Calvin Hosey of Regpack On How To Use Digital Transformation To Take Your Company To The Next Level

The initial benefit is that it can expand your reach. For most people, if they don’t have any digital presence and undergo a digital transformation, they’ll immediately go from a local entity to a global one. So whether or not you want to have customers in Japan when you’re based in Alabama is on you, but any business can immediately expand their reach right then and there.

As part of our series about “How To Use Digital Transformation To Take Your Company To The Next Level,” I had the pleasure of interviewing Calvin Hosey.

Calvin Hosey is the Head of Operations and Payment Partnerships at Regpack, an online payment management platform. His experience leading and training teams at Google, Kaiser Permanente, and Enterprise has translated directly to his role at Regpack, where he oversees the company’s support, payments, and onboarding teams and manages payment gateway partnerships. With honed strategic and leadership skills from his college years at UC Berkeley, Calvin’s talents have helped garner hundreds of positive reviews for Regpack’s customer support.

Thank you so much for joining us in this interview series. Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I was born and raised in Bakersfield, California, and ever since I was a kid, I’ve always been good at getting into different things. I was also swole and athletic, making me a prime candidate for football. Playing football earned me a scholarship at UC Berkeley, where I met tons of people and friends. It was also where I realized I didn’t want to play football as a professional. During my third year, I wanted to be an economics major, but I only had prerequisites for a few things and still needed to take a math class. So instead, I became a social science major, which has helped me tremendously throughout my career. I learned the statistical, mental, and laborious sides of sociology and how I could apply this knowledge to the work I do every day.

My social science degree led me to live in different places for a while — Canada, Seattle, and the Bay Area. I now live in San Diego, but I’ll probably be going to LA or Portland next. With each previous move, I held a different position or role in various industries, starting with sales. I was in construction before returning to sales again and held positions in training and operations, ultimately leading me here at Regpack.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

When I was contracted at Google, I learned the lesson that it’s probably not the best idea to be too blatantly honest when it comes to explaining things to people in higher positions than me, especially if it’s slightly unorthodox.

When leading a team, I treat everyone like they’re adults, so I don’t micromanage. I can when it’s necessary, but I personally don’t want to do it. So, during a meeting with the higher-ups at Google, they asked me, “How do you get your team motivated?” I gave them a blunt answer and said, “I give them more breaks.” The lead at the time pulled me aside afterwards and basically said that it’s fine if I do it because my team produces results. However, when the higher-ups ask what makes your team effective, telling them you give more breaks than are allowed is probably not the best strategy to explain productivity.

But my reasoning behind more breaks was to combat decision fatigue and choice overload that can occur in typically high-volume situations. If people are dredging all day, clicking things, and trying to figure it out, nobody pays attention to how much of a drag that actually is on productivity. So, the idea was to give them a break every so often, and I would find a flash game online that everybody could play on a browser. We would just have a team video game competition as a break to reset their brains and allow them to keep going faster and more effectively than everyone else.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I was still on the football team in my senior year at Berkeley when we had a coaching switch. The new coach, Jeff Tedford, a coach from Oregon, brought a boatload of people, including Paul Shea, the head of football operations. One day, Paul pulled me aside and said he wanted to keep an eye on me because he felt I had an aptitude for business. I don’t know where he got it from, but from then on, he would pull me aside and try to explain how loans work, the concepts behind them, and managing money.

He was a very successful businessman doing the football job for fun because he knew Jeff. He told me the story about his first business: a brake business. He said, “You need to choose a business that, no matter what happens as technology progresses, it’ll still be relevant. So why brakes? Well, it doesn’t matter how cars, technology, and all that fun stuff progresses; cars will always need a way to stop.”

Applying that same knowledge to Regpack, it doesn’t matter how businesses progress or things change; companies will always need to be able to collect payments and manage their users. Paul’s original philosophy was that you need to make sure you’re not going to be trapped as a middleman. If you’re running a business, you want to ensure that no matter what happens, you’re not going to become obsolete just because progression exists.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

When I was six or seven years old, I read a lot of Aesop’s fables. Every time I tried to sit and think of a scenario and how I would’ve handled it differently. So, from a very young age, I was always trying to figure out my own sense of self based on Greek mythology. I also read the Berenstain Bears, the Bible, and everything just to try and form a solid, comfortable sense of who I was going to be. I think I pulled it off.

As far as podcasts go, I listen to a bunch of them, but nothing really business-related. I had a discussion with somebody around a decade ago, and she always pointed out business books she felt I should read. However, I would always avoid listening to or reading books where somebody is telling me, “Hey, this is how you handle this situation,” because it’s never the same situation; the variables are always different. And if you try to take something that somebody wrote in a book three years ago and apply it to your situation without tweaking the context or adjusting for the variables you’re dealing with, it most likely won’t work. The internet age changes things almost daily now. Occasionally I will listen to a podcast where this professor talks about different business stuff and business news. I will listen to that to stay aware of how people manage companies — what they’re doing right, what I think they’re doing wrong, and what things I could potentially steal and apply to Regpack.

Extensive research suggests that “purpose-driven businesses” are more successful in many areas. When your company started, what was its vision, what was its purpose?

The simple answer is when our CEO Asaf Darash started Regpack, he knew he wanted to build a billion-dollar business. I joined Regpack initially because I had the idea that I would retire by 40 — I’m 41 now. I didn’t quite hit that goal, but the initial thing for me was could this company be the vehicle that would allow me to retire when I’m 40? At the time, I asked myself, “What are people going to need 10 to 15 years from now?” They’ll need a way to process payments and manage their portfolio. So those two elements, and the desire to retire early so I could wander the world, were why I hopped on. It’s been an eventful 10 years, but I still think the path is there. Maybe the new target is 45 now.

Are you working on any new, exciting projects now? How do you think that might help people?

One thing that I will keep working out is what I call Regpack’s “translation problem.” The “translation problem” exists because Regpack, like the internet, has the inherent ability to cause choice overload and decision fatigue. Because there are so many toggles and it’s formless, the system can be overwhelming for most people dealing with that environment. The specific group of people who understand its formless nature are developers. When they are developing things, there is a structure of language, but the developer can basically make whatever they want if they have the talent to do so. So, it’s still formless in a way.

I want to create a webpage for developers explaining all the fun things they can do in Regpack in a way they can better understand. That way, they can see how you can connect the information, collect payments, and facilitate data across platforms. Speaking directly to that niche group of people will help push Regpack to the next level of visibility and revenue we want because we don’t have to translate — it’s a language and concepts they already understand. All we have to do is say, “Hey, look at all the fun developer stuff. Now go to town.” From there, it’s just collecting payments from them and letting them go to town.

Thank you for all that. Let’s now turn to the main focus of our discussion about Digital Transformation. For the benefit of our readers, can you help explain what exactly Digital Transformation means? On a practical level, what does it look like to engage in a Digital Transformation?

The simple version is having a conduit online that your customers can see your product and purchase your product. You just need a medium where users can see your stuff and pay. It’s all digital. The one thing that I think people are starting to get in the past few years, or maybe they might not, is that the U.S. dollar is a digital currency now. If you really think about it, we used to take out cash to pay for things. Now it’s debit cards and phones, indicating we’re currently using digital currency. Eventually, there won’t be cash. Right now, a lot of banks are phasing out paper checks. All of this is a sign of digital transformation and being online in some form or fashion.

Which companies can most benefit from a Digital Transformation?

Businesses that could benefit the most would be the middle-class companies. If you had to give them a category, they are the mom-and-pop shops and the companies within the local and regional range that are used to being the connective tissue in their community. They usually have people who’ve been doing business with them for a very long time, and they’re experts in their products. They also have established pricing, which is one of those things people vastly underestimate. So, these types of businesses would primarily benefit the most from digital transformation because their established prices will almost always translate across all mediums, whether it’s in-person or online.

Major conglomerates are always going to have a presence in the world. They have an army of people to ensure those major businesses are always omnipresent. Entry-level entrepreneurs are usually people born in the digital age, so they’re not going to have an issue setting up on Etsy or Shopify. They’re okay with starting an account and throwing something up there. But, the people who’ve been around for 10, 15, or 20 years know their product and what they’re doing. They’re the ones who would probably benefit the most.

We’d love to hear about your experiences helping others with Digital Transformation. In your experience, how has Digital Transformation helped improve operations, processes and customer experiences? We’d love to hear some stories if possible.

One thing Regpack does very well is that we allow for payment collection, but not just in the traditional sense of making payments. Regpack is kind of its own self-contained money collection machine and allows for a diversity of payments which leads to a diversity of payment options.

For example, let’s say a client has five trips, each requiring a different deposit, payment date, and set of payment dates. One of their users selected two trips, essentially creating two different deposits and payment schedules that needed to happen simultaneously, based on different end dates. What our clients could do through Regpack is set that process up, so when someone chooses the trips, we could combine the payment schedules. For the user, it looks like one combined payment plan from our client, while our client only sees one combined payment. So as the user pays, we show our client how the money is allocated, and, in the end, they get the money they want by the due date they wanted.

Whatever combination of trips a user selects creates a payment schedule unique to them based on their choices. For us, when somebody enrolls in one of those payment plans from the client, it’s just a few clicks of a button to set up their products inside the plans. For the user, it’s only a few clicks to set up their cart, add the trips, and then make the payment. All anyone has to do after that is just sit and make sure the user has the money in their account and the client has their bank account tied to their merchant account. For Regpack, it’s just a script that somebody runs and cycles all the payments. So, it makes life easier for the user, the client, and us, too, since there’s just a script running in the background.

Has integrating Digital Transformation been a challenging process for some companies? What are the challenges? How do you help resolve them?

The biggest challenges arise with companies that are coming from paper. They don’t realize the translation issue paper does with digital. With paper, it is the ultimate flexible tool. You can write whatever price you want if you have a piece of paper. It can be $400 for this person, $700 for the next, and a 14% discount for whomever you choose solely on a whim. The problem is that the flexibility to create an entirely different experience for everyone you talk to doesn’t translate to a platform properly.

It can translate digitally, but if you say, “I want a discount on every third and seventh child at this camp, but only if they select this camp and this camp,” then that’s where you’ll see the most problems. Something unorthodox in terms of pricing has difficulty translating, and they know it’s unorthodox, but their audience is used to it. When this happens, they usually have to tell their customers that their prices will slightly change because of the new processes or commit to a wholly customizable system. Sometimes, they have to run into a wall a little bit because some things from paper just won’t transfer.

Ok. Thank you. Here is the primary question of our discussion. Based on your experience and success, what are “Five Ways a Company Can Use Digital Transformation To Take It To The Next Level”? Please share a story or an example for each.

The initial benefit is that it can expand your reach. For most people, if they don’t have any digital presence and undergo a digital transformation, they’ll immediately go from a local entity to a global one. So whether or not you want to have customers in Japan when you’re based in Alabama is on you, but any business can immediately expand their reach right then and there.

The second way digital transformation can elevate your business is by increasing your revenue. Returning to the first benefit, more customers can equal more revenue when you expand your reach.

Next, your processes can become more efficient. Most platforms and digital-based entities are built on the philosophy of optimizing what you’re doing, not just from the business’s process side but also the user’s side. Like the example I mentioned earlier, everything became easier for the user and the client with just a few clicks. It creates ease of use instead of having to type everything out.

Cash flow is another way to take your company to the next level. It’s related to revenue differently in that people want a consistent flow across most of the months in their calendar or fiscal year. If you’re a heavy Q1 and Q2 in-person, local business trying to find a way to stay afloat during Q3 and Q4, having that online presence can be a good way to buffer those months when your business isn’t as strong.

Lastly, the world is headed in a digital direction; that’s just the way humanity is structured. The internet’s not going away, so a digital transformation is like a ride you want to get on now. Unfortunately, if you are a business and don’t somewhat have that presence, you won’t be a business for much longer.

In your opinion, how can companies best create a “culture of innovation” in order to create new competitive advantages?

Innovation is just a buzzword; it doesn’t mean you’re constantly thinking up new ideas. It just means that you’re looking at your process and system in place every day and trying to make it that much better. You don’t have to adopt new technology or invent some new way to use rocket boots to get around a city. It’s fine just to walk. So I think all you have to do is make sure that with whatever process you build, you always make sure that everybody is just mindful and has the same idea.

I do a monthly meeting with my team where we discuss concepts to think about when brainstorming for ideas. As you’re going through day-to-day stuff, decision fatigue can hit you. So we want to ensure that we’re not creating a situation where the client is exasperated because they don’t know where to go. That’s not innovation, but it’s ensuring we’re mindful. It’s not about innovation. It’s all about making sure that everybody is aware of whatever product you’re doing internally. Everybody is aware and trying to ensure that you’re trying to get better. Sometimes that involves folding in new technology or integrating with a new system or company. It helps translate what we do better to the people who will use it.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My grandma, Dorothy, had a lot of sayings. She always said, “All money ain’t good money,” meaning that just because you can make money from something doesn’t mean you should. If somebody comes to my door right now and offers me a suitcase with half a million dollars in it, I’m not just going to take it. Coming from a guy who loves money, my first reaction would be, what’s the catch? What’s this about? That’s how I operate personally but with businesses too. So, looking at it from that perspective, you’ll see it’s always about figuring out what outliers you’re willing to accept when you’re getting a business and its revenue and problems. And so when I look at stuff, “All money ain’t good money” is usually the number one thing.

How can our readers further follow your work?

You can stay up to date on our latest work through the Regpack blog.

Thank you so much for sharing these important insights. We wish you continued success and good health!

No problem! Thanks for your time!