Key challenges of managing a team of CSMs

Being a customer success manager means that you’re willing to face new challenges and embrace the change on a daily basis. The role implies that you have customer-facing experience and are already a professional. But the most challenging thing is managing a team of CSMs.

What problems does a manager of a CSM team have to solve, what are the specifics of this work, and what skills are required to be good at this role? Today, we’re speaking with Matt Williams, manager of our CSM team in San Diego, who has recently celebrated his fifth Wrike-a-versary.

— How long have you been working for Wrike to date?

— My five-year anniversary was just two days ago. Five years. I opened up the San Diego office. I think that’s probably my biggest claim to fame here; I started in our Mountain View office, then opened up the San Diego office, and then moved to four different office locations in San Diego. So I’ve been around the block a few times during my time at Wrike.

— Prior to becoming a manager of the CSM team, you were a CSM yourself. How important is it, in your opinion, to get that experience personally before moving into the leadership role?

— I’ll try and answer that in a couple of different ways. My journey here at Wrike started as a junior CSM. So I was hired at the bottom of the totem pole, so to speak. I continually worked my way up. I do think that that experience was incredibly valuable for me, particularly in being able to coach my team through difficult situations they would get into with their customers. Is this experience necessary to be a good manager? Is this experience something of a prerequisite? I don’t think that you have to be a CSM at that particular company before moving into a leadership role, but I do think you need to be a CSM at some point in your career to be able to leverage that experience in order to coach your team.

I would say that continuing to be customer-facing is really important in this role. Otherwise, as a leader, it’s really easy to get lost in the world of leadership. In managing a team there’s a lot of logistics, planning, business growth, and business development that needs to happen, and you’re responsible for all of that as a leader. And it’s really easy just to get focused on that stuff and lose track of what we’re really here to do, which is to provide value in order to make our customers incredibly successful with Wrike.

— Did you have any people management experience before Wrike? If yes, how relevant do you think it was to the things you’re doing today?

Matt: That’s a great question. The short answer to your question is no. In a business capacity, was I a leader before Wrike? No. But, did I have leadership experience? Yes. And it came through a lot of different things that I did. I think a lot of folks have similar experiences and they just look over it, and think that they’ve never been a leader. But some of these things that I’ve done in my childhood and early adult life were incredibly instrumental to me being an effective and successful leader.

One great example was when I managed a bunch of ten-year-old kids as a golf camp counselor. Figuring out how to get a bunch of young children to play nicely together, not injure themselves with a bunch of golf clubs, and to successfully complete objectives that we want them to do — it’s very similar to what we do in leadership. Even though I was still just a teenager, (this experience) taught me some of the key fundamentals of leadership, like how to direct a group, how to get people motivated, and how to incentivize someone to do the actions that you wanted. That was really important.

Beyond that, I was also the president and treasurer of my fraternity in college. That was a direct leadership experience that I would translate quite closely to what I do at Wrike. We had 100 members of our fraternity. And you had to manage a budget of thousands of dollars for them, get everyone to come to meetings, participate in events, plan events, pay dues, and train new members. We had to get everyone certified and go through different programs. All of that was very similar to what we do here at Wrike. So, all of those things I think kind of naturally built up my leadership acumen and my leadership skills.

As I got to Wrike I had all those fundamentals that were in my back pocket. And as our company was beginning to grow, and as our CS team was beginning to grow, we needed a team lead in San Diego. I just naturally became the team leader because I had all those skills. I didn’t go apply and fight for that position. I was the first person to open up the San Diego office. And people I think looked at me as a figurehead there. I just continued to lead and cultivate the group. I basically filled the need for the business and became a leader out of that, from those skill sets I had previously built. So did I think that my previous experience was a formal leadership experience? No. But did I have leadership experience? I think I had a lot of it.

— What, in your opinion, are key differences between managing a CSM team versus managing a team of account managers, sales representatives — so, other customer-facing teams?

— So, I would say, between sales and CS… One of the biggest things about sales is that salespeople have quotas. You have very strict performance criteria and everyone is judged on a monthly, quarterly, annual basis. Beyond that deal, cycles are quicker than CS touchpoints — in sales your customer interaction points are happening on a very quick turnaround. Your actions (in sales) have a direct impact on that customer, on whether they’re going to purchase or not.

That really varies from customer success, where most of the actions that we’re taking are happening six months in advance of any outcome we’re hoping to get. And hopefully, those outcomes are going to get (the customer) in the right place where they are going to see a lot of value from our tool and the services that we’re providing. All of that needs to come together in order for (the customer) to renew down the road. A lot of that necessary CS work can’t happen three weeks, a month, six weeks before that renewal happens. Because it’s too late. The client will already say, “Hey, we’re not getting value here, I’m going to take this time and figure out a new tool that I can use instead.” So, our work is very forward-thinking.

In today’s modern world, everyone thrives off of instant gratification, and on the CS side, there’s so little instant gratification for all the work that you do with your client. Managing CSMs is all about keeping your team motivated, keeping them focused on the right accounts to be working on, the right actions to be taken with those accounts, and beyond that, making sure that everyone feels they’re getting recognized when that positive result does happen six months down the road. That’s really important — that CS leaders — need to make sure that their team feels recognized and empowered and that the work that they’re doing is making a difference even though it’s not happening right then and there.

— Does the fact that you’re now managing other customer success managers imply that you no longer have your own book of business? Or was it like that from the very beginning of you working in the new role that there was a certain transition period when you initially had a certain book of business, then it became smaller and then you completely transitioned to just people management?

— This question is very much related to my experience here at Wrike. But yes, when I first started (at Wrike) — like I mentioned — I didn’t ask to be a leader. I just stepped into that role and became a de facto leader. So, back in 2016 when I was first working in San Diego I had a full book. I had over 300 accounts that were like, top-tier enterprise clients. And on top of that, I was basically managing four other people. So during that time, I was working 70-hour weeks. My friends thought that I was going to quit, they all thought that I was overworking myself, that I was going to burn out, and that I wasn’t doing anything good for myself trying to do two jobs at once.

But at the end of the day, my focus was just to do what was right for the customer, and that was enabling my team. I needed to multiply my efforts. The struggle for me was trying to balance that between having a full book and managing a team. So, that was a crazy experience, because my schedule was nuts… You had to book me three weeks out. I was constantly traveling, I was doing my one-on-ones with my team from airports, and all kinds of crazy stuff. I was taking red eyes to New York and meeting with the client that day and flying right back. Would I recommend that to anyone? Absolutely not.

I think that it’s critically important for leaders to understand that you don’t actually need to be assigned to a particular account in order to make a big impact with that customer. Giving that hands-on relationship helps you as a leader stay involved; it keeps you on the front lines understanding directly what’s happening with your customer base but also makes your customers feel that they’re, you know, a VIP. And if we’re determining them to be VIP, then I feel that it’s my job as a leader to make them feel that they are truly important to our company and to our business.

— So, how do you measure the efficiency of your customer success managers and what are the key metrics? Especially from the perspective of what you mentioned earlier when the results are not visible immediately.

— It’s another good question. Here’s a thing. I’ll touch on this from a couple of different perspectives, first from the Wrike perspective and then from the general CS lens on how the industry takes on this topic. At Wrike, we really measure the effectiveness of our CSMs on multiple different criteria. We’re held accountable for renewal metrics, specifically gross retention and net retention — how many renewals are we bringing in, how much of our team’s book is renewing on a quarterly basis, and how much of that book is expanding.

Those are the numbers the board is looking at, and those are kind of the objective numbers our C-levels are looking at to see the performance of our organization as a whole. I don’t necessarily judge a particular CSM’s performance on whether they’re hitting their number quarter after quarter, or if they have a bad quarter — as sometimes in sales — put them on some sort of performance improvement plan. We don’t do any of that. What I try to measure the effectiveness of my CSMs are: how well are you managing your book of business, how well are you dealing with conflict situations, are you escalating accounts at the right time, and are you creating executive relationships? Are you taking your accounts that were at risk and are you taking them from that at-risk state to a steady-state? Those are the things that I really hone in on and how many times those events happen.

Same thing with NPS. I try to get an idea of how well that CSM is performing in terms of whether their customers like them and their ability to create advocates out of our Wrike champions. How many of those customers are doing case studies; how many of those customers are participating in our conferences like Collaborate or customer marketing events; and how much of this external motion is transforming our relationship with our customers to where (Wrike is) truly becoming a trusted advisor?

The other big thing that I judge our CSMs on is how well they’re able to spread the knowledge of their client success stories across our team. Are they able to create playbooks? Are they able to do knowledge share sessions? If the CSM keeps that information to him or herself, the whole team loses. And that to me is a huge miss. I think it’s partially my job as a leader is to facilitate some of that knowledge share. But it’s also on the CSM to be able to say, “Hey, I’m seeing some success here. How do we make this something that’s a little bit more widespread?”

— If you would need to increase the headcount and hire a new team member, what professional qualities would you be looking for?

— I have a really specific philosophy on this one. My philosophy is this: You can hire a hard-working, good person and teach them how to be a successful CSM. You can’t hire a successful CSM and teach them how to be a good person and a team player. So, because of that, I’m always looking for culture fit. I’m always looking for soft skills. I’m always looking for their motivation of “why.” I always want to know the “why.” Every interview I start the exact same way. I ask, “Why do you want to work at Wrike, and why do you want to work as a CSM?” And also, “Why do you like being a CSM?” If they can’t answer any of those three with any kind of clear logic, then they’re out of contention.

I don’t care how well (a candidate) performed at any of their previous roles. I’ve seen it happen where we can take pretty unskilled people, teach them a few things, give them the right opportunity to grow, and they grow into a role they would have previously never been experienced enough to get. We took a risk, and now we’ve built that experience for them. Everyone wins. So I’m almost never looking for really experienced and skilled people to try and come into our org — I’m looking for people that are hungry, that are motivated, that are team players, that are honest and, lastly, really want to be here. When we get these culture elements satisfied and you can do it across an entire team — that’s when you can start building some synergy where the sum is greater than the parts of the whole.

— So, does it mean that you would never hire a superstar asshole?

— Basically, yes. It’s 100% what it means.

— What, in your opinion, are the main challenges of managing a team of customer success managers?

Matt: Number one I would say is definitely what we talked about earlier — around motivation and gratification. It’s hard to say that what we’re doing has an immediate effect on our customers so I’m always trying to make sure that everyone stays motivated, they feel respected, accomplished, and recognized for the work that they’re doing. That’s super important. I think that can become really challenging to consistently do, and it’s still a nut that I think we haven’t cracked very well here at Wrike. It’s definitely difficult.

I think that the other big challenge is having to balance the needs of the company with the needs of my team. How do I balance that whole world of trying to build the business and further our organization with actually managing the team. My day consists of having one-on-ones, dealing with escalation calls, helping our team strategize with their books of business, figuring out account distribution, figuring out training for new CSMs, and so much more. You’re having to consistently pick and choose between what activities are going to give you the highest impact from your time spent. What am I going to do that will have the biggest impact on my team and the biggest impact across the entire customer success org? So that’s really, you know, that’s a huge challenge.

I think the last challenge that I’ve noticed — and this is something that I would never have said as a challenge two years ago — is maintaining our culture when we continue to bring in folks with different backgrounds and experience levels. As the requirements and the nature of the CS role is shifting, you have to know how to properly message and get everyone behind you on that kind of stuff. It was really easy to do that when we had a really small team of four to five people who are really close to it, right? We all were incredibly good at communicating with each other and we could have very honest, open conversations.

Now our team is built up of people from different walks of life, experience levels, and interests. They’re culturally very different. But trying to bring all of those folks together, unify them for a single mission, move that forward — especially for some of the more veteran folks who are used to an old way that we did things –capture the needs of new people, and crowd them all in a single direction is probably one of the most challenging things for the leader. Especially when I’m being asked to move everyone in a particular direction from our leadership that I do not agree with. That’s where I have to bite my upper lip to figure out the best way forward because that’s what the business is asking of me.

— And the last question. What do you like most about what you do in the management role?

— Yeah, that’s a good question. What I like the most about management is definitely being able to work with people and grow them into something way bigger than when they started. It’s really satisfying to see someone who came in with a skill set that was pretty narrow and watch them grow and evolve. It’s a blessing to coach the team, mentor them, and see them turn into someone way more skilled, successful, and capable than they were when they started. That’s really empowering. That’s really cool. That’s the kind of stuff I like doing. And especially if you have folks who are willing to work with you, listen to you, and really want to take that next step — it’s a blast. That part of it is super fun.

And I also think just being able to lead the team, bring everyone together, hold sessions where we take people and push them into their challenge zones, see them kind of struggle with the challenge, and come out on the other side and be successful — that’s also super rewarding as a manager. Because you know that some of the skills that (your team) learns will stay with them, whether or not they stay at Wrike or continue their career as a CSM. They’re going to take those skills and they’re going to have them forever. And I think that — for a manager — it is super rewarding.