So I believe a lot of the mishires are because the CEO, me, didn't do our job.
I think culture, as I've talked to a lot of other executives, is a critical foundation for building teams. One of the things over time I learned about culture is it's got to be really unique and kind of weird.
What is the hardest executive role to hire for in enterprise software?
Taylor Swift was on stage and I turned to everyone. I was like, did Nick hire the real person? The entire hour I was like, dude, we just had Taylor Swift at this concert. Only afterwards I realized it was an impersonator.
These back channels are so critical. Doing them early before you've kind of fallen in love with the candidate. Don't do your back channels when you've already made your decision. That's just a waste of time. The right executive for the job makes an impact right away.
Welcome to Whispered Hiring, the podcast where we talk with senior leaders about how they find, vet, attract, and grow go-to-market talent. I'm Andy, founder of Whispered. Today I'm joined by Nick Mehta. Nick is one of the most inspiring leaders I know. He just wrapped an amazing run at Gainsight where he defined the category of CS. I met him at, I think it was the second Pulse conference, where I got to watch Nick on stage singing to Taylor Swift. I knew some great folks that had joined him from Box as well. I learned about dinners, community, bringing people together from Nick that inspired me in a lot of ways. Nick's also written and spoken extensively about careers and networking. If you have checked out some of Whisper's playbooks, you'll see his thoughts woven throughout. He's got a lot of great podcasts. So today I'm excited to deep dive with Nick on how he builds great teams. Nick, great to see you.
Andy, it's awesome to see you. I remember those early days too. And you've always been such a first-principles thinker. So I love learning from you.
I'm excited for this one. I've been waiting for a while. So congrats, man. And congrats on the run you had at Gainsight.
Thanks. Yeah, it seems so funny. I stepped down on August 20th, and that seems like a long time ago now. But I appreciate having the chance to be part of that incredible community and company.
You've inspired so many people. At Gainsight, one of the things that really stood out to me when I first met you was the culture you built, the excitement you bring. I knew some of your senior leadership team as well, Allison, Ashvin, Anthony, they've all become friends. I think culture, as I've talked to a lot of other executives, is a critical foundation for building teams. Before we dive into how you hire, I'd be fascinated to hear your thoughts on what is a great executive culture and what do you need before you start thinking about bringing on great execs.
Yeah, it's interesting because culture is such a tough one because it's so open-ended. Hiring is a little clearer. A big part of the challenge is I'm a big believer that pretty much everything in life you have to define your why. What's the why? We all know that's start with why. If you haven't seen the Simon Sinek talk, it's great. For me, the key thing with culture is why does culture matter to you? One of the things that worked for us at Gainsight is people getting into their why and being very vulnerable about it. What's my why? Let's just do the therapist thing here and say I was a very lonely kid. Didn't have any friends growing up kindergarten through 12th grade. Ate alone every day. So people not feeling lonely was part of my why. That's only after I'm 48, so it took a long time to understand in hindsight what brought me here. And what did that mean? For me, the culture of the company was part of the why. It wasn't just to make the company successful. Some people, I respect it, it's like, hey, I want a successful company, therefore I need great people, therefore I need a great culture so I can attract those great people. Good for that. I like when people are very honest about that because one of the challenges with culture is where it doesn't feel like there's a deep alignment between the why of the founders or CEO and the company and what the culture is, and then it feels very thin. That's why you end up with these very plastic cultures that feel like, oh, I just found it on somebody's website, I'm just going to copy it. Versus you look at Bridgewater, which is a very famous hedge fund, Ray Dalio, and their culture is exceptionally well-defined, and some people hate it and some people live by it. One of the things over time I learned about culture is it's got to be really unique and kind of weird. Those are the ones that really stand out. Then it becomes clear, should you work here or not? Our company values were things like childlike joy, golden rule, success for all. If you were the kind of person who just wanted to make a ton of money and kill the competition, you would see those on their website and literally never even apply. I think that's success because those people would not have fun there and they also would not connect with the people there. So a sign of a good culture is it actually makes it really clear whether somebody fits, whether they should be there.
I love it. I remember you and I talked a lot when I was at Culture Amp because you guys were using the software and thinking about that. We always had this belief that if a value was something that there was no obvious con, like do good work, it was not good. I think you took a step further which I really liked, which is the values in culture should actually repel some people. We had a really cool guest on, Heather Dosier from Signal Fire Talent, and she said, I'd say 70% of people that apply to Whispered, we ask their dream job, and they say OpenAI and Anthropic. Her point was those have totally different cultures.
I was going to say the same thing. I'm like, how could you possibly believe that those are the same? My gosh.
One's 996 focused on consumer, and the other one's very enterprise, very kind of different vibe.
Yeah, exactly. I think that's a really good test actually, a cultural litmus test. Which door do you choose? And Google could be a third door.
Ah, you're right. Now it's a legit third AI door.
Legit third door. Yeah. Or Grok is a fourth door.
Fourth door. So you built a great leadership team. They had a lot of longevity. I sense that they've all stayed in deep touch with you. How did you get your leadership team aligned? It's a constant thing, right? I did Gainsight for 13 years, so I don't know how many leadership teams I had. It's sobering to even count. You mentioned some of the earlier ones, Allison Thickens, Anthony Canada, Ashvin. And then there were leadership teams after that. We had incredible luck selling to Vista Private Equity. I had new leadership teams as I went through that. I brought in new people. So it's that cheesy expression about a river, it's always changing. The leadership team's always changing. So what did we do well? I think one thing is you have to respect that it's always changing and assume that as new people, especially key people, come in, you have to be willing to have a beginner's mindset, which was actually one of our values, and reset the thinking on it. I had a secret weapon, one of the very few things in my career I'll be universally good at. I have the best coach ever. Her name's Kaylee Clamper, and she is one of the GOATs of coaching. Her dad is one of the most famous coaches ever. She was my coach, and I would bring her in to do executive team alignment. Over the years I learned some stuff myself. I'm nothing compared to her, but I learned things about questions that open people up. A simple question that we don't have to do right now, but you can do, and it's a great question, is three rounds of this question with your management team: If you really knew me, you would know X. If you really, really knew me, you'd know X. If you really, really knew me, you'd know X. I know that's a very obvious simple question. Do it. In my experience, 100% of the time on the third round, people are crying in a vulnerable, opening way. By the way, you should do this when people feel safe and you have a good culture. Don't do this for people that don't feel ready. I don't want to make anyone feel uncomfortable, but there are techniques like that that are really good at getting people to open up and align. Then you get into the tactical stuff like goal setting. I don't think I was ever great at that, I'm okay at it. But the human alignment really matters.
That is powerful. I know Allison from your leadership team was at Stanford Business School where they do all the touchy-feely stuff.
Yeah, it's touchy-feely. Exactly. What is the hardest executive role to hire for?
Oh, you're asking such good questions, no surprise because this is what you do. In enterprise software, I think it's marketing. One way to think about it is over 13 years, which role did you have the most of, which means you screwed up? It's not because those people you hired weren't good, they were good. It's actually because you didn't know what you needed. Among a lot of software CEOs I know in B2B, they screw up in the marketing role over and over again. I don't think it's the marketer's fault. I think it's the CEO's fault.
I could not agree more. We've got a whole playbook on how do you ask those questions. I was talking to a super senior marketer and he said, you have to have a CEO that's willing to take risks and fail. You did that over and over again with Anthony. You did stuff that people would be like, that's crazy, but it worked. I was talking to this guy, G Kaban or whatever, I don't know if you know him, but he works with Ramp, works with different people. He said most CEOs... I was like, how do you determine if you're going to work with a CEO? He said exactly, most CEOs, if I take eight risks and fail on all of them, will you be okay? I feel like Nick and Anthony in my earlier experience at Gainsight, you guys took crazy risks. You did things like build a conference for a function that didn't even yet exist, which some people would say should be shot down, but you did it versus plain vanilla stuff, and it was awesome.
Thank you. And Anthony is one of the best ever, actually the best ever in B2B marketing, and still a dear friend. But if you looked at after Anthony, who was an early CMO, I had a lot of people I brought in who were really talented and I would recommend over and over again. But if they're watching, it's like, the problem is me, not you. I don't think we really understood what we needed. So I'll use this as a perfect example. Anthony had a kind of right-hand person, Mike Nanimer, who went on to BC. You met him, right?
Oh, I know Mike really well.
I'm still in touch with Mike. I've told him most of the story. I remember after Anthony was stepping down, I was thinking about bringing in an outside CMO. The on-paper reason was we need more leads. Every CEO says we need more leads. Bring me more leads, people. Mike lives in Phoenix. He draws a little circle and gate. We sold software to customer success teams, and back then there weren't that many. Mike draws a circle and says, this is the number of customer success teams out there. This is the number of people we've marketed to. Basically, we've saturated our market. Nick, the reason you're not getting more leads is there aren't more leads to get. I was not smart enough to actually listen to Mike and brought in several other awesome CMOs over the next few years. My fault, the leads didn't go up. Brought in new CMO, same thing.
One thing I was always really impressed by you, the TAM of CS was this, Nick made it bigger because you went out and sold the vision of CS to Cisco and to people.
Totally. You can only do it so far. The lesson for me is that you have to really define that job. Not just, oh, we're a company, we need this role, but what practically can they do? Sit down and think in first principles about what you need. You might not end up saying I need that job. You might say I need a different job. I think new founders of these new companies are doing this really well. They're not all like, oh, I need a sales leader, marketing C, or even CS. They're just saying, from a first-principles perspective, what do I need for this company? When you don't do that as a CEO, you're doing a disservice to your shareholders and to the candidate themselves. So I believe a lot of the mishires are because the CEO, me, didn't do our job.
I couldn't agree more that marketers fail often not because of something they did. Manheimer was great. I remember calling him up one time. Gainsight had built this job board for the CS community. I was like, dude, how'd you do that? He explained how we wired the Indeed APIs and I learned so much. Okay, you said there were no questions off the table. I got one for you.
Marketing is more successful when you can take real risks. As you take on an investor and get more mature like Vista, and growth expectations start to get locked in and your company starts to mature, does the amount of risks you can take on marketing go down?
Yes, but not because of the investor like Vista. The fundamental thing is you can take more risks early at a company when you're growing really fast. I'll tell you my greatest regret at Gainsight ever. Do you know what it is?
I could never guess, but I'm excited to know.
It truly is very simple. It's not listening to Anthony, our first CMO. I don't know if AK is going to be watching this, but in 2015, we had a whopping probably $15 million of ARR and we had raised whatever $40 or $50 million, and maybe we had $20 or $30 in the bank. He said for Pulse, our conference this year, he booked Backstreet Boys for the party, and it was like $750,000. I was like no, we can't do that, it doesn't make sense, we're spending too much money. Of course we never did Backstreet Boys later on, we could never afford them again because we had to get more and more optimized. I'm tongue in cheek, that wouldn't have changed our trajectory, but those risks you can take when you're really young are harder later, especially if most companies are decelerating growth, it's pretty natural. So you want to take a lot of risks early. I think on the margin, CEOs can take risks later too, like little risks that don't cost you, how you communicate your public persona, what you speak about at your conference, being more cutting edge on your messaging. There are risks that involve capital, those are harder as you get more mature. There are risks that involve you taking a personal risk, you always have that in your control.
Dude, I love this. I remember the second Pulse when Taylor Swift was on stage and I turned to everyone. I was like, I've only heard this person once on the radio. Clearly Nick knew his music better than I did. I was like, did Nick hire the real person? For the entire hour, I was like, dude, we just had Taylor Swift at this concert. Only afterwards I realized it was an impersonator.
One of my happiest moments is how many people during... we had a really good Taylor Swift impersonator in 2015. I rewrote Blank Space, which is one of her famous songs, to be about customer success, and she performed it. I was so happy that all these people somehow thought we could afford Taylor Swift. Funnily enough, if we couldn't afford Taylor Swift then, we still can't, we definitely couldn't afford her now. So we should have gotten her then.
I love it. Before we dive into hiring, I have one more kind of fun question. When I asked you what was the hardest role to hire for and you didn't say CS, I love the honesty. I'm curious where you think the CS profession is now. I was talking to a top talent partner the other day and they were saying a lot of these hot startups are just rolling it into sales. You hear a lot of buzz right now around all these zero to $100 million AI startups that haven't even thought about CS and they're going to get smacked in the face by it. But I'm seeing a lot of great senior CS people kind of struggle in being third fiddle now more than I've seen in a long time. I'd be curious your take on the CS profession and the advice you have for our senior CS listeners.
Yeah, I think there are multiple pieces to this. There's the importance of retention, the need for a leader and where they fit, and the actual motion of what they do. Let me break it into three parts. What we are in now in AI, every investor you talk to says retention is going to be really important because there's a very unique thing happening that not everyone fully appreciates. Companies big and small have been told they have to buy AI technology by their boards, so they are buying a lot of stuff. Therefore, the vendors are growing really fast because they have infinite capital. It's a little bit crazy. The best analogy is like COVID with consumer, where restaurants boomed because everyone got thousands of dollars of stimulus checks.
