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‘I do wonder how long it will take until we have a wholly female board’ – Leadership interview with Abigail Kenny, Head of Global Strategy at Stripe

By Business & Finance
16 December 2024

Business & Finance was founded in 1964 and to celebrate our 60th anniversary, we are running a series of Leadership interviews with business leaders who are creating lasting legacies across the corporate landscape of Ireland. Abigail Kenny is Head of Global Strategy and Analytics at Stripe, the billion dollar FinTech enterprise founded by the two Collison brothers from Dromineer, Tipperary. Sarah Freeman speaks with her about leaning into the strength of mentorship. 


“I’m working with incredibly talented people who choose to work with me day in day out, some over decades now, and I have the opportunity to lead them, champion them, grow them and get them seats at the table.”

Kenny believes that the opportunities her senior position affords her should be used to broaden and diversify who the company is hiring. 

“I’m very deliberate about that. I spend a lot of time thinking about how I can provide equal opportunities to succeed and create a very strong sense of belonging in the teams I have the honour of leading.”

Asked whether her experience of leadership is different because she is a woman, Kenny acknowledges that the business landscape is still not the most level playing field. 

“In Ireland, it wasn’t until 1973 that the marriage ban in the Irish Civil Service and informally in the private sector was removed. So there are not many women like me, and more senior to me, compared to the amount of men that there are in senior leadership roles.”

She is, still, often the only woman in the room and references the ‘motherload’ that many women with children are familiar with, whereby the small details of family life fall to them to organise. 

“I do wonder how long it will take until we have a wholly female board or an entire leadership team of just women…We have a long way to go,” concedes Kenny, herself the mother of two young children.

Resilience

Kenny has seen her fair share of challenges over the course of her career and believes that building resilience is critical to success. 

“I think you can learn tips and tricks along the way that will help when you hit adversity because, undoubtedly, in a very long career, you face lots of different challenges.”

What works for her is a very well developed set of relationships in her network that can help either navigate or rebound from work setbacks. 

“Whether you’re dealing with a lot of pushback from a business partner or a stakeholder, having someone that you can have a sparring partner relationship with and who might be able to give perspective and look at it differently is key.”. 

She’s a believer in the value of simple pleasures like a quick, daily walk with the dog and some sense of gratitude.

“That ten minutes outside every day in the fresh air always gives you perspective.” She adds, “If I’ve had a particularly hard day, I will try and write down three good things that happened that day. It reminds me that failure isn’t permanent.”

Kenny’s first marriage broke down in her twenties, an experience, she says, taught her a lotalot about failure and resilience. 

“Life doesn’t always go as planned,” she says. 

While about to embark on a new chapter by starting a new job at Facebook, she received the divorce paperwork. 

“The paperwork symbolised my failure. Looking back though, that experience was one of my most powerful teachers because I had to do a lot of self-discovery. A lotAlot of friends were getting engaged as I was going through this and I had to let go of comparison. It’s true that comparison is the thief of joy.”

Kenny says she would have had perfectionist tendencies until that point and it was at this juncture that she had to rethink that approach. Ultimately, it helped refine how she handled difficult situations and people. 

“I always assume positive intent. Most people aren’t going out of their way to make your day difficult.

The divorce did, in a roundabout way, lead to one of the most influential mentoring opportunities that Kenny was given. 

“I was at a women’s leadership talk with Sheryl Sandberg and she spoke about how her first marriage break down was her biggest failure but that she was ok with it not working out because one of the most important decisions you can make as a woman who wants to have a partner and have kids is who your partner is and that they help take the load.”

Kenny sent her a note, saying she’d just gone through the same circumstances. Sandberg wrote back and invited her to meet. 

They had a 30 minute meeting where they shared life stories and Sandberg encouraged Kenny to approach her if she ever needed anything in the future. Kenny did subsequently ask her for advice when approaching a promotion and Sandberg invited her to be part of her lean-in programme. 

“It was about allyship across the company and it’s really action orientated. It’s not lip service. It’s about how you would use your positional power or your position of privilege to help people from historically underrepresented groups to find more belonging and equity in the workplace.”

It was 2015 and, Kenny says, it really resonated with her. 

“I heard a stat that said it would be another hundred years before equality in the boardroom. I didn’t have a daughter at the time, but I thought of my nieces and all the young girls who would just keep hitting that glass ceiling and I felt this really needs to change.”

Kenny’s upbringing was also instrumental in crystallising the need for equality. 

I’m one of six kids and I have four older brothers. I never saw a difference, gender-wise, between us until much later on in my career. I came back from my first maternity leave and one of my male colleagues asked me, ‘how was my holiday?’. It was cruel because actually, coming to work was like a holiday.”

She experienced subtle but significantly different treatment on return from maternity leave, including exclusion from trips. 

“I wondered, why am I being written off the script when I’m still here and I can actually do this. SO I really want to help break down some of these biases. 

It’s important to Kenny to continue this fight for equality. 

“If I’m in a room and I’m the only female sitting at the table, I’ll make it my job that there is a second woman involved the next time we come to that meeting.

Women are seeing the value of an equivalent ‘old boys club;. 

“Women are learning that muscle, over time, to  lift each other up and pull the next generation. Our power is our ability to make an impact. So for those of us who are in positional power, we should use it to the advantage of women coming up.”

Her advice to younger women is to understand the difference between mentorship and sponsorship. 

“It’s really well understood by my male colleagues and not so well understood by female colleagues.

Kenny parses the difference. 

“Sponsorship might be, I want you to help me get promoted. I want to get to the next level. Can you help me figure out what I need to do to get there and be very, you know, specific about it. Whereas mentorship is trying to figure out something that you need help with in terms of certain resources or supports around a challenge you might be facing.”

Kenny sponsors a wide variety of people and says it’s quite common for her younger male colleagues to declare their interest in becoming a director in the space of three years and ask how they can achieve that. 

“Women aren’t as forthcoming about that. I really encourage women to have that voice.”


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