From The Editor | April 9, 2018

Being Successful At Customer Success

A conversation with Allison Pickens, CCO, Gainsight

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Customer Success is no buzzword — it’s become the mantra of every software company interested in measurable growth. Yet, if you ask two different software company leaders to define “customer success,” you’re likely to get two different responses. In order to clarify — and elevate — the conversation around Customer Success, we sat down with Allison Pickens, Chief Customer Officer, at Gainsight. We picked her brain on all-things-CS — from pitfalls and best practices to structuring a CS team and more. Here’s what she had to say.

As an industry-recognized thought leader on Customer Success, how should software companies define customer success?  

Pickens: We define Customer Success through a fun equation: CS = CO + CX. The left-hand side of the equation stands for the benefits of customer success to your company as a vendor: increased retention, expansion, and advocacy. The right-hand side shows the two things you have to generate in order to achieve those results: strong Customer Outcomes (CO) and strong Customer Experiences (CX). If you don’t generate both CO and CX, you won’t achieve the results you want. As an example, we can all think of a client who loved our team (had a terrific CX) but never achieved quantifiable ROI (CO) from our product, so they couldn’t justify the renewal to their procurement team. It’s also possible that a client has achieved value (CO), but we as the vendor made it challenging for them (poor CX), so that client declines to advocate on our behalf.

Note that we don’t define Customer Success purely as a function. Customer Success is everything your company does — across Product Management, Engineering, Sales, Marketing, Professional Services, Support, Finance, etc. — to generate strong outcomes and experiences for your clients. 

What is now considered table stakes to ensure customer success?  

Pickens: We’ve defined a Maturity Curve for Customer Success that includes 4 stages: (1) Reactive, (2) Insights & Actions, (3) Outcomes, and (4) Transformation. In the first stage, vendors are in fire-fighting mode, reacting to escalations from their clients. That’s a terrible mode to be in — both for clients and for employees. So most companies that value Customer Success are pushing hard to complete the Insights & Actions stage in which they gather all the data they track about customers into a 360-degree view. This allows them to take actions and make decisions based on the data. At this point, achieving the Insights & Actions stage has become table stakes. 

Most software companies are in the Outcomes stage. They’re aiming to be proactive in generating strong outcomes for their clients by launching internal initiatives focused on Success Planning, Tech Touch, Advocate Engagement, and others. We launched what we call a “Periodic Table of Customer Success Elements” that enumerates these crucial initiatives. 

And finally — the pinnacle of Customer Success is the Transformation stage, where you’re making Customer Success a company-wide imperative. I’ve seen a few companies achieve this stage, and it’s pretty magical. One of those companies is a fast-growing Brazilian SaaS company called Resultados Digitais that has implemented Customer Success best practices across many teams, including Professional Services, Partner Account Management, and others. 

What has changed on your Customer Success team most over the past few years, and why? To what do you attribute those changes?

Pickens: I joined Gainsight when we had about $1 million in revenue — about four years ago. A lot has changed since then. The most important change is that the Customer Success industry has grown up. Four years ago, not everyone agreed that we should use metrics to track our effectiveness in CS, or that systems were important. Today, that’s taken for granted. Customer Success has “crossed the chasm,” as Geoffrey Moore (who’s an advisor to Gainsight) likes to say.

For my team, the maturing of the CS industry means that we have an opportunity to gather many more success stories in the industry and share those stories with others.

How is your customer success team structured?

Pickens: In total we’re 140 people spread across a number of functions and locations. We have a VP of Client Outcomes, which is what we call our Customer Success Management team, since that team is focused on driving outcomes for our clients. We have a VP of Professional Services, who manages several functions, including Advisory Services, Education, Project Management, Solution Architects and Technical Architects, Data Science Services, Services Sales, and Services Operations. We have a Support department and also a Customer Engineering department, which builds out-of-the-box configurations on top of the Gainsight platform to meet standard business objectives that our clients typically have. We have a Customer Success Operations department, which administers our own instance of Gainsight, manages internal enablement, conducts analysis and reporting, and builds cross-functional processes. About 30% of my team is based in India, so I also have a Customer Success leader there who manages a cross-functional group.

In your role as CCO, what are your top focus areas, and why?

Pickens: I’m always looking to focus my time on the intersection of three areas: (1) What I’m great at, relative to others, (2) What I’m energized by, and (3) What our company needs. That intersection tends to include engaging our Customer Success community (through speaking events, blog posts, podcasts, and client meetings), sponsoring new internal innovations (such as the cross-functional initiative that launched the Periodic Table of CS Elements), and ensuring that my team is set up for success (including designing my organizational structure, managing through change, and providing transparency).

As CCO, what Gainsight executives do you collaborate with most and why?

Pickens: I think the CCO role may be one of the most cross-functional roles at a company. You have to collaborate with every department. I work with our Sales leader on services sales strategy; with our Product and Engineering leaders on ensuring strong processes for discussing client feedback between our teams; with our Chief People Officer on teammate success (happy teammates lead to happy clients); with our Marketing leader on our strategy for communicating our thought leadership to the industry; and with our CFO on forecasting and budgeting. So my calendar is pretty full.

What are some best practices for software companies looking to improve CS?

Pickens: Take a look at the Periodic Table of Customer Success Elements. It represents all the best practices we’ve accumulated over the years by speaking with other CS leaders and incubating innovations within our own team. We did a benchmarking analysis across 100 Customer Success leaders that showed that if you build out these Elements and progress through the 4 stages of the Customer Success Maturity Curve, your Gross Retention on average improves from 80% to 93%, and your Net Retention on average improves from 92% to 125%. So there’s data that supports the idea that these are truly “best” practices.

What are some common pitfalls software companies should avoid regarding CS, and how can they go about avoiding them?

Pickens: The biggest mistake that software companies make is not to invest enough in Customer Success. But fortunately, at this point in the industry’s maturation, I see this mistake happening less and less frequently. We’re on the right path.


Allison PickensAllison Pickens is a recognized thought leader in Customer Success and scaling teams during hyper growth. As the Chief Customer Officer at the leading Customer Success software company, Gainsight, Allison is responsible for managing all post-sales functions. She is a national speaker and blogger, advisor to prominent companies, and was named one of the top 50 people in the sales and business development industry. She started her career in management consulting for Fortune 500 companies while at Boston Consulting Group and later worked in private equity investing at Bain Capital. At both companies, she helped organizations drive change and scale effectively. She has a passion for helping companies create and lead exceptional Customer Success programs and teams. Allison has a BA in Ethics, Politics, and Economics from Yale University, as well as an MBA in Entrepreneurship from Stanford University.