Stripe CRO Eileen O'Mara: Serving The Enterprise
Today's enterprises are yesterday's disruptors
Hey friends! I’m Akash 👋. I love learning about how great companies are built and I aim to share those learnings on startup strategy here. You can always reach me at firstname.lastname@example.org to exchange notes and share feedback.
Current subscribers: 3,420
Learn about startup strategy along with 3,400+ founders and operators
Today we’re speaking to Eileen O’Mara.
Eileen O’Mara is Chief Revenue Officer at Stripe, where she is responsible for the go-to-market function. Based in Dublin—Stripe’s dual HQ—Eileen leads a global team that helps millions of companies, from the world’s largest enterprises to the most ambitious startups, use Stripe to accept payments, grow their revenue, and accelerate new business opportunities.
Prior to joining Stripe, Eileen held a number of roles at Salesforce, including International CMO and head of commercial revenue for APAC & EMEA, where she led large teams across diverse markets. Eileen also held senior leadership roles at Oracle.
Eileen, to start with, your career started with roles at Oracle and Salesforce to finding yourself as chief revenue officer at Stripe. How linear was this journey?
I’m a big fan of Charlie Munger’s quote:
“You’ve got to have models in your head. And you’ve got to array your experience—both vicarious and direct—on this latticework of models.”
I’ve tried to use each opportunity throughout my career as preparation for what’s coming next.
I’ve been lucky to spend many years working with enterprises, and as Stripe has expanded to serve this segment it’s incredibly satisfying to draw on that experience, and to help build out that side of our business. It makes my role all the more exciting.
Stripe has had lots of success in moving upmarket into the enterprise, but traditionally it is best known for serving the start-up segment of the market. To what extent do traditional enterprises resemble the young startups that matured into enterprise-sized accounts (and as a consequence, how many of these learnings are transferable)?
Today's enterprises are yesterday's disruptors. Think of Uber, Airbnb, Instacart, DoorDash, Deliveroo, and others. Many of our users have been with us for over a decade, and so they've made that journey, and brought us along with them. At the same time, we now serve the largest and most progressive traditional companies.
A surprising amount of the world's ambition resides in enterprise businesses, many of whom are reshaping industries they've long dominated.
It might sound simple, but I spend a lot of time talking with our users and I hear time and again that enterprise needs are surprisingly similar to those of start-ups.
For instance, no matter the size of the business, leaders always care about reliability, security, ease of integration, rapid access to support, and a community of like-minded people who share their ambition.
Take Mountain Warehouse as an example. As it was gearing up for the annual Black Friday holiday sales rush, one of its payments providers experienced hours of downtime. It couldn’t risk the lost sales or added stress which an outage would cause. They came to Stripe for our ‘five 9s reliability’ record.
Drawing on our experience in serving start-ups, we’ve become the financial springboard for traditional enterprises reinventing their entire business models as they fight back against disruption.
We support them as they adopt the same tools and mindset that their disruptors have to compete and stay ahead.
Stripe has developed a compelling product portfolio as you’ve moved upmarket. I’m sure many Stripe enterprise customers use multiple Stripe products in multiple countries, but how important has it been that Stripe already was a multi-product company with 20+ SKUs in its portfolio before you started serving the enterprise?
Being multi-product is all well and good——last year we shipped 244 new user-facing features and 336 API updates—but enterprises don't buy products off the shelf, they need tailor-made solutions. The breadth and extensibility of the Stripe platform means we can build those bespoke solutions.
But every company is at a different stage of its transformation. We generally see traditional enterprises come to us at three distinct maturity levels:
Beginning of their digital transformation journey: companies just starting to sell their products online or upgrade their legacy systems. These companies will typically request a simple check-out to capture revenue online—they’re often not ready to become fully digital
Establishing a new distribution channel: companies who are rethinking the way they sell and distribute products on digital platforms. For example, Lotus Cars creating a direct-to-consumer channel to sell its new electric car
Launching a whole new business model: companies who are creating new complementary business models to generate additional revenue streams that are only possible in the digital age. For example, Zara launching a pre-owned online clothing marketplace
Whether they are considering moving onto digital platforms for the first time, or building new revenue streams, we work with these enterprises to support their transformation and, ultimately, accelerate their revenue growth.
The enterprises you serve run the gamut from innovative companies to traditional enterprises such as Ford, BMW, and Hertz. Stripe has already been recognised as the best solution for tech-forward merchants, but how much education do traditional merchants need on how Stripe unlocks value compared to traditional acquirers? How much education was required for traditional enterprises to view payments as a strategic lever rather than a cost centre?
Enterprises in every corner of the economy are staring down disruption and need to act now. Ask any enterprise CEO and they'll tell you that digital transformation is no longer a fluffy idea for the future: it's an urgent requirement for survival.
And this transformation is key to unlocking growth: businesses that switched to Stripe's newest payments integration saw a 10.5% increase in revenue on average compared to those that did not. How many levers can you pull that would give you that sort of revenue growth?
Our position within the ecosystem means we drive the entire disruption flywheel supporting both start-ups and enterprises simultaneously. We power disruptors such as OpenAI, we power the disruptors that have transformed into enterprises such as Amazon, and now we’re supporting traditional enterprises—such as Maersk—as they look to catch-up to the disruptors once again.
One challenge with selling to the enterprise is the focus on pricing, particularly with traditional enterprises. How has Stripe approached this challenge of payments being perceived as a commodity in order to avoid a race to the bottom?
If you're buying payments as a commodity, or just looking at payments providers as a cost center, you're doing it wrong! The vast majority of businesses have long since understood payments as a strategic lever to grow their revenue.
And Stripe supports enterprises in areas well beyond payments. The most sophisticated companies see the value of financial infrastructure as sitting in a similar category to cloud infrastructure: having the right financial infrastructure in place is essential to their future.
One example is in Stripe’s revenue and finance automation suite. Its automated revenue recovery features alone earned Stripe businesses an additional $3.8 billion in revenue in 2022 by reducing customer churn and payment failures. And Stripe Billing has been adopted by hundreds of thousands of businesses, including Slack, Atlassian, Deliveroo, and Figma.
I personally get excited when the world’s oldest companies come to us to partner on their transformation. It’s a privilege to support companies such as Ford, MAN, Le Monde, EDF, and others as they rethink decades—sometimes centuries—old systems for the modern digital age.
Many software companies attempt to widen their aperture by expanding beyond selling into other tech companies into traditional enterprises. Can you share your most important piece of advice for entrepreneurs about when to expand (in terms of product maturity or penetration of tech-forward enterprises).
Don't go upmarket because you want to grow your TAM; go upmarket because your users demand it.
At Stripe, we couldn’t continue to serve our most ambitious users without addressing the needs of larger companies.
Figure out what you solve for your current users and if these same challenges exist in other segments—in many cases that will lead you to the door of the world’s largest enterprises.
Thank you Eileen for this wonderful interview, and to the amazing people at Stripe who made this happen.
The days are long but the decades are short Sam Altman
Will AI Save Inefficient Software Companies? Will Bennett
Quote of the week
‘I often refer to the importance of product velocity and momentum as 🔑 indicators of early success for a startup but often overlooked is the rate of founder learning. When it comes the search for PMF, founder learning is often manifested in the speed to hone the core value proposition and pitch as the best founders are able to find signal from noise and iterate quickly and multiple times before PMF. So much goes into that succinct value proposition.’