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September 15, 2021Executive Interview Series

Executive Interview Series: Head of Clover Solutions, Jeff Dickerson

The Executive Interview Series provides readers with exclusive insights from movers and shakers in the payments industry. The Payments Industry is under continuous transformation, as such this series provides diverse perspectives on everything from strategy to payments technology and to the future of the industry.

In this interview, TSG’s Market Intelligence team-member Alex Ferguson sat down with the Head of Clover Solutions, Jeff Dickerson, to learn more about Clover and how it has taken the SMB payments industry by storm.

Background: Jeff has been in the software industry for over 30 years and has led companies as CEO through various stages of growth that have resulted in either an acquisition, merger or an IPO. Having grown up in the Sales and Marketing side of the business, his leadership approach remains constant despite guiding companies with various technologies ranging from SMB to payments to cloud-based services. His focus is always employees, partners, customers, and investors — and in that order. He comes to Clover/Fiserv by way of DaySmart Software, where in his less than 4 years there he led the 45-employee company that was under $10M in ARR to become one with approximately 300 employees and now $50M in ARR. DaySmart is one of CardConnect/Fiserv’s largest ISVs. When not building companies, you can find Jeff mountain biking, cycling, working out, golfing (although not very well), or perhaps shark fishing off the back of Martha’s Vineyard.

Q. TSG’s Alex Ferguson
How did you get your start in the payments industry?

A: Jeff Dickerson
I ended up taking a private equity owned company called DaySmart and I took it over as CEO. What they ended up having is a very interesting offering based around scheduling appointments for the salon industry and the pet industry. Now, when I first was approached for the position, they described a pretty interesting opportunity. I asked what they did, and they said – salons and pets. I kind of chuckled and I said something like, ‘I think he got the wrong guy.’ I’ve never spent more than 20 bucks in my life on a haircut and some people would think I overpaid for that. And they said, ‘no, no, no, your background with SMB is perfect.’

I was really hesitant. I talked to a good friend of mine who was at Bain Capital, and he said, ‘you know Jeff, there’s this wave that’s happening with payments and going in directly to the small and medium businesses and implementing that as an integral part of a solution. When I took over this company, they didn’t have any. When I left, we had grown to almost 50,000 customers, and $50 million+. The first thing I did in the first week is we went out for an RFP to bring in a card processing partner. We went out to the big ones and ended up choosing CardConnect. We became addicted to what that allowed us to deliver as far as a seamless integrated solution with payments, and the rest is history. It’s been a crazy ride I think in a lot of aspects, but the ride is accelerating believe it or not.

Q. TSG’s Alex Ferguson
Looking into your background, you have extensive experience in leading C-Level positions at software companies involved in a variety of different industries over the past 15+ years including eCredit, Metatomix, Sonian, The Neat Company, Nutonian, and DaySmart Software. How have these experiences helped you in your new role and influenced the strategic direction of Clover?

A: Jeff Dickerson
So historically I have taken small VC backed companies, usually under 100 employees, and grew them. Some have had some great exits. There’s been a flame out in there, which is an interview all by itself, because I do believe you learn more from your failures than you do your victories. But what that allowed me to do is really get an understanding and appreciation of SMB’s requirements. These SMB owners, as we all know, are the backbone of our country. It takes a lot of guts to open up your own business. These folks who open up the business have the exact same needs as a Fortune 500 company, they just don’t have 500 people in operations. They have to schedule an appointment, or a service, or shipment of a product. They have to get paid. They have to manage their accounting, the personnel, the everything. So, with the experience that I got from there, I was able to glean and then merge it with the payments and take all the benefits that that seamless solution can offer and get it to the customers. I think I’m better positioned than a lot of people that come in just with a payment background or just with a software background. I think the merging and melding of these two prepares me and probably puts me at a better advantage than a lot of folks.

Q. TSG’s Alex Ferguson
Looking back at your experiences, what do you feel is your biggest contribution to the payments industry thus far?

A: Jeff Dickerson
You know, there’s been so many contributions out there from a technology standpoint and the likes. That’s not what I bring to the party. I think it goes back to what we just talked about, and that is bringing a focus on a seamless solution for merchants and including payments. Not just payments individually, but the whole total solution. So, you go into one of these SMBs, the last thing they want is multiple devices on their countertop. Whether it’s a coffee shop, a salon, a veterinarian, a practice management, it could be any small business out there. They could have a screen for your next schedule, they could have one for payments to their insurance company, you could have a card reader on the front, it looks like Frankenstein stitched something together. There are cables everywhere, we’ve all seen it. I think the eloquence is in its simplicity. Having a total solution that allows an SMB to run their business, because most of these SMB they’re not savvy businesspeople, they’re artists that are passionate about their business. Whether it’s food, whether it’s a medical spa, or something else. What I think I certainly have brought here to Clover and a few other places is the focus of a total business solution, a total business platform that doesn’t come with just payments. But the platform shouldn’t be the lead actor, it should be the best supporting actor or actress and allowing SMBs to run their business as the primary goal.

Q. TSG’s Alex Ferguson
What do you feel has been the biggest draw for merchants choosing Clover compared to other SMB focused competitors like Square or Lightspeed?

A: Jeff Dickerson
I think that just is a continuation of what we’ve been talking about. We have over 550 apps that are in our Clover App Market. When you purchase a Clover, you know I’m a little biased, but it is by far the best-looking device out there and I don’t want to overlook that.

I was up mountain biking in Stowe, Vermont this summer and I walked into a coffee shop. It was pretty cool – the shop was all eclectic. They had two big Clover stations, one on each side. I went up and I said, ‘so how do you like this?’ And the woman behind the counter said ‘Oh, it’s really cool.’ I said, ‘so why did you buy a Clover?’ And she goes ‘it was the prettiest one out there. It is so cool look at this thing!’ And I’m sitting there thinking ‘okay, well, that’s kind of neat.’ And then I said, ‘so why do you keep it?’ She replied ‘oh because it works and it’s so easy and intuitive. I’m not a tech person, and I was like a rock star within 20 minutes of using this thing, and it always works.’

So, you know, it’s a combination of things. We have a great form factor that catches everybody’s eye. But really, it’s the platform. It’s the platform that allows businesses to do business. We just finished a 60-city tour throughout the United States of the Clover van and acknowledging a lot of our businesses, partners, and financial institutions. They concluded out here in Sunnyvale, and I had a chance to meet with a Hawaiian barbecue place. We pulled in and we presented the award, and I talked to him, and I said, ‘how did you guys do during the pandemic?’ And she said, ‘well, we’ve only had the Clover for about 10 months.’ I said, ‘you switched during the pandemic?’ And she said ‘yes’, and I said ‘why?’ And she said, ‘well, we started to switch to online ordering to keep things going, and the system we had couldn’t differentiate whether DoorDash, or GrubHub, or between anyone. We had all these drivers coming in for delivery pickups and we couldn’t even match them. It was just a fiasco.’ She went on to say ‘our sister company has been using Clovers for six years. We got it, brought it in, and it just speaks restaurant. They understand what we do for business.’ That was perfect – they understand that we speak restaurant. We also speak a variety of others whether it is payroll or whether it is time management for employees, or reputation management. We even have specific pizza shop oriented capabilities. We have all these features that allows our customers to take what they need to not only survive during the pandemic, but to thrive.

Q. TSG’s Alex Ferguson
At this point, Clover is a household name in the payments industry. But what is an aspect or capability of Clover most don’t know or consider, in your opinion?

A: Jeff Dickerson
I think the vastness, the depth, and the applicability to specific small and medium businesses. It’s not just one generic software, we have a deep platform. I think we were known originally because of the form factor we have, and we’ve kept that, but it’s just the the vastness of our solutions. Merchants can take as little or as much as they want, depending on the complexity of their business. It is the true business platform. Our goal here is if we do this right, we never give a small or medium business a reason to leave our screen. They will have everything there for them. They won’t have to spend time toggling back and forth, they’ll be able to successfully run their business, service their customers, and get paid for all of their efforts. Then continued, whether they’re sent marketing, or you can set and forget different things for yourself in managing your customer base, our solutions allow you to run a specific business.

Q. TSG’s Alex Ferguson
Where do you see Clover five years down the line? What is next on the strategic roadmap?

A: Jeff Dickerson
Clover is in a very, very unique position, and that is we are owned by Fiserv. We are seamless with Fiserv under the covers. We have over 5,000 financial institutions that resell our offering, we have a variety of ISVs that are out there. We have a go-to-market that’s staggering by most measurements. Yet we run Clover as an entrepreneurial driven organization. We are not of mindset of Fortune 200. We start every day as if we’re an entrepreneurial startup type environment and with that, it gives birth to a lot of creation, a lot of development, a lot of innovation. We have several initiatives underway that we believe will be industry first. The one thing I can tell you about it, it’s going to be our platform. Our platform is going to be able to sit on whatever go-to-market mechanisms or partnership we work with here. So, Clover is going to continue to push the envelope and to innovate. I see that the market is going to continue to get closer and closer between payments and business solutions. The customers are demanding it. They want to seamless offering and we will race towards that. We also have a very good international presence, and we are going to be doubling down on that. If you and I chat five years from now I see some significant growth from a global standpoint, and just continued innovation.

Q. TSG’s Alex Ferguson
Clover and Carat were recently recognized as the driving factors that led to Fiserv being awarded omnichannel provider of the Year by TSG earlier this year. Tell us more about how Clover is offering an effective omnichannel solution.

A: Jeff Dickerson
The go-to-market for Clover just sets itself up to for omnichannel. It all has to do with having a core offering and not trying to create something different for each opportunity out there. The way Clover was architected, and our base platform is architected, is extremely transferable and mobile not only to devices and to non-devices, but to different geographical locations and different partnerships. We are going to be lighting up the ISV channels that are out there that are currently using our card processing so that they will be able to take their specific solutions, put it in the Clover, and have what I call a business in a box. A small customer should be able to open up a box, inside is a Clover, you plug it in with any internet connection within two minutes, whatever software solution you have purchased through our ISV channels loads up, and you’re ready to go. That is something that is scalable and something that the merchants and customers out there are screaming for. So, I think it goes back to the platform being flexible and allowing others to connect in seamlessly.

Q. TSG’s Alex Ferguson
How have Fiserv and Clover dealt with the COVID-19 pandemic? What has the impact looked like from Clover’s perspective with its emphasis on SMB?

A: Jeff Dickerson
I got to tell you, I’ve got the luxury of looking back on this now, and I do so with tremendous pride and a little bit of awe with how quickly Clover adapted to what the market needed. Basically, online ordering. The whole world shifted. Nobody was going into places of business, but they still have to conduct business. So, the whole online ordering and order fulfillment component, whether it is from a retail business shipping a product online, whether it’s a food service business, or whether it is some other type of business, we quickly broadened our abilities there. When I say quickly, we work in two weeks sprints where Scrum agile shop. There are some features that came out in less than 30 days, where the features were developed in two weeks, they went to QA for another two weeks, and then they were shipped. I mean, there were some competitors out there that were still drawing on the board what they wanted to do.

But a lot of it was the hands-free component and the no-touch component that we responded to very quickly. One of the things that we are seeing right now with our merchants, is there are some things that post-pandemic you’re just not going to put the genie back in the bottle. With online ordering, there are things called dark kitchens now that never existed before where they don’t have any seating. They just order and people pick up or they’re delivered. Out here in the Bay Area, I was having dinner the other night in Mountain View. And I see this little robot, something out of Star Wars, coming down the sidewalks. And they’re robotic delivery systems. So, the world is changing quickly. No longer is there somebody in a car delivering a pizza. This robot comes in, it has a built-in warming oven, comes to your door, you have a cell phone barcode, open it up, take your food, and the robot is driven back with the help of GPS. You know, coming from the northeast, I didn’t see the tires equipped with snow tread, so I don’t know how it’s going to expand. But these are the type of things that at Clover we’re working with. We’re working with folks to be on the leading edge of some of these technologies to give businesses the advantage they need with Clover.

Q. TSG’s Alex Ferguson
Excellent. Well, Jeff, that concludes all the questions I have for you. Do you have any closing thoughts or comments before we conclude?

A: Jeff Dickerson
I think that the payments market at the end of the day is about the customers and the merchants winning. I think the suppliers, the providers, and the technology folks that can seamlessly integrate a payment solution into a business solution are going to win. I’ve had customers say, ‘I don’t want to stitch together a Frankenstein – I want a business in a box.’ That is what we are driving towards. And again, I think the eloquence of all this is in its simplicity. We can deliver a very powerful solution for SMBs to succeed and to act like a Fortune 250 without all the efforts.

Want more from this series? Catch up on more executive interviews.

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