Here’s a new episode from our podcast – Mastering CS, Candid Leader Insights. Irina Cismas, Head of Marketing at Custify, discussed with Amy Newbury, the Head of Customer Success at Kleene.
In this episode, Amy shares amazing insights about her journey in CS, the challenges she overcame, and the strategies she implemented.
What You’ll Learn:
- How to scale your CS department
- How to structure the CS customer success team
- What to prioritize in customer success
- The importance of the right tool stack for CS
- How to upsell and cross-sell
Key insights and takeaways for CSMs based on the interview:
Strategic Focus on Retention and Upselling: The discussions emphasize the importance of having a clear strategy focused on customer retention and upselling. Identifying high-risk accounts and working strategically to retain them is crucial, as is the excitement around shifting toward a more upsell-driven approach in the future.
Balancing Experimentation with Core Objectives: While it’s important to remain open to new ideas and experimentation, there’s also a need to maintain a strong focus on core objectives. This involves carefully selecting which new initiatives to pursue without derailing the team’s primary goals.
Importance of Customer Relationships and Trust: Building and maintaining strong, trust-based relationships with customers is critical. These relationships make conversations easier, help mitigate risks, and are essential for long-term customer success, even in the face of potential churn.
Cautious Scaling and Tooling: Rapid scaling and adding new tools or people to the CS team can lead to inefficiencies. Instead, the focus should be on training existing team members to be highly effective, using tools strategically, and ensuring that any added complexity truly adds value.
AI and the Future of Customer Success: While AI is increasingly becoming part of the customer success landscape, its role in fully replacing human interactions is still distant. There remains significant value in having key players within a CS team who can provide a consultative and trusted voice, which technology cannot yet replicate.
Podcast transcript
Irina 00:00
Amy, welcome to Mastering CS – Candid Leader Insights, the podcast where we deep dive into the world of customer success with industry leaders. I’m your host, Irina Cismas and today’s guest is Amy Newbury, Head of Customer Success at Kleene. Amy, welcome, and thanks for joining us today!
Amy 00:19
Thanks for having me, Irina!
Streamlining and scaling the CS department
Irina 00:24
Let’s jump right in. You were promoted to Head of Customer Success again to streamline and scale the department. What was the first thing you did when you stepped into this role?
Amy 00:35
I guess there were a couple of things. I moved into the role at the start of June, and I had a conversation with my C-suite to understand the risk levels they were looking for and the key objectives they wanted me to hit. Having worked in the team previously, before moving up to Head of, I felt there was quite a lot of slack we could trim when it came to client interaction. This might sound controversial in customer success, but being a startup, I noticed a lot of nervousness around not speaking to customers.
I did some analysis into my team’s activity and my own, and found that a lot of legacy customers were receiving a much higher touch experience simply because we were scared of losing them, rather than because they actually required that level of attention or were high-value or high-risk.
So, my first step was to tell my team to get rid of every weekly or monthly meeting in their diaries. Our new standard became quarterly meetings. Essentially, I reduced my team’s workload by a quarter in a single day.
The reasoning behind this was simple: what’s the worst that could happen if we tell a customer, with whom we’ve been having monthly or bi-weekly meetings for years, that we should have fewer but more valuable calls? Most of them responded positively, saying it was a great idea.
This approach was about changing not just the format of how we talk to customers, but also the cadence. By doing more with less, our team gained more headspace and the ability to scale without needing to constantly add more people to the team, which I believe is a common pitfall for customer success teams. But we can get into that later.
Irina 02:43
You mentioned removing the meetings. We’re trying to do more with less customer interactions. I want to put deep dive into this area. So tell me, what does a rock solid plan for scaling the CS department look like in your in your experience?
Amy 03:02
Yeah, I think if anybody had the finite answer on that one, the world of CS would be solved. I’d say that, for me, it is about really creating that value and value-driving conversations when it comes to speaking with customers. A lot of the work that I’ve done with my team has been helping them to feel empowered and feel almost like a consultant.
I think a lot of what we were doing previously ended up being, we’ve joked about it, “vibes-based” conversations. They were transactional conversations. We spoke a lot about maybe people’s personal lives or listened to feedback, and didn’t really know what to do with it.
But I think that actually switching those conversations into being—my line has been always ask that extra question. If a customer is talking about something that they’re working on, feel free to interrogate it. Don’t feel like you need to have all the answers. You can just say to them, “Actually, could you explain a bit more about that?” or “What does that mean for the business by you doing that?”
That means that you start to get into the deeper value-driving conversations that then help you spot opportunities, spot risks, and then allow the customer to come away saying, “Actually, that was a really useful call. I’m glad I was on that,” as opposed to, “I have to have this call.”
Structuring the CS team
Irina 04:33
How did you structure your team to make sure that they are efficient, I would say, and they are working, I would say smarter, not harder?
Amy 04:47
Yeah. So I think a lot of what it’s been for me over the past year and a bit has been around training up my team, empowering them, and promoting them. It’s about making sure that they feel valued in their role, but also have a very clear path for them to progress.
Because, like, I know with a lot of startups, people can end up having—everyone’s a VP, right? Everyone’s got this lofty title, but I think there’s actually no greater feeling than saying, “You’re here now, and you need to be here.” If we build this framework together, agree on it, and then check in one month, three months, whatever it is you think that person needs to do, and assess that criteria that you’ve set out, then it means that you, as a leader, end up having more people who operate in the way that you need them to.
So, I know that some customer success teams end up having people who come in and negotiate for them. Personally, that’s not how we’re set up anyway. We’re not a big enough team to warrant that, but I think that being able to negotiate, hold your ground, and know where our line is, is a really empowering thing for a customer success manager to then move up into being a senior customer success manager, or even a head.
So, I think that the idea is that you help your team rise around you, so that you can do more again with less, which seems to be the theme so far today.
Irina 06:22
Do you think it’s much easier when you are promoted internally? And when I say easier, I mean you are more successful in the role of holding up if you were initially part of the team, and you know how it works. So you’ve been there.
Switching roles in CS
What are the pains of the CEO of a CSM when you get promoted as head of CS and when you run, actually, the team? Would you consider this as your advantage, the fact that you’ve been part of the team?
Amy 06:58
You know, as you were asking that, I was actually thinking—not to sound like a politician—but there’s a yes and a no to this. One of the problems with getting promoted internally is getting people’s mindsets to switch to see you as a person who can offer this new thing, as opposed to what you were offering before in your previous role. I think that’s the same with any promotion. There’s always going to be that person in the company who remembers you from day one when you made a huge mistake or didn’t say the right thing in a meeting.
It’s almost like that youngest sibling thing—everyone remembers you when you were four years old, as opposed to now when you’re a grown adult with a four-year-old. I think that’s something you need to overcome on a personal level. You need to think, “I need to have this executive presence, and I need to go into these meetings with the C-suite that I was never privy to before and hold myself accountable for my department in a way I didn’t have to engage with before.”
But on the flip side, if I were to just start fresh in this job, clean, it’s an incredibly complicated tool, and the fact that I didn’t need to learn what it does, and I didn’t need to learn the customer base, meant that I actually was able to say, “These are all things I’ve been wishing I could change before and couldn’t.” I didn’t have to think about that. So, I think there’s good and bad to both sides of that situation.
How to balance clients and leading a CS team
Irina 08:39
How do you manage the balance between being hands-on with clients, I know that you still are, regardless of the bottle of the head, but also leading the team at the same time. How do you balance the two parts?
Amy 08:56
Yeah, I think it’s something that, at first, when I took over the role, I was potentially struggling with a little bit more. For full disclosure, I didn’t lose any of my customers when I took on additional responsibilities. Actually, my customer base has grown in the time that I’ve been Head of. I remember having a conversation with my CEO, and he was like, “You’re just going to have to learn to change hats.”
At any point, you put on your CSM hat, and you are a CSM—that’s all that you do. You listen to customers, you have those value-driving conversations, and you keep your eyes on renewals. Then sometimes you’ve just got to put on that other hat and deal with a difficult situation with your team, whether it’s dealing with a difficult situation for one of your team members’ customers, thinking strategically, projecting, or doing all of those things that you need to do as a manager.
But equally, I think you should never let your experience in one role affect the other too much. I think you need to retain a certain sense of separation. If I interacted with all of my customers like they were more important than my team’s customers, that would make my team incredibly demotivated. Similarly, if I let all the baggage of my day as a CSM—like hearing some bad news from a customer or going through a tricky time with a renewal—affect my direction and plan as a manager, that would then impact my team. It might also impact the conversation that I then move into as a manager.
I don’t want to create a biased opinion when I go into a management meeting, for example. I need to keep that balance, and I think basically separating the roles is the only way you can do it.
How to focus on what matters
Irina 10:48
How do you make sure that your team is focused on what really matters?
Amy 10:56
I think it is about working out those priorities with the company as a whole. To give an example, when I took over the team, we’d had a really tough year in 2023, as I think a lot of SaaS businesses had, and a lot of businesses in general. This meant people had been made redundant in our customers’ teams, and people were more nervous about buying long-term contracts. So, it had been a really tough year for retention.
Basically, the task that I set, and also agreed upon with my C-suite, was retention. We were going to improve retention by X percent. I think keeping people focused, therefore, is about removing all that extra stuff. Particularly in small companies, sometimes you can end up spending ages on a project, whether it’s a health scoring system or revamping how we work cross-communicatively with another department. And actually, you don’t always know what the long-term goal for that is, or it doesn’t necessarily go anywhere, because it’s not the key thing that’s going to move the dial for the business or the department.
So, I think it’s about starting each week with a one-to-one or a kind of huddle with your team and saying, “Right, what’s everyone going to do to fix this problem this week? What is your focus? What are the two or three key objectives that you think will help with this?” I think it helps to recalibrate everybody’s overwhelming sense of having too many things to do back down to some simple ones, like, “Right, we’re going to retain customers. Which conversations this week are you having that are going to help you achieve that?”
Negotiating with the C-suite and managing a CS team
Irina 12:49
I feel like, in some cases, because I do know a lot of stuff end up on the plate of customer success. The role of the manager is to be like a guardian that says, No, this does not affect our KPIs, or this action can wait, because it doesn’t impact the retention. In your case, do you feel like your role in some cases is to say, No, this is not a priority because it’s in between. You are like a buffer between the C suite and your team, and your role is to protect them and make sure that okay, they work on what’s important. How does the negotiation, or this level of negotiation, between C suite and your team work out?
Amy 13:41
Yeah, I think you need to pick your battles. In some cases, it’s about not being too rigid—you need to still be open to experimentation. If you were to shut down every idea that comes up as not relevant to the single goal you’ve set out, I don’t think that’s a particularly startup or growth mindset. You do need to create a certain capacity in your team, or within a month, to say, “Let’s pull this out and not make it a daily thing,” and go, “You know what? We’re willing to give that a go.”
Equally, though, I think you need to have a very strong line as to where those requests are going to derail the key focuses. Sometimes you find if another head of department, who’s new, joins and comes in with amazing new ideas, they might start firing them at CS: “Can you provide us with loads of case studies? Can you provide us with all these stats on our customer base? Can you provide me with XYZ?” And it’s like, “Wow, these would be so many great things to have, but actually, for my team to spend the time to compile this information, I don’t know if it’s going to be better than, potentially, this person living in a certain role,” and just letting my team propagate through, and then learning how to do that.
So, I think sometimes it’s a balance of going, “Hmm, this is worth giving a shot,” and saying, “As long as everybody’s aware of the risk, we’ve got these three really important renewals happening this week—do you want us to take some time out in order to do this thing? Yes, no.”
Then the other side is going, “Hmm, is this request a long-term request, or is it just a short-term sugar hit that someone’s asking for, that’s actually probably going to annoy your team?” Because as they’re doing it, they’ll be thinking, “Do they actually need this? Is this just a plaster over a bigger problem, for example?”
How to prove the value of CS internally?
Irina 15:59
Now, as the Head of CS, you are interacting more with the senior management team. How do you make sure that they see the real value of the customer success, and how do you prove internally, the value of the CS?
Amy 16:20
yeah, I think that is a very good question in that I think as somebody who works in a tech SaaS startup, you want that product to essentially mean that you don’t need to exist right as a company that needs to Be the mindset that something is so good that people stay with it and pay more for it year on year, whether you’re there or not. The true fact of that is that one that’s not how a lot of other businesses work, and I think there needs to be a level of respect across the business about what that means, and therefore the expectation from your customers that CS needs to be there as their wingman, as their confidant, as the conduit, etc.
So I think that some of it goes without saying, however, in terms of proving value, like honestly, money speaks loudly. So if your team is consistently delivering in terms of renewals, upsells, whatever it is, you know, partnerships, referrals, whatever it is, that is actually driving real monetary value back into the business like nobody can argue with the value of that team if you’re you know, if you’re delivering X, like, how the X over what your salary headcount is.
Irina 17:54
Speaking about revenue targets, how do you approach setting them for your team? Is it the top-down directive or a bottom-up approach? I’m curious about how those internal negotiations go.
Amy 18:04
Yeah, we’re actually kind of going through a bit of an interesting transition, which I’m excited about. Historically, we’ve always retained NRR targets, which have been mostly around retention because we haven’t had a clear upsell strategy. We haven’t necessarily had a product suite geared towards significant upsells. We’ve now shifted the product focus, which is really exciting. It’s taken a few iterations, of course, but we’re in a really good go-to-market place. Having gotten ourselves to Q3, we’re hitting our NRR targets that we set out in advance, or thereabouts, according to my projections. We’ve got another quarter and a half to go.
Now we’re looking into next year, and next year is going to be really fun, I hope, because it’ll be all about the upsell value-driving kind of strategy. I think the level we’re going to hit is going to be quite cross-functional. Me and our VP of Revenue, who looks after our sales team in particular, have been starting some interesting conversations around how the two teams can actually work together in a more cross-functional way than we have done before.
But again, it is about being open to other people’s ideas, while keeping that core belief inside yourself about the reality of what your team can do and the reality of what your customer base is like. I know we’d all love to say, “Hey, we can sell 30% more of everybody’s contract value onto every single customer.” But you know that this team downsized last month, or you know that this company has really undersold on their budget this year, and actually retaining them is a much higher priority than upselling to them.
So again, I think it’s about combining your knowledge within the company’s big vision and working out a compromise when it comes to that. Targets are good, but I’d say unachievable targets are actually demotivating, particularly for CSMs who have to manage risk a lot more than the sales team, who are taking on new business, and each deal is brand new.
Delivering on your targets in CS
Irina 20:30
Because you’ve been on both on both sides. I want to ask you, when you’ve consistently hit your targets as a CSM, what’s your secret to achieving that even when the market conditions are not in your favor? What’s your advice for CSMs who are struggling to deliver on their targets?
Amy 20:53
Focus and then mitigate risk. I think one thing that we’ve done much better in the past year has been to keep a really close eye on those higher-risk accounts and work them into renewal in a much more strategic way than before. Previously, we maybe weren’t as focused on this one specific thing, which was retention. Now we’ve got a very clear path to renewal, but also an escalation path as well, and we can find different combinations of people who can really help get these deals over the line.
On a personal level, building a really strong relationship with a lot of my clients has been really helpful. It’s the strength of the product, of course, but it’s also about making sure that you stay really close to your customers, develop that trust, and develop an understanding of their business. Help them understand the value of the platform, and then it makes all of your conversations a lot easier.
I know that’s a really simple thing to say, but it genuinely is true—you’ve just got to gain that trust, be a part of their team, and then your life is a lot easier.
Dealing with customers who are ghosting you
Irina 22:22
Did you also have a situation where customers you had in your portfolio were ghosting you and they were like, I don’t need you. I know my way. I don’t need I don’t want to talk to anyone. Where did you have this approach as well, and how did you deal with those type of customers?
Amy 22:39
Yeah, you’ve got to leave yourself at the door. I think, with a lot of CS management, if someone’s telling you everything’s fine and they just don’t want this call, you’ve got to listen to them. Even if you’re like, “Yeah, but I’ve been told I need to meet with somebody once a quarter to get these five pieces of criteria from each of these calls. Otherwise, you’re going to churn.”
I think the other thing is to take people at their word. I’ve got a stakeholder who’s a customer, and they have an engineering team. They are an engineer at heart, so they’ll meet with me quarterly. But honestly, I’ve shortened our calls. Normally, they’re an hour long for those more general stakeholder-led meetings where you might have people from multiple departments on it. If it’s just a one-to-one chat, feel free to make it a 20-minute catch-up. You’ve got to listen to that appetite from your customers.
Equally, some customers aren’t keen to meet at all. You’ve probably got to put those guys more in the risk bucket and understand that there’s very little you can do if you can’t speak to them and they have no interest in speaking to you. You just need to be responsive to that and then try to engage them across multiple other departments. So, is there a marketing campaign that you think they might be interested in? Are you hosting a webinar that they might want to listen to? You just then have to take that slightly more distant approach to engaging them, rather than expecting that everybody has the time or interest in speaking with you.
Irina 24:17
Did you also get the opposite? And by opposite, I mean, you had a very good relationship with your customer, but in the end, they still decided to part ways.
Amy 24:29
Yeah, we’ve had this as a team, to be honest, and it’s heartbreaking. It’s the best way to put it because you never go down easily. I feel like part of what you do is always try to mitigate this through, you know, looking at their contract value or additional things that you can throw into their contract that will help bring them value. Or can you deliver that one piece of insight that’s going to help make it click?
I think as we scale, we’re becoming a bit more confident at forming that criteria by which you can say, “Listen, the risk to this account is this amount. We believe we’d need to put in this amount in order to save it. And even then, there’s no guarantee that this is going to work. Is this worthwhile?” It will also probably cost about X amount of hours in meetings and preparations. Again, is this worth it?
And I think it’s really sad because you’ve spent such a long time working on these accounts. But at the end of the day, people’s priorities can change, and you’ve just got to start thinking about it more like a business than like a personal relationship. Again, I tell this to my team all the time: “It’s not personal, it’s business.” But it’s hard when you’ve got a customer-facing role because you know where they went on holiday, you know when they got married, that kind of thing, and they become almost like your colleagues in a way.
So, yeah, I think there’s no easy situation when a customer decides to move away from the business. It’s just about making it more of a strategic conversation rather than a personal one.
Account expansion
Irina 26:22
Let’s also talk a bit about the account expansion part, because I know that you’ve had a big role. How do you go about identifying and pursuing opportunities to grow existing accounts? What’s your playbook?
Amy 26:40
Yeah, so as I said at the start, we operate almost entirely on a quarterly cadence with that customer, but within that, a lot has to happen in that quarterly meeting. So, I think it’s about making that an incredibly valuable conversation with them and maybe setting out some objectives at the beginning.
One of the things that I’ve coached my team into is thinking, “What’s the best thing that could come out of this conversation?” So essentially, draw out a few objectives like, “Wow, they could want to proceed with this project. They could want to buy this piece of software.” These are things that I want to get out of this—this is the best case.
What are the worst things that could come out of this conversation? So again, you almost prepare yourself for, “Are they going to say, you know what, we thought about it, we’re not actually sure we’re going to proceed?” Then, going into this conversation, how can you turn this into maybe another call or a different type of conversation that actually turns into saving the account or even upselling them to a different model, or whatever it is that’s not working for them?
Does that answer the question? I slightly drifted from it.
Using the right tech stack
Irina 27:59
It does it. You mentioned that the expansion part is something that will be accommodated in the future as well.
How do you work? Do you also use technology in order to help you identify those opportunities, where to drive that meaningful conversation, because I know that you are a technical person, so I’m curious, how do you use the tools in order to identify those opportunities, upsell opportunities, where account expansion opportunities and not only, maybe also mitigate, where, identify some word, predict some churn.
Amy 28:49
So we don’t have any CS-specific tooling in-house at the moment. I think it’s probably something that we’d look into next year. We’ve gone through quite a lot of change—we’ve got changes in sales, changes in our product offering, that kind of thing. So I think we don’t really have enough evidence to support what the next 3, 6, or 12 months would look like for me to then tool up to make any predictive responses. That was my thinking in keeping this slightly more analog for the time being.
What we do do—so, I am obsessed with projections. I love projecting, and I constantly do it. One of the exercises that we’re going through at the moment is pulling out those opportunities versus our product base, just as a baseline for it. So I think we’re going step by step. One step is to identify some opportunities and test them. If you test them on a certain set of criteria that we’ve set out—five different points—then does that work or does it not work?
From there, you can almost turn that into something a bit more programmatic. Until you’ve worked out what that criteria is, you could spend all this time building analytics, reporting, or whatever, and it could actually do not very much in terms of your decision-making, or it could make you make the wrong decisions because you’re not assessing it on the right criteria. So I think we’re quite early in this, but it’s an exciting possibility. When the time comes and we’re like, “You know what, we’re pretty clear on these key indicators,” that’s when we can bring in more of a technical approach—bring in one of our analysts, for example, or even bring in our tech team to help us move this forward.
But, I mean, we’ve done a lot around pulling out app usage stats and bringing out touchpoints from our CRM system. But again, it doesn’t always lead to the same thing. If someone’s contacting because they’re having loads of technical problems, it doesn’t mean it’s the same thing as someone’s messaging you because they’re really engaged in a positive way. So again, the data isn’t always smart data, and I think we need to test out a few different ways before we can really settle on what good would look like and where the opportunities sit.
Irina 31:26
I think you are perfectly right. And a lot of CSMs that they’ve been talking to are very keen on gathering or monitoring, measuring a lot of data. They have the reports, and unfortunately, they don’t know what the data mean and what’s the story, and you end up in a situation where, and now, what? Okay, so I saw this metric, but I’m monitoring it. I’m looking every week, month, quarter. But what do I do? What does the data tell me? So I think it’s a very smart decision, and we’ll gonna coach you on this, because it’s a smart advice to be able to first of all, test it, understand it, pivot. And then when you know for sure, then try to bring the tools in order to take it to the next level. Yeah. Speaking of advice, because we are almost ending our conversation. What’s one piece of advice on scaling a customer success department that you would like to share with our audience?
Advice for scaling the CS department
Amy 32:43
I think, don’t scale too quickly. This is tough to say to your CSMs, right? Because everybody wants to be part of a bigger team or have fewer problem accounts or whatever. But I think one of the most valuable things, or the happiest place the team can be in, is where everybody’s got a set role. They know what it is they’re doing, and they can do it effectively.
Quite a lot of the time, you can add a bunch of tools to CS, or you can add a bunch of people to CS, and you end up with quite an ineffective mix. I think if you can train up your team to be really effective at what they’re doing, you don’t need as many of them from a financial perspective and to keep your C-suite happy. But also, what they’re doing is more valuable, and each of the conversations they’re having is better. It’s more fun for them. They feel empowered. They’re not nervous going into calls. Equally, they can handle renewals on their own. They can handle tough, mitigating situations on their own as well.
That is one side of it. I think that also, as I mentioned before, not adding a bunch of extra sheets and reporting or tools where they’re not needed can also be quite valuable. You need to have your key northbound metrics, and you need to track them. At the moment, for me, it’s projecting. I’m obsessed with it. I love my projection calculations, and I play with them a lot. But equally, that’s not to say next year it’ll be the same.
I think, again, it’s just about keeping that focus on what you really need to be able to succeed, rather than adding layers of complexity that ultimately just add time into everyone’s week that, quite frankly, you might not always have.
Irina 34:46
Finally, where do you see the role of CS heading in the next few years? And how are you preparing your team for that future?
Amy 34:57
Yeah, I mean, I think anybody who uses tools such as LinkedIn will know that AI is coming in hard to CS. There are lots of AI bots being built that can do the customer-facing role and that kind of thing. But I think, genuinely, that’s quite a long way off, and I believe there will always be value in having some really critical key players within a CS team. It’s just how business works.
I think that you need to be able to master tooling and potentially remove extra items from your job that can be done by technology. But I’d also say that you need to really make sure to become that consultative voice, become that trusted voice, and your job will always be vital to a business.
Irina 35:52
Thank you so much, Amy, for sharing your insights with us today! A big thank you to everyone who is actually listening. We hope you found this conversation as valuable and inspiring as I did, until next time, stay safe and keep mastering customer success. Bye, bye, everyone!
