Author Susan Cain writes that “Everybody shines, given the right lighting”.
And shine Eileen O’Mara does. As a highly experienced leader in technology, the Irish-American has navigated a brilliant career since 1997 working at dynamic, founder-led companies including Oracle, Salesforce, and now as the Chief Revenue Officer at financial technology company Stripe.
As a natural introvert, Eileen shared on High Agency Women that she’s had to find a way to express her unique voice and insights around some seriously high-powered tables.
“To my younger self, I would say even though it’s uncomfortable, and your natural preference might be to be quieter and to observe, and then contribute in a different way later, that’s not the role you play. If you have that opportunity, and you have that seat at the table, you have to find the will within to be able to articulate and contribute. Be yourself – but don’t pass on that moment,” she says.
We caught up with the Irish-American tech executive while she was in Sydney from her usual homebase of New York. Her perception of the local tech scene? “Vibrant”, with founders from companies like AI startup Ignition to Aussie classics like Canva and MYOB standing “shoulder to shoulder” with their US counterparts.
Eileen generously imparted insights from how to cultivate a leadership style that’s unique to your essence, how Stripe actually puts into practice its user-first approach to building, and what it feels like to have borne witness to the different tech waves including the desktop revolution, rise of mobile, and now the week-to-week breakthroughs happening in generative AI.
Missing Perspectives readers, here’s Eileen O’Mara.
Natasha Gillezeau: Before we go into the journey of Stripe and where we’re at today, I’d love to start with who you were when you were younger. Where were you born, and what were your early years like?
Eileen O’Mara: Geez, that’s really a long time ago now. I’m Irish, you probably picked that up from my accent. Essentially, my education and schooling was all in Ireland, and maybe the thing that is a little bit different, is that my parents met in the United States. And I have three older siblings. It was very unusual that an Irish-American legal family in the US would decide to move back to Ireland in the 1970s. I think we all grew up with a very “American” mindset because of their experience, and them having their first few children in the US. But essentially, very much a messy Irish family and upbringing in the West, but with a global outlook from the outset.
I’m the fourth of five children, with three brothers. Another thing that was assumed was equality for all in the house, and my expectations were that you’re as good if not better than your brothers. It wasn’t initially what I considered fundamental to the type of leader or executive I would later become, but I do think it was probably foundational to my thinking in terms of why me or anyone like me should have the same types of opportunities, and that those should be based on your merit and contributions.
I was a very geeky little girl, always reading business books, which is crazy in hindsight. But that was always my passion: how to grow things.
Something that struck me is you share the Irish-American heritage of the Stripe co-founders. Is that something you share with many other Stripe leaders? Do many of them share that dual heritage or that understanding of those two worldviews?
I don’t think it’s relevant at all actually. What I admire about Stripe and the founders is that we’re really here to serve companies to grow on the platform, and that’s probably what really anchors us as a company is this growth, curiosity mindset. This is a company built on a set of principles that we live and breathe every day. You might say: are there some Irish values or principles in that? Maybe to some degree, but that feels less relevant than the global ambition of looking out. You grow up in Ireland, and it’s an island to the west of Europe, people always either had to leave, or it wasn’t until my generation of graduates that you could even build a career in Ireland. But I think culturally, we’ve always been wanderers. That could certainly be a thread you could pull on.
You’ve worked at these different tech companies – Stripe, Oracle, Salesforce – and you mentioned that there have been those different tech waves that you’ve witnessed and been a part of. How would you compare those different companies when you reflect on your time there?
I like to work with companies that are number one, or on the way to number one, and I recognise that about myself now I have more experience behind me. I didn’t know that when I was in those companies at that time.
When I joined Salesforce in 2012 – they definitely weren’t number one. But to be in a culture and an environment where you have founders like Larry Elison, who was still at Oracle… and I really like that because founder-led companies have this drive and ambition and they see through things that I think is very unique. The innovation that comes from tech-led founder companies I think are a very special place. In terms of what I’ve seen and observed, these are generational companies that will be written into history books. And I’ve been fortunate enough to be at three very big ones.
But innovation, founder-led curiosity, and most importantly, always solving for someone else. Solving for a customer, solving for a user, and not putting the company at the centre.
I think that’s something that’s palpable about Stripe, and when Phoebe (the founder of Missing Perspectives) and I attended Stripe Tour last year, we really noticed that outward focus, whether it was Black Sheep Wines or Leonardo.ai and how much they were foregrounded in the presentations. I’m still curious as to what does that actually mean, how do you practically focus on the users and customers in the week-to-week and make sure that you don’t move back to thinking too much about Stripe, but you maintain the outward gaze?
We have a lot of mechanisms across the company that bring that to life, but on a practical level we start our Monday morning meetings at 8am with a user. And usually that user might not be super happy with us, or have a problem, but we start the meeting in the cold light of day and it’s like, okay thank you for being candid, tell us what’s going on, what’s working, what’s not working, and get get all the go-to-market leaders, product leaders, and we’re there to listen and learn. And I think that sets the tone at a founder level: okay, this is how important this is.
Patrick and John [Stripe’s co-founders and the CEO and President of Stripe respectively] host a one-hour meeting every Friday. And every Friday, that meeting starts with a user, and the whole company can tune in or if they can’t make it they can catch up on the recording. Again, it’s another strong signal that the user is the heart of everything that we do. So those kind of mechanisms make sure that it’s deeply engrained and embedded in the company.
And then every product that we build in our roadmap is based on user asks and feedback. And I was sharing this week – I met with lots of different users and prospects – Patrick and John told me I don’t need to be too clever when I joined the company. They said – just ask these companies and entrepreneurs what do we need to build? What do we need to build that is going to make you more successful?
And that is the company culture. Most of my job is to be the voice of the user. And that gives me a lot of licence to be really loud and get attention and say “I’ve heard this, or there’s an adjacency that’s not being considered, or this is a requirement”. So it’s a very refreshing way to build and scale a company, and that’s really at the heart of everything that we do.
I love that, I can totally image the Monday morning and the Friday meeting. That brings it to life so nicely. On the road to IPO [initial public offering], is there a concern that that user obsession or customer obsession could shift to a shareholder focus and how do you think about that right?
All we think about in the company that we have, and the company that we want to build is how can we solve hard problems for users. We don’t think about anything else, we don’t think about IPOs, potential IPOs, or not – it’s not on the agenda. So we believe that if we continue to focus on that, that will solve all the problems we might see or encounter and will ultimately be the right thing for the company.
In Australia, is there a good example of a user problem or a fragmentation issue that you’re solving for users that you recently worked on?
There are a ton of Australian AI-based startups bringing new products to market, and one of the requirements that we heard was we really want utility-based billing.
They’re always trying to be in front of the next wave of requirements from users. I had lunch with AI users this week, and the number one thing that’s challenging them is the path to growth, monetisation, and profitability. So that’s one thing.
I also heard some feedback today that was, “I think you should have another layer of sophistication around your fraud products”. And I was like, really good feedback for us. I can then go back with credibility into Stripe and say, “Listen, I’ve heard this thematically a couple of times, I think we really need to pay attention to it and learn more.”
How do you think about innovation and technological revolutions like AI about bringing all citizens and customers on the journey? Because I think some critics or commentators worry that in a world where there is already a wealth gap or accessing capability gaps, even if it’s access to different technologies, that that bifurcation could enlarge? For example, if a whole lot of people get on a different set of train tracks if we want to use Stripe’s metaphor of ‘the economic infrastructure of the internet’ and then a lot of other people, citizens, businesses and customers don’t? How do you think about that? Does Stripe have a responsibility here?
Yep, I mean that’s kind of fundamental to the mission of Stripe – to grow the GDP of the internet. If you think, well, what does that mean? It means to grow the GDP of the internet. And so it doesn’t matter if you’re in Bangalore or Boston. You should have access to this technology.
And I think that’s one of the things that really attracted me to Stripe – the values around that. When you think, do I have to be the largest company in the world to access this technology? And the answer is no – you’re accessing the same technology whether you’re a big company or you’re just starting something in your garden shed or bedroom.
We think this technology should be democratised and accessible to users of all sizes – whether you’re just starting something all the way up to your Amazon’s or Ford’s or the General Motors.
So, do we take it seriously? Yes, we do, I would say. And it’s embedded into our business model and how we think about it. Irrespective of where you are, and I’ve been through every wave, a lot of places bypass the desktop and went straight to mobile. That is the core of the company, making it democratised wherever people are.
Do you have any grounding rituals for yourself to literally do the job?
I’m not sure if I’ve cracked any secret sauce on this – I’ve got a few hacks to make sure I’m centred, and present. Obviously if a user is showing up and giving me their time, you have to be very engaged and very prepared. I especially spend a significant amount of time preparing and I’m current so I can bring some value to that conversation. So that’s one thing, preparation is key. And the other thing is being present to wherever you are, and that includes being attuned to wherever you are. I also need to plug myself out and recharge – I’m a natural introvert. So that means I need to find my space and go into a dark room for a period of time before I can emerge again. Those are the rituals specific to me, so I say work out your rituals so that you can recharge and show up and be the best you can be. I take that responsibility seriously.
Have you read Susan Cain’s Quiet?
I have. I have.
What did you think of it?
For me, I loved it. Have you read it?
It was recommended to us by one of our contributors Dr Linny Phuong, who wrote an article about the power of introverted leaders in healthcare. And she said at least in the Australian medical system, there is a very extroverted Anglo-Australian culture. That was her observation. And I’m not suggesting all Vietnamese-Australian women are introverted by any means, but she was talking about her nature not really being fit for that purpose.
And that environment, yeah.
I’m conscious from a women in leadership perspective of not perpetuating a certain archetype of women leadership, and not seeing or witnessing other types. I do think that more airtime is given to that more extroverted type of leader. Do you have ideas on how we can render more visibility in the culture, maybe what you resonate with more deeply? Does that make sense?
It does make sense. I may think about it differently now than I did like 10 or 20 years ago – for me in this role and for the roles that I’ve done I’ve been fortunate to be in very senior roles where I have been invited into environments where my voice matters and is sought after. I think what I’d say to myself when I was younger is that even though it’s really uncomfortable and your natural preference might be to be a bit quieter, and to observe, and then contribute in a different way later, that’s not the role you play.
From my perspective, if you have that opportunity and you have that seat at the table, you have to find the will within to be able to contribute and be able to articulate, and to be yourself of course, but not pass on that moment. Because it’s very important that we do contribute, and that there’s an equal share of voice – male, female, introverts, extroverts. It took me personally a while to figure out that and build enough confidence to say I know my stuff, I have a particular perspective and I need to share that and it will add value. In my experience and view of the world, we want all these types of personalities and people. But there was a point a number of years ago where it was all – oh, make the space and make sure you’re saying to Eileen ‘have you got anything to say?’. And that was more like – please don’t do that to me, that’s actually putting me on the spot, which is worse and aggravating the issue. And there was like a wave where people would ask: ‘Did everybody contribute today”.
People need to find the inner strength, if you’re in a room, you need to find a way to contribute. And it would be such a shame if introverted leaders didn’t do that. In the same way we believe that the world is made up of diverse set of skills, minds and attitudes, like you need to be able to contribute. But it’s not that easy, it definitely takes time and it takes practice.
One thing that has taken up oxygen in the news is that the current US administration has been vocal about rolling back diversity and inclusion and there has been an attack on the concept. Where do you stand at Stripe on diversity and inclusion?
One of the things that I really like about Stripe is we live and breathe our principles and in every way we believe everyone is equal, so it wasn’t having any focus on DEI, because it was just how we built the company. We have a great representation of men and women, we have equal pay for equal work, and that’s the kind of company that we are. So in terms of the current mood and tone in the US, we’re running the company in a way we feel comfortable with, which is based on work and merit, and that’s what counts.
In 2021, Stripe halted payment processing for Trump campaign donations for inciting violence. That was a while ago, we’re in 2025 now, but what’s your relationship like now with the administration? Do you have things that you would definitely do, that you wouldn’t do?
Listen, we’ve always had a democratic platform if you will, so we’re governed by regulations and rules, and as long as the users on Stripe are operating within the rules of that jurisdiction, we process for them. That’s the same now as it was when Patrick and John started the company. But we’re not trying to pick anybody’s side, all we’re trying to do is support merchants’ growth on the platform and support them in being really successful. We think that’s the right position to take.
Are there any exciting merchants you’d like to give a shoutout to?
The Australian tech scene is so vibrant. You have very big tech companies in their own right like Canva, or Atlassian, or MYOB, and then you have a ton of new startups coming through like Ignition and some of the other companies I met this morning like the AI companies. It seems to be a hotbed of innovation. Yesterday I met with the Tech Council of Australia, and there seems to be so many great companies both inbound and outbound, it just seems to be quite vibrant to be honest.
Where is Stripe headed to next, what are the priorities for the next year let’s say?
We’ve been pretty consistent with our mission to try and really create this global platform of payments treasury management, and with that to make it as seamless as possible for users to go wherever they want to go and grow their business. So that’s the North Star that we’ll continue to stay really focused on. We have our annual event coming up in San Francisco in May, Stripe Sessions, and we’ll announce a ton of new innovations on the product side that have come about from conversations around the world. We’re going to double down on innovation and investment around payments and how we’re using AI to make that smarter, faster and cheaper. We have a financial automation suite, but particularly usage-based billing.
So usage-based billing is a new framework to subscription-based billing?
Yeah, so we’ve long had a model of a subscription-based billing model and engine, which has been widely used. But with the new wave of AI companies and this need for utility or usage based billing, we think that this is a business model now that’s already taking hold. We’re powering a lot of that with this recent product that we launched – UBB – and putting a lot of energy into that. The beauty of this is it can take a lot of traditional businesses that could monetise content on a usage based rather than seats or licences. That’s an emerging area that we believe we can continue to drive and be at the centre of.
Okay, this is really interesting because we were talking about what a Chief Revenue Officer do. This feels at the heart of innovation. In the most fundamental level do you mind explaining what usage-based billing is? I think I understand.
It’s what you’d think, if you’re running a company, you have the opportunity to run different monetisation models within your company.
If you think about a traditional subscription-based company that might be based on a seat or a licence base, particularly with the emergence of SaaS, and now we think usage-based billing is the next wave. In order to be able to do that say for example some of your customers, it might be like, “Well I don’t want to be a full subscriber but I do want to pay for some of the content, how can you monetise that to make some of the content, how can you monetise that by having a usage based monetisation model that supports a company anywhere to make their services or products or content available in that way.”
And you think, God, what could it look like? Well, it could look like anything. And that’s why we think it’s going to be an emergent of new business models. Because if you can bill for it and monetise it, it means you can unlock a lot of value in a different way than was traditionally done.
If someone was listening to this and wanted to one day be a Chief Revenue Officer at one of the most exciting fintech companies in the world, what would you say?
I think a CRO role is a great role to be in because you’re at the frontline of what’s happening in the markets. I would say pick where you want to play, and then be really current on what are the dynamics of the economy or that user profile or that solution that you’re thinking about. I think that’s a core fundamental of anybody being successful… to really, really, really know and understand the challenges within the market so you can help drive the solution and the growth within it. So that’s one area.
The other is I often think that companies underestimate the value of listening to users or listening to the market. And fundamentally understanding and listening deeply to what are some of the challenges companies are looking to grow. I’m coming from a unique place of tech or fintech. If you obsess about your user I think you’re on the right path to success within your field. And that I think is not often at the top of the playbook, and I think it probably should be. You do not get to growth and high profitability unless you figure out first, what is your first line of defence.
And then the other thing is, people are everything. There are two channels to market. One, you can have a product growth platform. And we have a very successful product growth platform and we obsess about that. And then the other side of it in those user cases where they are more complex, we spend a lot of time making sure that when Stripes show up, they come in with an informed perspective and really delight that founder, entrepreneur, or executive.
Amazing. Thank you so much for your time Eileen.
Eileen O’Mara on … three women to stay across in tech
- Oracle CEO Safra Catz
“Safra is an incredible business leader.” - Claire Hughes Johnson, the former chief operating officer of Stripe and author of Scaling People: Tactics for Management and Company Building
“She’s so creative and personable in how she guides and shows up. She’s a natural teacher in everything that she does.” - The upcoming generation of women in tech
“They know their stuff, and they deserve to make it all the way. They have a lot of confidence, and they should have a lot of confidence. I’m really encouraged by what I see pulling through in the industry.”
