Issue #69: The Fast & Furious Career Path of Kellie Capote

Despite working in an industry where job postings for VPs ask for 10+ years of experience, Gainsight’s Kellie Capote moved from a Strategic CSM to Director to VP to CCO... in only 4.5 years. So just as you’re probably thinking “How did she achieve that?”— we wanted to know, too. 

My cofounder Nick and I recently spoke with Kellie to reflect on her rapid rise to the top. Below you’ll find a summary of some of that discussion, where she recalls three distinct tactics that helped her scale herself at fast-growing Gainsight. 

Want to listen to the conversation with Kellie instead? Head to the ‘nuffsaid podcast and catch the full interview here.

…

CHRIS: You started as a CSM at Gainsight in 2017 and now only four and a half years later, you're the CCO at the most well-known Customer Success software company on the planet. How did that happen? 

KELLIE: You're not the first person to wonder how the heck this all happened. I'll start by saying it's certainly been a fun, fast, and furious journey with tons of professional growth and learnings along the way. 

Previous to Gainsight, I was working in a people management role, leading teams at ADP. But behind the scenes I was geeking out on all things Customer Success. I knew Customer Success was a fit for me—and it made sense from a business perspective, with the massive shift in SaaS to the recurring subscription model.

But I also felt so energized thinking about Customer Success; my strengths are in working with customers and consistently challenging them to achieve their next level of desired outcomes. And at that point in time, I had two young daughters and thought it would be good for me to reground myself in an individual contributor role for a bit. I thought I was going to take a breath of fresh air as an IC, but quickly found myself gravitating right back to people management.

I’ll admit that timing was certainly on my side. Gainsight’s CSM team hit a rapid clip of growth and we were a super small, mean, and mighty team when I joined. I had the opportunity to help build out a few of our strategic enterprise teams. Then, I led all of enterprise CS. After that we just continued to grow and improve: we streamlined the org structure, brought CS Operations into the remit, and eventually I stepped into a VP role to lead the global CSM organization.

Then, about six months ago, I had the opportunity to become Gainsight’s CCO where my role would extend over the broader post-sales organization. I had (and have) some very big shoes to fill from our former CCO, Ashvin Vaidyanathan, who is near and dear to my heart. 

And now, sometimes I pinch myself when I wake up because I am truly living my dream. But by the same token, I know that this is a large responsibility, not only to Gainsight, but to the broader space of Customer Success. That's what keeps me energized day in and day out. 

NICK: I'll speak for everyone in the world and ask, are there any specific learnings that we can all take away from that meteoric rise? 

KELLIE: I'll share three things that come to mind the most. Ironically, I host a CCO fireside chat at Gainsight with new Gainsters (as we call them) and they often ask this same question. Here’s what I say: 

1. Number one, don't underestimate the power of cross-functional relationships from day one in your career. Back in my early days at Gainsight, I can recall one customer situation that required me to work with essentially a counterpart from each department in the org. We all had to group up and rally together to resolve the issue. 

That one situation had a lasting effect because the relationships I instilled with other department heads ended up paying off in dividends over the course of my career. My peers in that moment ended up becoming advocates for me internally, especially at the executive level, as we all rose together.

When you think of a future VP of CS or CCO, it absolutely must be someone who can rally around the notion of cross-functional collaboration. 

2. The second one is just a bias for action. I like to call it the “bulldog mentality.” You can slice it two ways: from an internal perspective and from an external perspective. Internally, I have an eye for process optimization, which was probably one of the key differentiators between me and my peers.

It’s not about saying, “Hey, this little thing over here, it's not working.” When you have a bulldog mentality, you actually go and do something about it. When you take ownership and initiative to constantly drive organizational progress, it not only benefits you by pushing you to be a more effective leader, but more importantly, it helps the broader team and company.

Some examples: I crafted Gainsight’s first true onboarding process doc for CSMs, I re-imagined our EBR templates, and restructured some of the KPIs for our team. I think one of the biggest things stepping into the VP of CS role is we had some high level metrics, but getting that operating rhythm in place was crucial. If you constantly drive towards operational excellence from an internal perspective, you will get attention from others in the org.

From a CS customer-facing perspective, I think the best CSMs have that same quality of a bias for action. The CSMs that continue up the leadership path are those who constantly challenge and push their customers up the maturity curve. They’re not okay with mediocrity. They truly embrace being the biggest advocate for their customers and infuse customer centricity across the organization. 

3. And last but not least, one aspect that has helped me in my career path is what I like to call the adaptability quotient. We often talk about IQ and EQ, but especially in the world of CS, I think we can all agree that a lot of the time it's like a rollercoaster ride. Every day is different. You don't know what's going to come out of left field, maybe even 30 minutes from now. There's the good, the bad, the ugly, and every emotion in between.

So being able to retain an even-keel mindset and say, ‘Okay, what's the next thing that I control? What can I do about this?’ rather than riding the emotional highs and lows, bodes very well from a CSM perspective, but also it increasingly becomes that much more important if you want to thrive in a CS leadership role.

NICK: It sounds like a really important part of being a CCO is your ability to execute. How do you figure out the biggest problems to solve? Do you go straight to Gainsight’s CEO, Nick Mehta—and if not, how do you navigate internally to figure out the most impactful problems to solve? 

KELLIE: There are a few parts of this question to unpack. First, we've done a good job at Gainsight of making sure there’s connective tissue from the highest level of the company down to entry-level roles. 

As a company we've created a one-page strategic plan, which succinctly synthesizes our mission, goals, and critical initiatives to drive the business forward. This is the backbone of purpose. But especially in the world of CS, I'm constantly looking at the headwinds and the tailwinds. I dig deep into our churn and expansion analysis to see what's working, what isn’t working, and in many cases this informs me on the most valuable problems to work on. 

In my role as CCO, my success depends upon how I go about solving cross-functional issues. I’m seeking out how Gainsight can be world-class when it comes to CS<> Product, Marketing, and Sales collaboration.

As the CCO, you are the responsible party for being the learning engine of the business. It's your job to make sure everyone at your company has a well-rounded view of what's truly happening to the customer. In CS, we are so close to our customers that we must be capable of injecting customer-centricity within the executive team, the board, and across the entire company.

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