How Upper Hand is Making an Important Impact on Wellness

Health Tech: Kevin MacCauley On How Upper Hand’s Technology Can Make An Important Impact In Our Overall Wellness

This article was initially published by Authority Magazine.

“Know yourself. What are you passionate about? What impact do you want to leave on society? What are your strengths and weaknesses as an entrepreneur? If you do what you’re great at (and get everyone else at your company doing what they’re great at), you’re able to grow and move faster.”


In recent years, Big Tech has gotten a bad rep. But of course many tech companies are doing important work making monumental positive changes to society, health, and the environment. To highlight these, we started a new interview series about “Technology Making An Important Positive Social Impact”. We are interviewing leaders of tech companies who are creating or have created a tech product that is helping to make a positive change in people’s lives or the environment. As a part of this series, I had the pleasure of interviewing Kevin MacCauley.

Kevin is an active businessman and entrepreneur in the startup tech community. He founded Upper Hand, a leading provider of sports and fitness management software, in 2012 after seeing an opportunity to revolutionize the industry while serving as a baseball coach. Kevin actively supports the startup and sports communities as a TechStar Sports Accelerator mentor and oversees a predictive analytics program with Butler University. To learn more, visit www.upperhand.com.


Thank you so much for joining us in this interview series. Before we dive in, our readers would love to learn a bit more about you. Can you tell us a bit about your childhood backstory and how you grew up?

I’m the second youngest of seven siblings. Growing up, I saw my older siblings as mentors, and I’ve always appreciated being able to learn from them. I’ve always had an entrepreneurial mindset and been very business-driven. Over time, I uncovered an opportunity to combine my passion for sports with my business-driven mindset.


Can you share the most interesting story that happened to you since you began your career?

When I was a Marketing Associate at Corporate Executive Board (CEB), now part of Gartner, a lot of the sales reps used to store a little liquid courage in the bottom drawer of their drawer at their desk. When closing out a month or quarter, etc. we would turn to that drawer to cold call the prospects on a file named “ANGRY HARD OPPS.xlsx”. I was able to book a meeting with the CTO of a Fortune 100 company on that list. And most importantly, I ended up winning a trip to Barcelona as one of the Top Sales Reps across the company, joining a handful of kickass sales folks. Then the real interesting stories start in Barcelona, but you gotta pour me a drink to get those.

Moral of the story, liquid courage works. Just remember, everything in moderation.


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 about that?

There are so many people that have helped me get to where I am today, but one person I am grateful towards is my older brother Ryan. I worked with Ryan for two years as he ran ClassWatch, a company that provided an alternative to class rings to graduating seniors. Throughout the hardships of raising money and building a business, Ryan was always calm and unwavering, even as we navigated the financial crisis in 2009. I really appreciated the time I got to spend sitting next to and learning from him every day.


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

Like everyone, it’s hard to say you have one true favorite. Our office is littered with quotes and your favorite may ebb and flow based on what you need to motivate yourself. That said, one quote that has stuck with me since college is by an author and writer from NYC Christian Bovee, “Doubt whom you will, but never yourself.” In work and in life this means so many things and is almost always relevant.


Whether fighting mental illness, trying to lose weight, manage people, or build a company from the ground up, it’s powerful to remind yourself of this. It does not mean you are never wrong, far from it, rather it reminds you that even when you are wrong, embrace it, learn from it and then have the conviction to believe in your ability to persevere. Cause haters are going to hate. As MLK Jr once said, a leader is the loneliest person in the room. So believe in yourself. Leave the doubt and negativity to others.


You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

  1. Work ethic. I may not be the smartest person in the room, but I will outwork the room.
  2. Naysayers motivate me. I excel when told it’s impossible or you can’t do that, no one’s done that, you don’t know that, on and on.
  3. Empathy. My work ethic is often viewed from the outside as being hard or difficult to approach (that’s actually part of my introverted personality). But inside, I approach every single decision with love for the person I am thinking about. I want the best for those who work with me, have worked for me, and everyone in between. Even enemies. They say when a man walks into a room they bring their whole life. I try to think about that when meeting with someone. Business may be business, but I can still care for you as a person. Everyone deserves to be happy in life. We only get one.


Ok super. Let’s now shift to the main part of our discussion about the tech tools that you are helping to create that can make a positive impact on our wellness. To begin, which particular problems are you aiming to solve?

At Upper Hand, we are committed to building innovative software solutions that make the management of sports and fitness effortless and contribute to a healthier, more active world. Especially in the past year, we have seen how important a healthy lifestyle is in reducing your risk of getting sick, or improving your chances of recovery. There has especially been a lot of disregard for the value of fitness in the face of COVID. One of the ways to recover from a disease like COVID is to be in shape. We’ve emphasized cleanliness and sanitation, but in some ways, we’ve forgotten about physical and mental health. Upper Hand has been able to help close that gap by helping sports and fitness business owners grow and retain clients, helping them lead active lives.


How do you think your technology can address this?

Upper Hand creates opportunities in the sports and fitness industry. Not only do we give our customers the upper hand in managing their business, but we also empower more athletes to stay committed to their personal development journey. For our customers, we help them optimize their business operations, so that they can reduce the time spent on admin tasks, and spend more time focused on their “why” — training their clients. On the client-facing side, the easy to use software makes it easy to schedule training sessions or coaching removes many barriers to entry to fitness. If it’s hard or frustrating to sign up for things, you won’t attract clients.


Can you tell us the backstory about what inspired you to originally feel passionate about this cause?

I’ve always loved the game of baseball. I played through high school, then became a youth baseball coach which continued to fuel my passion for the game. Over time, I started to build relationships with the athletes and parents, and began coaching private lessons outside of practice. While I loved getting to mentor the next generation of young athletes, I often found myself in awkward, transactional conversations about payments as opposed to athlete development. This friction inspired me to launch a software to help connect athletes with coaches to make business easier, and improve both the coach and athlete experience. Over time, the software has developed into a robust sports and fitness management platform that helps sports and fitness business owners of all sizes manage their operations and deliver positive member experiences.

Related: Read how one baseball academy returned to Upper Hand to accelerate growth.


How do you think this might change the world?

The more access people have to sports and fitness, the greater opportunity there is for all. What started as a simple problem of mitigating awkward conversations has really exploded into much more than that. By providing sports and fitness business owners with the tools they need to promote active and healthy lifestyles, we play a small role in contributing to the health and fitness of our world, as well as inspiring the next generation of kids to be active.


Keeping “Black Mirror” and the “Law of Unintended Consequences” in mind, can you see any potential drawbacks about this technology that people should think more deeply about?

Depending on who is behind the technology, there could be potential drawbacks that concern me deeply. I am a huge early adopter of technology and over the last couple of years that has gotten harder to do as you see more and more of our privacy being taken away from us. From Google to Facebook, you name it, the capability of these technologies to know every single thing about us. Now that said, there are two sides to every coin. And the value of the deep learning from fitness technology and data is incredible. From a business perspective, you almost have no choice but to be thinking about using the latest technology if you want to survive and thrive with your customers.


Here is the main question for our discussion. Based on your experience and success, can you please share “Five things you need to know to successfully create technology that can make a positive social impact”?

  1. Know yourself. What are you passionate about? What impact do you want to leave on society? What are your strengths and weaknesses as an entrepreneur? If you do what you’re great at (and get everyone else at your company doing what they’re great at), you’re able to grow and move faster.
  2. Know the market. It can be easy to fall in the trap of building new features or making changes just because your competitors are doing so. But innovation stems from a true understanding of your customers and their problems — those problems may well be the foundation for the solution your technology will provide. Visit and talk to your customers. Understand where the market is going and how you can develop your technology to help them continue to make an impact on society.
  3. You need to know how a business makes money. In order to provide a long term solution that will make a positive social impact on the world, it’s imperative that you set your business up for success and longevity. Make data-backed decisions that will fuel revenue growth for the future.
  4. Know what success looks like. Regardless of what metrics you choose to track, you need to define what success looks like for your business. Once you begin to collect this data, you will be able to track the health of your business, and if needed, make adjustments to fuel greater success moving forward
  5. Trust the data. We initially launched as Bookacoach, a way to provide a great online booking experience for coaches and athletes. However, as Bookacoach grew, so did the need for additional tools to help coaches manage their businesses. I’m big on metrics, and we saw the data pointing us in that direction. After pivoting to Upper Hand in order to offer a full-scale solution for sports and fitness businesses, we were able to help more coaches manage their operations. This has made a bigger and more positive social impact than our original offering. The moral of the story? Trust the data.


If you could tell other young people one thing about why they should consider making a positive impact on our environment or society, like you, what would you tell them?

One piece of advice I have is to just get started. Yes, it’s important to do research, but you can also spend way too much time on your business plan. You will learn so much more by getting your product out in front of your customers and getting their feedback. Once you get your product to market, you can start collecting feedback and iterating on it quickly.


Is there a person in the world, or in the US with whom you would like to have a private breakfast or lunch, and why?

Elon Musk’s mother. To understand how she “doubted whom she wanted, but never herself”. Just hearing stories about how she handled all the things parents nowadays are afraid of for their own kids would be powerful. She raised and fueled the growth, energy and work ethic of perhaps the greatest innovator of our time. How did she discipline? How did she know when to let her son start flying on his own? Letting your kid have wings is one of the hardest things to do as a parent. She did that and still has an amazing relationship with her son. That’s what wealth looks like. Not dollars and cents, it’s those momma bear hugs!


See why studios, gyms, and academies trust Upper Hand to deliver a premium client experience. Get a demo today.

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