Blog Webinars and Podcasts

Mistakes to Avoid When Scaling Your CS Operations | Webinar

Updated on April 30, 2024 36 minutes read

Summary points:

What mistakes should you be avoiding when scaling your customer success operations? We talked to Jennifer Chiang, author of The Startup’s Guide to Customer Success, about what it takes to grow your customer success team from one jack-of-all-trades to tens or hundreds of people.
Below are the main topics we covered during the webinar:

  • Building the customer success foundations for scaling
  • Getting executive buy-in for your tech stack
  • Scaling customer success
  • Q&A.


Irina 00:01

Good morning! Good afternoon, everyone! And thank you all for attending this webinar session. Can everyone hear me? And if so, can you actually give me a thumbs up? You have an emoji here. Awesome. Managing a growing customer base is not an easy job, but it is a good problem to have. And it comes with great responsibility. My name is Irina Cismas, I’m Head of Marketing at Custify, and today I teamed up with Jennifer Chiang, which is the author of the book “The Startup’s Guide to Customer Success”, and also Head of Customer Success at Seso, and in the following hour, we will try to crack the code of scaling customer success operations.

Before we dive into Jennifer’s presentation, I want to address a few housekeeping items. All the lines are muted for a better listening experience. We have the question tab, please, on the bottom right of your device. Please feel free to ask questions; we’ll try to answer all of them or as many as we can, depending on the timing. We reserved a generous time at the end of the presentation. A recording of this event will be sent to all of you who registered, and we’ll also publish the transcript of the event on our blog.

Jennifer, thank you for accepting our invitation and being our guest in today’s webinar. I know the audience is eager to listen to your presentation; I am as well. So I suggest we dive in directly, and I’ll pass it on to you. The stage is yours.

Jennifer 02:01

Awesome. Well, thank you guys so much. Thank you, Irina, for the wonderful introduction. Super, super excited to be talking to you guys today about what customer success looks like, especially when it comes to scaling. As Irina said, my name is Jennifer. I’m the author of the Amazon bestseller seller, “The Startup’s Guide to Customer Success”. Also, the Head of Customer Success at Seso. And before Seso, I was the Head of Customer Success at Yep. I’m a veteran of startups specializing in early-stage. So that is your pre-seed, seed-stage, series A, Series B startups. (You) can find me oftentimes consulting for early-stage startups and startup accelerators. It’s really helpful to build their customer success functions, and most so that they can bring in and, most importantly, retain customers.

I’ve created Customer Success teams from zero multiple times and helped to reorganize, refocus and refresh customer organizations to help you get focused back in the game. Of course, throughout all this work, I wore multiple hats, from being responsible for sales motions to the support functions and building internal data infrastructure. After all that startup life, I love that everyone’s putting it where they’re calling in from in the chat. I’m currently based out of the San Francisco Bay area but have lived over half my life, or actually around almost half my life, on the east coast and a few years outside the United States. Now that you know a little bit more about me, I do have a quick poll just to get to know you guys better. Let’s see if we can get this.

Irina 03:35

Do you want me Jennifer to publish it?


Yes, that’d be great.


Awesome. So we have the first poll. Can everyone see it? Super, you can start voting.


Jennifer 04:26

Awesome, we’ll wait maybe 10 more seconds for folks again their votes. Awesome. Awesome. So love that we have, you know, almost half of you guys are also heads of customer success. That’s awesome. Awesome. We got some CSMs in the house. Love it. We have startup founders non-customer successful as customer success ops folks. I’m this is going to be such a fun day. I’m so excited. Let’s go ahead and pull up our next poll, actually.

Irina 04:57

Okay, one sec. Publish poll.

Jennifer 05:06

So let’s see how many startups we have here today. Give it about 10 more seconds to get in your votes.

Jennifer 05:44

All right, awesome. Not surprisingly, as some folks fairly follow me on LinkedIn and see that I talk a lot about startups, we have almost everyone is from the startup here, love that. Love that so much. And we also got some people from Seso outside the startup space. So everyone’s welcome. I think there’s still a lot of really, really great tips and tricks for everyone, though I will say for startups is a lot more applicable.

Alright, we have one more poll; you can get that go in as well. Yep. All right. And this was all about what are some of the customer success scaling challenges that you’re facing today. I mean, we’re all here to talk about mistakes to avoid. And let’s get on the same page of where we are at. So let’s go ahead, and it’s a multiple-choice or not multiple is multi-select. So go ahead and choose as many as apply.

Jennifer 06:49

This one’s a little longer. So I’m gonna give you another 15 seconds to put in your votes.

Jennifer 07:08

All right, five more seconds. Awesome, awesome. So I’m hearing seeing here, you know, a quarter of us have too many things to do. And not enough time, I feel you; I’m in the same boat. And next, it’s like we have a tight or triple tie for hiring, setting up new hires for success, getting good data, as well as retention. Of course, these are all things that we are here to help really help with as customer success functions. And I’m just so excited to be having these discussions with you today. All right, let’s go ahead and get started with some more. And now that we know a little bit about ourselves.

So today, there is a slide so that we’ll be talking all about customer success, you know, building customer success, particularly if you’re as you’re setting up the foundation for scaling, as well as scaling and how to measure throughout. Today, I will also be sprinkling in some common mistakes that I see young Customer Success teams do in each of these sections.

I also want to hear and help you guys on what is the most pressing thing on your mind. So we’ll also be sure to leave plenty of time for Q&A as well. So please do start thinking of any and all questions that you may have and putting them in the question section as you think of them. So let’s go ahead and get started, love.

Oh, wow, we have so many people from all over Colombia, Paris, Germany, and Greece. Wow, I love this. Alright, let’s go ahead and get started.

Building Customer Success Foundations for Scaling

So first, let’s talk about how to build customer success foundations so that you can scale. When building customer success, it is really, really easy to get distracted by all the things that you need to do, and really easy to also get overwhelmed very quickly. And from you know, hiring, building relationships with internal stakeholders building playbooks, segmentation, working with customers managing renewals, and you know, I think you guys can probably all help me make the lives even longer and longer. And, you know, not to mention all the others that just come up at the most inconvenient times. And so, how do we build strong foundations for our customer success teams so that we can scale more quickly?

I gave the answer away in my agenda. But this is where focus comes in. There is a focus that comes with prioritization, understanding how you can spend your time in the most effective way possible to push customer objectives forward. But within that, there’s also different objectives that focus based on the stakeholder. It really is important to get these right.

So three focuses essentially, to build a good foundation for scaling, I really recommend focusing on these three things in this order. So first, on the customer success team level, it is important to understand your charter, you know, what is the purpose of your team in the eyes of the customer. So without understanding how you fit into the customer’s puzzle, you’re more likely to be scaling in the wrong direction or getting inconclusive results more often.

You know, everyone and everything must be rooted in the customer and to be delivering true value. That also includes not delivering so much that can take away from the core value and or model in your core value; a little bit more on that in a moment.

Next, on the company team level, you must have a strong focus on championing the customer. You know, this means that you should be getting buy-in from your leadership as well as your whole company around the power of customer success. And you know, without the buy-in of the power of customer success, you’re going to be spending exponentially more energy and effort. So these relationships are key for scaling.

Lastly, for customers, you want to focus on architecting a complete customer experience. You know, how are you planning to wow your customers and create evangelists in the long term. You know, and without a clear understanding of this, of, you know, the full complete customer experience, you’re going to be building a plane while flying it. And you know, that’s not great for you, your team, your business, or the customers. So each of these things are critical to have in place before you can really scale. And you know, when I work with startups and they’re struggling to scale their customer success operations, it’s usually because one of these focuses are not in place. So let’s go ahead and dive into each of these in a little bit more detail.

Understand Your Charter

Jennifer 11:40

So the first thing is really understanding your charter. So simply put, you know, what is the purpose of your team. And in my book, “The Startup’s Guide to Customer Success”, I talk about a simple framework to help any team determine this, which, you know, the management consultant in me has pitch flooded into a two-by-two matrix.

On one axis, we have product complexity; this is referring to how complex your product is for your customer to use. So, for example, you know, I would say Salesforce is pretty high in product complexity; there are even special roles for Salesforce administrators and Salesforce engineers because it’s just such a complex project to even implement.

An example of how something is low in product complexity could be like a document tracking system. Of course, this is not to say that these things are simple, but rather on the user side is easy to use and understand. You know, I have a document, it tracks how many views and clicks there are much simpler than Salesforce.

Going back to our chart, we can also see that the other axis we have is something called user complexity, which refers to how deeply or emotionally your product impacts your customer. So, for example, you know, a picture retouching tool has a lower user complexity because if say, the service goes down, I can probably wait or hack a workaround. But how are we going to a product like a dog walking service that has a much higher user complexity? Because if anything were to happen to my dog, I would be incredibly upset, and you guys would too.

After we figure out where your company lies on this, it will tell you what your charter is, you know, automate, revolutionize, simplify, or delight. In my book, I also include this fun quiz that you can take with your company to understand where your company falls on this match matrix. I also heard of CS teams having all CSMs to complete this quiz together to kind of see where the consensus is. Also, it’s kind of fun.

To quickly go through each of these four quadrants, I’m not going to go into these in so much detail. But for companies that are high in both product and user complexity, so that top right-hand corner, the customer success team’s focus is to really revolutionize. Revolutionize a way to think about the problem that your product will help them solve and to help guide them throughout that journey.

For those that have not so high product complexity but high end-user complexity, so that’s a bottom right-hand corner, the customer success team’s focus is to really delight. Delight your customers so that they feel valued and taken care of and so that your users, you know, trust you with something that’s very dear to them.

And then for companies that are high in product complexity but low in user complexity, so that top left-hand corner, the customer success team’s focus is then to automate, you know, automate processes that have been headaches for your customers so that they can be more efficient.

And last but certainly not least, for companies who have low product complexity and end-user complexity, so the bottom left-hand corner, the customer success team’s focus is to simplify. So simplify your customers’ lives by making these so easy to understand and process.

So, typically, I see two mistakes when people are trying to use this matrix. The first mistake is that folks forget to put themselves in the shoes of the customer when thinking about product and user complexity. And so remember, the product and user complexity is in the eyes of the customer, not you. Just because you think your product is easy to use doesn’t mean that your customers would necessarily agree.

And then the second mistake that I see people make here is forgetting that things are all a spectrum. If you have something that has a medium user complexity but high product complexity, then you’re probably taking playbooks from both to automate and revolutionize quadrants. Of course, I go into more detail about each of these quadrants in my book, but I hope this helps to kind of set the stage a little bit, you know, again, without understanding how you fit into the customer’s puzzle, you’re going to be scaling in all sorts of different directions, which means that your is not as efficient as not, especially when you’re scaling and there’s so much going on. So, you know, being rooted and understanding what your charter is will help a lot in those moments.

Champion the Customer

Once you’ve understood your charter, the second focus is really to help champion the customer. And it really boils down to two things. First is executive buy-in and overall team buy-in. Of course, the more people that you have, the tougher it is, but even if you’re a one-woman shop, this still needs to be done along with sharing this with every, you know, contractor stakeholder that you work with. And you know, why is executive buy-in and support so important is because if your leadership team doesn’t fully understand the power of customer success and the potential that it has, it’s going to be really tough for you to get leverage, to get resources to really help you and your team and your customers succeed.

Jennifer 16:27

I think Emily Hayes puts it really well here, you know, show your executives how it could have been different. If only someone had been paying closer attention; don’t just focus on this loss, show the potential.

And I think, you know, one of the primary power drivers with executive buy-in is that you can work cross-departmental so much more smoothly when everyone’s also along that same drumbeat. And that kind of ties into this next thing around customer-centric mindset, which, you know, we talked a little bit here and there, and to call my book here, to flourish, customer success must become the company mindset to unlock the biggest opportunities in business.

So we know we started talking a little bit about this, but when customer success becomes that mindset within your company, not only will your customers be able to tell the difference, but you will, too. And, you know, you might be asking, “well, why is that?” It’s because there is that mindset when you aren’t in the room, you know, say that product feature prioritization meeting, or good marketing value prop meeting, you know, even when you aren’t in the room, there’s always someone there championing the customer. And this means that even when you’re a small customer success team, and even a team of one, your customer success function, you can still thrive.

Remember, you know, I hope these, like quick examples, help to illustrate this. But you know, without the buy-in on, you know, the power of customer success, you’re going to be spending a lot more energy, you know, when it comes to scaling because you will have that buy-in already.

Architect a Complete Customer Experience

Lastly, once you’ve understood your charter and champion the customer, and you know, got that buy-in that you needed, the third focus is really architect a complete customer experience. And this is complete in the sense that it’s end to end, not in the sense that it’s perfect, because for sure, as we all know, this is an iterative process.

So I think Christian summarized it really well here; you know, if you want to stand out from the 83 other people that your client interacts with on a day-to-day basis, you must maintain a high level of geniality, even in the most insignificant interactions.

So we really need to be looking at the customer journey holistically, you know, from the very beginning of what ad they see, you know, as early as possible, to, you know, the point when they refer their friends after they’ve been with you for a few years, or, you know, even for a few days. By doing so, you know, you can not only make sure that it flows well but also keep notes on what areas may need more attention.

You know, we’ve also talked about, you know, the, you probably have heard of developing a trusted adviser relationship with the customer and showing your customers that you care, and this helps a lot with that. And again, you know, if you don’t understand, you know, what that customer journey customer experience is like, you’re gonna be building a plane while flying it, which is not great for your team when it comes to scaling.

Alright, great. And now we have a rough idea of how focus can help us set those good foundations for customer success scaling, you know, kind of going back to, you know, we just have so much going on and not enough time. So that helps a little bit with that. Now, let’s go into another thing that you know, some of you guys also chose – executive buy-in for tech stack.

Executive Buy-In for Tech Stack

You know, we won’t do a full poll for this, but many of you guys have had issues getting executive buy-in for the customer success tech stack. Go ahead and either put in the chat or emoji if you’ve had issues with this either recently or you’re currently having issues with this. All right. Seeing a couple of them. Ooh, a lot of thumbs-ups. Yeah. Or yet never, never want to see tech stack as a big issue.

Yeah, this is actually something that even if you’ve never worked with a CS tech stack before, it’s going to come out. Even when you have amazing, amazing buy-in, you still need to get executive buy-in for tech, especially when it’s high-budget items. Yeah, I’m seeing a lot. And, you know, it really is important that we continue to push this forward. As Catherine Blackmore puts it here, you know, it really is time to marry our customer data with programs, technology, and automation. And in that case, it is really important that we work with our executives to get them to see this as well. And before we kind of dive too deep into it, I want to define tech stack a little bit more here, especially for those who have never worked with a CS tech stack before, before we go into how to kind of get that to scale.

Jennifer 21:08

So when it comes to tech stack, you really want to supercharge your team by using tech efficiently. And there’s really four main functions that you want to cover here. So the first is a CRM, the ability to manage accounts. Second is email automation, the ability to automate success. Their data visualization, ability to understand trends. And then fourth is self-service help center, so ability for customers to quickly get that help.

So you know, when you’re small, I really recommend using your flexibility and adaptability to take advantage of the many, many free options that are out there for these things before graduating into more robust systems. This is not only for you to save on costs, but it’s also better for you to understand how customer success can most efficiently function to hit objectives. And I think now, in 2022, there’s a lot of really great customer success technologies out there; there are low costs and flexible options for, you know, customer success platforms, for example.

And even before, you know, talking to your leadership, you also should have a crystal clear clarity in your criteria for getting certain customer success tools. You know, this is not only to help you because sales folks are absolutely amazing in their jobs. And so you need to keep an eye on your keep your eyes on the prize, but also because you need to be able to communicate that same clarity to your executives when you’re getting that sign-off.

And, you know, there’s really three important things that I consider when evaluating tech stack. And that is, what is your current process? what does your team need? and what is your customer value?

I’m gonna quickly elaborate more on each of these things because it can be unclear. So first is what is your current process. It’s really important to understand and feel comfortable with the process so you know that it works. You know, too often, I see folks conforming to the technology instead of having the technology help them. So you know, examples of this is when you start seeing people, you know, even outside of the customer success sphere, say, “oh, I can’t do that because my system doesn’t allow me to”. We don’t want that to happen to us; we want our technology to help us to help our customers as much as we can.

And the other thing that’s really important to understand processes is we need to know if the process is or is not working. Because in order to make things more efficient, we have to understand what it is that we’re trying to make more efficient.

The second thing here is to understand what your team needs. So we’ve probably all seen the problem where we have too many apps on our phone that we end up forgetting or underutilizing over half of them. So we don’t want that problem to occur to our team, especially when, you know, as many of us are heads of customer success. We don’t want that to hurt our team, especially when each new tech item that we add is not only additional research time and budget but also additional training and implementation time.

So before you even start diving into the research, and you know, after you understand the team’s processes, understand what were the biggest levers to help your team. Is it having more accessible data? is it preparing for kickoff calls? whatever it might be, we want to make sure that whatever tech you’re bringing on actually addresses the needs of the team.

Last but not least, you know, the third one here, what is your customer value? So we talked a little bit about processes, and we talked about team needs, but also, you know, the important thing is the customer. So, you know, for example, we can have all the data, the visualization tools in the world, but our customer wants to just understand how to reset their password. Maybe we need to invest a little bit more time into a, you know, self-serve help center, for example.

So you know, these are just three things that you can go into when you’re thinking about tech research so that you have a lot more clarity and confidence. So I hope this framework helps a little bit as you approach your tech stack.

Common Reasons for Lack of Executive Buy-In

Jennifer 25:01

And, you know, even when that’s the case, like, you might be asking, you know, why aren’t all executives jumping in for Customer Success tech stack? Especially even when they have that executive buy-in, and, you know, I usually see three main reasons why they aren’t.

So the first one is not communicating in their language. First, and as customer success, we should all know this, we need to communicate in their language and provide them with the context that they need to understand how a tool could help us. So, for example, the other day, I was working with a CEO who didn’t know what a customer success platform was. And his first guess was Zendesk, and his second guess was Salesforce. And so, you know, this is a really great example of how we need to ensure that we’re all on the same page of what each tool is and why it matters.

And they will also not know and understand the processes of customer success. So translate that for them as well, so that they will understand. So, for example, instead of saying, “oh, yeah, it’s gonna help them prep for ERS in a timely manner”, you know, they might be like, “okay, that sounds good, but I don’t know what that is”. You’re saying things like, we can build stronger key stakeholder relationships if it can provide clients with better, more actionable updates. And to do this at a scale, we need to evaluate this tool.

You can see how that’s a lot more. You know, we’re talking about their language around scaling and building relationships and providing clients with better actionable updates.

So you know, similarly, this goes for getting buy-in from other executives, not only your CEO, your immediate boss but also, you know, how can this tool help marketing get more testimonials? or leads for sales? or even product feedback for the product? You know, how can you communicate the value that it will bring not only to your team but for others.

The second common reason why there’s a lack of executive buy-in here is not communicating the ROI. Too often, we are just putting them on a demo and be like, “you can see the value yourself”. But you’re kind of using the alas frame, or you’ve already done that research. And you know, based on that last bullet point, you’ve also been able to chat with other execs from other departments on why this is important. Well, you need to be crystal clear on the ROI as well. You know, how would this help burn rates? How does this fit into your budget? You know, for example, the most common CS example is that you can get a CSP or a customer success platform. And so, perhaps with a CSP, each CSM can handle more accounts, and therefore you will need to grow your team as quickly, therefore, saving time and energy spent into recruiting as well as headcount.

Oftentimes, we typically put these into dollar numbers such as, you know, if this platform is 25K a year, you know, this can unlock 50% more efficiency, which will save us two headcounts in the next year. And two headcounts alone would be more than 25K a year, so you have a much more compelling argument.

The last mistake I see here is probably one of the most common ones. Just like any of our other customer relationships, you need to show the value early and often. You know, it’s really important for your executive team to understand, from a 10,000-foot perspective, what is and isn’t working for your team, and you know, how they can help you unlock more. And, you know, by having these conversations early, and often, again, you know, at the high-level perspective, when you do propose a tool, it isn’t, you know, out of left field. And you also have advocates in the executive team that can help vouch for you.

Scaling Customer Success

So I want to make sure that we have enough time for Q&A. But one last thing I want to talk about today is metrics. That is something that is another really, really important topic when it comes to scaling. So as much as I want to be able to say, you know, this is definitely how, you know, if you’re scaling, a customer success team, well, you know better by now that every team is different, every product is different, every company is different, so there isn’t an easy way to say X metric will tell you exactly how you’re doing. Yes, there are metrics like retention expansions, NPS, but those metrics are more outcome-focused, a little bit of lag; these measure things that happen after they happen. And while hopefully correlated, it actually doesn’t tell you about the success of your team as you scale and whether your team is actually doing a great job, or maybe you’re probably just so awesome, that everyone’s just, you know, everyone loves renewing, and it’s not because your customer success team is doing much.

So on this slide, I actually want to talk about how I felt about metrics, as I’ve scaled and currently scaling my team to help me better understand how customer success is doing and sort of what our outcomes are. This means that I’m not tracking those other metrics. It just means this is how I’m focusing my time.

Jennifer 29:50

So the first thing is, as I was just saying, have focused metrics. So, you know, like we were adding focus to our customer success organization stuff that we were talking about a little bit earlier, we also want to add focus to our metrics. It’s so easy to get bogged down by, you know, hundreds of metrics if we wanted to, and we want to make sure that we’re focusing our efforts on, you know, I usually recommend like three metrics to start off. Eventually, your team’s gonna get bigger, and as your customer success organization matures, you can ramp that up to five and ten, and so on and so forth.

What I always recommend to folks, especially early on, is not to have a ton of metrics; you want to have three that you can really focus on, and you want to make them a little bit earlier on in the process. Typically, I like to see an adoption metric; you know, how do you make sure that folks are getting onto your platform? Secondly, I like to see an engagement metric; you know, how do you know if folks are still using it time after time? And thirdly, how do you know if folks are coming back, what commitment are they making?

So typically, you see this as renewals or something similar, like a pilot renewal or a trial churn or something like that. So yeah, so because, you know, again, I want to make sure that we’re focusing on slightly earlier metrics because if they’re not onboarding properly, they’re also probably not renewing. So that’s why we put a little bit more focus there.

This ties into my second bullet point, which is graduate metrics early and often. What I mean by that is to keep moving metrics along. So don’t be shy to, what I call, graduate from metrics. For example, for my adoption metric, I can say my very first version is to have people sign into the platform. Great. If only 20% of people are signing on right now, you know, I want to get that number as high as possible, and maybe 90% of whatever percentage makes sense for my product, before I feel comfortable graduating. And then graduation can then maybe look at a customer sign-ins, and then they have to click two buttons because, you know, if they click those two buttons, they’re more set up for success.

You know, I think using a concrete example might help. So assume I assume all people here use Slack. So if I were Slack, my first adoption metric could be a Slack login, and then I might graduate into looking at people who sent their first message, then graduate into looking at the number of people who have joined at least three channels, or whatever that is, so you can start seeing graduate metrics so that you’re going towards that North Star, and really understand what’s going on.

Ties into my last point here; there you go. You want to use metrics to reflect on how the business is evolving. So scaling organizations goes really, really quickly. And so it’s really important to understand how the business, the customer success business, your company’s business, your customer’s business is evolving as you scale. But if you stay stuck, and I’m always a high touch customer success function mentality, without realizing that your data is showing you that your customers don’t care that you’re high touch, you might be scaling in the wrong direction. So you want to make sure that you keep using these metrics to reflect on how your business is evolving.

So it is at least 9:03 where I am; I want to make sure we have more than enough time to do some Q&A. That’s always the most exciting part for all of us. And I already see there’s a couple of questions in the chat. So while I would love to keep going, keep adding more and more questions to that, I know I covered a lot today in our conversation from, you know, mistakes in setting up your customer success foundation for scaling, how you can avoid that, how to get executive buy-in for your tech stack as you grow, and also how to think of metrics that you scale so that you’re not focused on only the outcomes of your hard work but also using those metrics to help evolve your organization as your company scales.

So let’s definitely continue this conversation in our Q&A right now. Also, on the slide, my contact info is up here as well. Let’s definitely connect on LinkedIn. Also, links to my book, “The Startup’s Guide to Customer Success”, is there as well, available on Amazon ebook and paperback. And with that, I’m going to turn it back over to Irina for some Q&A.


1. Examples of non-outcome-focused metrics?

Irina 34:22

Yes, I started gathering the questions in the question tab. I think we can start with me, as you should see the question on the screen. What are some examples of non-outcome-focused metrics?

Jennifer 34:46

Yeah, so non-outcome-focused metrics. When I say outcome-focused, it’s more like, you know, retention, churn, things at the very end of like, that is the outcome, but then something there like little bit not as outcome-focused is, how many people are, you know, using the service day after day? How many people are coming in? Yes, you could argue that those are a little bit more, those are technically still outcomes, you can argue that all of them are outcomes. But I’m not here to argue semantics, but more so about, you know, what is something that is a result of a lot of things going on? Or what is the metric that focuses on? What are those things that are going on? Are they logging into, you know, that step four of your product at a reasonable time? And how does that and then, you know, being able to tie that back in, you know, with your churn or retention, things like that.

I think another one is also like customer sentiment is another example of non-outcome-focused metrics. You know, customer sentiment is such an important thing, you know, keeping that pulse on customers of like, hey, you know, we have, maybe one of our stakeholders is about to retire, or whatever it is, and just like, that’s not necessarily a metric that you need to like, make sure that all customers like X, but it is something that you need to start focusing on, especially, you know, earlier on, we don’t know what is going on, you know, with your customers or whether or not you’re scaling properly is like really looking to like sentiment. So I think those are some examples of non-outcome-focused metrics.

2. Working on new ideas instead of fixing current issues

Irina 36:25

Super. Another question, as a company, I feel we’ll always want to work on new clients, new products, new ideas, but we don’t focus too much on fixing current issues that hamper customer success a lot. Any suggestions here?

Jennifer 36:44

Yeah, typically, when I see this, it’s because, you know, there is a lack of internal stakeholder buy-in or executive buy-in. You know, why are folks not interested in fixing current issues which is hampering customer success? Do they understand the power of customers? Who says “if we’re able to really provide a good experience, aka not a super buggy experience, that actually helps them and helps, you know, helps the business even more?”.

And so I would actually dig in a little bit there, figuring out how they feel about customer success, how old they are, how they view these current issues, especially if they’re really, really big issues, you know, we can always talk about like, the little bug here or whatever, but like, you know, fundamental core product issues or core customer experience issues, of course, sales, whatever it is. That tells me that there’s something a little bit off in terms of the buy-in and making sure that not only you have executive buy-in now, your CEO, CFO, and all that stuff, but also, you know, does product understand? Does engineering understand? You know, does marketing understand? Making sure that we’re all on that same page.

So that, you know, you can make that case of, “hey, you know that big issue that we have right now? We should actually focus on that because that can unlock even more opportunities, more so than, you know, that shiny new thing over there”. So that’s kind of what I say. And that’s kind of what I’m seeing here in this question. Hopefully, that helps.

3. The right customer to CSM ratio

Irina 38:27

For a typical SaaS company, what will you recommend as a proper ratio of paid customers to a customer success manager to drive efficiency and avoid things falling through the cracks?

Jennifer 38:38

Yeah, great question. So this is where, you know, it really depends. And I know this is not the best answer, but it really depends on what your product is and what your users are. So going back to that product complexity – user complexity matrix earlier, that will help you determine what that ratio should be.

So what I mean by that is, and I can try to go back to that slide, if your product complexity is higher, your ratio is going to be a lower ratio, it might be like 1 to 10, hyperbolically speaking, or even 1 to 2, even more hyperbolically speaking. Because, you know, your product is just so, so complex.

But of course, you also have to understand where your users are and kind of that user complexity, how does this tie into the day-to-day? Do they want to build a relationship with you because you’re a really, really core product to them, and they don’t want to have anything happen between you and your product, they want to keep and really have a really good relationship, or are you a sign-and-forget vendor for them? Or are you just helping automate a lot of things and simplify their life so that so they can just move on with their day? That really helps you figure out what you need to do: more high touch, medium touch, low touch, tech touch. And then that will help determine your ratio of the paying customers to a customer success manager to help really drive efficiency.

So typically, you see, with tech touch, you’re getting to 1 to 1000, things like that. For really, really high touch, that’s where you see your 1 to 50s; I’ve seen even 1 to 20s, I’ve seen 1 to 100s, for even high touch. And that’s because you really want to develop those relationships with your customers, and that’s why it’s more high touch. Oh, you know why we’re on that point, high touch, you know, low touch tech touch, it doesn’t mean you have to do just one. If you’re doing high-touch things, you can still do a little bit of tech touch. But what we mean by high touch is that you’re more you’re doing more high touch.

4. Communicating Downtime Issues

Irina 40:59

We have a question from Zack, how do you approach customer communication when your platform is down for more than 24 hours? Who should be sending mass communication? How often should we communicate what’s going on? What this is for a product that is high complexity across the board?

Jennifer 41:19

Oh, well, I mean, if it’s high complexity across the board, I was wondering why your platform is down for more than 24 hours? Especially since, you know, as a customer success leader, I would want to make sure that my engineering team knows like, “hey, this goes down, you know, it’s going down, like on our side as well”. And so that’s a little bit weird.

Who should be sending mass communications – it really depends on your company and how big it is. Typically, I would say it is usually more on the customer success side because you want to maintain that relationship. We’ve seen folks come from their CSM so that they can have that conversation, and it seems a lot more personal, that they understand, especially when it’s super high user complexity. If Salesforce goes down like, “oh, no, I was supposed to close a huge deal today or something”, for that, you want to make sure that folks understand what’s going on, what you’re doing to help, and that’s where you want to be a lot more, high touch, so to speak, and really curate that experience.

Maybe Salesforce is not the best example there because it’s super SaaS, but I currently work in the agriculture industry for an agriculture company. And we deal with a lot of farmer’s livelihoods and when crops go bad, or, you know, crop yields are really good or anything like that, like, they care a lot. And so we need to make sure that we’re communicating things super clearly, we have next steps, it’s super clear what we’re asking them to do. Like, for us, you know, that high touch is really, really important when it comes to, you know, if something’s down for 24 hours, thankfully, it hasn’t been the case, but you know, if something were to happen, I would probably have the customer success managers, and obviously, we automate that. But yeah, I would probably do something along those lines.

How often – I think this is where it really depends on how often this is happening. If it’s happening really, really often, and people are really pissed off, this is where you probably need, you know, have like a site, I know, you’ve probably seen a lot of those, like status at that or, where you can log in and see the status. You can see that they are typically updating every, you know, 15 minutes to 30 minutes to an hour, depending on what the severity of the situation is. And then being able to, even if you’re still having that high touch mass communication, being able to be like, “hey, you know, I will keep you in the loop. This is where you can also check”. You know, making sure that they’re feeling comfortable, as comfortable as possible in this situation like this. It’s really, really tough.

But to kind of summarize, first figure out why it is happening in the first place. I know things happen, but you want to make sure that folks, especially in the engineering side of teams, know that it’s something that’s super high complexity, this is really important, this should never really happen. And then, you know, when it comes to mass communication, understanding, you know, how do you want to build that relationship, how you want to build that trust advisor relationship and how this has played into that. And then also making sure that communication aligns with the relationship type that you’re working with.

5. Project Management Tools & Strategies for Customer Success Teams

Irina 44:46

A question from Katie. She says, “great presentation”. Thank you. When building out the CS function from a project point of view, what tools do you use to help project manage and how progress to leadership tip?

Jennifer 45:04

Yeah, yeah. So, at the very beginning, this is where we had to talk in the leadership team’s lingo; what language do they speak? Not just like English versus Spanish or something, but more so like, what did they care about? Why do they want to know the progress on this? And like, what matters most to them? And also, what help do you need from them? And then how can you make sure that they know those things?

So most of the time depends on your leadership. Some leadership teams tend to be a lot more like, “hey, I trust you, you got it. I’m gonna just like keep me posted once a week”, and then there’s folks like, “I want to know, every single little detail”. And so find out what works best.

I’ve seen, you know, Gantt charts, I’ve seen, you know, even Google Spreadsheets to keep things simple. So you don’t want a huge thing. But I’ve also seen people use Asanas and Trellos and things like that as well. I would say like, you know, again, kind of going back to understanding what language they’re speaking, what do they care about? And what do you need? What type of things do you need help from them. So like, for example, I need help for sign-off, or whatever it is. So they have a heads up of how they can best help you. So that’s kind of what I recommend.

I also, to be honest, sometimes, especially when it’s, you know, super, super important, they want to be in the weeds. Sometimes it’s not a tool, and it’s just a meeting, and then you just have like a meeting doc, and then you just put, you know, 15 minutes on the calendar or something like that, so that you can check-in.

6. Who Should Engage in Monthly Subscription Renewal

Irina 46:53

Another question from Prince, would you recommend customer success actively engaging in the monthly renewal of paid subscription? Or is that a sales-focused task?

Jennifer 47:05

Yeah, I think this has been kind of going back to this little chart here from my book, it depends on the product complexity and the user complexity. So the reason why customer success should engage in a monthly renewal of paid subscriptions is when it’s really, really high complexity, high product complexity, or high user complexity. And that’s because you want to build that relationship with them and also leverage that relationship that you have with them to talk about their renewal.

I would say, typically, if you’re high touch, I would then question why it’s a monthly renewal, but that’s a separate story. Or if it’s especially with monthly, you may want to think a little bit more about the tech side, or like a tech touch side, because that is pretty frequent. In terms of sales, I think sales will come in if it’s a lot more transactional. And that’s because sales has so many things going on that we want to make sure that we’re also leveraging them for everything that they do so well, but also just kind of balancing like, who are we? Who do we want to build a relationship with our customers? And how do we make that super clear? This is, you know, possibly a really good example of using tech touch customer success. So that you can always have that build, keep building that relationship.

7. Building Your Customer Success Team

Irina 48:27

Another question; going from a team of 1-2 people to, let’s say, 5 or more can be challenging. Any advice on how to handle this part? How do you move from being a one-man show into actually building a team around you?

Jennifer 48:49

Oh, yeah, I mean, this is such a great question. And something that I’ve definitely made mistakes on as I was growing my first team. And so I love that you’re asking those.

So when it comes to growing from 1 to 2 to 5 or more, and I’m assuming these are all CS people, not not the whole company, there’s a really great kind framework that I use from Andreessen Horowitz, the VC (they use it for sales, but I think it applies very much to customer success as well); they call this the Renaissance sales rep. Your first one to two people are jack-of-all-trades, really hungry to really figure out processes, and build things, and break things, and rebuild them, and they can thrive in that ambiguity. And then once you get to that five and more (people), when you’re starting to scale, you actually go away from the Renaissance. Because once you get to five, you’re starting to build a lot more processes, so you need people who are a lot more operational, like efficiency-focused, instead of people who are really great at dealing with ambiguity.

So first I would say that, because you want to make sure that you bring in the right people, especially when you’re scaling, bad hires can really, really hurt you. And so, when I say bad, it doesn’t mean that they’re bad people, but more so that this doesn’t fit your company or your needs or their career trajectory or whatever it is.

So I think first, really understand what type of person you need and how you bring that person in? Do you need someone who is really good at dealing with ambiguity? Do you need someone who’s really good at efficiency? Do you need someone who comes from industry or is really good at customer success, or whatever it is; being really crystal clear on how you’re hiring. Because that is always probably the most challenging part, the most hurtful thing is bringing in the wrong hire. It could be the right hire at a later time or a different time, but it was the wrong hire at the moment. So that’s like the biggest thing.

Once you have that tea, I think, as a manager, as a head of customer success, it’s really understanding how you can unlock the most potential possible, especially when you’re dealing with 1 to 5 team members. That’s where I highly recommend meeting with everyone on a regular basis, so you understand what they’re dealing with, what they’re working on, what I call my 1:1 on what are the hot topics of the week, what is really on their mind? What are they spending the most energy and effort on? Because that will help me better understand how my team is thinking of moving customers to success objectives forward. But also, how can I help unblock them? How can I help uncover a lot of, you know, the data points or the tasks that they need to do? Or whatever it is. How can I help them walk? Because once you’re getting to five, it really is all about how you can help unblock things? Is sales bringing in a bunch of bad-fit customers? And maybe the best unlock is not to hire more people because there’s more customers, but working with sales and figuring out what’s going on. Is it to get a new tool? Going back to our tech stack conversation, you better understand what that is. So that was a lot of different advice, but hopefully, that helps. And I’m really, really excited for you, by the way.

8. Tackling Discrepancies Between CS Team’s Workflow and Client’s Team Workflow

Irina 52:38

So we have two more questions. As a startup, our culture is very open, approachable, and hardworking. But at the client’s end, it is extremely laidback, slow, and bureaucratic. Any tricks on how to tackle that?

Jennifer 52:54

Yeah, that’s a great, great question. So that’s really interesting. I like that it is, at least, you know, open, approachable, hardworking for yourself instead of the other way around, because that’d be something. So I think you’re already in a good position.

How do you tackle that? Yes, they can be laidback, slow, and bureaucratic, but like, how can we give them structure to help them realize and motivate them to hit, you know, shared customer goals? Right. And what I mean by that is, sometimes, when they’re extremely laidback and slow and bureaucratic, you know, maybe they need a little bit more structure and a little bit more clarity on why we need to get things done by when.

And so maybe a shared, you know, implementation playbook would be really, really important here. Or, you know, maybe it also could be a lack of a customer champion at that client. Yeah, they are extremely slow, laid back, and bureaucratic, but you know, who is really pushing things forward there? Really understanding who is that key stakeholder, even if it’s not the person with the purse strings. And I think, if you have a culture that is very open, approachable, and hardworking, you can really be able to pinpoint that pretty quickly and then build around that. So that would probably be my trick to tackle that. It seems like they’re extremely laidback, slow, and bureaucratic. How do we, how do we help them and give them the context that they need so that we can, you know, hit customer goals and achieve more with them?

9. Scaling Onboarding without Losing Personal Touch

Irina 54:35

Question from Abby. Hi, Jennifer. What is your suggestion for scaling the onboarding with a low touch strategy for a high user, low product complexity scenario? What mistakes do we look out for if we are pursuing automation to get our customers running quickly during this phase without losing the personal touch?

Jennifer 54:58

Yeah, so high user complexity, low product complexity. Okay, so we’re in that delight category right here. There you go, you can’t see my cursor, never mind. So we’re then in the delight category and that quadrant. So yeah, you typically are looking into more automation on that side, and that’s just because there’s a lot going on, it’s a lot easier to understand. So when you send that email that says, “hey, when you click on this button, this is what will happen”, most people understand that, and it’s not too hard.

So when it comes to scaling onboarding with that low touch strategy, I think you have to really understand your customer. Again, going back to a common mistake that I’m seeing when people use this matrix, you can be on the spectrum, it doesn’t have to be you’re always high complexity, or it’s not binary, it’s not you have either high or low user complexity, it’s somewhere on that spectrum.

So I would better pinpoint, as you’re scaling onboarding, where they are on that user complexity side. Is it that they absolutely care, you know, the example I always use is, a dog walking service, like, if something happens to my dog, I want to know right now sort of thing? Versus is it like high user complexity, but it’s not the end of the world. So something that’s very, very high, but something I wouldn’t necessarily be super scared about. Something like Slack – super high, I care a lot about what I do on Slack, I use it all the time, but at the same time, if it were to go down, I can still live my day. So better understanding how you scale, where you are on that user complexity, and how they react to certain things either when things go really wrong or when things go really well.

And then mistakes to look out for when you’re pursuing automation to get customers running quickly during this phase without losing that personal touch. Yeah, I think you’re hitting the nail on the head right there. How can you automate while having that personal touch? So, you know, this is beyond just instead of having it come from support at, having it come from Irina at; it’s beyond that. Right? We all know that personal touch is more than just changing email, having their name and email, and things like that. It’s like, remember this quadrant delight? How are you still building in delight in all of that?

For example, sometimes I get a text a little bit out of the blue, there’s an automation of a picture of my dog, just like being super happy in the park. I love that, you know, that was absolutely wonderful, that’s a personal touch. It took maybe two seconds of their time, it was completely automated, but it brought me a lot of delight, gave me a lot of confidence, and that kind of, even though it wasn’t with a real person, or I guess it was with a dog walker, but it wasn’t, you know, I was still communicating through a platform, I was able to build that trust with them. So there’s different ways to automate without losing that personal touch. So definitely think a little bit creatively and don’t get stuck into “oh, just personalize the name every single time”; do more than that.

10. How Sales and CS Can Work Together

Irina 58:45

The last question. I work for a company with a large team of CSMs. Think around 100, with a sales team of over 400. What would you advise on how to deal with salespeople who move their work to CSMs, although it doesn’t fall into the CSM bucket?

Jennifer 59:04

Oh, yeah, wow. Well, I’m sorry to hear that, you know, folks are just dumping the work on the CSMs. But going back to buy-in, this is where you need your executive buy-in, but also the sales team’s buy-in, or when I say sales team’s, I’m also typically referring to sales leadership. Because that tells me that we’re not on the same page, and so if I were the head of customer success there, that’d be a huge priority for me. Unblocking 100 CSMs’ work is for me to talk with the head of sales and better understand, “hey, this is a problem I’m seeing, here are some examples, and here are some solutions. I think I want to work with you to figure out how we can improve our processes so that we can unlock a lot more efficiencies on both of our sides”. Understanding what was the root cause of this. Of course, none of this is to put blame, it’s more about how we can move forward so that we’re providing a much better customer experience, which will not only help sales but also help CS. So I think I would really much focus on that. Again, very tough situation; I completely feel for you. And hopefully, you’ll get out of that soon, but get that buy-in and get the executive team, exactly the team, not just the C Suite, all the leaders across the board, and all the different departments.

Irina 1:00:32

I think that’s a wrap. And thank you, Jennifer, for being our awesome guest and for a very inspirational presentation that you did for us. Thank you all, the ones who joined; it was a pleasure having you all here. And we’ll definitely keep in touch.

Jennifer 1:00:56

Thanks, guys. Definitely connect with me. Thank you guys so much for coming.

Irina 1:01:01

Thank you all, have an awesome day. Bye-bye!

Do you have any topic requests you’d like us to cover in future webinars? Reach out to us and let us know.

Victor Antiu

Written by Victor Antiu

Victor Antiu is the Marketing Manager at Custify. With nearly 10 years experience, his focus is SEO, product marketing, and B2B inbound strategy. When he’s not trying to fix websites and automate processes, he’s traveling and sailing around the world.


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