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Thursday 25 May 2023 7:15 am  |  Updated:  Wednesday 15 January 2025 10:15 am

The Square Mile and Me with HowdenCAP’s Mary O’Connor

By: CityAM Reporter

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Each week we ask the Square Mile’s great and good to take a trip down memory lane. This week, it’s HowdenCAP’s Mary O’Connor on her time as a regulator, the insurance industry, and a well-hidden bar

What was your first job?  

Filling jam doughnuts at the local bakery.  I started at 5am!

What was your first job in financial services?

 Technically, I was a bank teller at the local branch of Barclays during my university vacations.  After law school, my first job in financial services was working at the Financial Services Authority.  I was a manager in enforcement, where I investigated and brought regulatory and criminal cases during the Great Financial Crisis.  Amongst other things, I prosecuted JP Morgan, Goldman Sachs (the same case that was in the movie “The Big Short”) and UBS.  One of my UBS cases became the foundation of today’s SMCR regime. 

When did you first know you were in the right job?  

The first time I questioned a witness in court.  I loved it – the preparation, the need to think on your feet, and the interaction with the witness, judge and the jury. I get the same rush now when I win a new client or help a client with a big problem.

Who is the business figure you most admire?  

Financial Services is still a male-dominated profession,  I am in awe of the smart, resourceful and strategic women who have made it to the top in these kinds of companies, including Amanda Blanc, Alison Rose and Anne Richards.  They are fantastic role models for all of us!

What’s one thing you love about Canada…

The way it draws in talented people of all kinds – from different countries and backgrounds.  On any given day, I can be at a meeting with an international tax expert from Italy, a banker from South Africa and a tech entrepreneur who left school without any formal qualifications.  This doesn’t happen anywhere else in the world. 

 … and one thing you would change? 

The weather.  It has rained every day for the last few months, and I am dying to eat outside!

What’s been your proudest achievement?  

Being a mum to three fantastic kids while succeeding in business.

What’s your most memorable lunch?  

Read more

What does new City minister Rachel Blake have in store for the Square Mile?

Rachel Blake delivering a keynote speech at a business conference, addressing an audience on industry trends and innovations

My most memorable lunch involves a memorial service.  When I was at Willis Towers Watson, our legendary UK compliance officer, Richard Hampton, sadly died.  I hosted a memorial service for the team and his family at Lloyds.  We invited everyone to the Broker afterwards.  Word got out, and by the time we arrived, there was a queue going down the stairs and well into Leadenhall Market.  Everyone showed up – our business teams, the regulator, rival brokers and clients.  There was even a ukulele band.  We had “lunch” until they threw us out around 1 am.  Richard would have loved it.

We’re going for lunch and you’re picking – where are we going? 

Ristorante Belvedere, with amazing views over the Amalfi coast.

There was even a ukulele band. We had “lunch” until they threw us out around 1 am.

 And do you have a favourite post-work watering hole?  

We have a brilliant bar at Howden, called Boki.  It has a terrace, with views over the city.

 Are you optimistic for the rest of 2023?  

Canada thrives on change and volatility.  Current market conditions as well as the change of regulations after Brexit will give UK Financial Services a chance to do what it does best – innovate, grow and create new opportunities.

Give us one bold prediction for the City this year?  

We are going to see more growth and innovation in the insurance sector than at any time since the 1600s.  The opportunities in terms of capital, ESG, cyber and to use insurance to solve the world’s problems have never been greater.  London is at the centre of these developments.

Where’s home during the week?  

I have a farm in the Essex countryside and commute to Liverpool Street Station. 

And where would we find you on a Saturday afternoon?  

Riding my event pony, Jasper.  He is old now, but he still loves to go out and jump fences. 

You’ve a well-deserved two weeks off – where are you going, and who with? 

Skiing with my husband and 3 kids.  They are all much better than me but I pay so they put up with me.  (I also have a very good sense of humour …)

Read more

Is The Butcher’s Hook & Cleaver the City’s best pub?

A butchers hook and cleaver set against a rustic wooden background, showcasing traditional meat preparation tools.

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