Clarity
and context,
that’s what incredible leaders
offer their teams.
This week we get Up-Close with Matthew Conroy, VP of WMG Technology at Warner Music Group and former Head of Product, EMEA at Stripe. Dive in to read about Matthew’s expertise on where the Fintech space has been and where it is going, as well as his unique approach to drawing inspiration from a plethora of sectors.
Career highlight to date? How has this influenced you as a leader?
Here is hoping that the best is yet to come!
I feel quite fortunate as rarely does a day go by where I do not feel a sense of gratitude that I get to work with incredibly smart and ambitious people on problems worth solving. I really do get a lot of my own personal and professional satisfaction out of the micro-moments of partnership and collaboration.
If I had to choose a highlight, I think it would probably be jumping head-first into teaching at UCLA Anderson on top of my day job. As someone who landed in tech somewhat by accident, it is humbling to have an opportunity to help others navigate this career path. For me, it feels like an opportunity to pay it forward.
“I really do get a lot of my own personal and professional satisfaction out of the micro-moments of partnership and collaboration”
What do you think are the top 3 attributes of a great digital leader?
When you say digital leader, the first thing I think of is ‘start by being a real human and not digital’. I think so much of what makes a leader successful is bringing humanity into the job. Empathy, communication, intellectual honesty, accountability and vulnerability, deployed at the right time, are important ingredients for creating and maintaining a great team. It does not matter whether you are making widgets or software or something in between, I think the core tenets are supporting and empowering smart, ambitious people around you.
Do you believe that you need different skill sets for different stages of business and business growth from start up to scale up, to listed, etc.?
For me, it’s less about a difference in skill sets and more about your patience for and tolerance of the things that make working in those specific environments unique and difficult. Each of those breakpoints have predictable patterns - how decisions get made, what often gets difficult, which challenges arise and what cracks appear first. I think if you want to be a generational company, you are going to have to move through all those stages and handle those transitions effectively. I think for product managers who are thinking about the arc of their career, you can learn so much from gaining exposure to so many different environments and companies at different lifecycle stages. Often, this guides my choice of what roles to take on more than industry or product.
How has the economic and market context of the last 3 years impacted your strategy?
These economic and humanitarian conditions really make me even more conscious of our responsibility toward our users and our customers. When you’re working in Fintech, in particular, you are dealing with peoples’ money. Therefore, we are part of every single one of our customers’ intimate lives, let alone their business operations, so even in the best of times we must always take that seriously. But I think given how many businesses are struggling, not just in the UK but around the world, this responsibility takes on even more resonance.
In practical terms, I think that does mean that the liability, security, support and responsiveness to each user’s needs becomes that much more important than in a ‘business as usual’ situation. Even the most flexible strategies and nimble teams will feel some disruption. We need to operate with more discipline and improve the speed with which we make important decisions. This is a muscle you not only need to develop, but also maintain with regular exercise - so that work is never truly over.
“we are part of every single one of our customers’ intimate lives, let alone their business operations, so even in the best of times we must always take that seriously”
What would your advice be for a leader leading through an economic challenge for the first time?
That is a good question and one that is getting plenty of attention right now. I hear a lot about the importance of being a ‘wartime operator’ these days and, frankly, I don’t like the term. It’s a violent proxy for operating in a time of great constraint, something we do all the time. For starters, we are not going to war, and so I think being flippant about that is unhelpful. They say, ‘war is a failure of diplomacy’, and I think in the wrong hands the notion of being a ‘wartime operator’ can mean one loses sight of the human element. You can give up on people and long-term bets very quickly and you can neglect change management under the guise of urgency. To me, what is important for leaders during this stretch is empathy, clarity and context. That’s what good leaders offer their teams, especially in challenging times. No business or sector will ever be ‘up and to the right’ forever. I think it is how you show up and show out for the people with and for whom you work that matters.
“When you say digital leader, the first thing I think of is ‘start by being a real human and not digital”
Looking backwards at the last 12 to 24 months, what emerging trends have stood out to you and then what does the future look like in 2025 and beyond?
One rude awakening I had working in Fintech was that the cycles of change are a bit slower than I was used to. When you’re working on financial infrastructure, big leaps forward actually take a really long time as you’re often upgrading big and complicated systems, alongside many partners, and within different regulatory regimes, and so on. It has been intellectually exciting, and occasionally maddening, to work in this sector.
Where is this all heading? I think it will mean money becomes more programmable - as easy to move, store and use as data, and done so in a secure and responsible way. If money becomes as easy to responsibly manipulate as data, you can unlock a lot of potential.
A big part of why I worked at Stripe was because every start-up I had ever worked with had treated payments as ‘Voldemort’, the iconic character from the Harry Potter series - an unspeakable source of danger and complexity. I think the implicit promise to the world’s entrepreneurs in Stripe’s mission to grow the GDP of the internet is, ‘Wherever you are in the world, focus on what you do best, and we’ll take care of the rest.’ Personally, I find that inspiring, even if you then have to do some pretty grungy work to make that possible.
So, what else? Definitely a ‘watch this space’ moment. A lot of the financial system is hard or impossible to access without size or an advocate. There is tremendous potential for companies like Stripe to be both of those companies of all sizes. In the short term, given the climate, payment companies must focus on the basics: building a global payments and treasury network, linking every country’s banking systems and adding payment methods, and so on. It is going to be a multi-year effort to get there.
How do you keep up to date in your sector?
I would love to sit here and tell you: “Here are the Fintech blogs I read”, and "Here is where I think the most interesting thought pieces are coming from”, but I can't do that. My honest answer is I learn through people, through other operators in the industry, and of course, by being a consumer. Everyone knows that it is good to get out there and use your own product as well as the products of your competitors, but one thing that was nice about working in payments is that I actually need these products all the time. I am originally from the US, but I have been in the UK and Europe for some time now and I am always surprised, in a positive way, about how different consumer behaviour is from a payment perspective in each market. As a practitioner, that makes the space a lot more fun to explore and help shape.
Having worked in product management for some time now, I find I get a lot of inspiration from seeing how other companies in other industries solve different types of problems, and then thinking about how I can bring that back to mine. An example off the top of my head is a coffee brand in San Francisco called Blue Bottle Coffee. They help you understand your preferences by taste profile. It is an artisan coffee shop and that is one way they nudge you into becoming a loyal customer. TCHO Chocolate does something very similar - they help you order chocolate by understanding your taste profile. A small example, I know, but you have two artisanal companies trying to understand how to hook consumers and encourage them to be loyal to their brand. If you think about running good design sprints, one of the ways that you can inspire your team is to showcase examples of companies from completely different fields that are dealing with some of the same challenges you are. This injects a little creativity in your own thinking.
Any suggestions of great books or podcasts? This can be about leadership, styles, anything that has informed you as a leader or even just as a person.
Many years ago, I had the pleasure of working with the late Professor Clayton Christensen from Harvard Business School. Most know him as the author of The Innovator’s Dilemma, but a book he wrote in his later years called How Will You Measure Your Life? has always inspired me. He was reflecting on not just his contributions to business, but who he became as a person. The self-awareness and perspective he brought to such a fundamental question really struck me, particularly as I had, and still do, hold him in such high regard.
In addition, the wisdom in Growth Mindset by Dr Carol Dweck is probably something that I aspire to live out every day.
There is another good book called Give and Take by Adam Grant. A key message of that book is that you make yourself successful by making others successful. I think that is a big part of how I have been guiding my own career and I very much see my job as enabling others to show up and do their best work. Growth Mindset by Dr Carol Dweck is another good read.
