically interesting”. But the people he works with are the key attraction.

“Insurance has great diversity and the people are egalitarian, practical and down to earth.”

Soul searching

Leaving a major firm to establish YPOL in 2007 required “a lot of soul searching” but it has proved a wise decision. As a director of a smaller firm, individuals have a greater say in how the business operates, even to the level of “what type of biscuits we’ll have in the tearoom”. That’s not possible, or practical, in large firms.

“It’s been less daunting than I expected,” he says.

Paul and his wife, Jenny, a lawyer whom he met at Minter Ellison, have a son, Tim, and a daughter, Julia. Both studied philosophy and law and Julia now works with her father at YPOL.

Outside work, Paul spends a lot of time trying to keep “the highest maintenance garden in the universe” under control.

He and Jenny love to travel, particularly to the UK and London, which is like a second home. Paul fondly remembers Christmas holidays in London when the children were young.

Avid reader

Although the Covid-19 pandemic temporarily curtailed the wanderlust, they’d like to resume travelling, particularly as Jenny, who had been working with Lawcover Insurance after a stint as corporate counsel at Macquarie University, retired in 2022.

Paul’s also an avid reader, currently devouring Victorian novelist Anthony Trollope’s The Eustace Diamonds about a court case over ownership of a diamond necklace.

He’s also keen on English writer Mick Herron’s Slough House series of spy novels, which also have been made into a TV series, Slow Horses.

There’s certainly nothing slow about Paul’s pace. He says work remains busy and enjoyable, so there are no plans yet to join Jenny in retirement.