Arjun Pillai | Docket AI (03:57.998)
Hi everybody, welcome to yet another episode of Rethink CRO podcast. Today we are excited to welcome Robert Clarkson to the podcast. Robert serves as the CRO for the Americas at Stripe. Stripe as you know is the largest private fintech company with about $65 billion in valuation and have processed more than a trillion dollars in just in 2023. Quite a lot of money that they are processing.
But Robert's FinTech experience is a little bit of a FinTech stalwart. He has a rich background in FinTech and payments. He has held three chief revenue officer roles previously at Pioneer. He has also done B2B, B2C and platform. He has also held key leadership roles at companies like American Express, PayPal, Norton LifeLock, which was previously Symantec and more.
Robert, thanks a lot for deciding to join us today. We are super excited to have you with us. And welcome to the podcast.
Robert Clarkson (04:58.858)
Well, thank you. Thank you for inviting me. I am anxious to either go through the questions and talk to your audience today.
Arjun Pillai | Docket AI (05:06.744)
Sounds good. Let's dive right in Robert. You are running a pretty big sales organization and you are the revenue leader for not only sales but more. What is keeping you at night? Keeping you up at night.
Robert Clarkson (05:19.733)
So, as a CRO, I am paid to stay up at night. This is a 24 by seven business. And I would say that every day, they kind of fall into different categories. One is, how do I keep the machine running effectively? Our machine, right? In this case, Stripe. We obviously have objectives, we have stretch goals, have intermediate goals and long-term goals. All those things need to be moving.
in the right direction at the right time and what am I doing to invest in those. But I also have external influences. So you have the new administration coming in, right? So you obviously have a new regulatory environment because we operate in many countries around the world. Not only is that the Americas, but my customers deal with their customers in 135 different countries around the world. And so...
I'm constantly reviewing and keeping myself updated on all things regulatory. For example, I'm heading down to Brazil in two weeks because there's some regulatory changes down there and I wanna make sure that our team and our customers are aligned with how to optimize for those new regulations. So that's kind of the second tier. And the third that keeps me up at night is keeping good people.
You know, at the end of the day, this is a people business and I reaffirm it with my team all the time. In fact, this morning I spent one of my second calls of the day on with my recruiting team within side of Stripe going over all the statistics. Like how many open recs do we have? How many people do we have in process? How many people are in the pipeline? What kind of offers are we making to those people? What kind of counter offers are they getting from their existing companies? All of that because at the end of the day,
Great people move a company forward and I'm privileged to work with great people at Stripe, we're always looking for more.
Arjun Pillai | Docket AI (07:15.96)
Awesome. And how big is your team and is it just sales or which all are the functions that are rolling up to you today?
Robert Clarkson (07:22.313)
So teams are 300 plus, we're adding another 60 or so this year, but it continues to grow. It is not just sales, we have sales and service. We also have the technical sales team as well, individual product expert teams, and then you have industry teams. They're all part of the kind of the overall go-to-market strategy.
But again, my team is anybody who either touches, influences, or can develop new channels for revenue. That falls into my work.
Arjun Pillai | Docket AI (07:58.67)
got it and stripe has like a PLG motion where a startup like I can start a company tomorrow and just go sign up for stripe and start using it. Does that eventually roll up to you like when I become a qualified lead to does your team touch me like how does that process work.
Robert Clarkson (08:06.182)
Absolutely.
Robert Clarkson (08:14.035)
Yeah, so very good point. Stripe has kind of built its reputation on kind of self-onboarding and making it very easy to get up and running and work in the payment space. So whatever it is, product, service you're selling anywhere in the world, you want to be able to get it up and running. And frankly, you want to be able to get it up and running easily and intuitively because one, whatever business you're in, that's your area of expertise. You want to kind of outsource the other stuff to Stripe.
And second is, we wanna make sure there's a familiar landing pad for your customers, right? If you're a startup, we're really concerned with your engagement with your customers. So we wanna make sure that when the customer comes to your site to buy your product or take your service or your subscription or whatever the model happens to be, they find a very familiar landing spot. In other words, they see all their credit cards they would normally use, any other payment types that are unique to their country or industry.
would be available there as well. then, know, bank to bank transfers and things like that that are all available. So for us, a lot of our customers originally in the early days of Stripe came in through this kind of self onboarding, self servicing. As they get larger, of course, their needs become more complex. They have more divisions, they have more people, they have millions of customers. Their scale becomes much more complex and intricate and they spend...
More time.
trying to develop a customer experience that really kind of emulates their overall company mission. And that's where they get turned over to my team. So I have basically four different channels within the go-to-market strategy. I have a startup group, which is not necessarily self-unboarded, but still startups. They're new, young, agile startups that are coming up through the system. Then I have kind of a mid-market or commercial group. Then I have an enterprise layer, which
Robert Clarkson (10:15.081)
You think of the biggest companies in the world. Those are the ones that our enterprise deals with. And then I have a platforms team. And the platforms team is any SaaS model that essentially small businesses would use to get their business running. And we power those payments on the back.
Arjun Pillai | Docket AI (10:31.566)
As a consumer when I see a Stripe landing page that asks for my credit card I am automatically at ease because I have seen it so many times the familiar blue color or purple color whatever is your color I'm not.
Robert Clarkson (10:42.621)
Mm-hmm. Yeah, well, the official color is blurple, so you actually got it right both ways because it's blue and purple, so it's blurple.
Arjun Pillai | Docket AI (10:48.556)
Yeah. awesome. So if I can rewind back to a point you mentioned about keeping and hiring the good people, do you involve really deep into the hiring process or is it only for your direct reports that you involve? How do you build your team?
Robert Clarkson (11:04.809)
I really try to stay very close to it. I think one of the most important decisions that you make as a CRO is who is selling your products, right? For many customers, this is the primary interface that they have with Stripe, right? Or with any business out there. And so it is really critical to me that not only these people very good and adept at understanding what the business model is and presenting the pricing and knowing the competitive landscape and all the things that salespeople need to do.
But they really are the flag carriers for the culture and the overall messaging of the business. And so, yes, we have a great marketing team. They do amazing work. They do brand marketing. They do events marketing. They do consumer and B2B marketing. But essentially, most customers' perception of Stripe is the folks on my team. They're the ones that they're interfacing with on a daily basis, either when they're new and they were...
kind of in the hunters segment, right? They were prospects or when they're existing customers for years and years and years, that AE team, that grower team is the one that they see on a regular basis. So to me, finding people who can do the what is easier than people who can do the how. In other words, I can find a lot of people who understand the FinTech space and the payment space.
But people who can do that and reflect kind of the values and the motivations of Stripe is more difficult and that's why I stay so involved in.
Arjun Pillai | Docket AI (12:41.112)
Do you have your own questions that you really like in the hiring process that tells you if this is the right person to be your ambassador or Stripes ambassador?
Robert Clarkson (12:53.824)
I try to probe a little bit about, I want people who can tell me a story. So what I tend to ask is things like,
Tell me about a time that a customer, an existing customer was upset with whatever the product and services you're representing right now. And how did you handle it, overcome it and grow from it, right? And I'm not looking for this, it could be somebody who sells literally, Coca-Cola or detergent or something that would be interviewing.
What I'm looking for is their ability to assess the IQ of the situation. In other words, what has actually happened to create this kind of unappealing sentiment in the short term. But more importantly, what's the EQ of the situation? Is the person feeling bad or let down about what they thought they were going to be able to accomplish and what they aren't? So I want people who can understand both sides of that fence.
And I find that the folks who understand the EQ of business, as well as they understand the IQ of business, are much more successful long term. And our customers have a better experience because of
Arjun Pillai | Docket AI (14:15.234)
Understood. If you can take a different direction a little bit in your sales execution process today, what is your biggest concern? What is top of your top mind for you?
Robert Clarkson (14:27.221)
For us, it's, so specifically Stripe, typically Stripe's reputation is embedded finance, right? It is taking, is powering somebody else's brand. So we're not a Coca-Cola or a McDonald's where that's the first name you think of when you think of payments, but in our space it is. So one of the things that I,
trying to evaluate is I harken back to the old days where they used to have Intel inside, right? So you would buy a PC or Dell or Compact, or could be 47 different brands in the logo, whatever it might be. But you actually looked for the fact that it was powered by an Intel chip. Now, could you and I tell the difference between an Intel chip and an AMD chip? No, but Intel did a great job of helping me understand actually what the differences were. And I think for me,
in the kind of space that we're in, which is not necessarily consumer facing brand, but definitely a B2B brand and a platform empowering brand. That became much more strategic. How do I make other people successful? And that's what I look for, both in terms of people who can translate that message and what Stripe can do for others.
Arjun Pillai | Docket AI (15:47.854)
In 2025, when we are executing your team, my team, we are executing on our sales execution, we know that the buying cycles are longer. The budgets are tighter and CROs are trying to figure it out. So how should they look at this transition? And what are some of the things that you have found to be successful in effectively selling in 2025?
Robert Clarkson (16:14.933)
We're just on that journey right now. fact, two weeks ago, we had our sales kickoff. So we kind of got our marching orders. We are a very high growth company. As I said, we serve every customer from the very smallest to the very largest. So we kind of get to experience a lot of the, don't have like a specific demographic or customer size that we go after. So we actually see the full spectrum of customers and we see global customers. So when I look forward to,
the challenges of 2025, it's about, it's almost about prioritizing appropriately because there's so many opportunities to grow the business, we can't focus on them all. And so you, I find that customers, I was just talking with a customer the other day and they said the turning point in their growth strategy was when they decided not to do things as opposed to try to do everything. And I think that
clearly the case here as well. We have to rigorously prioritize. There's a lot of great opportunities in front of us, but in order for us to be able to have the go-to-market strategy, the product strategy, the marketing strategy, and the integration strategy fully aligned, you can only do a number of those. And our job is to make sure that we pick the right avenues, the right lanes to swim in that have both huge, you know,
TAM, right, the size of the potential audience, and margin, right? So can't be just go after giant ones that have no margin and have cross-sell, up-sell opportunity as well. So we're literally, we went through that list over the last three weeks or so and prioritized just like we did in 2024. And we anticipate growing the business significantly again this year.
Arjun Pillai | Docket AI (18:10.008)
Was there something in that list that historically was obvious that you decided not to do this year? Just curious.
Robert Clarkson (18:18.549)
Nothing obvious that was in last year's list. I would say that...
Robert Clarkson (18:30.217)
When we build a plan,
We didn't necessarily figure in marketing support like we do this year. And I'll give you a sense of it. Stripe has a product called Link, if you check out on customers that have Stripe, think of it as a digital wallet for you that you would use at any Stripe merchant. And so in past years, we really haven't pushed forward on that. We built it, 130 million customers use it.
But this year we're actually supporting with marketing and I think that's going to take a different tact for us because normally we spoke on behalf of the efficiencies of the merchant and the experience that they're trying to create. This year we're actually adding to that which is a consumer experience that we can bring to those merchants and it kind of doubles our effectiveness with a
Arjun Pillai | Docket AI (19:29.55)
It is not everyday that I get to talk to a revenue leader who sells to SMB mid market, enterprise and even the biggest of one. So let me ask this question. When you look at some of these numbers that you are seeing, do you think that one segment has terribly slowed down comparatively to not for strike generally as a market. If I were to target SMB versus mid market versus enterprise, here is where you should and where you shouldn't.
Robert Clarkson (19:56.904)
It's interesting. the startup market is as alive and vibrant as it has ever been. And we feel very positive about it. And we're seeing that all the time. It's interesting, AI in general has spawned an entire, know, cadre of new entrants into the market. And we're seeing, even if you were to say, you know, traditional startups like,
staff businesses and services and all that, they were still growing at a very healthy rate, but then you layer on top of all the AI-driven startups, it is at another layer, multiple percentage points of growth to that group as well. So I don't think there's been any slowdown there, and in fact, it's probably healthier than it's been in many years. Also, I think interest rates coming down helps as well. When interest rates ticked up a little bit, it was a little tougher to get money.
Now you're starting to see some of that money flow back into the system, which I think always helps startups. At the very, very top of the market, the biggest enterprises, a lot of them are going through transformations. So, and you're seeing it now, like they're tooling for AI or they're tooling for potential tariff implications, right, to and from the US. So we're...
we're seeing a little more caution in the buying signals or the buying cycles getting longer at the top of the market, just because they have enormous enterprises to watch out for. They also are their multi-country and they have supply chain issues that they're very, very cognizant of the sensitivities to and they're making changes in supply chain, whether it's from China to Vietnam or South America or whatever it might be, you're starting to see those things. I think the...
pattern that we're seeing is that the largest enterprises
Robert Clarkson (21:58.273)
have kind of multiple pressure points on their business. Payments and consumer engagement is always kind of always one, but other ones have kind of popped up recently just because, you know, political changes in regulatory.
Arjun Pillai | Docket AI (22:14.798)
That's very interesting. And you mentioned AI, and there's no podcast today that we can complete without talking about AI. Given your vantage point as the CRO, how do you think about AI addressing some of the challenges that you or your team have today?
Robert Clarkson (22:19.765)
Right exactly.
Robert Clarkson (22:33.846)
Well, first of all, we are a partner of most of the AI companies that you could think of. So we are in the thick of it with them. As fast as they're growing, we need to make sure that we're keeping up with their growth. It's a very exciting time for us. But I'm finding multiple uses for AI. In fact, I just talked to somebody the other day. said, it's kind of like the old adage where you say,
I have an inside voice and an outside voice. And you kind of in an outside AI, and then you have an inside AI. And the outside AI is efficiency in marketing, being able to target and recognize clients more or potential clients more quickly and prospects. It's all your communications outside are starting to go through so that they are kind of the overall flavor of.
values and the core beliefs of the company that can be translated into these communications. But internally, we're also seeing tremendous advantages in AI. So we use it for a lot of our end of the year, kind of the talent assessments, right? it's always kind of like a near term bias when you're doing those things, but AI doesn't have that. AI says,
Look over the results in the entire year, tell me how we're doing, let's see how that fits, let's see how that translates into whatever ranking or rating you get for an individual employee, that's one. Two, I have a couple folks on my team that have fed all of my emails that I have sent internally through AI in the tone and the measure in those particular emails. So it's hundreds and hundreds of emails.
and they run it through AI, and then when I have to make another email, they send me a template of an email that sometimes I can't even tell, I can't even remember if I wrote it or not. It is so accurate to my voice that it is frightening. Like the...
Robert Clarkson (24:44.819)
or the...
in to a current event or something along those lines are all built into it. So that's one that I think really helps. The second though, and probably more important is, as you mentioned, we do over a trillion dollars a year in payment volume. So there was an incredible amount of data that we need to sift through to make decisions in this business, right? Both for our customers and for our own internal roadmap. AI has...
turn that from a week long or 10 day long process into literally minutes. So now when I go and ask what's happening in this particular segment in this particular country with this particular client base, it's not like an assignment that I send out and then somebody turns through it and sends it back to me. It literally comes right back on my screen. to me, it's going to make not only
decision making faster, but significantly more fortified with true data and up to the minute data. Because you can ingest, know, we work with a number of the AI companies, the amount of data that they can pull into a decision is more than you and I could do in a year, and they can do it in 30 seconds, right? So that has really changed the game.
Arjun Pillai | Docket AI (26:17.23)
So these are all like amazing things that you're doing with AI as in your specific role other than the email and the data that you are let's say the BI business intelligence that you're deriving through AI if you could automate one part of your job with AI automate what would that part would you like AI to automate
Robert Clarkson (26:38.416)
I would love to be able to, and we're working on this, everything, customers always ask us for, think of it like indexes. In other words, how is their business doing against the overall industry that they're in, right? If you're, you know, if it's snack foods, then you wanna know the snack food industry and then how your snack food's doing. And if it's a teaching platform, then you wanna know what,
you know, how are all platforms doing in the education space and then how is your platform growing, customer base, that kind of thing. And so that kind of benchmarking is enormously important. And it's always been hard to one, consolidate the right data and two, homogenize the data so that people are willing to put the data in because they get a lot of data out without me knowing exactly that it's sourced by you.
We never want to have competitive data in there, but we want to have composite data. And so I work on that a lot. And I think that's one of those things where every industry will be able to, every industry that sells and has a competitor will be able to kind of set up a system to be able to, as a customer, can grade my own performance because I can kind of see the average, right? So think of it as a FICO score for your company, right?
Yeah, if you're an 850, you're amazing. If you're a 450, you probably got to make some adjustments. And I think that's one of those areas that has been very elusive over the past many years and is now really coming into focus quickly. And I tell people all the time that customers don't just buy our products. They want to buy our advice on our products. Like, how is our product going to make the maximum impact for them?
Arjun Pillai | Docket AI (28:23.148)
Interesting.
Robert Clarkson (28:35.785)
not just our product does cool stuff, but what does it actually do for them and does it give them an advantage in their go-to-market strategy, their communications, their...
Arjun Pillai | Docket AI (28:47.008)
It also helps Stripe in the sense that Stripe is probably one of the few companies who have ubiquitous penetration. When you do that benchmarking, we can trust the data because it is statistically valid levels of samples across not only US, but also the rest of the world. it's.
Robert Clarkson (29:04.809)
Yeah, greater than 1 % of all the world's GADP flow through Stripe. So we have a big reach. And we can homogenize data so that you can't figure out what your specific competitors are doing, but you know if you're doing better or worse than the average.
Arjun Pillai | Docket AI (29:26.03)
Absolutely. And people love benchmarking in general. If somebody tells me that I have six more to hit against my benchmark, I'll go and hit that six. So I can only see the value in making the competition also in that. Other than the things that we discussed, Robert, is there anything that you would like to tell the upcoming revenue leaders or your peer revenue leaders that you think is relevant?
Robert Clarkson (29:35.349)
Exactly. Exactly.
Robert Clarkson (29:49.878)
So I gave a commencement speech to a college a few years ago, which was a tremendous bucket list item for me, and I was very excited to do it. And these were new graduates. So these were literally people just entering the workforce, actually hadn't even entered it yet because they were literally graduating that day. And I told them three things that I think I still try to live by myself all the time. And the three things were this.
that. The first one was
Problems are the opportunity. In other words, fixing someone else's problem is the job. And certainly as a CRO, my job is to not just watch out for the revenue of Stripe, but to watch out for the revenue of my customers. I have millions of customers. I literally am accountable for their revenue growth, not just mine. And in fact, my revenue growth is merely a byproduct of the success of those customers, right?
That was the first thing. Find the problem you're trying to solve, because that's where the opportunity is. Things that are running smoothly don't need people. They just need somebody to kind of monitor the process. But the actual problems are the career itself. The second was, the book, good to great, Jim Collins, the author, kind of stated,
he talked to successful CEOs over the years and CIOs and CROs over many, years. And he said they always kind of referenced, because he would say, well, you what was critical to you to get to this position? And she would say, well, know, it's such and such, but they would always reference luck. They'd just say, well, I was lucky because I got to join IBM at the early days. Or, oh my goodness, I can't believe it. I joined Microsoft, you know, six weeks after it started, and it was the greatest thing ever.
Robert Clarkson (31:49.119)
But what he found was, it wasn't really luck that...
healthy people's career and eventually their title. But it was actually the return on luck. It was the ability to see luck for what it was, which is an opportunity for something good to happen. Like luck is in a bag of money that falls off the truck. Luck is, and I was literally with the guy the other week at our SKO, and he said he went to a party. He sat down next to guy. They just had a conversation.
It turned out the guy was a CEO of a huge software company, but they had just bumped into each other and he had no idea who this person was. But the luck was the fact that they were able to engage in this conversation. Of course, he ended up working for him and accelerating up through his career and now he's tremendously successful. He's a CRO. But the luck wasn't that the person gave him a job. The luck was that they happened to sit next to each other at this party, right? And started small talk. So I always believe in that. So the second one was, you know,
Luck isn't a thing that happens to you. It's something that you start with and build from. And the third one was that it's always about people. Like, I don't care what business you're in, unless you're literally a writer in the middle of the woods or a painter up on the mountaintop, you need people, right? In fact, if you're a painter on the mountaintop, somebody has to bring you food. But it is always about people, and it kind of relates to your
question or one of earlier questions about headcount and what I look for in people. You work for people, you work with people, and people work for you. And so if you can understand what motivates those people to do the right thing, you're going to be successful. My number one axiom for my job is when people ask me what I do for a living, I tell them,
Robert Clarkson (33:52.244)
My job is to make other people successful, right? The people that are on my team, obviously that's fairly obvious. The people that I work with across the business, risk and compliance and finance and all of that and marketing. But more importantly, my customers and their customers. Those are the people that I want to be most successful because that is my success. And so those were the three things. was, know, problems are the opportunity. Luck is a thing that you, is a tool you work with, not something that happens to you. And the third one is it's all about people.
Arjun Pillai | Docket AI (34:23.36)
Awesome. That's awesome. Now what if our folks want to learn more about you, contact you, where should they go?
Robert Clarkson (34:31.765)
You can Robert Clarkson at Stripe.com or actually R Clarkson at Stripe.com. R Clarkson at Stripe.com, you can always reach out to me. Happy to mentor a lot of folks. I work with a lot of startups. I'm an advisor to a lot of companies. So at the end of the day, it is a people business and the more people I know, the better I feel about what the impact I'm making.
Arjun Pillai | Docket AI (34:56.354)
That's awesome. There you go everybody. Robert Clarkson. Robert, thanks a lot for joining today. We really appreciated the conversation and the insights.
Robert Clarkson (35:04.138)
Thank you.
Arjun Pillai | Docket AI (35:05.666)
Thank you for the listeners for joining in. See you in the next episode.
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