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Executive Interview Series: Founder and CEO of CCSalesPro and ISO Amp, James Shepherd

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 James Shepherd, Founder and CEO of CCSalesPro and ISO Amp to learn more about his journey through the payments industry providing training, education, and technology to the ISO/Agent community.

Background: James Shepherd is Founder and CEO of CCSalesPro and ISO Amp. James has spoken to over 3,000 sales professionals and completed consulting engagements for dozens of processing companies since CCSalesPro’s inception in 2008 and their knowledge base contains over 40 hours of video/audio training programs on various sales tactics and industry topics. His YouTube channel has received over a million views since its inception, and James hosts the “Merchant Sales Podcast” weekly with guests from across the payments ecosystem.

Q. TSG’s Alex Ferguson:

Tell me about yourself. How did you get your start in the payments industry?

James Shepherd:

You know, I think most people in the industry kind of fall in by accident, and that was the case for me. I was living in Chicago, and I’ve always been a serial entrepreneur and have had a string of different businesses and different positions.

When I left Chicago, I was a regional sales manager for ServiceMaster and running a door-to-door sales team there and doing some sales training. When I moved out to Central Pennsylvania after I got married, I was looking for a new business to start or some kind of opportunity. An ISO reached out to me (I think I posted my resume on or something) to recruit me, and I thought, “Well, this looks like something I could do for a little while, while I look for something legitimate.” And here I am, 13 years later, still doing it. So that’s how I got in and had a minimal interview process. It was like, “hey, good luck, go sell these terminals.” So that’s how I got in and just kind of kind of fell into it and fell in love with it at the same time.

Q. TSG’s Alex Ferguson:

Tell me about CCSalesPro. How did the idea for this venture begin?

James Shepherd:

Yeah, so really it began when I got into the industry, again, my background was in sales training. And I’m the type of person that I want to be an expert at what I’m selling. It gives me a lot of confidence to know what I’m talking about. I’m not somebody that enjoys pretending I know what I’m talking about, I like to really know it.

So, as I got into this industry, the training I received from the ISO that recruited me (a really small ISO they’re not even in existence anymore) basically consisted of a two-hour webinar, where they showed me how I could lease the old Hypercom terminal, the 220. They showed me how I could lease that for $99 a month times 60 months – that was my training. Then they said, “get out there in the field and good luck.” I was really good at it, I sold a lot of accounts, having no idea that this may or may not be the best deal for the merchant.

I really struggled to find information. I’m looking online searching “what is interchange? and “what’s the level two?” and “how does this work?” So, my thought was, if I’m searching for this, and I’m having a really hard time, there’s got to be other people doing that. I did that for, I think around six or eight months, and by that time I had switched to a more professional relationship with a payment company that was respected.

I started building a good-sized portfolio and I thought, “you know what, why don’t I take all these things that I finally figured out myself and let me start posting content on YouTube.” Which at that point, I was on YouTube before it was cool to be on YouTube. We started putting this content out and started the CCSalesPro blog. So, from the very beginning, it was really started as a resource to be the resource I wish I had when I had first started. To give people that edge to learn what they needed to learn about the industry, but mostly how to sell payment processing.

Q. TSG’s Alex Ferguson:

In addition to sales agent training through CCSalesPro, you offer an automated statement analysis tool called ISO Amp. Tell us more about the tool and what makes it such a difference maker for agents.

James Shepherd:

Sure. So, we have CCSalesPro which is primarily training, consulting, coaching, that type of thing. And the reason that I started ISO Amp was, as an agent myself, I felt like the statement analysis process was really archaic and frustrating for everybody. It was frustrating for the statement analysis department at the company I was selling for, and it was very frustrating for me. We started building, about six years ago, a software solution that could instantly come up with an estimated savings amount. Then we realized that image recognition and OCR was really coming along, and AI and all these things that the technology was there for. Then we built out where you can upload your statement and get an analysis done that way.

What we have to understand is when we talk about agents and we say a value proposition for agents in this industry today, we have to recognize that there are three different categories of value propositions that exist. The first one is payment processing. When I started the industry that was 100%. So, all the sales I made were because I can save them money, I can do interchange optimization, I can recognize interchange padding, I can eliminate junk fees, all of these things tied directly to payment processing.

Today that still exists, but it’s probably only about a third of the sales that are made are related to that specific value proposition as the primary. Now for those agents that are selling those mostly larger accounts, where being accurate really matters, they need a custom proposal template – That’s what we do there. So, they can upload their statement, we have a team of W2 expert employees. We try to automate the process as much as we can and then we have humans that do the rest. We’ve kind of taken the idea of the statement analysis department, and you now have the ability to outsource that, to free up some of your best people to do other things within the organization, and really help the agents close deals and get things done. So that’s one, that’s about a third.

Another third, is going to be technology. That’s where the payment processing is important, but only as it relates to the integration with the technology. For that we have our custom proposal templates. We work with our clients to be able to put in a little bit of information, maybe they want to upload a statement, whatever they want to do, but we can help them generate a fully customized proposal template with marketing information, data from the payment processing, and how much they can save – things like that.

Then the final third is going to be just the really simple pitch. This is where we’re competing with Square. It’s the idea of flat rate pricing, cash discounting, compliance surcharging, dual pricing, where we’re going after these merchants in the $30,000 a month and under range. Those merchants today, really, what they care about as far as payment processing is concerned is they care about simplicity. So, again, we have custom proposal templates, and we still have our instant functionality that we’ve had for years, where they can go in and put total volume in there for the merchant and hit create. They’ll get some basic information that they can put into a real nice proposal template that highlights the simplicity of it.

So, I think the answer to your question is, we cater to those three primary types of value proposition, and I think that’s what agents and ISOs are really looking for today.

Q. TSG’s Alex Ferguson:

In your opinion, what makes selling payment processing different from selling in other industries?

James Shepherd:

I like this question. When I started out in the industry 13 years ago, I would say that it actually was very similar to selling other things. I really felt like there was a lot of similarity. I think what makes it so different today (that it’s kind of good and bad) is that there is so much opportunity. But at the same time, there’s very little accountability and structure.

So, it’s very different, because as an agent, you come in, and it’s like, “Well, you say you sell payment processing, what does that mean?” Are you saying that you sell a point-of-sale systems to restaurants? Or you sell gateway solutions to B2B companies? Or do you sell an API solution to software companies that need recurring payments?  Saying you sell payment processing today could mean so many different things. So, I think it’s an amazing opportunity because number one, you’ve got all these different things that you can do, and different things you can focus on. But then also, you have this recurring income and I really believe the payment processing industry is one of the few industries left that really gives the ISO or the agents the opportunity to make a significant cut out of this recurring revenue that’s generated.

I think that’s the big opportunity. But again, when you say you sell payment processing, that’s not enough anymore. Now you need to be able to say, not that I sell payment processing, but specifically, what am I focusing on within that developing sphere.

Q. TSG’s Alex Ferguson:

You have an impressive YouTube catalogue with over a million collective views that I’m sure has covered this topic before, but what do you think is the most common difficulty new participants and agents in the industry experience?

James Shepherd:

Yeah, so it’s interesting, it really goes back to the last question and what sets this apart. It’s this idea of unlimited opportunity, but having unlimited opportunity is actually not a great thing when you’re starting something. When you’re starting out, you really need a clear path to success. You need to know this is what I should do today. This is what I should do tomorrow. What business should I go to next? So that practical question, unfortunately, it’s very challenging in our industry because so many people come to our industry through recruiting and straight commission to 1099 positions, where there’s really very little structure if any and no accountability.

Again, there’s good things to that: there’s flexibility, there’s work life balance, there’s things that can happen there that are good. But when you’re first starting out, I think the big challenge is, people see the opportunity. They’re like, “wow, this is an amazing industry, look at all the different things I can do.” But they struggle with understanding, what should I do next? When we look at that question, that’s where a lot of my content has been geared. Picking your vertical you’re going to go after, picking your prospecting strategy, and then really deeply understanding what’s the next action that you need to take.

I think that is just really, really a crucial thing. And then once you understand, this is going to be how I’m going to go prospecting, or this is the type of businesses I’m going to go after, this is the type of technology I’m going to offer, right? Like most of these agents, they have 20 different potential POS systems they could sell through their processor. That sounds great, but that’s terrible. If you’re new, that’s overwhelming. Well, which one do I sell? How do they work? What features do they have? So, I think it’s about narrowing that a bit and finding your path to success, and then staying on that path for a while so you can actually get some traction.

Q. TSG’s Alex Ferguson:

Speaking of your impressive catalogue, in addition to your YouTube channel, you host a weekly podcast that has published over 180 episodes to date. What’s the key to keeping your content fresh? Do you ever feel like you’ll run out of payments topics to cover?

James Shepherd:

Definitely not. In fact, you know, I think the key is focusing on topics and not on the people you’re going to interview. And what I mean by that is, you start with the topic. For me, the topics that can be discussed in the payments industry are really just never ending. It’s always evolving, which is what I love about the payment space.

But as far as having that content, to me the key is I start by thinking about what are the topics that appeal to my audience. It’s the “Merchant Sales Podcast,” so my audience is going to be people that are involved in selling merchant services, whether that’s agents or ISOs, or managers of salespeople, or executives or processing companies – anybody involved in in selling new accounts. So, I ask what are the topics they are going to find interesting?

Then once I start with the topic, then I start searching around, usually through LinkedIn and through my network and say, “Okay, who would be somebody that I could interview about this topic, that would be, creating insights and giving us ideas and creativity that my audience would find valuable.” I love doing the podcast, actually one of my favorite things to do. I try to record one a week and it’s a lot of fun. Again, I’m not worried about running out of content, because we live in an industry that’s always reinventing itself and evolving.

Q. TSG’s Alex Ferguson:

Do you feel how payment processing is sold has shifted over your time in the industry? Have newer entrants like Square and recent events like the pandemic shifted the formula of selling payment processing?

James Shepherd:

So, I think everyone knows the answer to this question, which of course is “yes, it has shifted over the last 13 years.” However, I think I would want to go a different direction with this answer, which is, I don’t believe it has shifted nearly enough as it should have. I’m actually shocked to be honest with you, that it has only shifted as far as it has. I think one thing that’s really heavy on my mind right now, is that the industry (when I say the industry, I don’t mean the payments industry, I mean, the ISOs and agents that are directly selling payment processing) has actually not done a great job of fully embracing integrated payments, selling software, picking certain verticals, and becoming experts and providing payment solutions to those verticals that integrate into their operation of their business.

That’s very concerning to me. I think that’s a huge threat, and you bring up Square, and you could talk about Stripe and Toast, and many others that are external companies coming in. Those companies are a huge threat, because they are built on the premise of integrated payments and that’s all they offer. That’s a big problem for our industry if we’re not going to adjust.

To answer your question, it has changed, obviously, a lot with the long-term trend being integrated payments. When I started 13 years ago, it didn’t matter what business I walked into, I could sell them on payment processing. They were all using a standalone terminal. A few of them would have some legacy point of sale system that I could integrate with. So, it was a question of, can I sell them on my rates, and my fees, and my cost savings, and my service, and my compliance, and whatever else? You’re related directly to payments.

That’s not the case anymore. You go out and walk down a street and walk into a bunch of businesses, you’re going to find that a significant percentage of those businesses already have an integrated software of some kind, whether that’s running through hardware, or a card not present environment, and they’re very happy with that. They’re not willing to change and all of the software companies have figured out how much money is in payments. So now they all have payment processing built in, and they’ve got the agents and ISOs locked out.

The sooner an individual agent or ISO embrace that, and say, “Okay, wait a minute, that’s the direction that everything is going, where’s my place in this? How do I embrace this?” – you’re going to dramatically change the way you’re doing things. I think that’s the change that’s going to have to happen over the next 36 months, in a major way, if the ISO agent model is really going to be something that’s going to be long term effective in the industry.

Q. TSG’s Alex Ferguson:

Looking back at your journey through payments, what do you feel is your biggest contribution to the industry thus far?

James Shepherd:

That’s a tough question. I think my biggest contribution has been that I’ve been able to answer two questions for the thousands of people who come into our industry every year whether that’s through recruiting or other various channels. Those two questions are, what is payment processing? And how do you sell it? Those are two questions that when I got started, I looked for the answer to those questions online, and I couldn’t find it.

I’m really proud of the fact that now when an agent comes into our industry, they can go to Google or YouTube or Facebook or wherever, any of these social media platforms, and they can search for those questions. There’s a lot of great resources now, not just mine, of course, I want to of course, acknowledge, there’s a lot of great resources, but my resources are there. And now they’re going to find those videos, and they can start watching those, and they can get an understanding of the basics of our industry.

I think that’s my greatest contribution to date, really just providing that online resource that helps people as they first get into our industry to just kind of understand the lay of the land and get some tips to be able to get started, because it’s such a fantastic opportunity. But as I mentioned earlier, you’ve got to get on that path to success if you really want to be effective.

Q. TSG’s Alex Ferguson:

What’s next for CCSalesPro? Where do you see yourself five years down the line?

James Shepherd:

The timing of this is so interesting. So right before this interview, I was having a conversation with my lead developer, and my business partner, his name is Jack Christiansen, a lot of people wouldn’t know him, he’s behind the scenes. But we have our own in-house developers that built ISO amp and built these other solutions, and we were just talking about this.

Really, the future of CCSalesPro is about integrated payments. What I mean by that is, our mission as a company is keeping merchant sales competitive. So, we’re trying to help merchants, sales organizations, ISOs, and merchant sales agents, remain competitive with Square, Stripe, Toast, PayPal, and many, many others. The only way to do that moving forward, as I mentioned in the last question, is really integrated payments.

So, we have a lot of things that we’re working on. We’re going to be doing more training and partnerships with processor agnostic ISVs, to help train the industry and help train ISOs on how to sell integrated payments. I have several companies of my own that, again, the industry is not really aware of, but I have different companies I’ve built and that work with ISVs that serve certain verticals. We’re talking about ways that we can help take that technology and bring that to the ISOs and agents to help give them more opportunities to sell integrated payments.

So that’s really what I see. I want to keep doing what I’m doing, putting out the content, doing the consulting practice, the training, and all of these different things that I do now, and of course, ISO Amp is going to be, I think, pretty large there in five years and have a dominant position in the market. Where I really see the organization headed is how can we solve this fundamental problem of helping ISOs and agents sell integrated payments and lock in their portfolios and future proof them? Because if we don’t solve that one problem, nothing else is really going to matter. None of these debates about anything is really going to matter. Because we’re going to lose the battle to the Squares and the Stripes and the Toasts of the of the economy.

Instead, we have to come out and say “wait a minute, we’ve got the distribution, we have thousands of individual salespeople and professionals that are business owners that are out in these communities, and they’re talking to business owners every day.” If we can get those people to sell the right solution and offer a higher level of service and support that these larger payment facilitators cannot offer remotely, we can actually win the larger battle which is the battle for integrated payments. What exactly that looks like, I don’t know yet, but I’ll tell you this: in five years from now, I want to be doing a lot more to help agents and ISOs solve the problem of selling integrated payments to business owners of all types card not present and present.

Q. TSG’s Alex Ferguson:

Excellent. Well James that’s all the questions I had for you. Did you have any closing thoughts before we conclude?

James Shepherd:

I just really appreciate the opportunity to be on here. I’m really passionate about the industry, and I always enjoy discussing it. I think our industry right now is in a really interesting place. You know, we’re in a place where there’s a lot of change. And when there’s a lot of change, there’s a lot of opportunity, and there’s a lot of risk. We’re in a high risk, high reward situation right now.

I feel like the ISOs and agents that pivot and embrace the change and say, “wait a second, I can’t do things the way I’ve done them for the last 10 years, I got to adjust.” They’re going to win big because there’s big opportunity right now. And those who say, “I’m going to keep doing things the way I’ve always done them,” I think those individuals are going to lose big because they’re going to get swept away with all the changes. I hope those that are reading this are going to change and are going to adjust with the market and I think if they do that, I feel like our future is very, very bright in this industry.