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Krista Anderson-Copperman is decidedly one of the most important pioneers in the Customer Success space. 20 years ago she joined Salesforce to play a core role in growing the Customer Success function (that was back when Salesforce coined the term “Customer Success” and built the largest CS function of that time).
She then went on to help Okta grow from $20M to $580M in ARR and through their IPO as their Chief Customer Officer. And now, she’s an advisor and board member to several prominent companies including Gainsight, Drift, Attentive, BetterCloud, and Benchling.
In case it wasn’t obvious, Krista has “been there”. She’s seen success and failure and has advised other CCOs experiencing the same.
In this interview, Krista explains how Customer Success has evolved and predicts where the role of the Chief Customer Officer is heading.
CHRIS: The powerful Customer Success function of the past was around on-prem and Professional Services. What did a good Account Manager look like during that time, and what does a good Account Manager look like now?
KRISTA: Back then the big difference was that when you sold someone software they had to install it on a box, physically in their building, and you had very little insight inside the customer experience outside of what they told you. But honestly, it didn't matter — they had already paid for it. You could sell it, set it up with professional services, and then walk away with very little account management. And unless a customer needed an upgrade, something was broken or you wanted to sell them a new piece of software, the customer experience didn’t matter because you already collected the money.
That’s overly simplistic, but from a SaaS perspective when we first started selling software as a service on the cloud at Salesforce, we knew it was different… But we didn't quite grasp how different it would be until we started losing renewals.
It was then that we realized we couldn’t just sell people on new products. We also had to sell people on the cloud itself: how to do business in the cloud, what the benefits were in terms of maintenance, security, productivity, cost as well as how to continuously take advantage of the constant flow of new features we were releasing. The CSM was born out of the need to regularly educate customers on these topics and, as you know, has evolved significantly from this simple definition. The best CSM’s today are product and people experts with varying levels of technical depth depending on the products they are supporting. They understand the different roles within accounts — champions, decision-makers, and end-users — and actively work to maintain and grow their company’s footprint in their accounts by understanding current and future challenges their customers are facing.
CHRIS: That was a great take on the past. I’d like to share Nuffsaid’s vision for the future and see if you agree or disagree with it.
One trend we’ve noticed is that investors of all types are now looking at retention rate as a key factor in the valuation and health of a company — which means that companies are now demanding a more powerful Chief Customer Officer. This shift in focus will also mean more companies will organize themselves around the success of the customer, and CCOs will not just be responsible for running a better CS department, but also for arming the company with the customer data it needs to drive better decisions.
What’s your reaction to that?
KRISTA: I 100% agree. The best CCO's are the ones who act as the glue across the organization by providing insights to drive growth and retention... But depending on a company’s stage, that can mean really different things. It can mean helping identify what the right product-market fit is for an earlier stage company. For later-stage companies, it's more about partnering with Product, Engineering, Sales, and Marketing to deeply understand and act upon customer needs to retain and grow their account base
They do that by training their teams on a couple of key deliverables. The first is developing relationships with both buyers and champions at their customers, so they can deeply understand the problems customers are facing and then partner with those customer execs to solve the problems. Sometimes with their own technology and sometimes with other tech. But the point is, the expectation is to seek to understand, partner, explore deeply, and solve the customer's issues. And to do that, you have to have those relationships inside your company across Product, Engineering, etcetera. You're the glue.
The bonus is, when you start to act that way where c-level execs at your customer start to think of you as a problem solver and ally, this almost always equates to greater wallet share and higher retention.
The second key piece around insights and being the glue is data. Every CCO should be measuring customer sentiment and every CCO should have a customer health or adoption metric. But the best CCO’s deeply analyze and act upon retention/churn, growth, and competitive data to increase win rates and grow their accounts. They're telling Product and Marketing where they are getting stuck competitively at the time of renewal and are providing suggestions on how to tweak the product or messaging to avoid such situations in the future. They're sharing insights with Product and Engineering around functionality that yields higher renewal rates and functionality that creates churn. What they aren’t doing is giving Product never-ending lists of feature requests — instead they're working cross-functionally to provide a prioritized list that will reduce churn and open up new ARR.
CHRIS: So, in an earlier stage company, the CCO’s job is primarily product-market fit. As the company scales, it shifts to more nuanced, product use cases and most importantly, future problems that need to be solved. And no matter what size the company is, the CCO needs to have a really good understanding of the competitive landscape and the needs of the product to fight against competitors, create moats, etc.
KRISTA: Yes - understanding, analyzing, and providing suggestions on how to avoid competitive pitfalls during renewal is critical for a CCO. But they also play a more subtle and unique role in having early access to competitive intel. There is a playbook for going head-to-head with a competitor for a new logo. You enable all GTM teams on that playbook, but in renewals, unique scenarios can unfold and CCO’s need to capitalize on them.
One scenario that everyone should be taking advantage of is when you are going into a renewal where your tech and relationships are rock solid and a competitor is trying to get in the door. Your champion will tell you if a competitor is there, so ask! And then ask for details. And keep track of those details. You will start to see trends emerge. Likely in how your competitor is positioning themselves in existing accounts vs. new logos but also around where they are headed. Competitors are forced to give more information when they are trying to win an existing logo from you, than when you are both competing for that logo as a new customer. Use that to your advantage.
All of that said, I’ll also note that, now that I’m working with companies as a board member and advisor, I spend about half of my working days talking to CEOs, CCOs, and COOs of high-growth, enterprise, B2B startups, usually anywhere from 40M-250M in revenue. And one noticeable challenge in enterprise software that has become clear to me is the need for more talent in the CCO role.
The CEOs I speak with are dying to meet people who can own the full scope that a CCO must own — from partners all the way through to upsells and renewals. There are very few people who have owned that large of a remit, can do it well at scale, and with the topics we have discussed today in mind, so there is abundant opportunity for people to build their careers in this area.
CHRIS: You talked about how CEOs want a more powerful CCO—someone who can just own that whole post-sale function, but there's a gap, right? Most VPs of CS or CCOs have grown up through a CSM track and they're often known as the nice person in the room. They haven't been trained in business in the same way that the CFO or the CPO or the CRO has. How do we close that gap?
KRISTA: One of the most impressive up-and-coming CCOs I advise today comes from a finance background, so my first piece of advice for anyone is to understand the financials of your company. How does your company generate revenue? Where does your company see future growth in products and customer segments? What financial metrics are important to your company from an overall performance perspective, not just the balance sheet? There is a shortlist of SaaS metrics that high-growth companies typically focus on. Know them, know which ones are important to your company performance and what you are doing to impact each one of them.
I start there because the biggest disconnect I see is exactly what you said. The people in these functions often don’t understand the fundamentals of how the company is run.
After that, the advice that I always give people early in their career and, in particular, in any of these post-sales functions is to go broad, don't go up. If you're in Professional Services, go take a lateral step to do something in the CSM world or in Voice of the Customer or in Sales. Whatever function you're in today, take a lateral step so you can better understand the full customer experience, not just one piece of it.
The Chief Customer Officers of today usually own anywhere between 4-6 functions: Professional Services, Support, CSMs, Education, Renewals, and Voice of the Customer (VOC). But when hiring for a CCO at a high-growth enterprise-focused company, three of those categories are more important to have expertise in.
The biggest CCO hiring mistakes happen when a CCO comes in without deep knowledge of these three areas. Professional Services and CSM leaders often have deep philosophical differences on how to make customers successful and someone who has run CSM’s but not renewals doesn’t always understand the commercials of the business. Imbalance or a heavier focus in any of those three areas relative to the others can create real customer experience issues.
Nuffsaid’s content, Gainsight’s content, and others are doing a good job of helping people understand what to look for, but companies need to be really conscious about developing people broadly across these practices versus continuing to develop deep expertise in a single area.
CHRIS: Let's take a peek at your vision for the next five years for Customer Success or CS leadership. Where is it going and what gaps do we need to close to get there?
KRISTA: We addressed a bit of this earlier so beyond continuing to invest in the function itself as well as the future leaders of the function, I think companies need to do a better job of educating the workforce on the ‘whole health’ of the company and the critical role CS plays in this. Strategic planning frameworks like OKR’s and V2MOM’s serve an important function in that they provide everyone in the company insight into the priorities and the metrics leaders are using to hold each other accountable to those priorities. This is so important for Customer Success as we are still very much so in the education phase of helping individual contributors and leaders across organizations understand the vital role good CS teams play in company health and success. And going back to our discussion about the best CCO’s being the glue, getting the whole company to understand that CS is not just about CSM’s or Pro serve doing their job — its about about coming together cross functionally to maintain and grow the customer base is critical.
But again, the problem is leadership. CEOs are recognizing the need for these really strong CCOs who can zoom out, who can analyze product and competitive dynamics, and who can understand the customer at the C-level and what's going on in their business. But there's nobody there to do it, so all the functions get put under a CRO.
The problem with this model is the majority of CROs have spent zero time in any of the CS functions as a leader or individual contributor. They know very little about what these functions should look like or how they should operate so they fall back on their sales experience and you end up with these well intentioned but wacky and wildly expensive models where companies are double and triple comping multiple teams on renewals and upsells. Not to mention, creating a mess of the customer experience.
So keep it simple. Keep your sales team focused on new logos and upsell/cross sells. Keep your CS teams focused on adoption and retention and do everything you can to develop those leaders into a CCO. That doesn’t always work, so recognize when the time is right to hire a CCO with a meaningful scope and make them a peer to your CRO. In addition to ensuring the right level of leadership and focus, this structure sends a very powerful message to your customers, sales and product teams. New business is not king — existing customers and new logos are of equal or greater importance to our company. That is the future of CS because that is the reality.
KRISTA: CCOs of the future will be experts in the practice areas I mentioned earlier, but they will also have very strong cross-functional, operational and execution-oriented minds. They will have a deep understanding of the economics of the business and the power of data in their role to drive customer retention and growth. They will have access to tech and data we only dream about today — this will definitely make their jobs easier but will also go a long way in developing future leaders in this space. Finally, they will have the people skills to connect with customers and peers to be the glue across an organization in the way we have discussed.
So think about your best CSM leader, then combine that person with your best sales leader, add equal parts operations leadership, data leadership, and product strategy and there you have it!
PLANNING
Executive Playbook: Planning and Budgeting in Customer Success
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STRATEGY
The Principles of a Remarkable Customer Experience
Xero’s CCO, Rachael Powell, leads the entire customer experience — including CS, Support, Education, Marketing, Sales, and more. She’s effectively managed such a massive scope of responsibility by instilling a core principle: the “inside-out” approach to improving the customer experience. Here, she breaks down how that philosophy works.
COMMUNICATION
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Adam Keys cuts straight to the point: “Never message someone on your team, ‘let’s talk when you get a minute’. That’s void of information and scary as heck!” This is a quick read with a good reminder for any manager. Avoid spookiness by giving your team context.
PLAYBOOKS
Is My Product a Must Have or Nice to Have?
We teamed up with Kristi Faltorusso (the Queen of Playbooks, in our opinion) to create a blueprint for figuring out how customers perceive your product and what playbooks to fire off if your product is deemed a “nice to have”.
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