Career Mobility Q&A with Mary Bonsor, CEO of Flex Legal

As part of a series of interviews we are showcasing the potential for lawyers beyond the ‘traditional role’. In Part 3 of the series, on International Women’s Day 2021 and during Women’s History Month 2021, Syed Nasser speaks to Mary Bonsor, a former property litigation lawyer, to discuss her experience transitioning out of private practice. Mary is an exceptional female role model and won Entrepreneur of the Year at the Women in Law Awards 2020 as well as winner of Entrepreneur Category at the Women in European Legal Tech Awards 2020.

What is your background and current role?

I am the CEO of Flex Legal – a platform to connect law firms and in house legal teams to lawyers and paralegals on a flexible basis. We have over 5,000 paralegals on the platform and 300 lawyers. Before setting up Flex Legal, I was a property litigator at Winckworth Sherwood for 4 years. I won Entrepreneur of the Year in the Women in Law Awards 2020 which was a great honour.

What led to you leaving private practice?

I didn’t fall out of love with the law, but I knew that if I did not set Flex Legal up when I did, I would never do it. I was 28 and did not have a mortgage at that stage, or children and thought it was the best time to take a leap of faith and take a risk. My mother always said “fortune favours the brave” and so I thought what was the worst thing that could happen and if it all goes terribly wrong, I will have learnt a lot along the way and could always go back to being a lawyer. I do love that I am still involved in the legal space, but just in a different way and have found a number of skills very transferrable.

Were there any challenges in making a move?

Yes! The first challenge was getting into the head space of taking a risk. It did not come naturally as most lawyers are quite risk adverse and it took 4 years of research and weekend work to take the jump. This is why it was important for me to raise some funds to check it was a good idea and that people I didn’t know were willing to invest in the idea and me. We only raised 120k to get going so tried to boot strap it which meant learning on the job rather than hiring lots of people to start with, so I had to learn how to be an accountant, a salesperson, a recruiter and a COO – you are the jack(ie) of all trades to start with!

What are some of your biggest challenges today?

Our biggest challenge is trying to ensure we can differentiate ourselves from some of our competitors, learning new skills such as managing a team rather than being involved in the day to day operations and scaling the business. This means we have to ensure our processes are efficient and things which were “in my head” are clearly on our platform so people can pick them up. A good example with this is account management and ensuring that all placements and how they go, are clearly recorded. This is a really important part of scaling and ensuring knowledge can easily be shared across teams. Our platform plays a key part in this.

How does your working day differ now?

My day is very different to when I was in PP. I spend a lot more time in excel then I did as a lawyer and spend a lot more of my time speaking to clients and really getting to know them. Weirdly I didn’t do enough of this as a lawyer and I actually think lawyers should spend as much time with their clients as possible to really understand their commercials and motivations which would make them a much better lawyer to that client so I am a really big fan of secondments.

Do you have any advice for those considering a similar change?

Just do it – you never regret it and continuing to be challenged is very important! Also don’t be afraid to ask for help and network, network, network.  I am amazed at how generous people are if you ask them for advice and have found having mentors incredibly important. I also could not have done it without my co-founder James, who is amazing – and the techy behind the idea. He is brilliant and we work very well as a team because we are incredibly different – he is brilliant at thinking things through, and I want to get on and do it (which means we can drive each other up the wall by challenging each other, but it works very well!) so I would also try and find someone to do it with who has a strength which you don’t as otherwise I imagine it could be very lonely!

Do you have any advice for start ups looking for investment?

My advice would be to also make sure your investors are right for you, and do your due diligence on them too. I always find it odd that the due diligence often only seems one way- from the investor side but it is crucial to make sure the investor is a good fit for you, supports your vision and can offer value otherwise it is not worth taking their money.

Do you have advice to law firms as a result of your experiences?

I think law firms have come a very long way in terms of innovation over the past 4 years but I think law firms could be more savvy with their data. They hold so much data and trying to analyse this more can help create a better service and make them more efficient. An example of when I was in PP where I could see this working is when I did a seat in real estate. Although each matter had time recording against it, the firm never looked across each case and looked at how long a transaction took and asked why did some deals take so much longer than others? Asking these sorts of questions could then lead to more efficiency, analysis and prioritisation of some clients over others. I think we will see a lot more data analysts in law firms over the next few years.


By Syed Nasser, Head of Technology Transactions

& Venture Capital


Mobile: +44 (0) 7960 739 158 

Direct Dial: +44 (0) 20 3642 1871

Flex Legal: Flex Legal

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