CONVO: What led you to Gainsight and your take on customer success?

NICK: My parents moved to America from India in the ‘70s. My dad got into the technology business. As a child I had more computers than friends — my computers were my friends! I was definitely a hardcore childhood nerd, into programming and science and math. With a classmate, I started an Internet company in college which we ended up moving to California. I ran a division at Symantec for a long time, then I ran a SaaS company called LiveOffice. In running my last company, I learned about customer success and how important it is. That’s why I’m doing Gainsight.

C: How did you make the transition from high school nerd to high-energy CEO?

N: I’m a very social, extroverted personality, and I love meeting people. But I was a complete wallflower as a child. Every day in middle school and high school, I ate alone because I didn’t have any friends – I don’t know if they were too picky or if I was too shy! I went through this metamorphosis as an adult.

C: Is being high-energy and authentic the secret to CEO success, or is it just your secret to CEO success?

N: In the NFL, Bill Belichek, the coach of the Patriots, is one of the best coaches of all time. He’s not a charismatic, seemingly nice person, but he’s probably the most brilliant mind ever. There are other coaches who have won Superbowls who are super nice and positive, and others who are tough on their players. I think being a CEO is the same way. It’s not like all CEOs are extroverts and authentic. I would flip it around and say, for almost everyone, things feel more comfortable if people are who they are. I have a lot of energy and I don’t know how to be anyone but myself.

C: How do you maintain a caring relationship with your team and still make tough decisions? Some people say that’s very difficult to manage.

N: The way I think about is, there are emotional connections and then there are friendships. I have an emotional connection and empathy and love for all of my teammates. I try to have a deep emotional connection to everyone at Gainsight. Now, being friends with your executives, I think it can work. I have unbelievable respect for them, but I don’t hang out with them outside of work. I think it’s healthy to have a little break. Work is all-consuming, especially if you’re a CEO. And you don’t want to create a perception of favoritism between your management team. If the CEO is buddies with people, it creates some potential awkwardness. Emotional connection? For sure. Friendship? I think most of my friends are people I don’t work with.

Q: You’ve done Carpool Karaoke videos with other tech executives. Some companies might think that’s frivolous but you see it as reflective of Gainsight’s culture. How so?

N: One of our values is child-like joy — bring the kid in you to work every day. Part of that is not taking yourself too seriously. We did this Carpool Karaoke series with a few well-known tech CEOs – Aaron Levie, the founder and CEO of Box, Keith Krach, the former CEO of DocuSign, and Jason Lemkin, the famous SaaS investor. It’s just talking and singing. I’m terrible at signing, but I love it, so I love karaoke. Aaron, the first victim, was totally game for it. We talked a lot about software and tech and customer success, and sang ABBA and Backstreet Boys and things like that.

C: You grew up a technology kid, but it seems like the secret sauce you’re counting on is human connection. How critical is that to success, and does it change what success looks like?

N: Our purpose is to be living proof that you can win in business while being human first. That translates into many different things for us. It translates into our culture, but it also translates into this concept of customer success. When a customer is frustrated and anxious on the phone, they’re not trying to be frustrated or anxious. Something’s going on. Maybe something tough is happening at home. Maybe their boss is really upset at them. Maybe they’re worried about their job. How can you have that empathy for them? The more you lean into them being a human being, yes it’s good for business, but forget that – it’s good for your soul.