Matt McCarrick of SkillSetz: “Cultivate and leverage your peer network”

Cultivate and leverage your peer network — especially the ones in different industries. My career has spanned multiple industries and it always amazes me how different industries look at the same business problems and it is interesting to see the different ways they approach and address them. There is a ton of wisdom, insight, perspective sitting out […]

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Cultivate and leverage your peer network — especially the ones in different industries. My career has spanned multiple industries and it always amazes me how different industries look at the same business problems and it is interesting to see the different ways they approach and address them. There is a ton of wisdom, insight, perspective sitting out there in your network right now that all relate to whatever business problem you are currently wrestling with. The good news is that most people are hardwired to be helpful and kind to others — especially when it comes to free advice — so just ask for it.


As part of my series about the “How Businesses Pivot and Stay Relevant In The Face of Disruptive Technologies”, I had the pleasure of interviewing Matt McCarrick who founded SkillSetz in June 2018 after spending more than fifteen years as a management consultant and B2B eCommerce technology leader serving Fortune 500 clients across a broad range of industries. Matt’s completely unplanned career path gives him a cross-dimensional understanding of the 1T dollars B2B Professional Services market given his time spent selling and delivering enterprise procurement advisory services, leading cross-functional digital transformation projects, and designing complex B2B eCommerce strategies for dozens of iconic, publicly-traded business customers. Matt currently leads the SkillSetz team from the company’s headquarters in Naperville, Illinois.


Thank you so much for joining us in this interview series. 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?

Sure. I have spent most of the last 18 years working as a B2B and Procurement technology advisor for (mostly) Fortune 500 companies and similarly sized private companies. My exclusive focus during my career has been helping these companies better control and manage their corporate spending while making the experience as painless and efficient as possible for their employees. Along the way, I learned an awful lot about how spending really works in large companies. In 2018, I founded SkillSetz which, in retrospect, was a natural evolution of my experience. It started out as a way for me to use my knowledge, experience, and (as my mother calls it) moxy to help my fellow business professionals by empowering them to transform their own unique natural abilities into meaningful economic value for themselves and their families.

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

This is going back 16 or 17 years, but I remember my first ever public speaking engagement. I had somehow finagled my way into the opportunity to make an hour long presentation to a large group of M&A and Litigation Lawyers at a conference down in Florida. At no point in my life had I ever done anything remotely close to what I signed up for and viewed it as my huge break-out professional moment. I must have spent well over 100 hours putting together my powerpoint with every possible animation and effect. My huge “AHA” slide was carefully planned with circles rising up, lightning bolts coming down, and an embedded wave file sound effect that resembled thunder. I was really impressed with it.

When the moment of truth comes I find myself up at the front of a windowless ballroom with more than 200 seasoned lawyers staring at me with rapt attention. Everything was going great until the slide right before my big moment. Suddenly — as is known to happen in Florida — there is a rapid series of very loud and unexpected claps of thunder. I am instantly knocked off my game because, in that moment — in that windowless ballroom — the only question my brain is able to ask is “OMG, did they plug my computer into the surround sound speakers in this room?”

Suffice it to say there was a good 30 seconds of extremely awkward silence as I stood there — stunned, speechless and confused — in front of this room full of high priced lawyers. Then, my perfectly timed big slide transitions on the massive screen behind me with the circles and lighting bolts. The only sound in the entire ballroom is the faint sound of thunder coming from the speaker on my 150lb laptop on the front table. The whole room completely lost it and it took them a full five minutes to regain their composure.

It was only a two hour flight from Orlando back to New York but I swear it felt like it took 10 hours. In the ensuing 16 years, I have never once used any animation or embedded files of any type in any of the thousands of subsequent powerpoints I have created. I am still traumatized by that experience. The unforgettable life lesson for me that day was “Less is More.”

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?

Honestly, so many people have helped me in so many ways throughout the course of my life and my career that it is really tough to do this. If pressed, I would probably have to say my older brother John whom I am happy to report is 10 years my senior, and it totally shows. While we have starkly contrasting personalities, he and I look at business, strategy, and humanity in very similar ways. For me, he has served in some ways as the voice of me 10 years from now. I can talk to him about any range of topics and I can always count on him for a measured, thoughtful opinion. As you can imagine, he is never concerned about hurting my feelings and he never gives me anything but his best thinking. From a professional standpoint, it is amazing to think back on how many times I went to him with questions or looking for a sounding board — at so many different times, and in so many different roles and situations. I guess he gets called out for his “diversity of value.”

The truth is John is only one of hundreds of people who I have been blessed to have in my life and who have helped me get to where I am today. That makes me the same as everyone else because no one gets anywhere alone — no matter what they tell you when they get to the mountain top.

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?

To be honest with you, when I first started building the company it was supposed to be a way for me to take advantage of an opportunity that I saw, leveraging the experience I had, to make a lot of money for my family. The reality is that when we started building SkillSetz in late 2018, the business had a different name and our hearts had a different motivation. Then COVID-19 changed everything.

It changed all the ways people work, and how they complete tasks in the new business world and, obviously, that dovetailed nicely with what we were doing. But COVID-19 also changed me and the company at a much more fundamental level. It changed our perspective on who our customers were and it changed the way we thought about our place and our responsibilities in this new world. I have saved big companies hundreds of millions of dollars over the course of my career, and no one remembered it by the time the next quarterly earnings call came around. Yes, it has been a ton of fun — but it has not been meaningful to me in any way and chasing dollars is not something I would consider purpose-driven.

Now I get out of bed every day with energy, optimism, and excitement. We have a real purpose now. SkillSetz is here to help people create economic value for themselves and their families based on their natural abilities. I can’t begin to explain the positive impact that has on energy and productivity for me personally. Also, it’s a pretty good reason to get excited about work every day.

Thank you for all that. Let’s now turn to the main focus of our discussion. Can you tell our readers a bit about what your business does? How do you help people?

Thank you for this opportunity. SkillSetz offers businesses of all sizes a one-stop shopping experience for all of their business service needs. Our business customers enjoy simple and transparent access to a deep network of world-class professionals whose experience, expertise, and talent are available for project-based work. Our purpose is to make it easy for Service Buyers and Providers to collaborate on project-based services opportunities, execute any mutually agreed upon work orders, and settle any related transactions — all while ensuring transparency and compliance. We believe that helping our fellow professionals commercialize their natural abilities to create value for themselves and their families is a business idea worth fighting for — especially right now. We also believe that the American workforce is the most powerful, creative, diverse, and innovative talent pool on the planet. In the last 12 months, we have also now proven that all of us can work from anywhere.

Which technological innovation has encroached or disrupted your industry? Can you explain why this has been disruptive?

From my perspective, today it is really about the rise of what they are calling “Platform as a Service” or “PaaS” offerings that we are seeing from companies like Slack, Stripe, Twilio and others. These players can enable really anyone with turn-key access to incredible capabilities and functionality — many which were not even possible a few years ago. It really has been stunning to watch and track how quickly almost all of the technology fundamentals are changing. One thing the leading PaaS players all do really well is they have created free or low-cost entry models that enable any customer to only pay as they scale up and almost all of them have responsible billing models. As a founder, why on earth would I be spending time and money building capabilities outside of my core competency when I can get the power of all these complimentary platforms and capabilities on a turn-key basis while laying off all the digital and compliance risk associated with hosting those capabilities?

What did you do to pivot as a result of this disruption?

It completely changed how we thought about our architecture and our software development roadmap. We proactively and aggressively reshaped our development efforts around our core strengths and competencies while making the conscious choice to lay off functionality and the associated risks that weren’t in our wheelhouse. This emerging PaaS capability which is still in its very early days completely changes the risk calculus for self-funded founders.

Was there a specific “Aha moment” that gave you the idea to start this new path? If yes, we’d love to hear the story.

Not really an “AHA” moment as much as a more gradual, and increasingly louder series of “Oh wows”. Once we made the decision to execute this architectural pivot, we began looking around at all of the other opportunities to enhance our platform and extend more capabilities to our users. The possibilities are truly amazing. This idea of extensibility and interoperability is actually the primary focus of our software development roadmap in 2021. It really is the quickest way to get value into the hands of our users.

So, how are things going with this new direction?

It’s still early but really good so far. It is a somewhat different experience working through the touchpoints and endpoints in this type of development model versus your typical persona-based U/X planning, but there is no substitute for the speed and low cost to implement things that add a ton of value to our users — which is what we are here to do in the first place.

Can you share the most interesting story that happened to you since you started this pivot?

One thing that is interesting is that I noticed an increasing number of organic transactions that came from our initial user community. By that I mean, when we were onboarding service providers prior to our launch, we weren’t thinking that they would start doing business with each other. We have seen a bunch of provider-to-provider work which tells me that we are really on to something here. They are collaborating and both sides of the transaction are benefiting from it. That is exactly what we are here to do.

What would you say is the most critical role of a leader during a disruptive period?

I was going to give a business-related answer but I think I will opt instead for just the human answer. Cognitive bias was very helpful in terms of keeping early humans alive but it is NOT helpful in the face of disruption. The most critical role the leader can play during a disruptive period is to demonstrate — through action — your awareness of the changing dynamics while communicating a clear and thoughtful strategy that lights the path forward for your team. No one expects you to be perfect but you are expected to lead them through the storm. When disruption comes, doing nothing is no longer an option.

When the future seems so uncertain, what is the best way to boost morale? What can a leader do to inspire, motivate and engage their team?

In my experience, good-natured humor and self-deprecation are the two leadership traits that most directly impact the morale of front-line workers. The first thing it does is de-stress any power dynamics. The second thing it does is make the leader more relatable. The third thing it does is make the team members feel like, well, a team.

Is there a “number one principle” that can help guide a company through the ups and downs of turbulent times?

The greatest teams in all walks of life do two things really well all the time. First, they trust each other. Second, they reward each other’s trust. All great teams do both every day.

Can you share 3 or 4 of the most common mistakes you have seen other businesses make when faced with a disruptive technology? What should one keep in mind to avoid that?

The number one mistake I see businesses make with disruptive technology is they lose sight of the product < > problem fit. It is very easy to fall in love with expensive sales presentations and product demos. It’s also very easy to fall in love with all the possibilities. One way to ensure you don’t fall into any honey traps is to keep your eye on the problem you are trying to solve..

Another common mistake I see businesses make is that they overreach in their implementation plans. Everyone, in the enterprise anyway, seems to struggle with the bias that a bigger bang gets you a bigger buck from a strategy standpoint but that is almost never the case. I would tell all businesses faced with technology decisions to consider the fact that far more baseball games are won by singles and doubles than are won by triples and home runs — and they are all facing the same pitchers.

The last mistake that comes to mind is a boring one but one that has a surprisingly severe impact on strategy, culture, and productivity. Communication. Far too often, business leaders completely fumble their communication plans and their change management strategy — overlooking it as a non-essential, non-critical component of an implementation plan and budget. In the real world of B2B technology, the sun rises and sets on user adoption as all of the implied value of those investments is supposed to manifest itself in usage. Don’t undervalue your communication and change management strategy because usage is your ultimate KPI.

Ok. Thank you. Here is the primary question of our discussion. Based on your experience and success, what are the five most important things a business leader should do to pivot and stay relevant in the face of disruptive technologies? Please share a story or an example for each.

Take some time to step outside of your day-to-day constraints to do some free thinking. You need to take the time to do whatever it is that you do to free your mind. Stepping away from the grind gives your brain time to breathe and process information. Not taking that time puts you at risk of falling into an infinite loop of cognitive bias that clouds your judgment.

Never stop reading quality content. Change is happening so fast now, especially in technology as we’ve discussed already. It is really important to always stay on top of emerging opportunities for and threats to your business. It is also necessary to reflect on history and absorb all those past lessons that someone else had to learn the hard way.

Effective communication has never been more important and, perhaps, never more difficult. To quote the great philosopher Tyrion Lannister, “What is it that unites people? Armies? Gold? Flags? No. Stories. There is nothing more powerful in the world than a good story.” Make sure your story is authentic and make sure it counts.

Cultivate and leverage your peer network — especially the ones in different industries. My career has spanned multiple industries and it always amazes me how different industries look at the same business problems and it is interesting to see the different ways they approach and address them. There is a ton of wisdom, insight, perspective sitting out there in your network right now that all relate to whatever business problem you are currently wrestling with. The good news is that most people are hardwired to be helpful and kind to others — especially when it comes to free advice — so just ask for it.

On the whole, people expect their business leaders to act and perform with confidence and humility. At the same time, no one expects anyone to be perfect. You will make mistakes and the most important thing you can do is own them in front of your team. It will make it much easier for them to own their own mistakes in front of their teammates. Ownership and accountability is what wins championships.

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

My favorite life lesson was taught to me by my parents when I was a child. They drilled into my head that every human being had something unique and special to give our world and that every human being was to be valued and respected equally. Well, all of that drilling seems to have hit something. Our tagline at SkillSetz.com is “Everyone is Great at Something!”

How can our readers further follow your work?

I plan on spending the rest of my professional life helping businesses and professionals find each other and create economic opportunity for themselves with SkillSetz. That is the only place I want to be and that is where you will always find me. (Also, we have a pretty cool two minute video on our homepage that provides a succinct overview). I’m also on LinkedIn!

This was very inspiring. Thank you so much for joining us!


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