The Infinite Game of Customer Success: Why Gainsight Partnered With Vista Image

The Infinite Game of Customer Success: Why Gainsight Partnered With Vista

[TL;DR: We’re thrilled to announce a partnership with Vista Equity Partners, valuing Gainsight as a “unicorn,” to take the Customer Success movement to new heights. And I’m personally all in as CEO for this next phase. If you want to read the boring version of this story, see our press release here. If you want to read fun commentary from Alex Konrad at Forbes, click here. Otherwise, read on…]


Memories are funny. Why do we remember some things and not others? Why are some images 4K-vivid in our brains while others feel like they are encoded in 8-bit? Why do I recall every single final play from every single Steelers playoff loss and yet forget peoples’ names :05 seconds after they tell them to me?

Over the course of my 7+ years being a part of the Customer Success movement, thousands of images have been etched into my brain, including:

  • The first Pulse conference in 2013 in San Francisco, with a gigantic-at-the-time 300 people in the audience.
  • Pulse events globally in London, Sydney, Atlanta, Boston, Chicago, Seattle, and New York.
  • The face of every Gainster past and present who has played a role in making the Customer Success movement a reality.
  • Hundreds of redeye flights to meet with members of the global Customer Success community.
  • Talking about my struggles with loneliness in front of 3,000 of my closest friends at Pulse 2017.
  • Hundreds of video and phone meetings coaching CS community members on career options.
  • And, of course, my ill-fated rap music debut (though I’m sure many would love to erase that memory!).

Yet, one messy and lonely image rivals all the rest. 

I remember walking into our first “real” (non-coworking) San Francisco Bay Area office in Mountain View, CA, in 2013. The space was conveniently stationed upstairs from a bar. We had just signed a 2-year lease coming off of our Series A round of financing. I remember asking the landlord who the previous tenants were, hoping that the location’s good omen would carry us forward. “I don’t think any of them are still around, to be honest,” he said. 

While outwardly, I, of course, projected infinite confidence in the inevitability of Customer Success, my inward monologue was somewhat different:

This is too much space. And 2 years is too long. Why did we sign that? Are we even going to be in business then? 3000 square feet? We’ll never use that. Is Customer Success really a thing?

Since I’m being real, I believe thousands of early members of the Customer Success community (and maybe even some to this day) shared this sense of “imposter syndrome.” Yet, we put on a brave face and powered forward. Here were our two older kids (7 and 5 at the time) wishing us good luck. Back then, I wouldn’t have dared to even imagine the success we’re celebrating today.

The Customer Success Mountain

The Customer Success community looked up at the top of an impossibly-high mountain in 2013, with the peak invisibly-obscured by clouds. Could we all make it up? Would we survive the journey? Was there even anything at the top?

Over the next 7 years, members of the Customer Success movement took on the challenge together, knowing that their companies’ futures (and valuations) depended on them:

At Gainsight, we consider the Customer Success movement’s success to be a big part of our mission, so we tried to contribute where we can. We have published and produced thousands of blog posts, hundreds of community events, and 3 books. Personally, it continues to be the thrill of a lifetime to have met thousands of Customer Success execs and to have spoken at hundreds of separate events and podcasts, big and small. And of course, we cannot forget the parody music videos.

In short, the climb so far has required a lot of steps by many people. But it has been incredibly rewarding, in particular because of the challenge. I hope that the members of the Customer Success movement feel that same pride as well. They deserve it.

And we all know the best days for Customer Success lie ahead of us. We are all just getting started. We see another mountain just ahead of us where Customer Success truly goes mainstream across all industries. It’s out there waiting for us.

The Next Climb with our New Sherpas

In the old days of business, a company had only two options at our stage. You could stay private and venture-backed and hope that the clock doesn’t run out for all of your stakeholders before you reach the next mountain. Or you could brave the public markets early. Sometimes the latter approach worked, but in many cases, it led companies to be optimized for the short term and unable to complete the next climb. We’re fortunate that today, there are other much more appealing choices available to us.

Over the last few years, a new category of investors has emerged to fund businesses built for the long term. First amongst them was Vista Equity Partners. We knew Vista because 24 of their portfolio companies use Gainsight. Vista was a huge proponent of Customer Success as a way to fuel long-term growth in their investments. Vista also had demonstrated industry-leading best practices in scaling companies by leveraging the collective knowledge of their hundreds of software investments. And Vista had proven it time and time again, including recent IPOs of Gainsight clients JAMF, and Ping Identity.

So when Vista preemptively approached us with an offer to partner for our next climb, we were flattered. Most importantly, we were proud that some of the smartest people in software agreed with us that Customer Success is existential to business success. Vista’s conviction validated the tireless efforts of the Customer Success community. After some careful thought, we decided they would be the best next “sherpas” to help us up this new, exciting and challenging path.

What does this mean for our clients and community? We’re going for it. We are going to double down on our innovation. We are going to push harder to drive Customer Success as a company-wide priority, incorporating important partners in Product and Sales. We are going to bring Customer Success to more companies, locations, and industries, leveraging Vista’s best practices for growth. And we are going to continue to bring the community and profession together so we can all win as one.

And to be crystal clear, I am personally doubling down and staying on as CEO. I have never been more excited about what we can all do together.


Thanksgiving was last week in the United States, so I’m still feeling the afterglow of good food and gratitude.

This first climb hasn’t been easy. Sure, from the top, it looks fun. But it wasn’t a straightforward path. We had to help invent (with many collaborators) a new industry on the fly. As such, we made many, many mistakes. Scratch that. I made many, many mistakes. But thanks to so many others, we were able to get there. 

Our founders, Jim Eberlin and Sreedhar Peddineni, saw the mountain before almost any of us, back when we were Jbara Software. 

Our first set of guides, our early investors, were a huge part of all of this being possible. Roger Lee from Battery Ventures was like a founder of Gainsight, coming in so early. Ajay Agarwal from Bain Capital Ventures bet on us as a fledgling company, with a vision for how this space could disrupt Sales and Marketing overall. Byron Deeter from Bessemer Venture Partners saw the need in his extensive SaaS portfolio and helped establish Customer Success as a critical play in the cloud. Jeff Lieberman from Insight Venture Partners helped us adopt the best practices of the many “scale up” companies they fund. Nakul Mandan from Lightspeed Venture Partners triple dipped, helping to spot Gainsight at Battery Ventures (along with Paul Morrissey) and then re-upping twice at Lightspeed. Greg Goldfarb and Harrison Miller from Summit Partners, Matt Garratt from Salesforce Ventures, Ben Johnston from Sixth Street Partners and Donald Tucker and Pegah Ebrahimi from Cisco Ventures were thoughtful and supportive guides throughout the journey. Finally, our independent Board Members Kirk Bowman, Kirsten Helvey and Sue Barsamian counseled us through countless important decisions and we’re forever thankful to them.

As with any company, particularly a Customer Success firm, none of this would be possible without the customers that trusted us and shaped us. There are far too many to name, but I will just say that a highlight for me has been to get to know our clients as the wonderful human beings they are.

At Gainsight, we’ve been fortunate to be in the middle of a software movement and bear witness to a new profession. As such, the first climb depended on the trust of the 100K+ members of the Customer Success profession who stepped into the ambiguity of a new role and embraced it.

And of course, I am personally forever-indebted to our team at Gainsight past and present. We’ve been a uniquely global company from day 1, with our founders hailing from the unlikely combination of St. Louis, Missouri and Hyderabad, India. Along the way, we added Gainsters in San Francisco, Bangalore, San Mateo, Phoenix, London, Tel Aviv and hundreds of “Gainsters Everywhere” that work from homes. Their ability to balance our five Values, most notably “Stay Thirsty, My Friends,” got us to this point. And this includes both the 700 current Gainsters and the hundreds of other Gainsters-for-Life in our alumni group. And on behalf of all of them, I know none of us would be here without the support of friends and family supporting us along the journey.

Indeed, this photo shows how our family has grown with the Customer Success movement, with our 5 and 7 years from the previous photo now magically grown to 14 and 11 – and an 8-year-old, too!

An Infinite Game

A few weeks ago, I interviewed Stewart Butterfield, Founder and CEO of Slack. Stewart and I both nerd out about philosophy, so we discussed the nature of companies and a book he had recently read called Finite and Infinite Games. I subsequently purchased the book and the core idea is “A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play.”

At Gainsight, we set out as our purpose “to be living proof that you can win in business while being human-first.” While we definitely think this news validates our objective, that kind of mission is truly infinite. We’ll always find another mountain to climb. We’re always going to want to keep going. It’s the climb that is the purpose, one step at a time.

Stop me before I write a Miley Cyrus parody…