International Women’s Day: A Q&A with MD, Holly Shepherd

International Women’s Day is a day to celebrate ALL women, their achievements and successes both personally, and professionally, their dedication, leadership, and rights to live in an inclusive society.

Like many other industries, insurance is paving the way for a more gender-inclusive workplace, with the number of female executives increasing year on year. In 2021, it was recorded that out of the 350 largest insurance organisations, 30% of the executive committee were women*. Of course, this could be classed as a success, not just for women, but also for the industry, but the figures show there is still a way to go before we reach inclusivity and equality. And whilst the numbers support progress, there is still no denying that women still face an abundance of challenges in the market.

In celebration of International Women’s Day, we host a Q&A with our Managing Director Holly Shepherd to talk about women in the industry, gender bias amongst our male colleagues, the opportunities and challenges women face, and more.

Q: Tell us a little more about your role and how you came to be Managing Director.

A: Around three years ago, I was tasked by the board of all three companies (Shepherd Compello, EPG & White Oak) to streamline the expense base, and the most efficient way for me to do that was to combine the central services of all companies – so, HR, finance, compliance etc. It took me about 18-months, and out of that came Shepherd Global whose ethos was to provide a superior service for all three businesses. I think, after that, I’d naturally got to a point where I was virtually running the operational side of each of the businesses, so I just asked the board if I could be called Managing Director… and they said yes.

Q: Do you think that you would have been given that title had you not asked?

A: The truth is, I really don’t know. It was always being said and I was always positioned in that role so I’d like to think so, but who knows.

Q: Let’s talk about work-life balance, how do you manage yours, and what’s most important?

A: The most important thing to me is doing everything that I’m doing well, whether that’s being a mum or managing a business. When I’m working, my head is 100% at work and when I’m with my family, my children have my undivided attention, so for me, it’s very much about keeping things separate. If I’m trying to work and I’m worried about my children, then I need to go be with them as I know I won’t be doing a good job at work whilst my mind is elsewhere. And it’s the same with work, if there is something that needs my attention, I’ll step away and focus on that. It takes a lot of prioritisation to establish what’s most important at that moment in time and to be able to forget the other thing temporarily. It’s definitely not a 9-5 and flexibility plays a huge role in it all.

Q: What do you think companies underestimate when it comes to supporting women in the workplace?

A: The confidence to ask what we really need. They definitely underestimate the power of communication and asking women what they need in terms of support. The majority of organisations will offer whatever you need, you just don’t know it because it’s not openly communicated, or it is, but not very well.

Q: Do you think there are enough opportunities for women in the industry and how can we bring certain issues around gender bias to light?

A: I think there are plenty of opportunities for women to get into the industry, but the massive hurdle arises when it comes to women having children. I feel like as though they’re written off and there’s not enough support for working parents. I’ve seen it on occasions, where women try to hide the fact that they have children, or if they do mention it, their first response is to try and justify it. If you do talk about your children, you’re kind of labelled as ‘just a mum’ and it’s as though you lose your professionalism and credibility a little bit.  We need to be upfront and accept that a lot of women do or will have children and it’s the most important thing in our lives, so we need to move past it and start to understand that women can do both and do it well.

Q: Do you think the culture at White Oak supports working mums?

A: Absolutely and not just working mums, working parents. We are very much a family business, in all aspects, we see our teams as family and appreciate how important family is to them, so we support the decisions they need to make for their family. It’s definitely a different culture from anything I have experienced before but I would feel so uncomfortable if any mum (or dad) felt like they were being pushed into a corner by having to choose their children over work or hide their children, because I know what it feels like. My team’s work-life balance is just as important to me as my own.

Q: What would you say have been some of your biggest challenges as a woman in the industry?

A: I think having the courage to call people out when something doesn’t sound or look right. It’s hard because sometimes it may mean losing business or upsetting clients and there have been times where I have gone away from a situation and felt embarrassed that I didn’t call it out.

Q: Have there been many situations you can recall where you’ve been treated unfairly because you were a woman?

A: Truthfully, yes. I’ve been in situations where international male clients won’t respond to my emails, they will go over my head and straight to my male colleagues and it’s like, ok how do I deal with this because it’s completely not ok, but how else am I going to do business with this client? Do we only do business with them through male members of the team now? I think this is where calling it out comes in, but sometimes it’s not that easy.

Q: Have you seen much change in the way women are treated in the industry over the years?

A: Yes and no is the perfect answer to this one. Yes, there are more women in the industry, yes there are more female executives, and of course yes there are more opportunities for women because generations are changing. But Insurance is still very much a boy’s club and I think there are things that people have learned that they can’t say out loud, but it’s still being said, now it’s behind closed doors.

Q: What do you think we can do to pave the way towards a more inclusive industry?

A: Having more women leaders! Sometimes men (even if they have the best intentions) don’t realise that what they’re doing or saying can be gender bias. So, it takes a woman to call it out for them to learn and kill those old habits.

Q: Do you have an example of a time when a male has been unintentionally gender-biased?

A: One that stands out is around traveling, a lot of men automatically assume you don’t want to travel for work because you have children at home. And yes, that may be true for some women, but others would love the opportunity. So ASK us!

Q: How can we encourage our male colleagues to do better to support women in the industry?

A: Probably by not being afraid to enlighten them on how some situations can make women feel and in which situations we need their support. I think we all want to see men calling out situations even when we’re not around and start seeing them make that hidden culture unacceptable.

Q: What advice would you give to younger women starting out in their career today and what can we do to encourage future leaders?

A: Be yourself and confident in who you are. Don’t worry about what other people think and don’t try and change yourself to be what other people want you to be. Success comes from you, if you’re being yourself and you work hard enough, you can be a successful leader.

Q: What’s important to you as a role model?

A: To be honest and not sugar-coat things to make them look easy. To normalise having a bad day or being open when I’m struggling with something, and just keeping it real – we’re all in the same boat!

Q: What do you do to support women in finance?

A: I’m on the board at BIBA, we support the women in finance initiative and as an organisation, we’ve made a number of commitments for women in finance, one of them being that we’ve committed to having at least 50% of women at an executive level. Naturally, I think we have a very diverse company, but it’s never been intentional, we just gravitate towards women, and I think it’s down to our company culture and how open we are with our values and recruitment process.

Q: This year’s theme is ‘break the bias’, what do you pledge to commit to break the bias and create a more inclusive world?

A: My pledge is having the confidence to continue to speak out because we can’t break the bias without challenging and speaking up.