CRO Spotlight: Interview with Paul Harapin, CRO Stripe, Asia Pacific
Paul shares his path to becoming CRO and reveals how he drives growth, navigates complexity and keeps the customer front and centre
In many ways, the CRO is the heartbeat of a company, acting as the bridge between business, sales, marketing and operations. As startups and scaleups face mounting pressure to achieve profitability at speed, the importance of this role has never been greater. In this interview series, we sit down with leading CROs to gain firsthand insight into the tenacity, creativity, and strategic thinking required to excel in this evolving role.
Our first conversation is with Paul Harapin, CRO of Stripe, Asia Pacific.
1. Tell us about yourself and how you ended up on the path to becoming a Chief Revenue Officer (CRO)?
I started my career at IBM, where the company had a very structured program that effectively gave employees an MBA within a year. A huge part of what we learnt was selling and how to sell value. At the time, we were selling mainframes and the technology pathway underpinning it. At the beginning, I really wanted a deeper understanding of the technology so I could really establish its value, so I went down the engineer path. During my 5 years in technology, I found myself selling more than the sales teams - in large part because I am a storyteller, but also because I deeply understood the problems that customers were trying to solve. As an engineer, I was speaking to customers regularly and naturally having conversations about what they were doing and what they needed. I used that understanding to tell stories about how we were going to solve their problems - this had nothing to do with the technology at all, that’s just an enabling function. It was all about understanding. After doing that consistently, leadership suggested I move into sales full time.
Over the years, I tell my teams repeatedly that clients don't really care about your product. What they care about is the problem they’re trying to solve or the value they’re trying to capture - and the more you understand that, the better. I naturally fell into a sales groove as I just loved solving problems for customers.
2. What does your role as CRO of Stripe, Asia Pacific, entail?
I would describe what we would do as being able to tie the customer’s business to the technology we have in a way that exchanges value on both sides. That’s really what we do. If we have a client, we start by understanding what they are trying to achieve, what creates value and what are the blockages. Then, we tie that all together so that fair exchange of value is there. For it to be win-win, we must be able to help solve a customer’s problems and they must be happy to pay for it.
It’s an important part of the CRO’s job to make sure everyone feels good about the exchange of value. It can’t be lopsided to build a true partnership. The last thing I ever want is for someone to regard us as a vendor, running a transactional relationship. As CRO, it’s your job to be customer-first and infuse that sentiment through the company.
In my current role, my involvement with product teams is focused on understanding what our global customers need in the APAC region, and ensuring those needs are met.
Managing all of this—along with customer success teams, technical account managers, and marketing teams—requires navigating significant complexity. As a result, the role requires a lot of time spent on planning, forecasting, and resource allocation. This becomes particularly complex in international organisations, where you're reporting to both local and global teams.
When I first joined Stripe four and a half years ago, we had a very straightforward structure: one team sold to fast-growing startups, while another sold to everyone else. Since then, the structure has evolved. We now have specialized teams focusing on startups, SMBs, large enterprises, and platforms. The enterprise market, for instance, has a very different set of requirements than startups. These customers, such as large Australian or Asian enterprises or government bodies, require a different approach. Similarly, platforms have their own unique business model and challenges. We also have a partner channel that involves collaboration with companies like Accenture, Deloitte, and smaller firms that work with our customers on a range of services.
3. How do you manage the complexity, especially when considering resource allocation and balancing short-term and long-term goals?
It definitely ebbs and flows throughout the year. Toward the end of the year, a lot of focus is on planning for the next year and beyond. At Stripe, we do both one-year and three-year planning cycles, constantly adjusting for changes. Three years may seem like a long time, but in our fast-paced industry, it's a necessary timeframe to ensure we're on the right track.
Balancing short-term revenue goals with longer-term objectives is a continuous challenge. My primary role is to remove obstacles for my leadership team, ensuring they have a clear path to execute business needs. Much of my work involves solving problems so that the teams can focus on growing the business and helping customers. We also work closely with product teams, as our revenue goals must align with new product developments. Together, we ensure that our product roadmap supports business goals in different regions.
Managing Stripe’s business is also much more complex than traditional software businesses because our revenue doesn't always reflect immediately after closing a deal. A customer may sign a contract, but they need to integrate our product into their systems, which can take time. We constantly assess these delays, looking for ways to accelerate the process, whether by identifying resource constraints, working with partners, or resolving friction points.
4. How do you think about the trade-off between chasing short-term returns versus investing in long-term opportunities?
We take a portfolio view of our customers and change strategy based on the company's phase. Early on, Stripe was a product-led, self-serve business model. The founders themselves were hands-on, engaging with customers directly. Over time, we saw that some of the smaller companies we started working with grew into large enterprises, which required a different engagement model. Today, we manage our startup and SMB communities knowing that although the immediate revenue may be smaller, many of these companies will eventually grow into significant customers.
On the other hand, larger enterprises require a longer sales cycle but can deliver substantial returns in the long run. For example, a startup might sign a deal and go live within a week, but a large enterprise might take years to go live. However, once they're up and running, they could be processing billions in transactions. This means making strategic investments and being patient is crucial, especially with larger customers.
In the early days, Stripe wouldn’t have had the resources to pursue large enterprises, but as we've grown, we've been able to make those investments, and they are now a significant part of our business.
5. Given the evolution of the revenue role, how do you see it changing in the future?
The revenue role has always been important, but it's increasingly becoming a more general management role. In my current position, my team and I are responsible for driving revenue, but we also work closely with governments, policymakers, and even the media. A lot of innovation, particularly in payments, is coming from the APAC region, and we actively collaborate with regulators to guide policy in the industry.
More than just driving revenue, my role involves shaping the direction of the business. It’s about identifying friction points in our processes and resolving them quickly. At Stripe, we analyse data constantly to identify bottlenecks, whether it's a delay in product integration or a lack of resources. By focusing on these friction points, we can speed up the customer journey and improve overall efficiency.
As for the sales function, while many companies, such as Atlassian and Canva, initially grow through product-led marketing, they eventually need dedicated sales teams to handle enterprise-level deals. Even early-stage companies with a product-led growth model will eventually need a skilled salesforce to manage larger deals and navigate the complexities of enterprise sales.
6. Reflecting on your career and the future of the revenue role, what advice do you have for founders, especially technical founders, as they grow their businesses?
As a founder, particularly a technical one, it's crucial to understand that the sales process will evolve. In the early stages, you may be doing everything yourself, from calling customers to leveraging your network. But over time, as your company grows, you’ll need to adapt your approach. The importance of having a dedicated sales team and understanding how to manage large enterprise contracts is something founders need to be prepared for. The evolution from a small, self-serve business to a more complex organisation with sales teams and enterprise deals is natural, but it’s also something that requires foresight and planning.
Being exposed to this evolution early on is valuable for founders. It’s about understanding what’s coming down the line and preparing for it. Many or most of the companies I work with appreciate this foresight because it helps them avoid surprises and better manage their growth. It’s a journey, and with the right strategies, it can be a smooth one.