Issue #80: Breaking into CS Ops and How to Grow From There, with Gainsight’s Seth Wylie

Seth Wylie kicked off his journey in CS Ops over 5 years ago at InsightSquared. During his time there he became a Gainsight “super fan” administrator, so when the opportunity to work at Gainsight in CS Ops opened, he jumped on it. At Gainsight, Seth has worn many hats: he’s been an individual contributor in CS Ops, the manager of their growing CS Ops team, and recently took up the opportunity of supporting and connecting the CS Ops Admin Community too.

We recently sat down with Seth, a self-proclaimed “full-flavor CS Ops geek”, to learn about his career path, how others can break into a CS Ops role, and the skills necessary to grow a career from there. 

If you’d rather listen than read, head over to the Nuffsaid podcast to listen to Seth’s full interview. 

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Breaking into CS Ops from another role

A lot of people look at CS Ops as a hard role to get into. It doesn’t help that CS Ops job postings often require 5+ years experience. But also, it generally isn’t a very well-known choice for a career path. So I do my best to shed light for others on how to get into CS Ops and share what types of skill sets are needed in CS Ops.

One path you can take to break into CS Ops is to transition from a different role within a company you already work for. This is how I got into CS Ops. At InsightSquared, my VP of CS knew that we needed to make our CS team more scalable. There are a number of different levers you can pull to do that, but the lever he pulled was by purchasing software. We bought Gainsight and he needed someone to help with the technical and strategic challenges of implementing that software. And at the time, I was leading the support, onboarding, and technical account management team, so I had experience in leadership, systems, and data, plus lots of customer-facing experience. I was teed up well to take on that new role.

Others might transition into CS Ops by first taking an opportunity to lead a project that’s usually part of the CS Ops cornucopia. Then that small project will lead to another small project, which ultimately leads to a bigger project.  

A final path I see some people take: moving from another Ops role into a CS Ops role. If you have experience in Ops whether it be Sales Ops, Dev Ops, etc. you can absolutely make a move into CS Op without first having been a tactician implementing CS-specific programs. I say that confidently because I know people who have been Salesforce administrators, but jumped over to become Gainsight administrators. People who have done analysis or different kinds of marketing have jumped directly into doing CS analysis or customer marketing, and have done really well.

With that said, there will be a responsibility that falls on you to level up your knowledge of the discipline of Customer Success. There are some great resources out there to do so including Gainsight's Pulse+ to rapidly level up your CS knowledge. You want to be able to have those conversations not just in a purely operational way, but in a way where you're thoughtful about the context of the subject matter.

Breaking into CS Ops as an early-stage hire

One question I get is whether or not someone can jump into a CS Ops role for the first time as a new employee instead of making the move at a company they already work for. Of course, I shared my experience about getting into the role directly, and there are a lot of folks who do make the gradual transition. But the direct hop into CS Ops, whether at your company or at a different company is absolutely something people do. The thing that makes it tricky is that instead of being able to figure out what you can add to CS Ops at your organization as you go, you need to understand enough about yourself in order to tell the story about how you can add value at the start. 

Let me share the four major areas where someone can enter CS Ops and add value immediately.

#1 Systems

Maybe you have systems administration experience, or if you're customer-facing on a very technical product, then you can make the case for stepping into a systems administrator role on a CS Ops team. You can also certainly build that up through certification programs. Gainsight offers certifications and Salesforce has Trailhead as another option. There are a lot of folks who are actively learning, so that they can bring a CS skill set from their current role into a more operational place. 

#2 Data and analytics

Again, looking back through your experience, you might have a lot of experience with spreadsheets, or you might have dabbled in SQL. If you have a strong background in data and analytics, you could be of great help to a CS Ops team. 

#3 Enablement 

Most CSMs know what it’s like to be given very few tools or instructions to do their job in a clear way. Oftentimes, CSMs are basically told to ‘figure it out.’ That's the way that a lot of CS teams operate, but of course, a well-enabled CS team is going to be much more effective.

So if you step into an enablement role, you need to be able to tell the story to a potential employer about how you are good at figuring out what people need to know, helping them to get better at certain skill sets, and understanding the best way to present information to others. 

#4 Retention marketing or expansion marketing

If you have experience in content writing, or working with systems like Marketo or Eloqua, you may be able to step into a CS Ops team and build programs to send automated emails to customers, build in-app notifications, or facilitate customer workshops. All those could be part of a 1:many role.

Overall, if you’re new to CS Ops, you need to be able to tell a story about how you have the skills to suit what a CS Ops team is looking for. The piece that makes this tricky is that you are potentially joining an organization where that CS leader has never had a CS Ops team before. They're likely doing their best to read content like this to learn from the best in the industry to describe what they're looking for. But you are one of two people in that interview conversation, or that exploratory networking conversation. So if you can describe what an effective CS Ops team does and show how you can contribute to that vision, then that’s compelling to a CS leader who has some clear needs, but has never seen it lived out before. 

The most valuable skills in CS Ops

1) Being a thought partner to the CS leader. One skill set I came to appreciate having as a CS Ops professional is the ability to sit down with a CS leader, pull up a whiteboard together, and talk through strategy. CS leaders need a thought partner who can help turn their vague pain points and goals into specific plans (and push back or poke holes when appropriate). I’m good at taking subjective information from a number of places and helping to organize it into a thoughtful plan, and I’ve found that skill to be common with other CS Ops professionals I admire as well.  

2) Being a systems thinker. I'm very much a systems thinker. For example, if someone who has a customer relationship challenge goes to their colleague, most people (and we need these people) are able to throw themselves at solving that particular customer situation. But I'm the kind of person that looks at that situation and thinks about how a problem is a symptom of a larger issue. I might think about how we need to improve our CSM training, the way we structure our EBRs, or whatever it is. I am fully oriented towards “how do we solve the system?” That sort of thinking is a hallmark of someone who does really well in CS Ops. 

3) Being comfortable with doing things for the first time. Solving problems that haven't been solved before. Learning software that hasn't been used before. Using existing software in a way that hasn't been done before. That discomfort of doing something for the first time is part and parcel with pushing your CS practice forward, which is ultimately the responsibility of a CS Ops person. You have to be open to what you might learn along the way. 

Moving from IC to manager in CS Ops

When I first stepped into CS Ops, I was a tactician. One of the first things that we did, for example, was to build out our list of playbooks in Gainsight. That was basically an interview process for me. I had to sit down with our CS manager and VP of CS and decide on what would be in our renewal playbook or our new customer playbook. Then I executed on setting those playbooks up in the system.

Whether it be a systems responsibility (like in my case), an analytics responsibility, an enablement responsibility, or customer marketing responsibility, it won't take too long for leadership, your peers, and other teams to stop asking you to execute, and start asking for your advice on how to execute. And not too long after that, people will stop asking you how to execute and start asking you what to execute on.

Pretend someone asks you, “We need to improve our new customer onboarding process—what should that look like to improve it?” Note that they're not offering you a suggested solution. They're asking you to go off and figure that out. Eventually, you’ll grow to a point where CS leaders will ask, “What are we gonna improve next quarter? Can you help me as the head of CS Ops, narrow down what the biggest areas for improvement should be on our CS team?”

At that point, you’ll understand the mechanics of your business, you’ll have the relationships with teams you need to work with, you’ll have a sense of the corporate strategy, and you’ll understand the pain points that the CS team experiences. Armed with that strategic vision, you’ll be in a great position to help your CS leader make big decisions and plan for the future.

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