4 Tactics to Building and Managing Customer Success with Allison Pickens

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Allison Pickens

One of the things I like most when talking to people about their career journeys is understanding how the skills they’ve learned along the way help them succeed in their current leadership role. Sometimes, my guests are surprised at how their trajectory, even if it seems nonlinear, has played a critical part in their professional development. In my conversation with Allison Pickens, the Chief Operating Officer at Gainsight, a customer success SaaS organization, you’ll hear how her background in strategy and management consulting, and investment banking, allowed her to thrive in her current position.

Not only is she making serious strides as the company’s COO, but her role is also inclusive of CCO responsibilities. Listen, as Allison shares tactics that have helped her excel at managing Gainsight’s cross-functional work and strengthening their customer success initiatives.



1. Define Roles and Expectations

Upon joining Gainsight, Allison tells us that the company had no revenue and lacked internal consistency. She explains that there were a lot of different people in their roles who had unclear charters, which I’m sure, is an observation many leaders notice in start-ups.

It wasn’t especially clear what each person’s role was and what they could depend on each other to deliver. According to Allison, it was important for her to start defining this portion of work, and she shares some of the steps she took to get organized during the process:

  • Define the charter for every function in the organization, inclusive of what metrics the function is responsible for.
  • Determine what activities the specific function manages so people know exactly what they should be doing when they get to work in the morning.
  • Include dependencies that involve other other functions and be sure that’s documented as well. Ex: if CSMs have expectations from the professional services team, that responsibility needs to be included.

The charter creation process helped Allison and Gainsight create an environment with more cross-functional gelling and trust. Additionally, she shares that it wasn’t simply just the exercise of writing the charter that helped improve the cross-functional relationships, there were a number of off-site bonding exercises, one-on-one conversations, and manager led discussions that created this outcome.

2. Build Customer Success Internally and Externally

Allison shares that she was able to really start implementing CX when she created a Customer Engineering Team (CET). With this team, she was able to create more automation processes in order to improve the customer experience, allowing for more consistency and reliability. For instance, when it came to onboarding, she noticed the professional services team would reinvent the wheel for each new client, which didn’t create a consistent, predictable client experience that they were aiming for.

I love when Allison mentions that she noticed Gainsight didn’t have enough prescriptive best practices for clients to achieve very particular goals that they had, such as renewal management, life cycle management, and advocacy engagement. Due to this lack in consistency, she wanted the CET to figure out scalable ways that they could easily help their internal team members advise clients on how to get these specific outcomes.

Allison worked with CET to create a few solutions to these problems:

  • They standardized the way data flows into Gainsight. CET created a standardized onboarding process which allowed people to create a 360-degree view of the client in a consistent, predictable way.
  • CET created a deployment application, which allowed team members to automatically configure certain best practice recommendation that would align with the clients’ needs, based on a  predetermined set of 16 objectives that CET saw as being common in their client base.
  • Created an internal application that allows CET members to monitor clients’ performance challenges and any improperly built configurations, which is a helpful preventative measure. If a Gainsight admin is administering the product in a way that doesn’t best serve the client, Allison’s team will know about it and be able to intervene right away to advise on how to best do so.

3. Unite Leaders Under A Shared Vision and Performance Metrics

A challenging facet of the COO and CCO is uniting the rest of the executive team under one vision. Allison believes this task is incumbent on the CCO to figure out, believing that the most successful CCOs are very effective cross-functionally. At the same time, she doesn’t think that the company should be solely reliant on the CCO to create an amazing client experience and client outcomes—everyone also has their part to play in ensuring CX success.



Allison shares that she wanted to overcome the challenge of customer success being viewed as a vague function—one that’s reasonably valuable, but maybe not as valuable as the other functions whose value was not able to be measured. Allison saw this as an opportunity to unite leaders under a metrics-driven cause.

4. Don’t Be Afraid Innovate

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As COO, Allison started building out a business operation function inclusive of a new initiative called Elements.

Elements is essentially a periodic table of customer success elements with a framework that her team released that could progress along a customer success maturity curve across functions.

Allison shares that Elements is inclusive of 16 different objectives that companies tend to have with customer success across their company. This framework was initially incubated within her department because she wanted to be sure they could consistently deliver against certain outcomes that clients were expecting to achieve.

According to Allison, this framework helps them consistently deliver against specific outcomes that clients were expecting to achieve.

What Do You Know Now That You Wish You Knew Then?

Allison says: 

“Be braver, and it’s interesting because I think a lot of folks think of me as being a brave person. I like to think of myself as a brave person, but I’m not always brave enough. When you know that there is a right thing that you have to do, the right decision that you have to make, do it as soon as you know, and not a minute longer. So, make that decision, whether it’s about promoting a team member, replacing a team member, making that organizational change, or having that difficult cross-functional conversation. Don’t wait. Just do it right then, because your gut’s telling you it’s the right thing.”



About Allison Pickens

Allison Pickens is an internationally known thought leader on Customer Success and scaling teams during hyper growth. As Gainsight’s Chief Operating Officer, Allison manages corporate strategic planning, corporate development, and operational responsibilities that are critical to the company and its customers’ success.

Allison was named one of the top 50 people in the sales and business development industry, is an international speaker and blogger, and the host of The Customer Success Podcast. She also serves as a Board Director at SaaS companies RainforestQA and eCompliance and is a Growth Operating Partner at Bessemer Venture Partners. She has a passion for helping companies create exceptional Customer Success initiatives across their company. Allison has a BA in Ethics, Politics, and Economics from Yale University, as well as an MBA from Stanford University.

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