Nov 29, 2022

Read Time 4 min

Three lessons I’ve learned building a Customer Success team from different backgrounds


This is a guest article by Michael Su, senior consultant of Customer Success, The Success League.

Customer Success is still a young field and a new concept for many companies. When I ventured out to build my first Customer Success department at a tech software company, my leadership team thought I was nuts.

At the time, I was a sales engineer, and my job was to close deals and move on to the next prospect. I was very successful in my work. However, I found there were two flaws in our customer management process.

First, it felt like I was abandoning my customers and punting them over to our professional services team once they signed a contract. I know customers shared my feelings because some of them flat-out told me so.

Second, we were leaving expansion opportunities on the table. We had a “land and expand” model, however, no one was actively working on expanding our customers’ deployments. Sometimes we’d get lucky, and the customer would come to us to ask for more products or services. But that did not happen very often.

There were also a number of customers who turned us into shelfware or essentially churned. This made it difficult to find referenceable customers to speak at events or provide case studies.

To fill the gaps in our service model, I went above and beyond what I was asked to do in my role: I continued working with existing customers. After getting slapped on the wrist a few times for my after-sales support, I knew things had to change.

Selling leadership on the concept of Customer Success

I approached the leadership team about my idea of creating a department designed specifically to address customer experience, adoption, renewal, expansion, and advocacy. Alas, they did not understand my pitch. We had presales, and we had post-sales. To them, there was no gap. It took a lot of data and a lot of selling to get them on board with this crazy new concept.

Like many early-stage Customer Success teams, I was working with limited resources and did not have any headcount to hire new talent. However, I was allowed to re-recruit current employees for the team. I talked to folks from various departments in hopes of seeking out that customer-centric mindset. I pulled the best of the best from support, professional services, and even sales! I was like Danny Ocean and ended up with what I truly believe was the best team ever (although I didn’t have 11 people…yet).

Diagnosing my new team’s problems

Everything was going well. Deals were coming in. Customers were happy. It was all coming together beautifully. We had the talent. We had the skill sets. We managed to power through our ramp-up period and proved to ourselves and the company that Customer Success was a crucial part of driving revenue retention and growth.

But we were missing alignment and strategy. The CSMs had a list of customers they were expected to renew and expand. However, they didn’t have a clear path or instructions on how to achieve those objectives. We were the poster child of “winging it.”  While the team was working harder, I, as their leader, was not working smarter.

Everyone was doing what they did best individually. The folks who came from support and professional services did a stellar job at answering technical questions or troubleshooting issues. The folks who came from sales were amazing at asking great questions to demonstrate the value we provided. But we’d need to get clear on team expectations to reach our full potential and scale.

Folks were getting pulled left and right into other processes outside of their responsibilities or book of business. I believe most CSMs have it ingrained in their DNA to say “yes” and lend a hand even when it may not make the most sense. Because of this natural inclination to help and our team’s undefined boundaries, CSMs took on the role of subject matter experts for their peers. This additional designation distracted them from their own work and product training.

Even though no one on the team was new to the company, they were new to the role. They’d transitioned from their previous job into something brand new and were expected to figure it out along the way. As a small team with a startup mentality, we were building the car while driving it. We got far, but eventually, we hit our limit.

Lessons learned from building a Customer Success team from the ground up

Fast-forward 10 years. I now build Customer Success teams from scratch for a living. I’ve worked with an array of companies from large enterprises to tech startups that just got their first paying customer. In all cases, I’ve needed to get creative when building my team, which almost always included internal recruiting. I’ve learned a few lessons and picked up some tricks along the way. I know what to do and what to avoid.

Here are my top three pieces of advice.

  • Get everyone on the same page. I’ve learned that there are many ways to answer the same question. To build customer trust, coach your team to be consistent in how they respond to and communicate with customers on all subjects. While your CSMs don’t need to read from a script, their underlying message should align with the team and the company’s goals. Don’t shy away from encouraging CSMs to lean into their uniqueness.
  • Align your team members’ goals with desired behaviors and outcomes. As humans, we naturally focus on what we are measured on, and more importantly, what we are compensated for. A variable compensation plan is an effective way to motivate your team to achieve their individual goals. But compensation plans are too large and complex of a topic to cover in a short blog. In fact, we teach an entire class on how to set team goals and structure compensation plans.
  • Extend Customer Success training beyond product and technical knowledge. As a Customer Success leader, you’ll have team members who excel in specific areas of expertise. Using these standout employees as on-call SMEs for your team and other departments is not scalable. Instead, develop competence across your team with structured training to build skills in interpersonal dynamics, negotiating tactics, and more. Ask yourself: are your CSMs empowered to communicate at the executive level? Are they prepared to conduct executive business reviews? Do they know the art of persuasion and how to ask great questions?

Attract Customer Success talent with compensation plans

As mentioned above, you’ll need to start thinking about compensation plans when you build the blueprint for your new Customer Success team. There are several different models to consider. Among them is the variable compensation model. It’s a popular option, and for good reason. Learn the benefits of variable pay, as well as how to design and transition to a performance-based model in our primer: “Craft Customer Success compensation plans that attract top tier talent.”


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