In this webinar, Irina Cismas, Head of Marketing at Custify, sat down with Irina Vatafu, Head of Customer Success at Custify, and Steve Finch, Customer Success leader at Thinqi, to discuss one of the most transformative stages in a CS career: stepping into leadership for the first time.
Together, they unpacked what it really takes to transition from CSM to CS Lead, how to balance strategy and operations, build trust with teams, align CS with business goals, and survive those chaotic first months as a new leader.
Summary Points
In this session, we explored what first-time CS leaders experience when taking on management roles, and how they can succeed despite the steep learning curve.
Key takeaways include:
- Transitioning from CSM to Leader: Moving from doing the work to enabling others requires a mindset change, patience, and empathy for yourself and your team.
- Building Trust First: Before driving big initiatives, focus on listening, setting expectations, and establishing credibility.
- Balancing Strategy and Operations: Learn to prioritize, delegate, and find small wins that show impact early on.
- Owning Mistakes and Failures: Every CS leader fails before they succeed—authenticity and reflection are key to long-term growth.
- Defining Proactive Strategy: Shifting from reactive support to proactive CS demands structure, clear processes, and business alignment.
- Internal Processes Matter: Healthy teams rely on well-designed internal workflows, clear OKRs, and cross-department collaboration.
- Proving CS Value to Leadership: Demonstrate CS impact using business metrics—show how you prevent churn and contribute to growth.
Transcript
Intro
Irina C (0:02)
I’m Irina Cismas, Head of Marketing at Custify, and I’ll try to be your host today, even though, as you can probably hear, I’ve almost lost my voice. But a cold and a half-working voice aren’t going to stop me from hosting this one. Not when, after more than 25 editions, I finally get to share the virtual stage with my awesome colleague, Irina Vatafu, Head of CS at Custify.
She’s been my partner in crime for so many of these sessions, the person I always go to when I plan the next thing. So, you could say she’s the mastermind behind quite a few of our past webinars. So, Irina, thank you for accepting the invite and stepping into prime time today.
Irina V (1:00)
Thank you so much for having me and for the surprise, because it was an awesome introduction. Thank you, Irina, for having me.
Irina C (1:08)
And, of course, you’re not alone, because you brought back up and joining us today is Steve from Thinqi, who’s been through the trenches of building and leading CS teams. So, Steve, thank you for taking the time to join us.
Steve (1:25)
It’s my pleasure, Irina. And, yeah, it’s a pleasure to join you both and be able to talk about this stuff to your audience. So, very excited to do this.
Irina C (1:34)
It will be interesting conversations, I promise you all. So, between the three of us, or maybe the two of you a bit more, depending on how long my voice holds up, you guys will hear a mix of real stories and hard-earned lessons about what it takes to survive your first year as a CS. And, of course, once you get all those takeaways, you’ll need a way to put them into practice.
And that’s where Custify comes in. It helps CS teams get full visibility into their customers, automate their busy work, and focus on what really matters, helping customers succeed. A couple of quick housekeeping notes before we start.
The session is being recorded. I know that’s the number one question I always get asked. So, yes, you’ll get the replay.
If you have questions, please drop them in the chat or in the dedicated Q&A. It doesn’t matter. We’ll grab them as we go.
This conversation is mainly for you guys, the ones that managed to join us live. So, you’ll have the chance to basically pick the mind of both Irina and Steve and ask all your questions. And if it makes sense, we’ll take them in the conversation.
If not, I will have a Q&A session dedicated to that. And let’s get things going. And like always, I want to know where are you right now in your CS journey.
So, give me a moment to basically publish the poll.
Okay, I’ll give a few moments for the audience to engage with the poll. It’s always a surprise on how things actually end up. I’m curious if the live audience is more towards first time CSMs or we have a mix.
I think it’s awesome because I know and I talked with both Steve and Irina. And they will talk about those first few chaotic months and how to find your footing when everything feels new.
Please share your experience and let us know what were those things that you would wanted to know when you were first time CS leader. So, you also have the chance to share your experience. Do it in the chat.
We have an international audience. People from Peru, from USA, from Brazil, from Scotland, from California.
So, let’s start the discussion with the transitions from CSM and head of CS.
Basically, one day you are handling customers and the next day you are handling people and expectations. Irina, what was the hardest shift for you?
Transition from CSM to Head of CS
Irina V (6:25)
So, that’s a great question and it raises very nice memories. Just as a quick introduction, I was first hired at Custify as a CSM five years ago. And my previous experience was mostly in training, learning and development and support.
I started as a CSM, but I was promoted fairly quickly to the head of CS position. So, I can tell you that the transition from CSM to head of CS for me was much harder than I expected. There’s a huge change that happens overnight.
One day you’re a CSM, working with customers and solving problems and the next day you step into the leadership role you’ve been working so hard toward. But suddenly the challenges are completely different and you are still the same person. So, that’s something that nobody tells you.
That basically you’re still the same person, but everyone’s expectations of you change instantly. And that’s, of course, especially true with internal promotions, but it can also apply when you are hired externally. People often expect you to come in and magically fix all the existing issues.
So, for me, the hardest part was waking up and talking to the same people I had spoken to the day before. But now they saw me differently. They expected me to have all the answers.
And I remember one of my first weeks in the role, a team member came to me expecting me to resolve a longstanding process issue that had existed for months. We actually talked about it a couple of days before the transition. And I was like, hey, look, I’m still Irina.
We completely talked about this before and now you’re expecting me to solve it. So, previously, I would have just flagged my manager and now I was the manager. So, it really hit me hard to see that I am the one now that has to fix that.
I’m not the doer. I’m the enabler. So, that was the toughest part for me.
Early Leadership Surprises
Irina C (8:31)
We are already starting receiving questions from the audience. Elizabeth, I need you to bear with us for a few more minutes. We’ll take your questions.
But not before asking also still, when you think back to your own move into leadership, what caught you off guard early on?
Steve (8:55)
Okay, well, I guess my journey wasn’t as straightforward as Irina’s. The path I’ve taken to my current position hasn’t been really linear or traditional. It’s gone forwards, it’s gone backwards, it’s gone sideways.
My first step into managing a team, which was some time ago and that was more focused on business development. My first steps into that made me realize that I really wasn’t very good at managing people at the time. And I think there was a bit of overconfidence, maybe it was hubris or Dunning-Kruger effect, whatever it was.
I assumed that because I could manage projects and manage customers well, that I’d be able to manage a team of people. And I think there’s things like the HR formalities that threw me the most, having to do appraisals and things like that, and the one-to-ones and the individual stuff. And it was asking questions of me that I didn’t have answers for.
And I hadn’t really prepared or trained for it very well. But then later I stepped into, took an unusual route, but I introduced customer success into our business at a point where we were shifting all of our focus on our software as a service. Before that we did contract service work as well.
So the business was changing and evolving. I introduced customer success into it and the team was pretty much me for a few years. Then we did expand the team.
I was keen to become the head of CS role. And to be honest, I really struggled. And I don’t think either I, myself or the business were properly prepared for that role and that team structure at the time.
I had a set of objectives for the new role set for me, that I had a time period I had to prove to the business I was capable of this. And that was managing my full portfolio of customers. Nothing had changed there at all.
So suddenly I’d gone from being, having my week full up with managing customers to my week full up with managing customers, plus the responsibilities ahead of CS role. And yeah, I didn’t do great at it. And I found it difficult to juggle both of those things at the same time, because I was kind of conditioned into my focus being on the customers and making sure that they have what they need.
But I had to then deliver on the objectives of the head of CS role. And that was very challenging for me.
First Steps & Balancing Strategy vs. Operations
Irina C (11:41)
To be honest, I like both of the answers. And I like to say that I’m glad that you struggled, because now I know that you are both successful. So I want to ask you, how did you do it?
So how did you move from suffering and from all that pain into where you are today? So I want to start with you, Irina. And I want to ask you, what’s the first step?
What’s the first thing that you did when you stepped into the head of CS role? What did you decide what to focus on first? And I’m not sure.
Elizabeth’s question was basically, and I’m going to start it live, because I think it correlates with this. Any advice on balancing strategy work versus operations, and struggling with the context switching? So we either go to this, and we build on how did you decide what to focus first?
I think the two of them are related.
Irina V (12:59)
Yes. So I will continue Steve’s idea that everybody’s struggling in the beginning. It’s the head of CS role for the first time.
And there are many, many things that can look like priorities. There are many expectations from the team. But the way I tried to think in order to put some clarity in my mind and to manage to obtain some to succeed, let’s say, in this role was to think that just like when you’re a CSM, because I had that experience, the CSM experience, just like when you’re a CSM building relationships with customers, as a new manager, you need to establish trust and clarity internally before making any major changes in the team or coming with new ideas and projects. So if with a customer, you have some success planning sessions, or one on ones in the beginning, some onboarding calls and whatnot, I started my role as a CSM by focusing on setting expectations and running discovery sessions with the team.
So I started by listening, even though I was promoted internally, and I already knew everyone, my new role gave me a different level of influence and responsibility. So I scheduled calls with everybody to understand what are the current pains? What is everybody expecting from me?
And what are my priorities? If there were overlaps between the teams, for example, sales having an issue product having an issue, my team having an issue, that’s the problem I would start with, I would try to find some small wins that I could deliver fast, but also establish some strategic projects that I could focus on in the upcoming weeks and months. So speaking about strategy and operations, I think it’s first you have to realize what is needed and to set some goals and expectations together with the team.
And then you’ll find the answer if it’s either strategic or operation, the one that the project that you will have to focus on in the first months as a leader.
Irina C (15:13)
Steve, was it different in your in your case?
Steve (15:19)
I guess it was. As we’ve talked about that challenge where you’ve got, you know, you’re firefighting, and you’ve got lots of different parts of the business asking you for different things. You’ve got to try and simplify that a little bit and be realistic about what you can deliver.
And also, you know, to get those early wins, you’ve got to set some goals that are actually achievable and not overly ambitious, because no matter how much time you think you’ve got, you’ll have less to actually do it. So and, you know, as Irina said, it’s about building trust. If you can take ownership of what those goals and objectives are, as opposed to have them dictated to you by the business, or at least co-construct them, then you can be realistic about what they are and take a bit of ownership of them.
For us, it was, you know, separating those things off, you’ve got the strategic, it’s all about who’s taking ownership of those strategic decisions. If it’s something that’s been entrusted to you, then you go, okay, well, I’m going to do it. And I’m going to take the time and plan out strategy.
It could be that, you know, the business needs something different on that short term. And something that we talk about with our customers, because we do learning and development, and something really pertinent recently is about understanding metrics that are important to the business, you know, impact metrics, as it were, we have our own little measures in CS that are great for us, and it helps us understand our customers better. But how do we show that that’s positively impacting the business.
So trying to find some metrics and some stats that show an actual impact to the business means that you’re just going to get more buy in from other stakeholders, you know, in the same way as the sales team have to prove what revenue they’re generating, and, and all of that, and how marketing activities convert into business opportunity, then a customer success team has to similarly demonstrate either something positive in terms of contributing towards revenue generation, or preventing negative, you know, reducing costs, reducing churn, but trying to do it in a in a language that the rest of the business and other stakeholders can understand and just pick some small wins, show that you’re achieving progress towards it and being realistic.
You know, it also plays into avoiding vanity stats and having true objective measures. And the first couple of times you measure that it’s not necessarily going to shed your team in a good light. As Irina said, you know, you inherited some problems or challenges or whatever, that were already there that then suddenly became your problem.
And, you know, so it’s kind of difficult, you’re not gonna, you’re not going to solve everything overnight. So just pick those early wins, ones that are going to give you the best sort of PR in the business to show that you’re achieving progress towards it. And doing that measurement and being honest and objective and authentic, so that you can, you know, you know, if you’re doing vanity metrics and stats and things that, you know, are a little bit sort of sprinkled with glitter, as it were, it’s hard to maintain that.
So trying to be honest and objective, but that again, depends on the culture of your organization. If they support that, if they let you make mistakes, if they let you fail in order to achieve a bigger goal, that’s quite an important thing. And I think one of those things that we did that’s managed to filter the things that we really needed to do, other than just the loud voices, was about setting up a framework for the team, which was using the OKRs model, which is objectives and key results, because we can always attribute the objectives towards organizational goals, but then that cascaded down and the key results are the things that were leading to the objectives, and then the tasks were the things that are leading to the key results. So we could then show that everything we were doing with our time being spent was attributing towards a greater goal.
And if there were requests coming in that didn’t correspond to our key results or objectives, we could say no and say this doesn’t contribute towards this. So we had backup by that framework.
Training, Failure & Growth
Irina C (19:40)
Steve, I really liked you touched several things that later on we’ll dive into. So we’ll dive into the data, into the reports. Hopefully the time will be generous with us.
I want to answer because you have a particular question, Steve. Somebody, Jesper asked you, did you follow any trainings when you were aware that things weren’t going as planned? You mentioned at the beginning your first time experience as a manager was not an ideal one.
So what did you do to reverse this this part?
Steve (20:23)
Yeah, so I previously, probably about, I don’t know, maybe about six or seven years before I’d adopted this role, done an ILM level five leadership and management course. But it was, I couldn’t really remember a lot of what I’d done in that. Things had moved on.
Everything that I’d done was really self-taught. I didn’t have any specific CS leader training programs or anything that I’d done. You know, when I started doing CS, it was quite fresh and it was quite new.
And I was learning from the practice that was out there in the community. So I was learning from my own mistakes. And there wasn’t, you know, there was no one really to sort of, sort of coach and mentor me in that role of doing that because there wasn’t any precedent.
You know, quite often it’s great if you’re operating as a CSM and you’ve got a head of and you can learn from them and learn how to do things and grow into that role when you’re just working it out and you’re pioneering and you’re trying it out. There’s no rule book or there’s no instruction manual, as it were. So you’re just trying to adapt as you go along.
You know, in terms of trying to turn that around, I spent a year being head of CS and I failed in that role. I didn’t achieve my objective. So I kind of moved sideways then.
And I then had to sort of swallow some humble pie, as it were, and then come back, as it were, and build and grow. So it was a different little route that I took. And I think also the business learned a bit more about it and about the role and the team, the department.
I had to kind of, yeah, take a different path and demonstrate results and move the team in a direction without it being a sort of recognized responsibility. I had to kind of re-establish my leadership within the team. So it was an interesting route.
But also what we needed from the team and customer success changed and evolved at that time as well. And we started recognizing our differentiators in customer success and what we were doing differently. And the actual configuration that we then evolved into was very different from that initial one.
So it was, yeah, an interesting route.
Irina C (22:51)
I think you are the first leader and the first guest that speaks directly and admits the fact that he failed in his role. And I think this shows, I don’t know, authenticity. And yeah, thank you for sharing.
Also, the part that we want to forget about it, where we are ashamed of sharing it, because we have the feeling that nobody went through this path. So yeah, I think I’m going to do a webinar about all the failures, and I’m going to challenge the guests to speak about the things that they didn’t manage to do. Yeah, it’s funny, isn’t it?
Steve (23:35)
Because we don’t talk about that. But that’s where the growth happens, isn’t it? It’s actually where a lot of the magic happens when you literally have to swallow your pride and admit that you’ve done it.
And it’s that being objective and authentic. And it is challenging at the time, as a human being. But then you look back, and it’s interesting, actually, revisiting that period of my life in preparation for coming to do this has been almost like a cathartic experience as well.
But yeah, I mean, I guess if that was it, I failed and I went off with my tail between my legs and ended up down an alleyway drinking vodka or something like that, then maybe I wouldn’t be sitting here talking to the audience. But thankfully, I managed to find another path and learn from that and grow from it.
Early Wins
Irina C (24:28)
But if you also see the wins, what were the first big wins look like when you managed to succeed in the role? Maybe something small, but that gave you momentum or confidence that you are heading in the right direction?
Steve (24:51)
Yeah, absolutely. You know, that first 12 months, I struggled to think back of where I had any wins. It felt like the whole 12 months was spent swimming against the tide.
For me, the big win actually came a little bit later, when I’d, you know, step back from that position. And it was a less formal sort of leadership. And it was, you know, maybe at the time, you know, when your career trajectory is just going like that all the time, you’re always chasing the next level and the next thing and whether there’s a bit of pride in the status or whatever.
But that having that sort of humility thing, then it was like, well, I don’t really care about the title or the status, I’m just going to try and do good things. And I know where this team needs to go. And I know what we need to be doing.
And putting in that structure, that framework of using the OKRs and being able to ensure that the team were all working together on the right things, the things that impacted the business. The big win for me was when we did our first quarter where the OKRs were in and everyone had bought in and we worked really hard as a team together to achieve that. And we hit all our objectives, you know, smashed our goals.
And we were able to communicate that and present that back to the business. I put a nice PowerPoint together to show what we’ve done. So I could communicate those wins.
That was really kind of a special moment for me, because it had everything. It had the ability to demonstrate what we’re doing is contributing towards the business, the tools to communicate it so that other people in the business could understand. There was the team cohesion and everyone, you know, feeling good about working towards the same thing.
So everything was all really clicked into place. And that was the first really big win for me.
Path to Head of CS in Small Teams
Irina C (26:44)
I’m going to pause for a second and have a look at the audience before we are moving to the next topic, because I want to make sure that we answer all the questions coming from the live audience. And I let the two of you decide who is picking up this. We have any tips for a CSM lead to achieve the head of CS position on small teams, potentially only managing one to CSM as the team is pretty small.
Irina, when you want to try, will you try to answer it? And then I’m going to let Steve continue.
Irina V (27:30)
Yes, for sure, for sure. So first of all, I think it’s important, even in a small team, to talk about this idea with your manager, make him know that you have this intention because your manager is there as your mentor and can guide you and help you with tips and tricks. And you can set together some goals in order to know what’s the path that you have to take in order to get there.
And second, if you are thinking you don’t want to share that with the internal team and you are looking to transition into a different company, I think you have to be prepared for chaos. But in the same time, you have to be super proactive and to be involved into the daily operations and into the daily things that are happening in order to already as a CSM to take some load from your manager and from the ones that are building the internal processes in order to have already the knowledge and the experience to be prepared for what the role requires.
Irina C (28:38)
Steve, what’s your advice?
Steve (28:42)
Yeah, I guess it’s you’ve got to be clear about the reasons why you want to do it and is that for you. And you know, it’s because it’s not something you kind of step into lightly, as we’ve already talked about. It’s quite a challenging thing.
And no matter how prepared you think you are, there’s a lot of unexpected things that happen. So I think you really need to be ready for that. So you need to take a look at yourself and see if you’re ready to if you really want it, because you’ve got to really want it because it’s something that you’ve got to kind of live, breathe, eat, sleep for the foreseeable future.
So you’ve really got to want to do that thing. You’ve got to build some resilience in yourself to be able to take the setbacks and be able to succeed in it. And does the business need that role?
You know, is it ticking over? Where’s the gap? What is it missing that that role is going to fulfill?
Because they’re not going to pay you extra money and create an extra role and give you that title unless the business actually needs it. So having those conversations with the business. But as Irina touched on there, it’s like, ooh, is someone else want to do that as well in the in the team?
Do you talk to them about it? Or do you, you know, and that’s an interesting one. Again, that depends on the culture of the team.
It might be clear that you’re automatically already stepping up and showing yourself to be a leader and the business might approach you and offer you that. So it depends on whether you, you go to the business and say, hey, I want this, or whether the business comes to you and say, hey, we’d like you to be this. So it really depends on your situation.
But either way, you’ve got to really want it. And it’s got to be something that motivates you to get out of bed in the morning and be realistic about the challenges ahead.
Pitching Yourself for the Role
Irina C (30:30)
Steve, I want to ask you an extra question on this topic. What if you decide that you want to take the role? How do you present it to the leadership team?
Do you go with, hey, I think I deserve it? And this is why I deserve it? Or how do you pitch it?
Do you prepare a business case? Do you show how do you, how do you prepare for the discussion of I want to take the role ahead of CS? How do you prepare for this conversation?
Steve (31:03)
Yeah, I proposed it to the business. And so I did go about doing that. And I think for me, it’s because I just saw this natural progression that I kind of wanted to be the next level in that role.
And I felt like I was doing a bunch of the things that a head of CS should do. And the reality then once the business makes, you know, if you’re pitching it to the business, I think you’ve got to work a bit harder to prove the value of yourself in that role. You know, later, when I came back into leadership role, it was something that the business then offered me.
So it was a different way around. It’s almost like I grew value in the business was offering me something to differentiate it from being a regular CSM role. But pitching it to the business, yeah, you got to be convincing, and show where the opportunity is, and why, you know, why the business needs that role, and why you’re the best fit for it.
But you’ve then got to back it up and prove it. So you can’t, you know, over promise and under deliver, you’ve got to manage that, but not set yourself up for a fall by promising too much to the business by picking up what your capability is in there. So it’s, it’s a fine balance, really.
Reactive to Proactive: Defining Strategy
Irina C (32:28)
Thank you for this addition on your on your answer. I remember the first time when I wanted to be the manager of the team. And the VP of marketing told me at that point, you aren’t ready.
And I was like, how can you say I’m not ready? I was the best specialist, I know all the metrics, and I was under the impression that the next best thing for me is leading the team. Well, only now I can say that leading a team is totally different than being a specialist.
But that’s my that’s my story. I want to put the analyst question on on screen, because it’s perfectly ties up with what I want to what I want to discuss. But before we go into what I have prepared, let’s answer her.
So she is sharing with us the challenge that myself and my team was to do a mind shift change as we come from a customer support background, those being reactive versus proactive. We are now at the stage of defining a strategy. And the question is, how does one define a strategy that makes sense to the business role players?
Irina V (33:46)
Yes, so I can take it if, if I may, because we were in the same situation at the beginning. So five years ago, when I took the role, we were still a small team, and we were covering both support and CS. And it was a continuous challenge.
But in the same time, it was a bit hard for us to define the separation and to draw a line between the support and the CS teams. And I can tell you that we are the CS team, we talk about productivity, and we talk about quiet time to spend on customer analysis about strategic guidance and all of that that requires focus. And if you have a lot of context switching, you will not be able to deliver on that.
So you will always be reactive in the end if you are handling both support and CS because you will not have the mental capacity, the mental space to do that. Imagine you start the day with the answers on email or Slack or tickets or whatever. And then at the end of the day, you have to focus on the proactive part, but you will for sure fail because your brain will not let you do that.
And you will say the next day and so on and so forth. And you will just postpone the proactive part. So in the end, you will fail because you will not do the CS job, you will still be a high level support or yeah.
So we realized that and you have to have a business case indeed to present a bit what to analyze, what is the proactive work that your team is doing, what are the proactive processes that you have in place and to estimate the time that your team needs to focus and then to build some start with some small processes to separate the things who should be in charge of the reactive things and who should actually focus on the proactive part and you will see immediate results.
In the beginning, it will sound like okay, but we will not have work to do for the CSMs anymore or something like this. But then you will realize the impact that taking out the reactive work from your CSMs will actually bring to the company.
Irina C (35:57)
Steve, you want to add on what Irina said?
Steve (36:01)
No, I think Irina covered it perfectly there and in nice detail as well. There’s nothing more to add to that.
Processes That Support Strategy
Irina C (36:09)
Okay, then I want to deep dive and I want to talk about the processes, basically the processes that supports the strategy and I want to divide them and allocate to different roles. So Irina, I want you to talk about the business processes, the customer facing processes, the onboarding, the renewal, how you build it and why you build it and what are the mandatory things when you first establish a team. And then Steve, I want you to talk about the internal team processes that you need to have into a team to make sure that it’s properly managed and managed and run.
And for a manager to be able to see if the team is at the full capacity, if it’s burnt out or not. So what do you need to have in place to make sure that your team is okay and what do you need to make place, what do you need to have in place to make sure that the CS is aligned with the business strategy and is delivering in line with what the company wants. Irina, we talked with the business side and then we switched to the team.
Irina V (37:26)
For sure. So first of all, when I started, I was lucky enough to have Custify and it was already fed with data. And the first thing that I did was to take some time to assess the current customer journey and see where are the gaps.
So this means that I started listening to calls, joining customer calls, reading feedback notes, analyze the reports and churn feedback and all the whatnot. And based on this, I identified the key friction points in the customer journey and where process would really make a difference. Based on those insights, my first focus became onboarding.
And I think everybody here in the audience heard about the fact that onboarding is crucial and usually determines whether a customer will renew later. So I sat down with the team to discuss how we could make it smoother and more consistent. And for example, a key part of this was the sales to CS handover.
From the first weeks, we streamlined the process and worked together with the sales team to ensure that all customer details were captured early on, that we went very well informed into the customer calls in the beginning. And yeah, we made sure the transition from sales to CS was good. Then we analyzed what other pain points were during onboarding that we realized customers needed more guidance.
So we reiterated in order to make the onboarding process as smooth as possible. And in the meantime, because I mentioned that I had to do an analysis and to come up with some ideas and to build the process. But in the meantime, we were still, we had to not be surprised by churn and to still have help customers, of course.
So in order to gain that time for the strategic work and for that analysis, we first actually implemented some triggers and alerts. So basically to not be surprised by customer behavior and by health drops, we started by creating some important, some alerts for the important triggers that we were seeing in the product, like health scores dropping or product usage decreased or things like this. So we were constantly being informed about the things that were happening and we could act on those, even if in the back end, we were working on other stuff.
And basically once we finished with the onboarding and once the onboarding became more consistent, we started mapping other key inflection points throughout the customer journey. And we prioritized processes that address the most critical gaps that we have. And I can tell you that our next focus was on adoption and customer success plans rather than renewals, because for us, the renewal is the natural outcome of the consistent engagement that we were offering.
And the renewal process itself, it’s fairly straightforward. We basically just run a call similar to a business review where we include the renewal details. But in reality, we work on the renewal all year long and I advise you to do the same through proactive touch points and success planning.
So again, by continuously engaging the customer, you don’t rely on that last month push before renewal to turn a detractor into a promoter. And yeah, again, make sure you don’t, you are not surprised by unhealthy customers.
Set some safety nets there to make sure you capture everything that can surprise you and in parallel, analyze the gaps that your customer journey has and act on those.
Irina C (41:25)
You know, you have a question. In your transition month, did the sales team stay involved with the customer for growth sales opportunity or did the CSM own the expansion sales? If sales and CS co-managed the accounts for growth, what friction points did you experience and how did you handle them?
Irina V (41:49)
That’s a very good question. So as I mentioned, for us, the transition from sales to CS was a critical point. And we even had in some situations, not always, sometimes it wasn’t needed, but we had the sales team staying involved during onboarding and even joining some calls, especially where there were more complicated use cases or where there was a long history in sales and we didn’t want the customer to repeat everything that was discussed.
And we discuss each case by case, but the sales team is available for help. And in the same time, we are available as a CS team to join the sales team when needed in order to make sure the prospects are really well handled. And we answer all the questions there.
And regarding the growth opportunities, we handle the renewals in the CS team. So the CSM handles that. But when it comes to expansions or other negotiation or anything like this, the sales team jumps in.
So basically, we identify the opportunity and then the sales team continues the conversation just as they have different skills and it’s more efficient like this. We collaborate, we are together there to ensure the best customer experience that’s possible.
Internal Team Processes & Cross-Functional Alignment
Irina C (43:14)
Thank you. Steve, you also have a question that I’m going to address after asking you about the internal team processes, the ones that keep the team running smoothly behind the scenes.
Steve (43:32)
I’ve already mentioned implementing OKRs so that all our actions align with organizational goals — that was a real game changer for us.
Another big shift has been what we call the three P’s: People, Process, and Practice. As you develop people and build trust, they start to demonstrate good practice. At that point, you can relax some of the process elements because it becomes muscle memory — people do it naturally.
When you implement a new process, you have to design it, implement it, pilot it, and police it until it’s embedded into daily practice. Once it becomes part of how people work, you need less oversight. I started noticing my new CS team could pick up and integrate new practices quickly.
Of course, introducing anything new comes with some pushback — you’re working with smart people who have opinions, and that’s a good thing. Healthy debate helps refine ideas. People will only adopt a new process if they believe in it, and one way to achieve that is through co-construction.
Let them contribute. Sit down, talk, listen, and share ideas. Often, they’ll come up with better solutions, which is a double win — you get better processes and greater buy-in because they helped create them.
Another key shift was opening processes beyond our department. For example, in our software release cycle, we run six-week sprints involving Product Design, Help Desk, Operations, Marketing, and CS. Everyone collaborates — from customer communications to media assets, webinars, and internal training.
This cross-department collaboration created real cross-pollination. Everyone now understands what’s being released, learns about new features, and upskills together. The CS team has to master new functionality before customers even see it, so being part of the release process helps tremendously.
We also invited other departments to engage more with customers. Our Product and Design teams now join customer calls, visits, pilots, and testing sessions to get direct feedback. They love it because it connects them to the real problems they’re solving instead of getting second-hand information.
So, one of the biggest internal shifts for us has been opening processes across teams and departments — creating alignment, collaboration, and a shared sense of ownership for customer success.
Making the Business Case for More Capacity
Irina C (48:41)
I really liked your answer and I really like the fact that you touch the cross-department thing not only into the team. I think you have a question and I think this is for you Steve, I know my team is at capacity but our ARR isn’t very high and the business doesn’t see another CSM as a reasonable investment but our churn is starting to grow and we need to act more proactively than ever.
How do I make the business case? I can relate to this, I know that Ana Maria is not the only one who is feeling this pain so I really wanted to put it on stage.
Steve (49:27)
I had exactly the same situation when I was Head of CS. I was pushing for a new CSM but also for resources in other areas. When the help desk or support teams were short-staffed, CSMs had to step in and fill those gaps.
Because we were responsible for customers, it often fell on us to cover for other departments — something that isn’t always obvious to the business.
So, it’s not always about hiring another CSM. Sometimes it’s about reducing the range of responsibilities your current CSMs have. Look at it differently — your goal is to make leadership aware there’s a problem.
If hiring another person isn’t possible, consider bringing in lower-cost roles, like support staff, who can take some workload off your CSMs. They don’t need to have the same skill level or salary, but they can relieve pressure so your CSMs can focus on strategic work. If they’re constantly dealing with reactive tasks, they can’t truly fulfill their role. So the solution may not be a new CSM, but redistributing responsibilities within your existing team.
Irina V (51:17)
Yes, I want to echo what Steve said and add that, until you convince management to hire another person, you still have to survive. Make your processes as efficient as possible, communicate clearly with your team, and prove the value you’re delivering.
The real challenge is that management doesn’t always see the value of the CS team. It’s our job to demonstrate it—just like we prove value to our customers, we need to prove it to leadership. Once they understand that value and you find the right way to communicate it, it becomes easier to negotiate for new resources when needed.
And as Steve mentioned, a new resource doesn’t always have to be another CSM—it could be someone in support or an assistant who takes some load off the CS team without adding high costs. Think creatively about how to make your team’s work more efficient without significant expense.
Steve (52:30)
Also, get clarity on what’s going wrong or not working. Is churn too high? What specific risk are you trying to solve with an additional CSM?
If you can gather that data, you can present a stronger, data-backed rationale for hiring. When you frame it as “we’re losing more revenue than the cost of a new CSM,” leadership is more likely to listen.
It’s challenging, especially when you’re already stretched thin supporting customers. We’ve faced similar issues with overloaded CSMs. The solution wasn’t always to hire—it was to adjust our practices. For example, we realized we were giving customers too much attention. By reducing meeting cadence—from weekly to biweekly or even monthly—we freed up capacity without hurting the customer experience.
Leadership Style & Self-Awareness
Irina C (54:01)
Steve, how do you stay direct, realistic, and aware of what’s going on while also working on the bigger picture—upsells, expansions, growth, and building strong customer relationships? What’s your secret, and how can I track its impact on overall growth?
Steve (54:31)
I don’t think it’s magic. I think, realistically, we often surprise ourselves as human beings. If you’re invested in a topic, if you have passion for something, the rest comes with experience and not being afraid to fail.
It’s also about being genuinely curious. If something’s not interesting, you’ll stay within what you know. But when you’re curious, you start asking — how does that work? How does this impact that?
My career path has been varied. I started as a graphic designer many years ago, then moved through roles like project manager, account manager, business development, sales, and marketing. That variety helped me understand different teams, what makes them tick, their impact metrics, and what matters to them. It helps me empathize, have real dialogue, and balance their needs with those of my team.
Don’t be afraid to get up, talk to people, and build relationships across the organization. The more you understand and learn, the better you can support others and succeed together. A business is more than the sum of its parts — it’s about everyone working together toward the same direction. If you’re only pulling the rope your way, you’ll struggle to get your voice heard.
Irina C (56:39)
I am going to take two more questions: Although I have a team I’m struggling to find information that explains how many roles a true CS team should consist of.
Irina V (57:01)
Yes, so you’re not the only one struggling with that I can tell you we work with the CS teams and I’ve talked to hundreds of people and everybody has the same issue and I can tell you that the role is defined by the business and the organization.
So there are CS teams that report to sales or to head of operations or to head of CS or whatever this depends of every business is so different and I think the definition has to come from the internal people that decide from the internal management team and you as a leader are also responsible to define that role and for your team because we cannot be everything.
We will not be good at doing everything you are responsible to analyze what really impacts the success of your customers and what are the things that you can own and if you feel that it’s something that you cannot control that then it’s probably not your job to do that because you will not succeed wearing so many hats in the same time so ask yourself does it help the customers succeed and if the answer is yes and you have control over that probably it’s it can be in the job description.
Irina C (58:14)
I think the next one is for you, Steve. What is your view on using an MLS instead of having CSM running platform trainings as part of the onboarding? That’s an interesting question.
Steve (58:33)
Our company is an LMS company so yes have an LMS I don’t know it’s an unusual question you know there’s two different modes of delivery there like in an LMS you can do lots of things with it and deliver different modes of learning and the CSM running training suggests it’s some sort of face-to-face workshop or something like that.
A CSM can run a workshop through an LMS so they’re not mutually exclusive but by any means but I think that’s more a learning and development question and it depends what the is trying to what knowledge is trying to be gained or what skill or competency it depends on the nature of the learning outcome and then you define the mode of delivery as a result.
If it’s just that people need to know some basic stuff and you’ve got some just some tick box learning then you could just do an e-learning module with a multiple choice question at the end you can distribute that out and replicate it multiple times with minimal effort that might be the tool for the job.
But if you’re trying to help people learn how to perform brain surgery then answering some multiple choice questions is not going to you wouldn’t let them loose on your brain after doing that so that might need some you know coaching mentoring support and a longer a longer journey of learning I think it’s the whatever the learning outcome is that you actually want what what you’re trying to help people do is it be better at something or or know more about something and I think it’s the outcome that then defines the mode of delivery.
CS Before Product-Market Fit & Closing
Irina C (1:00:18)
With the permission of everyone I know that we basically ended the session I want to answer because I promised that we’ll take all the questions I want to answer Alicia and then we’ll wrap up and I want to propose a thing for all of you so bear with us don’t jump well because I have an offer that I want to propose to everyone who is watching us live because we only managed to go through 33 percent of the things that we have prepared for you so we want to announce a take two but bear with us for a take two not before we are answering Alicia’s question what are some best practices for leading CS before product market fit how to
Steve (1:01:07)
I’m not sure what that question means is it that you’ve got a CS team and you’ve got CSMs and you’ve got a product but you haven’t really found a market for it yet and you’re you want the team to be promoting and encouraging the use of the product and trying to achieve success with it but you don’t even know who you’re selling it to yet
Irina C (1:01:42)
Exactly I think you cover it up pretty well I think you discover I think you describe this very well. Alicia can confirm it she’s still online with with us I think that here.
Irina V (1:01:55)
We cannot talk about renewals or anything else it’s only about the customer journey itself and the way they adopt and learn how your product works I guess so everything else applies um a proper onboarding proper success plans in order to make sure the the customer successfully adopts the product and yeah any insights are welcome here in order to understand exactly what you’re
Irina C (1:02:29)
I think we can take it also offline and we can come and we can come back also I want Juliana to let us come back offline she is asking about specific tips for those leading the CS team for a service not a product our case is a business membership so we’ll we’ll take this we’ll take this offline and because we’ve reached out the end of our time today and I don’t want to rush through the rest just to squeeze things I’m thinking how about we do a part two of this session in a few weeks we can pick it up right where we left off and go even deeper plus it will give you time to think about what you’d like to ask Irina and Steve directly next time so you ask the questions instead of instead of me let me know in the chat for those of you who didn’t drop if there’s something this is something that you’d like us to to happen and for sure we can organize it in in a few weeks and while you are typing that in for the ones who are still with us I want to take a moment to thank both Irina and Steve for sharing so many honest and practical insights and of course to everyone who joined us live today if you want to revisit anything don’t worry the recording will land in your inbox soon and if you want to keep learning check out the other sessions our Custify webinars series.
