Featuring Kellie Capote, Chief Customer Officer at Gainsight
This article is part of our 2.0 Leadership Series, where we provide practical insight into what strategic Chief Customer Officers are doing so the rest of us can level up more quickly.



A “fun, fast, and furious journey” is how Kellie Capote describes her career. But make no mistake: she’s being humble.  


Kellie grew from Strategic CSM to CCO at Gainsight—the most well-known Customer Success company in the world—in only four and half years. A more accurate word for her career would be meteoric

Before Gainsight, Kellie led account management and partner management teams at ADP. But behind the scenes, she said she was geeking out on all things Customer Success. “I knew Customer Success was the right fit because of how energized I felt by the idea of it; my strengths are in working with customers and consistently challenging them to achieve their next level of desired outcomes.” CS also made sense to her from a business perspective, with the massive shift in SaaS to the recurring revenue model.

Kellie had two young daughters at the time when she joined Gainsight. The idea of learning the business from the ground up combined with the flexibility of an IC role, proved to be a great landing point for Kellie to start her career at Gainsight. Little did she know that a thriving customer success movement and an innate passion for leadership would find herself gravitating right back to people management.

Her timing was flawless. Not long after she joined, Gainsight’s “small, mean, and mighty CSM team” hit a rapid clip of growth. She kept up. She went from building out multiple Enterprise CSM teams, to leading all of Enterprise CS. Then, “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.” Six months ago Kellie became Gainsight’s CCO.  

In this interview, Kellie takes us through her career, articulating what exactly helped her grow so quickly and how her responsibilities and focus have changed.  


    • Specific habits have helped Kellie grow quickly, like: building cross-functional relationships even as an IC, operating with a mentality of taking ownership over problems that aren’t necessarily in your remit, and being able to quickly bounce back from unanticipated changes. 
    • You’ll need to prove your capabilities, so leadership wants to place a bet on you at each level and stage of the company. Start measuring your progress now and your impact on metrics the company cares about. 
    • There are key differences between the VP and CCO role: they require two completely different skill sets (execution and managing down versus strategy and managing sideways and up).

Habits that will accelerate your career

When I’m coaching others and need to share what I did to accelerate my career, I always come back to these four habits. 


1) Build cross-functional relationships right now 


Relationship-building has always been one of my strong suits. But I was fortunate to be thrown into a critical customer situation early in my career at Gainsight that afforded me the opportunity to develop relationships with counterparts from essentially each department in the org. We worked as a team to get through this challenge.

The experience had a lasting effect—those same peers later became advocates for me internally, and we all rose together. We all know this habit is foundational to the role of the CCO. But you can practice building that habit now and it’ll benefit you over the long-term. 


2) Operate with a “bulldog mentality” 


Having a bulldog mentality, or a bias for action, is about taking responsibility for problems even if they’re not technically “owned” by you. 


Instead of pointing out problems (“Hey, this little thing over here, it's not working”), you actually go and do something about it. When you take ownership and initiative to constantly drive organizational progress, it benefits you by pushing yourself to be a more effective leader, and 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. When I stepped into the VP of CS role, 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."

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) Develop your adaptability quotient 


IQ and EQ are talked about all the time but on a day-to-day, especially in the world of CS, I think we can all agree that it's often a rollercoaster. Every day is different. You don't know what's going to come out of left field; there's the good, the bad, the ugly, and every emotion in between. So developing your AQ (adaptability quotient)—your ability to adjust course in the face of unanticipated changes—will help you scale yourself in a rapidly changing company. 

Being able to keep an even keel 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 in Customer Success and in leadership.


4) Build out your selling skillset 

If we really embrace what Customer Success means at its core—that it's a growth engine for the business—and we all orient ourselves around the north star metric of NRR, then CS is really just a continuous sales motion of the original deal. There’s the first sale, the second, the third... We’re constantly driving and bringing more value to customers.

CS can learn a lot from Sales to help with this continuous sales motion. The fundamental sales skill sets, like having a challenger mentality, objection handling, understanding the value proposition, negotiation, and presentation skills, help differentiate “good” from “great” CSMs.



Taken at Gainsight’s 2021 Pulse Everywhere conference


Anyone can build their selling mindset—you don’t have to have a background in Sales. It requires a focus on metrics, being entrepreneurial (this is “your business”), and developing a mentality of taking ownership and accountability. 


Two ideas to help you build a selling mindset right now:

a) Do your homework. There is so much content available for salespeople—who says you and your team can’t learn from it, too? Study up on books such as The Challenger Sale, sit in on demos, listen to call recordings, roll out professional development with a focus on selling, go through the same training your sales team, or talk to your colleagues and ask questions about how they’ve handled negotiation conversations, upselling, and navigating specific objections.

We're seeing more CS organizations roll out professional development courses with similar soft skills training. The more CS can learn about sales methodologies, the better.

b) Require your peers, mentors, or even your boss to hold you accountable to metrics. Too often, Customer Success isn’t required to be data-driven and held accountable for numbers that matter to the business. If you don’t personally own a number that matters to the business, ask someone to hold you accountable to one and apply pressure on you. 

Proving your capability so leadership wants to bet on you

When a new investor comes into a company, and in our case it was Vista Equity Partners in 2020, the conversation often centers around whether the current executive team that brought the company here will be the same team that drives the business forward into new realms. The common action is to bring in people with more experience.


Presenting yourself as someone leadership can place a bet on takes a dual approach: there’s the business aspect (“can this person perform?”) and the relationship aspect (“what’s their connection to their team, their peers?”).

From a business standpoint, I have a few tips for others who want to 1) be kept on after an acquisition, 2) do well in an interview, or 3) make the case of why you are deserving of a promotion.

1) Carry yourself with conviction

I encourage everyone reading this to constantly advocate for yourself. You need to bring a lot of confidence to these types of conversations. It may sound trivial, but it honestly goes really far. After the decision had been made to promote me to CCO, Nick Mehta’s feedback was that he loved how much conviction I had.


One small but powerful tactic here: replace passive words (e.g. I think, maybe, kind of, probably) with power words (e.g. I expect, I’ve demonstrated, plan, drive, achieve). 


2) Be more prepared than you need to be

I suggest to always come with more than you’re asked to bring. During my interview for the CCO position, Nick didn't ask for it, but I came with a plan for Gainsight’s future. When you come prepared, it shows a level of professionalism, passion, and your ability to think strategically about the business. 


Along that vein, even if you’re a CSM, start to think about how things would be different in your team or company if processes, team structure, or culture were different. How would things change if your goal was on expansions not renewals? How would things change if you reported to the CRO not CCO? Considering your opinion on these types of questions now will help you be prepared for strategic discussions in the future. 


3) Bring historical data and demonstrate experience

Prove what you've already done by the numbers. This is where having a consistent operating rhythm becomes important. I had clear data points to showcase what stages I’d led the team through and the progress we’d made since I started at Gainsight. 


In that interview to become CCO, I was very specific. I showed the team where we are today, and with a SWOT analysis, what we needed to do to get to the next level. Then I built a bridge to where we wanted to be from both a gross and net retention perspective.  


Another tactic I used in my conversations with leadership about the CCO role, was presenting Gainsight’s former CCO’s One-Page Strategic Plan (OPSP). I shared what I already had influence over within the doc and how I would attack goals as the new CCO.


4) Stretch yourself

No matter what role you are in, I recommend stretching yourself, as much as you can, to do the tasks and take on the responsibilities of your next role. As a VP, if I had not taken on some heavy responsibility, such as presenting in the Board of Directors meetings, I would not have been as prepared as I was stepping into the CCO role.

It goes back to having that bulldog mindset—if you consistently volunteer to work on issues that aren’t technically yours to deal with, not only will you be noticed as someone who can execute, you will be preparing yourself to succeed in the future. 

As for the relationship side: When the time came for me to advocate for taking the CCO role, it was a natural fit from a relationship standpoint. I’d already been doing the work of a CCO, and my peers and my team recognized that. 

How your focus changes as CCO

The role of the CCO is defined differently by every organization. But I envision the best CCOs as having two qualities in specific:

1) They have the ability to extend customer-centricity into every area of a business. At Gainsight, it’s my job to make sure there’s “customer connective tissue” from the highest level of the company down to entry-level roles.

"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." 

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.


2) They have the capacity to detect the most important problems to solve. In any business, there’s not enough time in the day to complete all things that need to be worked on. Therefore, prioritization and knowing what the right things to focus on are key to any CCOs success.

One thing I constantly look at is Gainsight’s one-page strategic plan, which succinctly synthesizes our mission, goals, and critical initiatives to drive the business forward. This is the backbone of our purpose. I refer to it often to decide ‘what’s most worth my time.’ 


CCOs also need to regularly look at the headwinds and the tailwinds of the business. 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. 


The difference between a VP of Customer Success and a CCO





Across the industry, there’s some confusion around the difference in responsibilities of a VP of Customer Success and a Chief Customer Officer. Since I've lived both roles, I now have a sense of the distinction.

1) As CCO, you spend more time managing up and sideways than managing down. 


One framework that I use with my leadership team in coaching conversations is this notion of managing down, managing up, and managing sideways. As you go up the career ladder, all three management techniques are important, but the distribution changes at different stages. 


As a CCO, I spend more of my time managing sideways and up than managing down. Of course, I have to empower those below me and make sure the right people are in the right roles and drive accountability, but when I was VP, most of my energy was spent on managing down. This doesn’t mean as CCO you should disengage from your ICs. But in order to scale, you must establish an operating rhythm of trust and empowerment within your team. 

2) As CCO, you must have skills outside of just “deep” Customer Success.

Obviously, the charter as CCO is just much bigger. You can't get too deep into one thing, like the CSM organization for example. It’s not good enough to understand all the ins and outs of Customer Success. You need to know enough to be dangerous and effective across multiple departments. So having the right structure in your day, frameworks, and metrics becomes really important. 


To have influence, you have to go wider in an organization. You have to have a longer reach. My success depends upon how I go about solving cross-functional issues. For example, my biggest initiative currently is to figure out how Gainsight can be world-class when it comes to CS<> Product collaboration. At the end of the day, there is a huge opportunity for businesses to tighten up the convergence of those teams by creating shared metrics and injecting more of the voice of the customer back into the product.


As a CS professional, if there are smaller initiatives that pop up to work cross-departmentally, volunteer for those. 

"It's not good enough to understand all the ins and outs of Customer Success. You need to know enough to be dangerous and effective across multiple departments." 

It will only benefit you in the end because that is ultimately the cornerstone of the CCO role—being able to drive customer-centricity across all departments. 


3) As CCO, you need an executive presence in the form of honing a much deeper understanding of company financials and having excellent board presentation skills.

I like to think about 3 buckets of success: investor success, company success, and teammate success. Investor success really shows up when you jump from VP to CCO.

That means, as a CCO you’ve got to understand the financial side of the business. If you’re a VP and don’t understand the financials of your company, I encourage you to go learn about it. 


My former boss, Ashvin Vaidyanathan, did a great job of slowly handing over those responsibilities. He let me build the board decks, be part of our due diligence cycle with Vista, and present to our board as a VP. And his mentorship paid off. In August 2021, as CCO, I presented to our Board of Directors (plus, I wrote this blog with a CS BOD Slide Pack Template for your use)—which was a big win for Gainsight and me. 


If you don’t have a mentor like this, I would challenge your leadership team to let you do more of these activities and ask to be put in situations that will push you to grow. This will build your confidence and will prepare you for the next step in your career. 



This article is an expanded (and lightly edited) version of Kellie’s appearance on our podcast for Customer Success leaders. If you haven’t listened to our show yet, be sure to check it out here






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