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Rebecca Mason

First openly Trans Woman in the Lloyd's market

When Rebecca Mason joined the Lloyd’s market in the late 1980s, Richard Rogers’ building in Lime Street had only recently been opened by the late Queen Elizabeth II. The 300 year-old Lloyd’s market offered many opportunities however the traditional working culture was not  always welcoming to everyone, particularly those from diverse communities.

Portrait of Rebecca Mason by Franklyn Rodgers, 2023

Rebecca’s transition began around the millennium. She had joined Aon Underwriting Managers and felt that she was in a working environment that would be a safe place to take the huge step of transitioning. ‘I had to do it for my mental wellbeing – and Aon were totally supportive.’ Rebecca also had a trusted female confidante and friend, who became an ‘Ally’ years before the term was coined;  ‘Sarah was brilliant. She answered all the questions that people had, but didn’t want to ask me directly. She brought people on board, and with her support I was able to involve HR and start the process formally.’ Aon’s HR team worked with senior management to make the process ‘as easy as possible, although I had to be reminded that it wasn’t just me that was getting used to this adjustment, my colleagues were as well.’

Rebecca Mason, 2022

Although Rebecca’s post-transition life has been extremely successful, both professionally and personally, it hasn’t all been straightforward. There were some mixed responses particularly in the early days. Nevertheless, she continues with an ethos based upon turning up and being the best woman she can be. She believes that changing people’s perceptions happens through being herself and openly talking to people.

Rebecca with the Tardis

Outside of the office, Rebecca’s transition inspired her to rekindle her love of theatre. Having studied English and Drama before starting her career in insurance, since 2006 she has been a member of a number of community theatre companies, gaining a reputation as a director and more recently using her affinity with words to create three plays, Another Christmas, Another Carol, Death Before Marriage and last year’s acclaimed ‘Incomplete’. Rebecca also enjoys live music, cycling and has recently started learning to play the piano.

Rebecca and cast for her play Incomplete

Since her transition over twenty years ago, Rebecca has seen a change in attitudes. She held a senior position at R&Q-Accredited, her previous employer, and recently moved to an prestigious role at MS Amlin where she has found herself in an organisation that embraces diversity.

“I look around the office and I see women, people of a non-European heritage and people from the LGBT community all holding senior roles. To me, this is the future of Lloyd’s and the London market.”