Blog Webinars and Podcasts

Mastering CS – Candid Leader Insights – Ep 5 – Will Stevenson

November 28, 2023 24 minutes read

Summary points:

In our new episode of the Mastering CS – Candid Leader Insights podcast, Irina Cismas, our Head of Marketing at Custify, sat down with Will Stevenson, Founder and COO at Will shared more about his journey in the SaaS and B2B space.

What You’ll Learn:

  • What to prioritize when you are starting out at a new company as a CSM
  • The importance of both focus and multitasking in CS
  • How Customer success looks in different industries
  • How to choose the right tools for your CS tech stack
  • How to build a CS team with essential skills
  • How to face challenges as a new CSM

Key insights and takeaways for CSMs based on the interview:

Early days in a new company: Embracing the analogy of curveballs in one’s professional journey, the key is to recognize that challenges can lead to significant successes. The initial interview phase is just the beginning, and the real test lies in navigating unexpected situations with a long-term perspective when starting or joining a company. The ability to adapt and persevere through curveballs is crucial for sustained success.

The power of prioritization: When taking on a new customer success challenge, prioritizing the learning process involves discerning which issues require immediate attention, which can be allowed to simmer, and which can be left to smolder. By engaging in open conversations with various stakeholders in the organization, both at the individual contributor and leadership levels, one can quickly compile a list of challenges. The crucial skill lies in then prioritizing and addressing these challenges based on their urgency and impact.

Adapting to the unique challenges: Adapting to surprises and shifts in strategy in customer success, much like navigating life’s unexpected curveballs, involves recognizing that challenges can lead to valuable outcomes. Drawing parallels to personal experiences, such as fostering children, underscores the notion that unexpected situations, though initially daunting, can result in significant rewards. In the realm of business, anticipating curveballs, both positive and negative, is part of the journey. The key lies in resilience and the understanding that, regardless of the nature of the curveball, the options are clear: either give up or keep going.

Choosing the right tech stack in CS: The choice of tools and technologies in customer success is crucial for enhancing team effectiveness. Despite the overwhelming variety of software options, it’s essential to recognize the specific needs of the team and seek solutions tailored to those requirements. The speaker emphasizes the importance of efficiency gains achieved by using tools designed for the particular challenges at hand.

The CS team in different companies: In building a customer success team, the roles evolve based on the company’s growth stage and specific needs. For startups with five people or fewer in customer success, generalists who handle various tasks are essential. As the company grows to 500 or 1000 people, the team becomes more specialized, with distinct roles such as onboarding, customer success management, support, and operational oversight for efficiency.

Podcast transcript


Irina 00:03
Well, thanks for taking the time to chat with me today. It’s always a pleasure to connect with fellow CS leaders, especially those navigating the exciting world of B2B SaaS. One of the things I really appreciate about these types of conversations is the chance to dive into not just the technical aspects of our work but also the personal journeys that shape our perspectives.

Speaking of personal journeys, I came across something interesting in my research about you. It turns out we have something else in common beyond customer success. We are both parents navigating the challenges and joys of parenting. I have one daughter who’s already teaching me more about management than any book or webinar ever could. I hear you are a proud dad of three daughters. That’s quite an amazing experience. I can barely manage one, so I bet managing three is even more challenging. How has this journey of fatherhood reshaped your approach to leadership in the B2B space?

Will 01:08
Yeah, quite a bit. I think the biggest lesson I’ve learned as a parent—my journey is kind of unique. Happy to discuss that, but the primary lesson is that being in charge is hard, right? There are a million decisions to be made. When we went through the foster-to-adopt process and first got our girls—four, three, and a newborn—life was a whirlwind of personalities and decisions.

We discovered that with three kids, we were 100 times busier than when it was just my wife and me. There were constant decisions: ‘I’m hungry, can I go outside, my sister stole my toy,’ and so on. However, we realized early on that our kids were really capable. By the time they were five, they were making their own breakfast, packing their own lunches, cleaning up their rooms—doing all the things we would have otherwise done.

So, if I had to give it a framework, it’s about working through arguments and empowering them to make decisions. This aligns with managing people in a company. You provide a framework, work with them, but ultimately empower them to make decisions and solve their problems. This reduces the manager’s decision load, and decision exhaustion starts to fade away. Making 20 decisions a day is much less exhausting than making 1000 decisions a day. That, I think, is the biggest parallel I’ve found. But being in charge is hard.

Starting out at a new company as a CSM

Irina 03:14
I never thought of implementing a proper framework, and interestingly, I find myself doing a similar thing with my kid. Starting a new company, especially as a CSM in the first 30 days, must be a bit like diving into parenting—lots of adapting and learning on the fly. How do these early days shape your approach to customer success?

Will 03:41
I think what we have to realize is that and I haven’t read a blog about this (I’m happy to send it over if you’re interested), but what I realized pretty early on is that curveballs can create home runs. Just because somebody throws a curveball at you doesn’t mean you can’t hit the ball. Our adoption journey was very similar. Even when you’re starting a new company or joining one, the reality is you spend a bunch of time interviewing and having conversations—that’s the honeymoon phase, right? You’re asking questions, they’re asking questions, you’re getting to know each other.

But when you get hired or start the company, you’ll realize that the two-week to six-week interview time period was nothing in the grand scheme of things. There are a million other things to learn. That’s where thinking long term shines through. If you’re thinking about it short term when you join or start a company, the challenge is that at the first sight of something unexpected, you might try to find a way to get out. So, you have to be prepared for those curveballs, be ready for unexpected situations, and be prepared to work through them in the long term.

Prioritizing the learning process

Irina 05:14
You mentioned learning in the first month, in the first weeks of taking on a new CS challenge. How do you prioritize the learning process? Because you have to talk with so many stakeholders, and besides your team and peers, you have to go through the product and processes if they exist. Where do you start? What’s the most important thing?

Will 05:48
Yeah, the key, I think, is to know which fires to put out, which fires to let burn, and which fires to let smolder. So, you have to prioritize. I think the way you do that is, when you first join, you’re going to learn about the problems really early on. Everyone’s going to tell you the problems; no one’s going to tell you the successes. That’s just human nature; we have a tendency to talk about issues rather than solutions.

So, I think the first week or two is really spent having conversations with everybody in the organization—anybody that’s currently in CES, that’s customer-facing, the sales team, the management team, product team. What are you hearing? Having those conversations with the individual contributors and the leaders of the company are really going to give you that problem list. And then the problem becomes prioritizing. It becomes figuring out, again, which fires absolutely have to be put out right now, which fires you can let burn over here that aren’t as important, and which fires to let smolder as they’re building up. You quickly learn your priority list just by having conversations; people are pretty open and transparent, especially about problems that affect them.

Irina 07:19
From what you said, it takes me to the concept of focus. And I think this is one of the most important aspects, not only in customer success but in all areas and I know that you second this. How do you apply this idea of focus to increase customer success and scale the business effectively?

Will 07:48
Yeah, I’m a big proponent of focus. The reality is, if you want to do anything with excellence, you have to focus, right? I have dozens of tricks and tactics that you can use, and I’m happy to talk through a few of those. But the overarching message is, if you want to do something of high quality, you simply can’t multitask. And that’s coming from someone who loves to multitask, right? It’s very much in my nature to work on 10 different things at once. But I have to rein myself in and realize that if I really want to get something done to the highest quality, it all comes down to focus.

So, when we talk about focus, it’s probably easier to start backward or start at the end and work our way backward. Why is focus important? Let’s start with the end result, right? The end result is I want to get more done, and I want to get it done to a higher quality and efficiently. So if that’s the end goal, what prevents you from getting there? Usually, it’s internal and external distractions. Decisions are a big one, which we’ve already talked about today. Making lots and lots and lots of decisions can be distracting and take away from your focus. Other work is constantly competing to get done. Meetings are a big distraction.

So, what do we do to eliminate those distractions? This is ultimately where we come full circle. For decisions, we just have to make fewer of them, right? We have to empower others to make decisions and reduce decision exhaustion. Here’s one of my tips around decision exhaustion: I have a uniform that I wear every day. It’s not literally a uniform, but I have this hat that I wear five or six days a week, and I have the same color T-shirt in this brand. I eat the same thing every day for lunch. It’s one less decision that I have to make. I’m eliminating those decisions, which reduces my decision exhaustion.

Other work creeping in at the wrong times: I have a one-tab rule. When I have something to get done, I’ll pull one tab off my browser and focus only on that one tab for a set period or until the task is complete, depending on the priority. I set my computer to do not disturb. No more 600 tabs across the top, bouncing around, getting notifications. One Tab is my way to zero in and focus only on that aspect.

The third is meetings. A lot of people talk about this, and it’s almost cliche, but it’s like just reduce the recurring meetings in your calendar. Time block, set specific blocks on your calendar for when you’re going to get work done versus when you’re going to meet with others. One thing based on scientific research is 10 a.m. is the most productive hour mentally for people in the normal workday. It’s been proven many times. So 10 a.m. on my calendar is blocked. No one can book 10 a.m. because I know that’s my time to get work done for that 60-minute period.

I think there are a million ways to optimize output, but focus is the vehicle that gets us there.

Multitasking in CS

Irina 12:23
I know that focus is important, but I often hear about multitasking. So, I have to take this information and try to see how you actually apply it in your CS role because, for me, it sounds very challenging. You have a lot of client meetings, there’s always an emergency in customer success, and there’s always a fire drill to handle. Could you delve deeper into how you organize, for instance, your day to maintain this focus?

Will 13:16
We have to go back to which fires do we let smolder, which fires do we put out, and which fires do we let burn, right? There’s always a fire in customer success. Absolutely, and these rules are going to get broken, but if you stick to these rules, 90% of the time, you will be more efficient. So, the 10 a.m. thing is non-negotiable for me. Unless someone calls me because I won’t see it if I don’t have Slack open, my email up, and our Help Desk open. If I don’t have all these things open and I’m only focusing on one thing, the only way somebody’s going to get a hold of me is to call me or text me, but I probably won’t see it if it’s a text, so call me, right? That’s a non-negotiable for me. That’s my one hour in the day. No one can disturb me during the workday, and I can get things done. I can narrow in and focus.

But at the end of the day, I think it really comes down to you have to set the rules for yourself to be productive. There will always be distractions, there will always be a fire, there will always be someone calling you trying to get your attention. A million things compete for your attention every day. The question is, what are you going to give your attention to? While it is difficult, for sure, it’s absolutely difficult in the sense that there are so many things competing for your time. You have to outline those rules that you’re going to follow, and you have to follow them. If you don’t follow them, it’s not a controlled experiment, and you won’t know if they work or not. So follow those for 30 days and see if they work. My guess is you’ll come out being more productive at the end of these 30 days.

Irina 15:14
In my case, the thing that I’ve learned from being a mom is that okay, focus is one thing. I cannot do my—I think I was a multitasking person before being a mom. But now I think it’s a combination between focus and multitasking. I’ve learned that I can do so many things in five minutes, and I’m not wasting it. I’ve learned that time is the most valuable resource that I have, and it is very limited. So yeah, indeed, I decide very well on where do I consume my energy.

Will 15:58
I love that time is your most valuable resource that you can offer to anyone. Because, again, there are so many things competing for your time, including your family and your kids. You have to make time for that. So I’m with you. Yeah, I agree.

Adapting to unpredictable situations in CS

Irina 16:19
Besides this, another thing that I had to adapt to is unpredictability. I was the person who was always doing plan A, plan B, and a backup plan. I had backup plans to backup plans. But I realized that what the kid basically learned is that I have to deal and adapt to all of those situations. Now, I want to ask you, and I do see a parallel. So I want to ask you, how do you adapt to surprises or shifts in strategy when it comes to customer success? Because priorities do change. How do you do this?

Will 16:56
Yeah, I mean, I think it goes back to curveballs can produce runs, right? Some of the craziest curveballs I’ve been thrown in life have produced home runs, have been the greatest things that have happened to me, including my kids. I’ll get back to that for a second, which is when my wife and I first started our foster care journey, we brought home a brand new little baby girl, right? Five months later, the state called us and said, “Can you take her two sisters?” Unexpectedly out of the blue. We had no idea that was even an option on the table. It was a massive curveball. We didn’t know what to do at first. And then we said, “Of course, it’s our two sisters, we have to do this, right?” Unexpected on our side, greatest reward ever.

The same thing goes for customer success and business in general. You’re going to get curveballs, right? It’s going to happen. You’re going to get unexpected situations, good news, bad news. 50% of the time, the thing you expect is going to happen. 25% of the time, you’re going to be pleasantly surprised, and 25% of the time, you’re going to be let down or discouraged. You just have to keep going. Like I tell my girls all the time, there are two options in life: you either give up or you keep going. And if giving up isn’t a realistic option, then you keep going. It really narrows it down for you when you boil it down to those two options.

Customer success in different industries

Irina 18:40
You’ve been working in different industries—from real estate, and health tech, to marketing automation. I’m curious, are customer success challenges unique to each industry, or do they overlap? Are there key differences or similarities that you’ve noticed?

Will 19:00
I think the challenges are the same, right? Challenges and goals are the same. There are certainly different strategies or tactics that you can use in each industry. But at the end of the day, CS wants less churn and more customer growth over time, right? When you really look at it, the key ingredients are the same as the key outputs at the end.

Those are the things that we want in customer success. So I think usually the way you get there is more customer usage, faster time to value, enhanced value over time. I think it’s universal, right? We sometimes overcomplicate these things and make them out to be something they’re not. The reality is if you pull 1000 Customer Success teams and say, “Here’s a multiple-choice question of what is most important,” everyone’s going to say, “I want less churn and I want more customer growth.” That’s how Customer Success works.

Irina 20:07
What are the biggest obstacles in gaining actionable insights for the CS team? And how to overcome those?

Will 20:15

I think this is a super important question, and something that not a lot of people are asking, or they might be asking it in slightly the wrong way. So what I mean by that is, everyone talks about the famous quote, right? “What isn’t measured isn’t managed.” I think, as an industry, we’ve kind of outgrown this quote because everything, to a degree, is measured today. The challenge most people are going through is that it’s not organized enough for them to understand the measurements or to have the key insights. So you have to get the metrics into one place. Chances are, they’re being measured already. You have to get them to a place where you can easily digest those, and they’re visible to everyone.

For the items that are less quantifiable, like customer sentiment, that’s a good one. I think AI is helping us with that already, and I think it’ll make it a lot better over time. But you just have to capture that. You have to have your CS team capture those sentiments across all your customer interactions and feed into the data model. Most of the time, people just aren’t good at seeing the data that’s being measured. And it’s not their fault, right? As a CS leader, manager, or team lead, you’re not a systems engineer; your job is not to build these systems. So you can easily see the data in most cases. But it is someone’s job to do that, or it should be someone’s job to do that. So we just have to work with those people to get the data that we need to make informed decisions in the right place where it’s easily accessible for the right people.

Irina 22:14
I often find that because we are chasing, we want numbers, we want to measure everything from everywhere, and everything is important. And then when we look at the data, we can’t answer the question and no one knows, “Now what do we do with all these numbers that we have, with all the reports? How do we make sure that we are not only collecting data for the sake of it? And then what you do with the results? And what the data tells you is another thing? How do we make sure that we are reading the data correctly?

Will 22:57
We have to measure consistently, that’s the challenge. It’s a challenge that a lot of people face; the data isn’t consistent, which ultimately changes where the goalpost is. So as long as you’re measuring data consistently, in my experience, even if you’re measuring it wrong to some degree, there’s some margin of error there. Even if you’re measuring it wrong, if you’re measuring consistently over time, you should see gaps shrinking where they should shrink and gaps growing where they should grow. But I think that’s the challenge. Everyone wants perfect data. Perfect data isn’t real; it’s kind of like the unicorn that everybody’s chasing. It’s not exactly a real thing most of the time, especially in smaller companies. When you’re talking about a company size of under 100 employees with $10 million ARR or something like that, your data is just not mature enough to be consistent in a way that you can make every decision off of. You should try to make as many data-driven decisions as possible. But at the end of the day, you just have to measure that data consistently and see incremental increases in getting better.

Tools and technologies for customer success

Irina 24:24
Thinking about data, I want to speak about tools that basically help us extract this data. How crucial is it to choose and use the right tools and technologies in customer success? And how much does this impact the effectiveness of our CS team?

Will 24:46

Well, I think it’s difficult today to choose the right tools in many cases. There’s just so much software out there, making the right decision is really hard. But I also find in the Customer Success world, onboarding world like us, that it’s probably the most undervalued, underfunded team in an organization. When you look at sales and engineering budgets, they are massive compared to CS budgets. Still today, I think the market is coming around, but it’s still a big discrepancy. That’s really why we created Board— I was looking around, and I saw that customer onboarding teams typically used Excel files or generic project management onboard. So I figured there had to be a better way. And if there wasn’t, then we’re going to create it.

But what I typically find, and just like a recommendation, I guess, for the listeners is, in any industry, in any department, in any department org, solutions that are geared for the specific problem that you’re trying to solve are likely going to cause more efficiency gain than wider solutions. I often equate it to bowling, and I’m not personally a bowler. But I know that if I’m bowling down a lane that has rails on it, I’m not going to go out of bounds. If I’m bowing down a lane that doesn’t have rails on it, I’m going to be out of bounds. So that’s the same way I think about it with software. If you’re going with a super-wide solution that can do everything for everyone, you’re going to find that it does nothing for anyone. When you’re using software specific to the problem that you’re trying to solve, usually, you’re going to be able to solve that problem. Now, I think that there’s something to be said about platforms versus point solutions. But I also think that there’s a reason that point solutions exist today because they solve a problem.

So I think from an impact perspective, in the customer success world, and the onboarding world, and the support world, technology makes you more efficient. It’s the same across every other department and every other org. So super crucial, unfortunately, harder to make a decision than it should be in today’s world. But I think that’ll change over time. I think as more software providers focus on customer success as a CIO or an organization that they want to support or a department they want to support, it’s going to become easier and more scalable to pick the right solution.

Choosing the right tools

Irina 27:58
I’m just curious now because you mentioned that it’s hard to pick the right solution. How do you make your decisions? How do SaaS products convince you to try them out? What do they need to do? What do they need to offer?

Will 28:15
I’ll tell you one thing; it’s rarely LinkedIn, email, or InMail, despite getting 60,000 in-mails a day. But I think the way that I’ve always purchased—and the interesting part about that question, I’ve kind of found myself falling into that role across every company that I’ve ever been at in the last 14 years—is an enterprise software purchaser. The way that I’ve done it is I usually identify the problem, design the solution, and then find the software that supports the solution. I always say “purpose before technology,” meaning like if we’re solving this one problem, what is the ideal solution for that? Now, let’s go find technology to support that. So again, it’s working backward. It’s the same thing we did earlier with focus. You kind of have to work backward in that scenario of what am I really trying to solve? What’s the ideal solution? And what can support that framework or that architecture that I’m putting in place? And then you just go out and do a lot of demos and ask a lot of questions and ultimately hope that you make the right decision.

Irina 29:36
And how do you get funded for this? How do you take the leadership buy-in for this? Leaders speak about being hard for them to be funded and you also mentioned that CS is actually the team that is the most unfunded in comparison.

Will 30:01
So I’m going to tie this into how do you make the right pitch to get the right software and get the budget for the software. I’m going to make the same argument for headcount here. And I’m going to make the same argument for if you, as an individual, want to move to a different role in the company, let’s say you want to go from a success team lead to a manager or director, right? It’s all the same process.

What’s funny about this is I literally just had this conversation on Monday with a CS team lead that wanted to move to Director at a different company. And it was a connection that we had made, and I had a conversation with them. So ultimately, it’s the same process.

So the process is, you have to evaluate the problem first. How big is this problem that we’re trying to solve? And is it a legitimate problem, and you have to quantify that. It may not be as simple as, “If we solve this problem, we gain two customers, and we retain two more customers,” right? It may not be that straightforward, but if it is, this problem takes 20 hours a month away from our team. On average, our team makes x dollars per hour. If we can reduce that by 75%, here is the tangible value of what we’re trying to do.

After you identify and quantify the problem, it then becomes making it easy for the person that you have to go get budget from to make the decision. The way that you do that is you outline the problem, outline the cost of the problem, outline the solution, outline the solution cost, and make it extremely easy for them to say yes.

So in moving from a team lead to a director, what you have to tell the person that’s making that decision, and what you have to convince them of is, “I’m going to be more valuable by being in a director level than I am in a team lead level,” and you have to quantify that. If you can’t quantify that, then you have to ask yourself, “Do I want this just because I want this? Or is this what’s best for the organization?”

The same thing when you’re trying to pitch getting funding for software or getting budget for software is, “Do I want this because I like it? Or do I want this because this is actually going to make an impact for my team and for my company, and it saves time and energy and effort down the road?” So I think that’s it.

As I see it, and I’ve seen it a million times, but it’s, “Hey, we really need the software.” And I say great, we need the software. Why do we need it? Well, we have this problem over here. Great, how much? How much money or time or resources is that problem costing us? I have no idea. It’s like, well, then how do you know that we need to pay for something to solve it? It may be costing us 15 minutes a month, which at the end of the day isn’t worth $1,000 a month in software. So I think that’s it.

I think you have to think through the problem, think through the cost savings of a solution. Make sure when you’re having that conversation that it’s actually justified. And it’s not a selfish decision to buy it. It’s going to make the organization better.

The Customer Success team

Essential roles in CS

Irina 33:45
You mentioned director’s roles and positions and I want to switch gears to another important pillar in customer success. And that’s the team we talked about. We talked about the foundation, we talked about the processes, the framework of technology. And now let’s talk about the people. What are the essential roles within our customer success team? And what stage in a company’s growth do you typically see these roles merging?

Will 34:18

Super great question. Different-stage companies need different things or different roles. I would say if you’re a startup, and when I say startup, five people or fewer in customer success, you’re gonna have generalists. That’s a really small company. They’re going to be doing everything—onboarding customers, managing them, supporting them. It’s a challenging time for sure. The end goal is, when you’re a 500-person or 1000-person company, the team setup is going to be more specialized. You’ll have onboarding, Customer Success management, support, and a layer of ops over top of them ensuring efficiency.

The question is when to start becoming specialized. I err on the side of early specialization. Once you have your fifth person in customer success, you should be thinking about splitting. There are two logical paths at that stage: onboarding and customer success management with CSMs handling support, or vice versa. Onboarding and support can be combined, and CSMs handle the ongoing management. This setup works for small teams (around five to 15 or 20 people).

After that, it splits into three roles: onboarding, success management, and support. The decision on which direction to go is based on your specific product. If your product is highly technical and has a lot of support questions, you might split roles differently than if the product is easy to implement, has rare support needs, but requires ongoing management for extending or adding use cases.

Personality is another factor. In the early stages (five to 10 people in the CS organization), you may design roles based on personalities. The personality of someone who enjoys onboarding is different from someone who excels at managing relationships. A person who is project-focused may not thrive in a long-term relationship management role. Matching the right people to the right roles is crucial throughout the lifecycle of the company.

Non-negotiable skills for CS people

Irina 38:24
Speaking about personalities, I want to ask you when you are recruiting, what are those skills that are you are looking for, and which is the thing that is nonnegotiable?

Will 38:39

Non-negotiables upfront. I am absolutely in there. Here’s a spoiler: they’re all every skill that I have, in my mind right now is a soft skill.

Right? So the two non-negotiables self-awareness, and situational awareness. So what I mean by those two things, if you are building a team, and you’re building a team full of people that have no self-awareness, that team is going to be very dysfunctional and not a joy to work on. Right? If you’re building a team full of people that have self-awareness, they know what they’re good at. They know what they’re not good at. Certainly helps that situational awareness on the other hand, also very important. If I’m on a call, and the customer is visibly angry, and I’m not picking up on those cues. That’s not a great personality trait to be lacking for customer success. Right.

So self-awareness, situational awareness, my two non-negotiables. Absolutely. Team has to have it or I can’t make the hire. I’ll go through kind of a few other things that I’ve had on previous like great teams that I’ve managed which are Are people that check their ego at the door? Right? I’m the same way, right? You gotta check your ego at the door. You can’t, you can’t think you’re the best at everything. And it kind of goes along with with self-awareness. But check your ego at the door, lifelong learners. I love hiring people that love to learn. I love to learn, I listen to podcasts, I listen audiobooks, right? Like, I’m constantly listening to something that I’m hoping increases my knowledge in life. But people that like to learn are typically great on the customer success team. And last, I’m gonna say team players, because again, it kind of comes back to if the team’s not functioning well. It’s, it’s really hard to hit goals, it’s really hard to have success as a group in customer success. If your team’s not playing well together.

Finding the right people for the job

Irina 41:00
The soft skills are the hardest to test in an interview process. What’s your secret recipe? How do you find out if they’re a good fit or not?

Will 41:11
So through a series of situational questions, I have a list of situational questions. And again, I’m happy to send this over if you want to share it out with your listeners as well. But I have a series of situational questions for CSMs and onboarding specialists. Basically, what I’m trying to figure out is, are you one, are you self-aware? Are you situational aware? And then also, for the split role of onboarding and CS, I’m trying to figure out, are you project-focused in life? Or are you relationship-focused in life?

One of my favorite questions to ask in an interview is, it’s a Saturday, midday, right, two o’clock in the afternoon, one o’clock in the afternoon, whatever. What are you doing? It’s a very open-ended question that can go a million different ways. But what I’m really looking for is, am I at home, building a shed? Or am I at a friend’s house watching a football game? The reason that I ask that is, if I’m at home building a shed, I’m very project-focused. I have a goal, I want to get something done. If I’m at a friend’s house watching a game, I’m relationship-focused, right? I want to spend time with my friends. Not saying people that focus on projects don’t want to spend time with their friends, but there are little indicators. You ask a bunch of these questions that are all kind of related and similar, and you figure out, does this person want to spend time building relationships? Or do they want to spend time executing projects in their own personal life? What are they interested in? It really helps figure out which seat that person should sit in on the customer success side.

Irina 44:00
I want to ask you, what’s your take on learning from mistakes? Because in my case, some of my most memorable lessons come from turning mistakes into learnings. Do you experience a similar thing? We are usually afraid of making mistakes.

Will 44:24

I mean, I’ve made a lot of mistakes. And I’ve learned a lot from them. So I agree. Ultimately, I kind of subscribe to the theory of if you’re not making mistakes, you’re not moving fast enough. Meaning like if you’re kind of wandering through life and not making any mistakes that’s like, well, then you’re just not making enough decisions. You’re not doing enough, right.

And maybe you’re doing a lot but you could do more. So I kind of subscribe to that. But I also just subscribe to the fact that knowledge sharing is king. So at my last company, I had 12 People in the Customer Success role. And what we would do is every week during our weekly meeting, every single person on the team had to bring a learning, 60-second learning from the week prior. So if you didn’t learn something in the last week, you like, didn’t pay attention, right? Like, you should learn a lot of things in a week.

But it’s the 60-second learning, very basic stuff, it can be a learning of it can be a soft skill learning, right? Like, how, you know, I found out that if I asked this question at this time, I get this response. And this is kind of what I want. Or it could be, hey, I learned something new about our software. If you do this, then this and this in this, right. But if you’re constantly sharing those learnings as a team, the team overall is going to make fewer mistakes. So if you have 10 people on your team, that’s 10 learnings a week, that’s 40 learnings a month, right? And you can multiply it off from there, 480 learnings a year. So I’m a big fan of sharing that across the team preventing some of those mistakes. But I also believe that everyone’s gonna make mistakes. And again, if you’re not making mistakes, you’re just not doing quite enough.

Facing challenges as a new CSM

Irina 46:32
If you were to give a piece of advice to a new CSM here to help them overcome common challenges, what would it be?

Will 46:40
So this is my favorite question of all time. And I’m going to, this is the reason it’s my favorite question of all time. I tell my teams this weekly, doesn’t matter if you’re new, or if you’re, you know, five years old or 10 years into a company. The answer is, you are the expert. This is the advice.

So if you’ve spent a few weeks learning apart from your brand new hire, right, you’re four weeks in, you spent four weeks learning the platform, you’ve on boarded one company, or two companies, you’ve taken 20 support cases, you are officially in the top 1% of people in the world with that platform. Officially, if you look at all the people in the world, and all the people that have solved 20 support cases, onboarding one or two customers, or learn the platform for four weeks, it’s a very, very, very small number.

So you have to have confidence in yourself as a new employee, as an employee 10 years down the line, you have to be confident that you are the expert and you know more than most people in the world. So when you get on the calls with customers or sending emails, or you’re having customer interactions, you should be confident that you’re the expert. It’s my one piece of advice that I believe everyone. Everyone should take it. And if you’re a manager listening to this, you should go tell your team that they’re experts, the morale boost, the competence boost that you’re going to see off of this is as massive.

Future of the CS

Irina 48:35
As you bring this interview to a close, I’d like to take a broader look and reflect on the evolution of the Customer Success industry as a whole and where it might be headed. What’s your vision for the future of CS and where should upcoming CSMs focus their energy to stay ahead?

Will 48:54
Great question. I’m going to go against the grain here. What I’m saying is, we overcomplicate customer success. Everyone’s looking for the latest, greatest metric to measure, or the buzzword. Some say CS is the new sales. I hate to burst everyone’s bubble, but sales is still sales and CS is still CS. They’re different but both awesome roles in themselves. I think the goals of CS are going to remain the same. The goals of CS are to retain customers and increase current growth or revenue. Sales goals are similar, aiming to increase baseline new revenue.

My advice to CS as a whole and CSMs is, don’t get distracted. Focus on the few things that matter most, providing a great experience for the customer, over-delivering on promises, and increasing usage. Pay attention to their usage patterns and help them increase it. Focus on renewals and demonstrate increased value to the customer. If you do these things, you’re a top-notch CSM. Hone in on these aspects and figure out the tactics that work for you. There are a million tactics to increase these numbers, but let’s focus on the most important things – the customer. Giving them an amazing experience and increasing their usage while driving results for them makes you the best CSM in the world. Technology and metrics will change in this industry, but the end goal remains the same.

Irina 51:30
Well, thank you very much for your time! It was a very nice discussion, and I’m glad we had the chance to do it.

Written by Nicoleta Niculescu

Nicoleta Niculescu is the Content Marketing Specialist at Custify. With over 6 years of experience, she likes to write about innovative tech products and B2B marketing. Besides writing, Nicoleta enjoys painting and reading thrillers.

You might also enjoy:

Webinars and Podcasts

Mastering CS – Candid Leader Insights – Con Cirillo | Ep 1 Podcast

In this episode of Mastering CS Candid Leader Insights, Irina is joined by Con Cirillo, the Director of Lifecycle Marketing at Funnel and an advisor for investment groups and companies.

Webinars and Podcasts

Mastering CS – Candid Leader Insights – Ep 8: Michael Boyd

In our new episode of the Mastering CS – Candid Leader Insights podcast, Irina Cismas, Custify’s Head of …

Webinars and Podcasts

2023 in CS: Heaven or Hell | Webinar

What to expect in 2023 from customer success? Is this ever-changing industry going to be “heaven or hell”? …


Notice: This website or its third-party tools use cookies, which are necessary to its functioning and required to achieve the purposes illustrated in the privacy policy. If you want to know more or withdraw your consent to all or some of the cookies, please refer to the privacy policy. By closing this banner, scrolling this page, clicking a link or continuing to browse otherwise, you agree to the use of cookies.