Fireside Chat with Matt Shobe, Product Design Leader and Serial Entrepreneur

Fireside Chat with Matt Shobe, Product Design Leader and Serial Entrepreneur

July 16, 2019
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This past week, we were honored to have startup veteran, Matt Shobe, join us in the Skilljar offices for our ongoing Chats with Interesting People Series (CHIPS).


Matt was most recently co-founder and Chief UX Officer of Mighty AI, a data management platform principally for the autonomous driving technology industry (acquired by Uber in June 2019). Prior to Mighty AI, Matt was a Venture Hacker at AngelList, a fundraising and talent platform for startups, and the co-founder and Chief Design Officer at FeedBurner, a web feed management platform (acquired by Google in 2007). You can find more detail about Matt’s background on his website, here. Matt is also an avid distance runner, private pilot, skier, and dad. 

Read on for some of Matt’s thoughts about startups and the evolution of his career.

You’ve been a co-founder of a startup many times. Why do you enjoy most about it?

There’s certainly an appeal, or a romance, to the idea that “I’m in charge of my own destiny.” In startup lingo, “I’m a numerator over a much smaller denominator.” I keep coming back because I love having a hand in establishing the culture & values of a given company and I want to do something meaningful with great people. Something that has always stood out to me in my startup experience is the feeling that when you look to your right and your left, you realize that you see nothing but other people you are hellbent to help succeed. 

Tell us about a really difficult time you’ve had at startup and a really joyous time.

One of these instances that comes to mind is from the late 2000s. I realized that at my previous startup, we didn’t do enough to celebrate success. When we accomplished something big, we briefly acknowledged the moment off as part of never-ending to-do list and sprinted forward; we spent enough time properly recognize the achievement and the hard work of the team responsible.

When we started Spare5 in 2014 (the company’s name prior to re-branding as Mighty AI), my co-founders and I decided that we needed to list the  values that the company would stand behind to hire, operate, and grow. As we developed that list, I fought for “celebrate success.” When we hit our first million tasks completed at Spare5, we went out and bought a cake to celebrate. From then on, whenever we hit a major milestone, the precedent was there (if not always a cake): celebrate and recognize. Employees always knew that hard work would be recognized and appreciated. 

Many startup founders have either an engineering background or a very sales-oriented perspective. You, like Skilljar’s CEO, Sandi, come from a product and design background. How have you seen the product and design aspect of technology companies evolve over your career?

When I was right out of college in the early 90s, most design teams were more like service bureaus. We felt like we were on the outside looking in, just waiting for projects to be thrown over the wall at us for one-off execution. Design was not necessarily strategic and it often felt like we didn’t truly have our own voice. This started to change as companies like Apple came into the foreground. The industry began to realize that design-driven organizations were producing really great products and that human-centered design thinking was a core element of those products’ success. 

Today, I see what I call the “wheel of product justice” — engineering, product, design, and operations/customer success are all equal “spokes” that support the wheel. This is based on the relatively recent recognition that while every team has its specialties, all of the spokes need to be strong to make the wheel turn. Engineering is still in charge of platform and code, the product team has to make sure the right deliverable is put out into the world, and design is accountable for the total customer experience. And, most critically, each team trusts the other spokes to make the right, most informed decisions. This partnership across teams is critical and wasn’t a given in technology companies when I started my career. 

Lightning Round

Favorite productivity tool?

(8 hours of ) Sleep

Favorite social network?


Favorite vacation spot?


Cats or dogs?


Any books you would recommend?

Ruined by Design: How Designers Destroyed the World, and What We Can Do to Fix It By Mike Monteiro

The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers By Ben Horowitz

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