The Right Connection: Nick Mehta, CEO of Gainsight

This week Mentorloop’s Co-founder and Chief of Operations, Heidi Holmes speaks with Nick Mehta, CEO of Gainsight.

They cover a variety of insights:

👉 The importance of being true and authentic to yourself to become a great leader
👉 How to engage your ‘ideal employee profile’ to reinforce your company culture
👉 Explore the New vs Old world of mentoring
👉 Nick shares who have influenced his career

Hear more life-changing mentoring stories on Mentorloop’s podcast ‘The Right Connection’ via Spotify, Google & Apple Podcasts.


[Heidi Homes]

Well, hello and welcome to Mentorloop moments. My name is Heidi Holmes, I’m co-founder and COO of Mentorloop. We’re a platform that helps organisations build a culture of mentoring for their people or communities.

So today I’m going to be having a moment with Nick Mehta. Nick is the CEO of Gainsight, the
customer success company, a five-time Forbes Cloud 100 recipient. He works with a team of 800 people who together have created the customer success category, that’s currently taking over the SaaS business model world.

Nick has been named one of the top SaaS CEOs, by the Software Report, three years in a row, and one of the top CEOs by Comparably in 2018.

We’ll be discussing how Nick has navigated his career over the years, the future of work in a post COVID world, and the role mentoring has to play across these themes.

Nick, welcome. And thank you for having a moment with me today, on your walk!

[Nick Mehta]

I know!

Heidi, it’s so great to be here, and for everyone watching, appreciate you joining
this conversation and yes, I’m on a walk, in Palo Alto, California. So trying to stay healthy
myself while we do this.

Yeah, that’s fantastic! So here we are. I’m in lockdown in Melbourne, Australia, and you’re out walking. So hopefully…

I know… I feel like I’m, I’m rubbing it in. That’s not fair, but yeah. Feeling for you. Can’t wait, for you to be able to go anywhere you want to get someday soon.

Yeah. Yes, someday soon, it’s coming. It’s coming. So look, let’s
jump straight into it. I wanted to run through a few questions today, to deep dive in, I guess to your career to date and obviously, you know, interweaving mentoring into that, both at an individual level and as the role of CEO of a global tech company, Gainsight.

So, you know, when I looked through your LinkedIn history, you’ve had a fascinating
career, you know, from founders, such as time in V.C. land to now, obviously CEO of a global tech company.

So when you think about how your career has progressed over the years, I mean, was it that
you had a plan in place from the start and, you know, were you always destined to be a leader?

I definitely don’t believe in destiny.

I think anyone can be a leader and I believe in a growth mindset for sure. But, did I always want to do it? Well, it’s interesting Heidi, somehow I, you know, 25 years later, I still have in my Dropbox the essay I wrote to apply to college in 1993.

So that’s a long time ago, most of you, many of you watching weren’t born yet.

The essay was about, where would you like to be 20 years from college? What do you want to be doing?

And it was basically about me running a company. So running a company, I guess, was what I wanted to do at least as, as per that essay.

Now, the company I always said I was gonna run was this biotech company that was going to cure all world disease.

Oh wow!

Typical entitled high schooler, thinking I was so much better. I didn’t think I was going
to be running an enterprise software company. I don’t think I knew what enterprise software was at 17 years old, but I guess I did want to be in business.

You know, the true part of that is, you know, my dad was an entrepreneur. He never had anything big. He ran some small companies, but I kind of grew up around small business, And, you know, I think I just sort of probably got into it that way.

And I guess when you think about your pathway, you know, especially starting as a founder and going through now to CEO, of… well, you’re CEO as a founder. You know, you’re CEO, COO, you’re every C when you’re a founder.

Yep. Yeah. Yep. (laughing)

You know, how do you describe yourself as a leader now? And what are some of the biggest challenges you’ve had to overcome in becoming that better version of yourself as you’ve grown into that role?

Yeah, it’s interesting. It’s funny because if I describe myself as a leader now, and I took that comment you made, “Better version of yourself.” I actually would say for me, not necessarily a better version of myself, but rather a truer version of myself.

So if you said, “What’s Nick’s leadership style?” at the core of it is just literally having a lot of confidence in who I am and what I am, and just being completely comfortable, being that and sharing that with the world and not having to hide it at all, being totally open to being vulnerable – all the things that are good, and some of the things that are challenging, and being able to talk to anyone about it.

So this confidence in who I am and my style and not seeing that I need to be somebody else. Right? So, that’s something that I think all of us end up trying to find.

Now, within that, what are the attributes?

If you ask people that know me, they would say, “High energy and passionate and, you know, big into communication, very positive.”

Like there’s a lot of things, but all of those touch on some core, of like, finding who I am, not trying to be better. Like, I actually don’t believe in that – there’s no better. I just know who I am and I hopefully can be fortunate enough to have jobs where, who I am, is valuable to that job.

Right? And, so I think I’ve figured out who I am.

But inevitably, I guess that continuous learning piece has to come into it.

Totally. Totally.

How do you keep yourself accountable around that, that personal development piece?

Well, yeah. I mean, so within that, like who I am, doesn’t have to be the same every day. I mean, you’re totally right Heidi. Like, it’s not like that’s a static thing.

In fact, just as a trivial thing, I used to be like the worst dressed person in the room, and now I’ve spent a lot of time on fashion, right? There’s a lot of things that have changed about me.

One of the ways I think about that from a work perspective is that I think about what the company needs right now. And like, in my case, the CEO job description, right?

I wrote a blog post a couple of years ago that was pretty popular, called Attention CEOs: Fire Yourself. The idea was, once a year, every quarter, however often you want to do it, imagine firing yourself, writing a job description for what the company needs then and hiring that CEO.

And then hopefully you can be that CEO or be that leader. Right? The same thing can apply to any job. And so for me, how’s that played out well, you know, over time I had to get better at like coaching executives versus doing things myself.

I’m sure, Heidi, you can relate to that.

Or get better at long-term strategy versus just executing on what’s there today. Being more thoughtful about decision-making, including more people in the process. These are things that you just learn.

And so I have, like right now, as an example, I have to figure out how to be a CEO of a company that has lots of different product lines versus we’re just in one business, because we actually sell into customer success teams and product teams, and we have a bunch of
different things we do.

And so I have to learn…I have to be that CEO. And so I talked to a lot of CEOs and say, “How do you do these things?”

I actually met a CEO at a conference just two days ago. And just like, like learned his whole model. Like, how does he run it? How does he decide who works on what? Right.

So one of the things I try to do is, I really try to learn from every single person I meet. It doesn’t matter by the way, if they’re a super experienced CEO or their first time.

Yeah. And I guess, you know, we’ll get to this a little bit later, but that’s definitely that peer mentoring piece that, that’s


Coming into play there and, you know, there’s such huge value in that. Where you can talk to someone that’s just, you know, in the trenches like you and going through some of the same experiences, you know, that can really be invaluable, that advice.

Right. Exactly.

So, changing tact here a little bit, and taking it a little bit higher level, you know, addressing the elephant in the room – I don’t know if we’re in a post-COVID world yet, or we’re still in the COVID world, but…

Still in it. Still in it. (laughs)

(laughs) I feel very much, still in it, but, you know, I think even pre-Covid we heard a lot about, the ‘Future of Work’ and what that’s going to look like. And, you know, the ‘Future of
Work’ this, the ‘Future of Work’ that, and we’re hearing even more about the ‘Future of Work’ now.

You know, cause everyone’s in kind of this, limbo-land. Some people are back in the office. Some people are still working remote. We’ve got large tech giants, like Atlassian coming out, going, “You know, we’re remote-first now.”

Now we’ve got some people sort of grappling in the middle as well within this, sort of trying to force people back as well, with a couple of days from home heading towards some sort of hybrid approach for the majority of companies.

I’m just keen to hear from you, I know it’s a big topic, but how do you think about this? I guess, in the immediate short term and how you’re navigating it and what you think the ‘Future of Work’ could look like for your people at Gainsight?

Yeah, totally. And I think you already had the right answer.
Cause I can’t say what the future of all work is and there’s going to be. Just like the present of work, there are many different kinds of work, right?

There are people that work in offices, work in stores, work at home, you know. I think there’ll always be some mix, but for our company, I think one of the things that we actually…

I was talking about this at the same conference I alluded to before, where I do think each company has a potentially unique kind of ‘ideal employee profile’.

You heard the term ‘ideal customer profile’, right? Who you target as a business. There’s a similar thing about ‘ideal employee profile’. What employee is the type of employee that would be uniquely happy and successful in your company?

The Gainsight story is that when we started, we were actually distributed from the beginning. So we had people in India, people in the US throughout. And so we basically have always been very distributed.

And one of the challenges there is obviously, there’s a lot of communication overhead, and a lot of video meetings and, you know, time zones, and all the things that you’d know all about. And then the upside is, even before the pandemic, we were a very flexible company.

Need to go take time off to go see your kid’s recital?
No problem.

Want to, you know, spend the day with your spouse and catch up later?
Totally Fine.

And, so we basically have leaned into that hardcore. I believe one of the really unique things Gainsight can do is be one of the most flexible employers in the world.

Cause we’re, essentially saying, “You can work wherever you want, permanently.”

We’ll probably have a few offices, because there’s some places people want to work in the office. But for me, I’m going to work from home forever. And that means all the meetings will be virtual and all that.

Or on a walk?

On a walk, exactly.

And the advantage is…and it’s funny, even this walking thing, I tell everyone, “Hey, take walks, do calls while walking.” I publish my step count every day to the company, so they know I’m taking care of myself too.

When I go take time off because my kid has a birthday party,I tell everyone about them.

And so I think that for us, our ideal employee profile is probably people that really value flexibility and like ‘the whole’ life.

But our ideal employee profile might not be somebody who is really early in their career, wants to be in an office with the energy of like 500 other people. That’s a valid profile too. That’s probably not going to be us, and will never be us – we’ll never be great at that.

And so I do think there’s some element of like, what employee population
can you be awesome for?

Not trying to be something for everyone, but be great for a certain type of people looking
for a certain type of company.

Yeah. It’s interesting, actually, you say that and you referenced the, younger employee looking for that, in-world experience of the office.


That’s something we’ve seen in organisations coming to us. Mentoring in the past has often been seen as a bit of a nice-to-have, or it’s something that’s only relevant for high potentials.

But they’re in this limbo-land – in a remote hybrid world where some of their employees, could be younger or mid-career as well. A lot of organisations going through a period where they’re remotely onboarding people and they’ve never done this before.

And so, you know, you’ve got tools like Zoom and Teams to communicate, but people almost becoming more siloed in a sense in that they’re communicating with their teams but how do you interact and meet with people outside your team?

Essentially, how do you have those water-cooler moments, remotely?

That’s where we’re starting to see mentoring come back as a kind of initiative to drive some of these connections outside your specific team.

What are some of the initiatives you’re doing internally as well to help create that sense of connection across teams?


First of all Heidi, you’re totally right – “connection” is the operative word for sure. Because I think that is the one thing you lose when you don’t see people in person and you have to find ways to do it.

I love seeing people in person, it’s awesome. I would love to meet you in person! But you know, sometimes the circumstance doesn’t allow it and there’s a trade-off. I don’t love being on the road every weekend, you know?

There are two sides to everything and so there are ways you can create connections that are never going to be the same (as in person), but they can still be very special.

And so that’s one of the big things I believe is, working remote’s never going to be the same as in person, but it doesn’t have to. It just needs to be good for certain kinds of people.

So for me, one thing is that every company event should really focus on connection. We were just talking about our All Hands, and the only purpose there is connection.

Cause you know, everything else, the communication of information, what’s happening at Mentorloop or Gainsight – people find out about that 24/7.

There’s Slack.
There’s, you know, email.
Whatever you’re doing, right?

So we spend our precious time on actually, like, just communicating information. And so for example, you know, we’ve had at our All Hands, this awesome DJ come in, right.

And the DJ comes in and puts on different…
(He’s a great DJ, by the way. His name is DJ Schematics. He’s so good.)

And he puts on all these like awesome songs and people on the Zoom chat are like having a lot of fun. And every meeting that we do at Gainsight, we have an icebreaker, every single one.

You know…
What song is in your head right now?
What’s your childhood dream?
What’s your favourite memory from Summer?

Every meeting has an icebreaker, and people do it in Zoom chat. And so there’s different ways to drive connection.

I love the peer to peer mentoring idea and like, I love what you guys do in it.

By the way, we at Gainsight use Mentorloop for our community, which we can talk more about separately. So I love that idea. Yeah.

Well, that’s probably a nice segue, because I was going to bring that up. So we obviously do what can we do to support CS Gainsight Community Mentoring Program. And, you know, it’s funny because we’re actually, again, seeing more and more companies sort of come to us and
thinking about mentoring, not just as an internal sort of tool to create connection and connectivity, but as part of its social impact strategy.

So yeah, I was wondering if you could just talk through a little bit more about the Gainsight CS Ops Mentoring Program and what sort of drove that initiative from your side?

Yeah, totally.

Let me say, overall, my philosophy, like in general, is today, most companies think of their company and their customers and kind of community as different things. I believe that concept is gone in the future. It’s gone, because it’s all one thing. It’s all just human beings, right?

And actually, you know, you might have already experienced this – we have customers that have become employees and employees that became customers and like everything, every permutation, right?

So to say it starts and stops here, it doesn’t make any sense. So we’ve always been a very
community-oriented company. And when we started, we created this community for the customer success profession called Pulse.

And that was, you know, the big, big thing was this big conference that we do in person every year, and obviously lots of other events. And what we found was okay, those events are kind of like the ops where just naturally, there’s a lot of community building that happens in person. And it’s great. It’s really cool. And water cooler talk, as you said, at the bar or whatever – how do you replicate some of that online and how do you sit and create that serendipity?

So we had a specific role within customer success, Customer Success Operations.

It’s kind of like the new part of customer success. Just as you have sales operations to help you scale sales, this is the same thing for customer success.

Everyone’s hiring customer success operations people, but they’re all kind of new to the job.

And so for a lot of them, they’re like, well, “What is my job supposed to be like?” And you know, one of the big things in community is people just want to feel less lonely, and they want to meet people like them, and they feel like they’re not the only ones going through this.

And what I love about Mentorloop is…

I’ve talked to so many of our people in our community that have used Mentorloop now,
paired up with a CS operations person who is a little further along in their journey and they love it. They love it.

And by the way, the people that are further along in the journey love being the mentor as well.

– Nick Mehta, CEO of Gainsight

I’m sure you hear this all the time, right? It’s a two way it gives both people benefit, you know?

Absolutely. There’s this kind of this old world view of mentoring that for a mentor, it’s just about this altruistic view, about giving back and feeling good about yourself – but it’s way more than that.

I always have this moment when I’m playing that role of mentor that if/when I’m giving advice or some guidance I think, “Oh, you know, I need to go and do that. Why aren’t I doing that?”

Heidi, literally today, I had that like an hour ago. A CEO was asking me (he has a smaller company), “What are your biggest learnings from when we were much smaller?” And then I rattled off a list of things, including three or four things I still haven’t done yet.

So I really was like, I need to do these now. (laughing)

So yeah, you’re totally right. You can learn from every conversation. It doesn’t even matter how
experienced the person is.

I’ll meet some CEOs who are running tiny, tiny startups and I learn tons from them, right?

And so I think that like one of our values at Gainsight is “shoshin”, which is the Japanese
word for “beginner’s mind”. And so beginner’s mind, the idea that we all can learn the most if we adopt the mindset of a beginner, right?

Because within beginner’s mind the possibilities are endless, so we love that.

It sort of aligns back to a sentiment we have at Mentorloop, that no one is self-made. Like there’s always a support act involved and you know, you’re never, you never stop learning.

So, I guess just on a personal level then, if you think about over the years, and we’ve had a chat about some key mentors, in terms of mentoring for you at a personal level, who have been some of the most impactful mentors that you’ve connected with over the years?

That’s very interesting. Cause you know, the term mentor has two different definitions like you alluded to, right?

And, and whenever I hear the term outside of your company, I have that old school definition, which is, oh, that one person, that’s the super wise person .that’s telling you everything
and passing on to the next generation. And I never had that.

Like I never had one person. I kind of say, I’m like a student of the world. I want to be mentored by everyone!

And so if I go through some people that specifically have helped me, I think of Jeremy Burton. I was at a software company called Baratos. I was a product manager. Jeremy was the president of the company. And, you know, he was incredible at taking technical complex ideas and making them exciting like in terms of marketing. And I learned so much from him.

There’s a guy named Mike Speiser, who was another one, a boss of mine. And he was a Director of Product Management or something, and he’s now a big, big-time venture capitalist.

And he just talked, talk to me so much about ambition and going for big ideas.

I’ve learned so much from so many different people. And so I love the idea that everyone can be a mentor and everyone can be mentored. That’s why I like what you do, because mentoring is not this thing where you just do it once and there’s one person. You want to be able to have access to everyone.

Yeah. That’s it, we have this image that we use which is this picture of Mark Zuckerberg, of Facebook, and Steve Jobs of Apple to demonstrate that this is how people typically see mentoring – as a hierarchical kind of relationship.

The idea that, I see something similar in you to me and I’m going to take you under my wing.

But you know, the problem with traditional hierarchial mentoring is that it excludes. That sort of mentality favours the bold, it favours people that already have these networks and actually makes mentoring feel like it’s an inaccessible proposition.

When in fact, you know, I’ve always found that the best mentors that I’ve had, particularly as a founder early on, were just those people that were 12 or 18 months ahead, that help you see around corners.

They’ve just gone through something you’re about to, that’s where I really the nuggets of advice come from.

Actually, I can give you a couple of other examples just to build on what you said…

So in my CEO role, Aaron Levie who is the CEO of Box, a well known SaaS company – he’s been incredible. By the way, not him sitting in mentoring me – more like us just talking and like hearing how he thinks, and you know…

He has this incredible resilience to just keep going.

Or I’ll pick a name that’s probably not as familiar.
There’s a woman named Rachel Carlson who’s the CEO of Guild Education. Guild is a company that’s actually younger than Gainsight, and Rachel’s younger than me but I’ve learned so much from her because she’s gotten to do her company in an even more modern way than we did because she only started five years ago.

And so, yeah, I totally agree with you.

There’s this thing about people that are on your journey, maybe a little bit further ahead, maybe the same level, and you can learn so much from them.

Yeah, absolutely.

So, to wrap up mentoring at an individual level, I know from people in our community, they’re often curious about how to go and connect with a mentor, and I’m sure you get approached all the time on LinkedIn.

I’m curious just to know when you are approached, how do you assess whether this is something you will take on? I know you’re very generous with your time but you obviously can’t mentor everyone. What advice would you give people that are going out and seeking mentorship, in how to approach someone?

That’s interesting.

One thing I would say is you probably don’t start out with the message, “Can you mentor me?” Because it’s sort of like, on a first date, proposing someone to marry them. You might want
to save that for later.

Instead, ask for 20 minutes of their time to just get their input on something.
I think that one thing to not undersell is to share – what can you bring to the table too?

So, you know, it doesn’t have to be positioned as a one-way street.

You know, if somebody emailed me and said, “Nick, you know, I’m a VP of customer success. I’m thinking about my next job. I’d love to get your advice, but I also love to get your feedback on what I’m hearing from the needs of CS leaders in the market right now.” And so I’ll be like, “Oh wow, great.” In that conversation, I’ve learned something, they learned something, that’s awesome.

I think that type of short conversation to build the relationship over time, a two-way street, just like in marketing, you know, you have that conversation, now nurture that person.

And what I mean by that is like, you don’t have to just ask for another meeting right away. You can, you know, a month later send that person that you met a note saying, “Hey, I really enjoyed our conversation. I saw this article and I thought of you,” Right?

It’s that ongoing relationship building that takes work. I think that’s, that’s what it’s all about.

Yeah, absolutely.

The best mentorships are reciprocal in nature. And I think it’s also important for mentors to come with an element of vulnerability to the table here as well, because there’s obviously something there for them to learn too.

We’ve all got something to learn. We’ve all got something to teach, but you know, it shouldn’t just be viewed as a one-sided relationship.

Love it. That’s such a great, great way to say it.

Well, Nick, I think that’s a wrap.
Thank you so much for taking the time to have a chat with me today and on your walk. I’m so jealous of the sunshine and you being out and about, but you know, it’s given me
energy for the day ahead. So I’ve really enjoyed chatting with you, and we look forward to supporting Gainsight mentoring initiatives going forward.

Thank you so much for inspiring people around mentorship, and thanks for being a great partner to us, and thanks for going on a walk with me. I really enjoyed it.

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Em is our Marketing Manager at Mentorloop. That's a lot of 'm's! | She is passionate about crafting messages, crafternoons and craft beer.

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