Whispered Hiring with Nick Mehta @ Gainsight

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? I think it's marketing.

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.

Andy, it's awesome to see you. I remember those early days, too. And you've always just been somebody such a first-principles thinker. So, I love learning from you.

Thanks. Yeah, it seems so funny though. I stepped down 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.

Yeah, I mean it's interesting because culture is such a tough one because it's so open-ended. Hiring is a little bit clearer. A big part of the challenge is, I think I'm a big believer in pretty much everything in life, you have to define your why, right? What's the why? And we all know that's start with why. If you haven't seen the Simon Sinek talk, right? It's great. And for me, I think the key thing is with culture, like why does culture matter to you? One of the things that I think worked for us at Gainsight is people getting into their why and being very vulnerable about it. Right? So it's like what's my why? Well, let's just do the therapist here and say okay, he was a very lonely kid. Didn't have any friends growing up kindergarten through 12th grade. Ate alone every day. And so people not feeling lonely was part of his why, right? That's kind of like, only after I'm 48. So it took a long time to understand in hindsight what brought me here. And then what did that mean? Well, okay, for me, the culture of the company was like part of the why. It wasn't actually just to make the company successful. Some people, I respect it. Some people 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, right? Good for that. And I like when people are very honest about that because I think 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 or whoever and then the company and then what the culture is and then it feels very thin. You know 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, you know, versus, you know, you look at obviously Bridgewater which is a very famous hedge fund for folks that don't know, Ray Dalio, and their culture is exceptionally well defined and some people hate it and some people live by it. I think 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? Like our company values were, you know, 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. And I think that's success because those people would not have fun there and they also would not connect with the people there. And so I think a sign of a good culture is it actually makes it really clear whether somebody fits, whether they should be there.

I was going to say the same thing. I'm like, how can you possibly believe that those are the same? My gosh.

Yeah, exactly. Yeah. I think that's a really good test actually. A cultural litmus test. Which door do you choose? Or and Google could be a third door.

Legit third door. Yeah. Or Grok is a fourth door. Third door. Fourth door.

You know, I mean, it's a constant thing, right? Because a leader, I mean, you know, I did Gainsight for 13 years. So, I don't know how many leadership teams I had. It's sobering to even call. You mentioned some of the earlier ones, you know, Allison Pickens, Anthony Cennina, Ashvin. Then you look at like then there were leadership teams after that. We had incredible luck of selling to Vista, private equity. I had new leadership teams as I went through that, that brought in new people and so yeah it always, it's that cheesy expression but a river, right? It's always changing and like it's the same thing here, the leadership team's always changing. So what did we do well? You know, I think one thing is that you have to respect that it's always changing and assume that like as new people, especially key people come in, you have to kind of be willing to have beginner's mindset, which was actually one of our values, and kind of reset the thinking on it. Now I had a secret weapon, who is the one, what very few things in my career will I be like universally good. I have like the best coach ever. Her name's Kaylee Clamp Warner and she is like one of the goats of coaching and even her dad is one of the most famous coaches ever. And so she was my coach and I would bring her in to do kind of executive team alignment. And over the years I learned some stuff myself. I'm not at nothing compared to her, but you know, learn things about questions that open people up, right? A simple question actually that we don't have to do right now, but you can do, and it's a great question, the Kaylee Clamp, 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. Now, I doubt that's a very, you're gonna be like, Nick, that's an obvious simple question. Do it. In my experience, 100% of the time on the third round, people are crying in a vulnerable opening way. You know, and 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. So, I don't want to make anyone feel uncomfortable, but oh my gosh, there's 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 and all that. And I don't think I was ever great at, I think I'm okay at that, but I think the human alignment really matters.

Yeah, it's just it's like touchy-feely. Exactly. Yeah.

Oh, you're asking such... I mean no surprise because this is what you do. In enterprise software, I think it's marketing.

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's like, you have to have a CEO that's willing to take risks and fail, which you were, man. You did that over and over and over again with Anthony. Like you did stuff that people would be like, that's crazy, but it worked. And I was talking to this guy, Gokul Rajaram, I don't know if you know him, but he does like works with Ramp, works with different people. And he's like most CEOs, you know, Gokul. Yeah. Most CEOs... I was like, how do you determine if you're going to work with a CEO? And he said exactly like most CEOs, like if I take eight risks and fail on all of them, will you be okay? And I feel like Nick and Anthony in my earlier experience on Gainsight, you guys took crazy risks. You did things like build a conference for a function that didn't even yet exist. Yeah. Which some people should be shot on, but you did it versus like plain vanilla stuff and it was awesome.

I know that's... Thank you. And Anthony's one of the best ever, actually the best ever, in B2B marketing and still a dear friend, really different. But if you kind of looked at after Anthony, who was an early CMO, you know, 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, where it's like I don't think we really understood what we need. So I'll use this as an example. So this is like a perfect example I heard. Anthony had a kind of a right-hand person, Mike Mannheimer, who went on to BC. You met him, right?

You know, I'm still in touch with Mike. He's... I've told him this most of the story. I told him all this story and I remember after Anthony was stepping down, Mike was... I was to think about, oh, you know, bringing in an outside CMO, etc. And he said, and the reason, you know, the on-paper reason was we need more leads. Right? Every CEO says, we need more leads. Bring me more leads, people. And so I'm in Mike's in Phoenix. He's got his whiteboard. He draws a little circle. And Gainsight, you don't need to know too much about Gainsight. We sold software to customer success teams, right? And back then there weren't that many. So Mike draws a circle. He's like, 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 and my fault, like the leads didn't go up, you know, and of course like brought in new CEO, Groundhog Day, same thing, right? And so a lot of...

Totally, all these, and you know you can only like do that so far and so that's the thing is like I think you... So 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 it's like what practically can they do, you know, sit down and be like what practically is possible, think in first principles of all the things about what you need and you might not end up saying I need that job, you might say I need a different job. I think new founders by the way of these new companies are doing this really well, they're just like oh I need a sales leader, marketing, you know, they're just like or even CS, right, which we can talk about, they're just saying what first from a first principles perspective what do I need for this company and 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.

Go.

I, yes, but not because of investor like Vista. I think the fundamental thing is you can take more risks early in your company and when you're growing really fast though and or when you're growing really fast. I so like I'll tell you. Do you know what my greatest regret in Gainsight is ever? Do you know what you want me to tell you?

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 like a whopping probably 15 million of ARR and we had raised, you know, whatever 40 or 50 million bucks, maybe we had 20 or 30 in the bank. And he said for Pulse, our conference this year, he booked Backstreet Boys for the party or whatever and it was like 750 grand and I was like no we can't do that it doesn't make sense we're earning too much money. And of course we never did Backstreet Boys later on, we didn't, we could never afford them again because we had to get more and more optimized, right? Now I'm tongue in cheek like that wouldn't have changed our, that would have been really fun but wouldn't have changed our trajectory but those risks that you can take when really young are harder later especially if you know most companies decelerating growth it's pretty natural right so yeah I mean you want to take a lot of risks early. Now I think on the margin CEOs can take risks later too like there's little risks that don't cost, you know how you communicate your public persona, you know what you speak about at your conference, being more cutting edge on your messaging. So there's risks that involve capital, those are harder as you get more mature. There's risks that involve you taking a personal risk. You always have that in your control.

One of my happiest moments is how many people during, we had a really good Taylor Swift person here 2015. I rewrote Blank Space, which is one of her famous songs, to be about customer success and then you know she performed it and I was so happy that these people all somehow thought we could afford Taylor Swift. So now funnily enough if we could afford Taylor Swift then, we still can't, we definitely couldn't afford her now. Oh, we should have got her then.

Yeah, and I think there's multiple pieces of this like there's the job, the importance of retention and then there's the need for a leader and where they fit and then there's the actual motion of what they do. Okay, so let me break it in three parts. What we are in AI now. I think every investor you talk to they are like yeah retention is going to be really important because there's a very unique thing that's happening that not everyone fully appreciates. Companies, big companies, small companies have been told you have to buy AI technology by their boards. So they are buying a lot of stuff so therefore the vendors are growing really fast because they have infinite capital. It's a little bit crazy right? It's like if you told, actually the probably the best analogy is like COVID with consumer where it's like of course restaurants boom because everyone got like a lot of people got thousands of dollars of stimulus checks in the mail.