This article is based on a presentation given by Rik when he held the position of Senior Director of Enterprise Customer Success at PayPal at our Customer Success Festival, Amsterdam in 2024.

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The payments industry is competitive, and retaining and growing your customer base is more challenging than ever. 

With businesses closely monitoring performance and constantly evaluating alternatives, it’s not enough to simply offer a service—you have to fight for your business every single day. 

As someone who has spent years leading global customer success teams at PayPal, I’ve seen firsthand how crucial it is to go beyond just processing transactions and focus on building deep, value-driven relationships with customers.

In this article, I’ll walk you through the strategies we use at PayPal to stay ahead in the dynamic world of payments, from driving growth to future-proofing our business through innovation. 

We’ll cover:

  • The scale of PayPal’s operations
  • The role of customer success managers at PayPal
  • The focus on retention and growth
  • The power of leveraging AI and customer feedback to future-proof our operations
  • How we’re positioning PayPal to revolutionize commerce, not just payments

The scale of PayPal’s operations

Most people are familiar with PayPal already, but I want to share with you what we are doing to be the best customer success organization in the payments industry. I’m going to show you what it really means to fight for your business every day, every hour, and every second, because that’s what we have to do in customer success at PayPal.

PayPal is 25 years old and as of 2024,operates in over 200 markets globally. We have 35 million merchants – online shops – using PayPal every single day. Additionally, we’ve reached 426 million PayPal accounts. Now that's a staggering number!

Last year, we processed $1.5 trillion in payments. To give you some context, that accounts for 25% of all global e-commerce outside of China. That’s a huge portion of the world’s online transactions flowing through PayPal.

This is what excites me about working for PayPal. We’re fueling the global economy, driving commerce not only for large platforms but for countless small and medium-sized businesses (SMBs). SMBs are truly the bedrock of PayPal. Our two-sided platform, which connects consumers and merchants, is what gets me and my team out of bed every morning.

The evolving role of a CSM at PayPal

Being a customer success manager (CSM) with PayPal 20 years ago was simple. Once a merchant had the PayPal button set up on their site, the job mainly involved checking in with them occasionally, making sure the button was working as expected. “Is it helping customers make payments?” That was the essential question.

However, things have become much more complex since then. Beyond the PayPal button, we now handle all forms of card processing – Visa, Amex, MasterCard –, but we also manage a wide range of alternative payment methods: Apple Pay, Google Pay, and many others. 

We process payments end-to-end for our merchants, both online and offline, and across mobile and apps.

Managing critical payments infrastructure

When you become responsible for processing all payments for a business, the stakes get much higher. 

If something breaks, if a payment fails, the merchant is out of business—literally. We play an absolutely critical role in the day-to-day, minute-to-minute operations of the businesses we serve. This isn’t just about processing transactions anymore; it’s about keeping businesses alive.

Over time, we started adding more services on top of payments to help merchants drive traffic and improve their performance. These additional features have made the job of a PayPal customer success manager far more intricate over the past eight to nine years. 

The breadth of knowledge required to do the job has expanded enormously, and it continues to grow.

The expansion of customer success at PayPal

A great example of how the role has evolved is our acquisition of Hyperwallet a few years ago. Hyperwallet handles payouts. So every time you take an Uber and wonder how the driver gets paid – that’s Hyperwallet at work. This is one of many products our customer success managers now need to support and understand.

The landscape for our CSMs has expanded dramatically, and so has their responsibility. We’re now at the very foundation of our customers’ businesses. If our service doesn’t perform, their business can’t perform, and the impact is immediate.

Real-time customer success

An important point to note is that, unlike many billing or subscription-based companies, PayPal charges for every transaction. 

If a transaction fails, we don’t get paid. And if it fails often enough, we might lose that customer entirely, as they’ll switch to a competitor. That’s why customer success at PayPal is real-time. 
We’re always on, 24/7. Every transaction matters, and every moment counts.

The focus on retention and growth

At PayPal, our strategy is built on two key pillars: cusomer retention and portfolio growth. 

Retention is absolutely critical for us because we are always “on.” This means we rely heavily on algorithms to monitor the performance of our systems, ensuring that we are continuously up and running for our merchants. 

Whether their customers are shopping online or using a service like a taxi, we need to make sure that payments are processed smoothly every single day.

We operate in a highly regulated environment, with rules that differ from country to country, and we work within a complex payment ecosystem involving many players – it’s a competitive landscape. 

Everything in this ecosystem has to work in real time because when you make an online purchase, you expect it to happen in seconds, not hours. That means there’s an incredible amount of complexity and infrastructure at the backend. Achieving operational excellence and constantly measuring and monitoring performance is key to staying on top.

Competing in a fast-paced payment ecosystem

The competitive nature of the payments market cannot be overstated. Most of our large customers have multiple payment providers, and they are closely monitoring our performance as well as that of our competitors. 

Sometimes, they are doing this in real-time, meaning they can shift their transaction volume from us to another provider within minutes if they see better performance elsewhere.

This is why fighting for our business in real-time is not just a saying, it’s a reality. It’s what makes customer success so essential. We have to be vigilant, responsive, and proactive at all times to ensure we’re delivering the best service possible. Otherwise, we risk losing business, and in payments, every transaction counts.

PayPal’s three pillars of success

  1. Retention
  2. Growth
  3. Future proofing 

Retention

Let’s start by diving into the first pillar: Retention. 

At the top level, we rely on a vast array of churn indicators and performance metrics. We have algorithms running in real-time to monitor the performance of our customers. These systems alert us when something isn’t working well, whether it’s a decline in transaction volume or a potential technical issue. 

Some of these alerts come through in real-time, while others are weekly or monthly, but they all help our CSMs engage with merchants at the right time, on the right topic.

Proactive engagement

Proactive engagement is absolutely critical in our approach. Our goal is to free up our CSMs from administrative tasks so they can spend more time on strategic, proactive activities with merchants. Every hour less spent on servicing means an hour more spent helping our merchants grow.

The real power here comes from knowing exactly when to talk to a merchant, what topic to address, and having the confidence to enter those conversations prepared and informed. It’s all about articulating value. 

In a fiercely competitive payments market, our competitors will actively try to sway our customers. They'll ask, "Why are you with PayPal?" and present their own alternatives. This is why we must consistently show the value PayPal brings to the table.

As a premium payment brand, we know PayPal isn’t the cheapest option, but we also believe that our merchants receive tremendous value in return. However, it’s crucial that we continually remind them of this value. Repetition is key here—especially when it comes to retention.

Red accounts

The last part of retention is handling what we call red accounts. This happens when a merchant signals that they’re unhappy with PayPal. Even the smallest sign of dissatisfaction triggers an alert, and we mark that account as “red.” This sets off alarm bells across our organization.

When a merchant becomes a red account, our CSMs create a "save plan" and choose the right playbook for that merchant’s specific situation. This becomes a collective effort. Much like the example of the onset team that rallied together, we bring together cross-functional teams to work on saving that account. 

Our CSMs are the leaders of this process, and we work diligently to get things back on track.

Our red account process is quite sophisticated. We categorize issues into tiers: yellow, amber, and red. As the severity increases, more people from across the organization get involved. We’ve done a solid job educating the wider PayPal team on the importance of red accounts. 

When someone flags an issue with a red account, we all need to lean in and work together to help that customer. This system has been working well for us, and we’re continuing to refine it as part of our ongoing journey to improve retention.

Growth

Now, let’s talk about growth. 

There’s a lot to say about growth, but here’s how I see it: as CSMs, we must take ownership of all growth for our customers, no matter where it originates. 

We need to create internal transparency, know exactly where growth is coming from, and have a complete view of how our customers are growing. This holistic perspective is crucial.

Data-driven and targeted

At the foundation of our growth strategy are CSM campaigns. These are highly targeted initiatives driven by data and insights, often created in collaboration with our product, go-to-market, and marketing teams. These campaigns are focused on specific groups of merchants, with the goal of driving growth—whether through value-added services or product expansion.

The key is to leverage data to identify where the opportunities lie. We spend significant time testing and piloting campaigns before scaling them. The governance around these campaigns is strict because we want to ensure that when a CSM is tasked with running a campaign, they feel confident and excited about it. They know we’ve done our homework, and we’re already halfway to success.

Of course, there are still some campaigns that miss the mark. Maybe the data wasn’t analyzed deeply enough, or the merchant is working with a partner where the functionality doesn’t fit yet. But getting the data right is essential.

Small-scale success leading to larger impact

What makes these campaigns so effective is that when they work, and the CSM receives great feedback from the merchant, the real fun begins. That success sparks a thought: "Who else in my portfolio can benefit from this?" It opens up new opportunities, and the autonomy of our CSMs comes into play.

This autonomy can make our product teams a bit nervous because it means that CSMs are in the driver’s seat. When they come to me wanting to launch a campaign to 2,000 customers, I always say, “Great! Start with the 200 most eligible, and let’s watch the magic happen.” And it does.

Today, about 10% of our growth is campaign-driven, while 90% is driven directly by the CSMs. Their autonomy is a huge part of our success. Campaigns help to fuel new product launches, providing that first nudge. But once CSMs get positive feedback from customers, they start looking for more opportunities to apply that success across their portfolio.

Dashboards and tools

We also work hard to support our CSMs with tools and data. Our dashboards are continually improving, helping to identify where the opportunities are, what the next best product or service is to offer, and where CSMs should focus their efforts. This “white space” analysis allows CSMs to see where growth potential exists and target it effectively.

At the top level, we also rely on marketing and other tools to help with self-onboarding. But the role of the CSM in this holistic approach is to make sure that for every merchant, we have an action plan in place. 

For example, encouraging a merchant to try our fraud products or customize a feature they haven’t used yet. While we can’t always hold our customers’ hands, we can guide them in the right direction.

Ultimately, our growth strategy is about taking a holistic view of the customer, owning that growth, driving small, targeted campaigns, and watching the magic happen in the middle of the process. It's an incredibly powerful approach. By empowering our CSMs and giving them the right tools and autonomy, we can ensure that growth happens organically and at scale.

Future-proofing

The final is future-proofing. 

In customer success, closing the feedback loop is essential. We conduct thousands of quarterly business reviews (QBRs) and have hundreds of daily conversations with our customers. With all of this feedback flowing in, we need an effective way to harness it and drive actionable insights.

That’s why we’ve launched the voice of the merchant program. We’ve been using Salesforce to capture feedback, starting with hashtags to categorize the insights. At first, hashtags seemed useful, and for a while, we were able to get a lot of mileage from them, even just using Excel to manage the data.

AI to the rescue

However, we’ve recently begun integrating AI to take this process to the next level. AI is now mining the feedback from our QBRs and the input our customer success managers provide through the Voice of the Merchant program. 

Hashtags aren't as helpful as we thought. AI doesn’t understand them well and prefers natural language. So, we’re shifting away from hashtags, and it’s allowing AI to mine meeting notes and conversations more effectively.

This opens up exciting new possibilities. Once we’ve mined all that feedback from our quarterly business reviews and other customer interactions, we can start asking the AI model-specific questions. For example, "What are the insights for our PayPal-branded button?" or "What feedback do we have on card processing through Braintree?" AI can pull these insights and feed them back into our product organization, enabling us to act on real customer needs.

Speed and efficiency

A great example of this in action is with our Hyperwallet product, which handles payouts. Just like with card processing or any other product, we can now easily gather and analyze customer feedback using AI. 

It’s extremely powerful. With a click of a button, we can generate a comprehensive report on customer feedback by product.

I experienced this firsthand when preparing for a meeting with Frank Keller, our Head of Product, in Ireland. I asked my team for a product-specific feedback download, and within 15 to 30 minutes, it was sitting in my inbox. 

AI had done the heavy lifting, processing vast amounts of feedback in record time. This is the kind of efficiency we need when you’re running a global customer success operation with 450 customer success managers.

AI is becoming a huge asset in helping us future-proof our customer success efforts. It allows us to capture and process insights at scale, ensuring that we stay connected with our customers and can quickly feed their feedback back into the organization. 

As we continue to teach and refine our AI models, the insights will only become more precise, allowing us to respond more effectively to our merchants’ needs and stay ahead in a competitive market.

The future of PayPal: Revolutionizing commerce

Lastly, let’s touch on PayPal’s ongoing journey. We started with something simple—the PayPal button. From there, we revolutionized global payments and processing, growing to handle 25% of all global e-commerce transactions outside of China. That’s an incredible achievement and something we’re very proud of. But, of course, that’s not the end of our story.

What’s next for PayPal?

So, what’s next? We’re not just stopping at payments. Our next goal is to revolutionize commerce itself. We want to leverage our vast amounts of data and AI not only to facilitate transactions but also to help merchants drive their overall commerce strategy.

For those of you following the latest developments like the Digital Markets Act or the shift away from cookies, you know the pressure businesses are under. SMBs, in particular, are feeling the rising costs of search ads and Google advertising. The current model is becoming unsustainable for many of them.

What we want to do is similar to what we did with payments—change the game. Instead of paying for clicks or impressions, merchants will only pay for actual transactions. We aim to drive the e-commerce funnel without requiring merchants to invest heavily in ads. 

With our new model, merchants will only pay us when a transaction is completed. This shift is going to be huge—allowing businesses to personalize ads using AI, but only paying when those ads convert into sales. It’s a much more effective and cost-efficient approach, especially for smaller businesses.

A new challenge for customer success

This new approach to commerce presents a significant opportunity for PayPal, but it also stretches us as a customer success organization. It raises new questions: How far can we take this? 

We’re dealing with the same merchants, the same webshops –but now, our customer success managers won’t just be speaking with payment managers. They’ll be engaging with marketing managers, treasury teams, fraud and risk managers, and more.

This new frontier in commerce will require us to expand our knowledge and expertise. It’s a great challenge for us as leaders in customer success, but also an incredible opportunity. It allows us to build deeper, more meaningful relationships with our customers by helping them across multiple facets of their business, not just payments.

The path forward

As we continue to grow and evolve, our goal is to revolutionize commerce just as we did with payments. By leveraging AI and shifting the cost burden from clicks to actual transactions, we’re creating a future where businesses, especially SMBs, can thrive in a more sustainable and efficient way. 

And as CSMs, we’ll be there every step of the way, ensuring our merchants not only stay with us but grow with us as we enter this exciting new chapter.