The perfect 30-60-90-day plan for a new customer success leader

Please note: This transcript was generated using an AI-assisted transcription tool and may contain errors, omissions or mistranslations

A 30-60-90-Day Plan for Customer Success Leaders

Ravi: Hi, everyone. Wanna welcome you to our webinar. My name is Ravi Pimplaskar. I am the senior director of revenue marketing at ChurnZero. I assume most of you are familiar with ChurnZero, but if you're not, really our mission is to help CS teams manage customer relationships and really drive retention and growth at scale.

And this webinar is really a big part of that mission. It's to really help customer success leaders lead well and not just execute well. Over the years, we've seen a shift, right? Customer success has gone from this reactive kind of support-adjacent function to something that's a strategic revenue-driving discipline that CROs really pay attention to.

Retention, expansion, advocacy. These are all now board-level metrics. And that sort of shift is exactly why a leadership transition, whether it's a new one, matters so much. What worked for customer success five years ago doesn't automatically work now. And so that's what makes this topic really important.

Most new or even tenured customer success leaders, they feel a pressure to act fast. But the leaders who build lasting credibility, they do the opposite first. And that's really what this framework's gonna do. They assess first, then they align, and then they act.

And our host is gonna show you how to do that mapped across the 90 days. And I do wanna point out that there's two audiences in the room. I know that this seems appropriate for those that are brand new to customer success leadership. But even those who've had that seat for a while, if you're looking to reset, reignite your team, I think this is certainly a very appropriate way to do that.

Wanna talk a little bit about Marley Wagner. She is the head of customer success programs and strategy at EverHealth, but a friend of ChurnZero for a long time. She is an award-winning customer success strategist, and she's known for scaling customer success both efficiently and effectively.

Before EverHealth, she actually ran her own fractional CS/CX consulting practice. She's seen this challenge really from both the vendor side and the boots-on-the-ground leadership side. She is a frequent speaker at customer success industry events, including, as she just told me, our ZERO-IN conference. She's done it several times, which is in Nashville in November, if you're interested. But she's spoken at those events about rebuilding customer strategy and leading CX redesigns. And on a little bit of a personal note, Marley is also on the board of the Make-A-Wish Colorado.

So without further ado, I'm gonna turn it over to you, Marley, to get us started.

Marley: Thank you, Ravi. Thank you so much for having me. Always a pleasure to work with my friends over at ChurnZero. And I'm super excited to talk about this topic today. As Ravi mentioned, I currently work for EverHealth.

I run our CS programs and strategy, supporting our customer success team. That means I actually don't personally run our CSM team. The wonderful leader who does that is my peer. I sit alongside her as her partner in crime, as her operational partner, as well as supporting our broader customer experience leadership team, the support team, and our onboarding and implementation team as well.

And as Ravi mentioned, prior to this role I did spend many years in consulting and fractional work, first through a customer success agency and then my own independent consultancy. So lots of experience seeing customer success leaders step into new roles, whether it's their first time as a CS leader or just hopping from one opportunity to the next.

And as Ravi pointed out, even just a little refresh. I personally recently returned from maternity leave with my second daughter and actually found myself using many of these tips and tricks as I got reacquainted with what I missed in the business while I was out. So I'm very excited to share this with you today.

I really want you to think about this session as a practical way to think about the first ninety days. Not necessarily a rigid checklist. Let's see. Any other housekeeping? Please feel free to pop questions or thoughts in the chat. Ravi and I will both try to keep an eye on that throughout.

We'll save time for questions at the end as well, but I always think it's a little more engaging if you have a question about something I'm talking about, I will try to address it in the moment. Here we go.

Thinking about stepping into that new role, again, regardless of how many other CS leadership roles you've had in the past, there can be a lot of pressure, right? We find ourselves feeling pressured to inspire the team, learn the product, understand the business, and show impact really quickly.

And this is the tension that I want to name upfront for all of us, right? And be open about throughout this conversation. We feel that need. I think a lot of folks in customer success also hold themselves to really high standards, right? We have risen to the position of becoming a leader or have been a leader for so long that we feel that internal pressure as well.

So we can tend to just jump in and start changing things, right? Processes, tooling, org structure, metrics, any of that, before we really know the why behind the current state. So I would encourage you to fight that urge. Don't fall into the trap of that pressure to prove yourself, because it can push you into big changes that may not be the best in the long run, right?

We need to gather the context and earn the trust in order to make those changes stick. So by going a little bit slow, I'm sure you've all heard the slow down to speed up framework. And that's really the gist of what we're gonna talk about today in this assess, align, act framework.

As I said, first thirty days assess, next thirty days align, last thirty days it's time to act, right? When I say assess, I mean are we listening? Are we learning? How are we building trust with our team, with our peers? And then that alignment phase, we'll talk more about this in a second, but align doesn't necessarily mean everyone agrees always.

But it does mean synthesizing and prioritizing and pointing everyone in the same direction. Then when it's time to act, then you can do the implementation, measuring. That's when you get to start really showing the impact. So this is the framework that we'll use throughout our hour together today.

And we will reference back to these three phases: assess, align, and act throughout.

Quick note before I move on to start talking about assess. Keep in mind as we talk about this, each phase really builds on another. So if you do them in the wrong order, it doesn't work. The order is very important here. Quick question for all of you. Feel free to pop in the chat what your first instinct would be stepping into a new customer success role, whether you have a new role that you're starting soon, you've recently started one, or you're just dreaming about what that next role would be.

What's your natural instinct on day one of starting a new customer success leadership role? Is it fixing what's broken? Is it listening and learning from your team and your peers? Is it diving into the data, or is it just all about meeting everybody that you can? What's your natural instinct of what you would do first?

No right or wrong answer. I'm just curious what folks would naturally do.

Ravi: I think we're getting a deluge mostly of B, listening and learning.

Marley: I love that. I see a few, though, and that's okay, right? It's okay that we have different natural instincts. We're all a little bit different. We all have different leadership styles.

We all lead our teams in slightly different ways. We're gonna talk about sort of the mix of how to incorporate all of these because all of these are a component of the plan. We're just gonna talk about, again, a practical framework of the order in which tends to work best.

Awesome. Thanks for sharing, folks.

Days 1-30: Assess Customers, Your CS Team and the Business

Marley: So thinking about that day one, the first thirty days in that new role. Again, this is all about assessing. We're not ready to prescribe anything or recommend anything yet. We're just here to understand what's happening. So you have three primary audiences for those first thirty days.

They are, number one, your customers, number two, your team, and number three, your cross-functional peers across the company. So within each of those categories you want to dive into some pretty specific things, right? Number one, with your customers, are you looking at health data? Are you looking at historic churn reasons?

Why did old customers leave you, right? So customers includes churned past customers as well, not just current. You're looking at NPS scores and comments and other survey responses and any other sort of voice of customer feedback that your company has gathered. What are the words that your customers are actually using about you?

And then you're sitting in live and listening to recordings of actual customer calls. Again, what are the words the customers are using? How are they interacting and engaging with your team? What does that look like? And a reminder: it is okay for you to join a call as a new leader, right? And you can let that customer know, "Hey, I am brand new.

I'm just sitting in to listen today. I'm so excited to meet you. I look forward to having more in-depth conversations with you in the future." You don't have to have all the answers in order to talk to a customer. It's a good reminder for us, right? Then when you talk about your team, what are you assessing within your team?

Number one, of course, you want to meet them all. You want to get to know who they are as people. But more strategically, you want to get to know their strengths, both individually and as your customer success team. Then you want to do the flip side. What are their frustrations? What's hard for them?

What gets in their way internally and with customers? What are their personal goals, professional goals, and what are the team goals that the company has assigned to customer success? And what are the ways that your team is working today? What do their processes look like? Then you want to go outside your team to the broader company and your cross-functional peers.

Understand your business model. Get to know the overall business strategy and cross-functional dynamics. How has customer success worked with those other teams in the past? And then start to know your products. Again, you do not have to be a product expert in order to understand the problems that your products solve, in order to understand why folks buy your products, in order to talk to customers.

But you do need to get that general overview. "Hey, what do our products do for our customers? What is the driving force behind them becoming a customer of ours?" So the goal here with all of these is to see the system before you start optimizing the system.

Customer Feedback, Health Data and Cross-Functional Discovery

Marley: Then looking at what questions can you ask within those three categories to unlock the rest of the plan, the next two phases? With your customers, if you're actually live on a call with them, asking them where they're getting value from your product, right? "Hey, what do you find the most valuable from our company, our team, our products?

What's working for you? And then where are you getting stuck," right? "Where are you running into issues? Where can I help support you better, customer?" It's okay to ask those questions even, again, if you don't have the solutions yet, and I would encourage you to be brave, if you will, and ask those questions before you have the answers.

That's how you get to the best version of the answer and the best solution. Then when you're talking to the team, asking them what they're proud of, right? What have their big accomplishments been recently? And then what do they wish was different? No company is perfect. No CS team is perfect, right? We all have frustrations.

We all have challenges, roadblocks that we run into, whether it's, "Oh, I really wish we had a customer success platform. Working out of Salesforce is really hard for me." Or it's something like, "Hey, I have so many accounts, and I just don't have enough time in my day to talk to all of them."

Whatever their frustrations or challenges are, I want you to be asking those questions as you get to know your team. Then thinking broader again outside of the team, asking your peers how customer success creates value within the company more broadly. Again, as Ravi mentioned in his introduction, customer success is a revenue-driving function, right?

We typically own the largest portion of revenue within a SaaS business as our current customer base. That renewal number is the largest number typically. So understand how other teams see customer success. Do they know that? Are they partnering with customer success to enable that retention and growth?

Or has there been friction in the past, right? We know the age-old tension between sales and customer success. There can also be challenges between product and engineering and customer success. And there's potential for challenges in any of those relationships. But understanding what the current state of the cross-functional partnerships are is a huge first step to improving them.

Even if they're already good, you have room to make them better, but you got to know where we stand first. And then again, on the flip side, where are we colliding? Where are we having conflict? And then you want to be listening for themes, patterns. What are you hearing across all of these groups of people that you're talking to?

You're not trying to just collect this giant notebook of comments, right? You're looking for recurring themes across the people and the data that you're looking at so that you can then start to use that as you build a plan in later phases.

So the output of the first thirty days should really just be a clear current state picture for you to understand, you to share with your leaders, you to share with your cross-functional peers, right? So one, a simple summary. What did you learn? Current state, strengths, pain points. You could do a SWOT if you like that format.

Something simple that works for your brain, easy to understand, easy for you to think about. Number two, a relationship map for your team and your cross-functional stakeholders. I've also seen some leaders start to incorporate customer stakeholder relationship maps. I think this is a tad early for that.

I think those are really important. I would stick to the internal relationship map for the time being and maybe do the customer one in the next phase or maybe in the ninety-day phase. But knowing, again, where you sit, who your key partners are internally, how do you get stuff done together, super important.

Then a kind of preliminary list of opportunities that you could start to work on in the next phase, the next two phases, right? What are some quick wins that you're seeing that you think might help make an impact quick? And what are some things that you're thinking about that might be good longer-term bets to make?

Again, we're not making decisions about those things yet, but starting to make a list of, hey, based on these patterns I'm noticing, I think we should dig into these opportunities for improvement. The point here, again, not to have every answer right away. You're just gathering information in order to build a credible point of view on the current state as well as the questions that still require further investigation.

Days 31-60: Align Your Customer Success Strategy and Customer Journey

Marley: So now we're entering phase two, the align phase, that thirty-one to sixty days. Second month in the role, been in seat for four and a half weeks, give or take. You no longer feel like you don't know anyone's name. You're starting to recognize people when they pop up in chats or in meeting invites.

You're starting to get to know folks a little bit as well, feeling a little more comfortable. So now before you start to accelerate, which can be easy to do after that thirty-day mark, we can be like, "Okay, we got it. I'm gonna start running." I would encourage you to continue holding on, pulling back on the reins a little bit longer to get alignment, right?

You met those cross-functional peers. You got to know them. You understand how they view customer success. And now we're shifting from discovery to planning. So you're starting to draft kind of a customer success vision, if you will, that's grounded in those company goals and culture and ideal customer segment, ideal customer outcomes.

Everything that you've discovered in that assess phase, now you're using it to start the planning. You're evaluating whether things like team structure and roles, customer segments, ratios of CSMs to customers, whether any of that needs to shift or should shift, and refining the future state customer journey.

I want to talk about customer journeys for a second. So this is my hot take on customer journeys. It's not about the document. The document is irrelevant at the end. It's about the process of you going through the process of mapping, right? That is how you understand. So even if you come into a new role and someone says, "Hey, we already have a customer journey.

Here you go." Awesome. Look at that. Definitely review it. But I still want you to go through the exercise of mapping it yourself 'cause that's the way you're gonna get to really know it and understand it. So I'm less worried about the output. It doesn't have to be, like, this beautiful customer journey at the end.

But I want you to understand it in a way that makes sense to your brain.

Customer Success Metrics: NRR, GRR, NPS and Time to First Value

Marley: And then I want you to start really partnering with customer success operations, RevOps, whoever handles metrics. Understand where your NRR, your GRR, your NPS, your onboarding duration, time to first value, accuracy of your renewal forecast. Understand where you are with all of those critical metrics, and then you can start to build a slightly longer-term, six to twelve-month plan, I would say, for how to potentially improve visibility of those metrics or actually increase the metrics themselves, right? Improve upon those outcomes.

But those are not wins you're gonna get in this first ninety-day period. So you're just planning for the future. You're aligning with those cross-functional peers. You are creating that vision for what customer success looks like moving forward, ensuring you have the right team design, not taking any actions on that design yet, but starting to map it out, and then choosing those few high-priority items that would matter most and that you want to start with when you do get to the act phase, right?

The strategy here becomes a reality. It's not just words. When other people, your team, your peers, your leaders can explain it back to you, right? So you're getting alignment on, "Hey, this is my vision for customer success now that I've stepped into this role." You're explaining it, and then you're saying, "Can you explain it back to me?

I wanna make sure you heard what I just said, right? And that we're in alignment here." We say alignment a lot in leadership meetings, and at a certain point it sounds like a ridiculous word. You're like, "What does that even mean anymore?" But I think that happens because it is so important, right?

So as I mentioned earlier, alignment is not always everyone agrees a hundred percent, especially not right away, right? It's okay to have healthy dialogue and healthy disagreement, respectful disagreement about who should own upsells, how renewals should be processed, who should be the approvers on exceptions to discounts or contract terms or what have you.

It's okay to have that dialogue, and it's okay for you to have a perspective, and it's okay if you get overruled, right? We as customer success fought for so long to get a seat at the table. We have that seat at the table now, but that doesn't mean we're always gonna win. And so having that dialogue is important.

And getting to a place where everyone can tolerate the answer, right? Everyone can tolerate the path forward and say, "Yep, this may not have been what I originally wanted, but I understand that this is what we're doing." So this is how I view, from a customer success-focused perspective.

This is how I view your key cross-functional peers, right? You, as the customer success leader, of course, own the customer success strategy, right? Your sales counterparts are your partners in that. They are a very important part of your customer success strategy succeeding. So I would view them as a partner.

Product, they are gonna give you input with, "Hey, this is how we recommend customers use this product," and you are gonna give them input back, "Hey, this is how customers are actually using this product or feature, and these are the suggestions that we have for optimizing based on their real lives." So that input is bidirectional with product.

Of course, you're gonna have an executive sponsor regardless of your organizational structure, whether you report to sales or revenue or operations or customer success reports directly to the CEO. You're gonna have some sort of executive sponsorship, and they are going to be, I would say, the most useful person on this list in continuing that alignment, right?

Alignment at the executive level is one of the most important things that we can do to ensure that we as customer success leaders can accomplish what we have been tasked with doing. And then one of my personal favorite cross-functional partners for CS, of course, is RevOps or CS Ops or your data team, whoever owns data and systems and tooling.

They're really gonna be your partners in the proof, right? The evidence. "Hey, this strategy that I designed and all these cross-functional peers that I worked with, it's working, and here are the numbers to prove it." Okay. So again, alignment here is just about being able to move faster later, right? We can certainly push through on our own and get a lot done really fast, but oftentimes we'll run into roadblocks down the road.

So taking the time to get this alignment with these cross-functional folks early can save you a lot of time down the road.

Still in that phase two section here, the output. At the end of 60 days, you've made it two months into your new role. The goal is to have an output that is something that people can start to act on in the next phase, right?

So number one, having a documented customer success strategy or charter. I love the charter sort of format for this. I think it's a really helpful guiding tool to use. Number two, having a recommended updated team design. It could be that you think the team is structured exactly as it should be, and that's okay.

You don't have to make team changes for the sake of making team changes. But having evaluated that and understanding the why and then making the decision, yes, this meets our needs for the future strategy, or no, this does not. That's the important thing here. So if you're saying, "Hey, no, I think the team is fantastic.

They just need some more guidance. We need some more processes, maybe some more tools," like whatever the thing is, the team does not have to change just because you came in as a new leader, right? And then if it does need to change, maybe it's the flip side. Maybe it needs to change a lot. The reality of being able to totally turn over a whole team, not super realistic immediately.

So what do we need now, today? And then what can wait until next fiscal year when we can incorporate it into the budget? That kind of thing. And then the third thing that's part of that sixty-day output is gonna be your roadmap, right? So I talked about your customer journey map. This is different.

This is your internal customer success roadmap. What are your sequenced set of initiatives, ideally with owners attached, as well as timing, that you really think are critical to accomplishing the goals that you've been brought on to lead, right? The initiatives that you've been brought on to lead.

What do you need? What initiatives and projects and what support do you need to go and accomplish those goals? When you're putting these things together, really think about including trade-offs, making those visible, right? If we do this now, we're gonna have to wait for this until later, right?

If we make this hire now, we're gonna have to wait to add more CSMs until XYZ quarter, right? Or if we pull time from RevOps to help us get clearer visibility on those bottom-line metrics like NRR and GRR, we recognize that's gonna be pulling their time from XYZ other project that they let me know that they're working on.

Including the trade-offs is really important, again, for continued company-level visibility and alignment and agreement. If you're just like, "I need these things," but there's no line of sight to what other gaps might pop up as a result of those, again, you're just gonna run into problems down the line, and eventually you'll hit walls that will slow you down.

So taking a little bit more time, I'm a broken record on that today. Taking a little bit more time upfront can serve you so well in the long run.

Days 61-90: Act on Customer Success Priorities and Quick Wins

Marley: Moving on. So that's the recap of 60 days. That's our output. Moving on to 90 days, that act phase, the part that we all have been itching to do for the last 60 days, right? Imagine yourself, or maybe you really are 60 days into a new role. And even if you have followed this phased approach so far, the assess and align, by 60 days you are itching to take action.

I know that. I'm the same way, right? Again, like I said, I just returned from maternity leave not even a month ago, and I'm like, "Oh, I should have slowed down a little more when I got back, guys." 'Cause I've been in act phase maybe for too long already. So thinking about act. Now you have all the information you need.

You have the plan. You have agreed upon the plan, and now the final 30 days of that 90-day window, it's time to start moving. Start launching new programs. Maybe it's a new onboarding framework. This could be… Side note, this could be an onboarding framework for your customers and/or your team. We sometimes forget about our internal teams when we think about onboarding, right?

This could be, "Hey, we really need a more structured QBR process," right? CSMs are having them, but this CSM is doing it this way, this CSM is doing it this way. We need a little more consistency. This could be, I evaluated our health scores, and everybody looks green, but we're still seeing customers churn.

So we really need some support from the data team to make some changes to the structure of our health score, the inputs of our health score. Whatever those projects are, you want to launch those highest priority items, process changes, programs, initiatives, whatever they are. You want to launch them with very clear owners, right?

You, as the new leader, are not going to be able to design every single thing yourself. So you may have dedicated operations folks or program managers or other specialized roles who are there specifically for designing initiatives like this. You might not. You might just have CSMs, right? And so if that's the case, you want to really be thoughtful about, hey, which CSMs are looking for growth opportunity?

Which CSMs have indicated interest in this particular topic? Who can I assign as the owner, at least of the initial V1 of this initiative that I find to be high priority? And then which are you going to own yourself 'cause there will be lots of that, right? Then which leading indicators can you track on those initiatives that can move within a quarter or so.

Things like NRR and GRR and even NPS, right? They're not really gonna move in the next ninety days. Those are longer-term metrics that it's gonna take through the next renewal cycle to see impact on. So what can you see impact on earlier? We'll get to more examples of that in a second, but start to think: What can I measure here during this thirty days of act at the end of the ninety-day period?

And then set up a communication plan. You want to make everything really visible to your organization. Particularly as you're new, there is a sense of proving yourself, right? And so you just want to be very transparent. You want to share as much as you possibly can. You want to make sure that you're not hoarding all this information that you're gathering from these initiatives that you are rolling out, and that you're then adapting based on what you learn.

Pilot, Measure, Learn and Scale Customer Success Programs

Marley: All right. Oh, at the bottom here, I want to call this out. This is a good way to think about entering into this act phase, the first actions that you're taking, right? Start with small wins. Gather proof, right? Those metrics. What can I show that is moving already, those leading metrics? That builds confidence in you that you are taking the right action, in your team that you are taking the right action, and in your peers and your leadership that you are guiding the customer success organization in the direction the company wants to go.

Then you will be able to move on to those bigger bets, right? And that doesn't mean you're not starting to plan and lay the framework and groundwork for those bigger bets. But starting with those smaller wins, "Hey, what can we accomplish quickly in the next two weeks?" "What changes can we make next week that will see the impact of this quarter?"

Thinking in that order will help you get to those bigger things and have bigger impact when you get to those larger initiatives. So as I said, really think about those quick wins. We don't want it to be chaotic, so we don't need to change a million things all at once. But think about one or two, maybe three targeted specific changes that you could pilot or just internal process changes that can create quick wins.

Again, hold off on building the larger, broader system. What can you accomplish now? What can you unblock for your team that they've felt blocked on? How can you help them push through something that they've been fighting for and that is really important to them, right? Maybe there's something manual that CSMs are doing, and there is a plan, theoretically, there was a plan in place to help them automate it, but it never happened.

It hasn't happened yet. How can you unblock what is blocked that they are really asking for, right? How can you remove CSM friction and frustration and save them time quickly? And then what can you pilot with your customers, right? Maybe it is we're gonna make these two changes to our customer onboarding flow.

Instead of five meetings that focus on these five topics, it's now only gonna be four, but we're gonna shift them from training sessions to working sessions, right? And we're gonna see how that works because we already have training videos that we can share with them, right?

Maybe you're gonna test that, pilot that with a cohort of new customers and see how it works. Then you'll establish a baseline. Did that work, right? Define those leading indicators. Did time to first value improve if you made those changes to that onboarding flow? Did your CSAT score for your onboarding team improve, right?

Are your customers coming to their CSM after onboarding more familiar with the product? I know that one's a little anecdotal, but there could be a score there, right? There could be a CSM customer readiness score when they graduate from onboarding to the CSM. It's a great example.

And then what can you learn from that? What worked? What didn't? Maybe you tried something that worked super well in your last company, and in this one, it just is not working for your team or your systems or your customers or their needs or whatever the case may be. What did you learn? And then how can you scale that?

What can you do to expand on that success? As you're identifying those pilots, be thinking about that scale component, right? Is there something that you think will be a bigger project, a bigger initiative? My mind personally always goes to digital customer success and automation. That is how I came into the customer success world.

And so thinking about, hey, are we meeting our customers where they are? Most companies are not. And so how can you pilot that in that quick win, and then eventually get to the scaled, larger program of rolling it out across your customer base and across journey phases. So this pilot, measure, learn, scale process is a safer way to start moving quickly because you're creating evidence, right?

You're demonstrating success rather than just accumulating change. Oftentimes when we just start to change stuff and we throw things at the team and we're like, "Hey, I need you to attend this training that I'm putting together, and I need you to—here's a new SOP for this thing and here's this and blah," and we're not then following through on the measurement and the learning, it can just become really exhausting for your team.

Change fatigue is real. I've seen it. I've felt it. And so think about using these four steps to avoid that change fatigue.

Leading Indicators and Customer Success Metrics for the First 90 Days

Marley: Awesome. So wanna hone in on measuring in that first 90 days. So again, we talked about these revenue outcomes, long-term metrics, NRR, GRR, et cetera, expansion revenue if you own expansion or CSQLs if you don't, if you just hand off to a sales team, all of those are critical metrics, but most of them are longer-term metrics.

You're not gonna see movement. Even if you did start changing stuff on day one when you started, you're not gonna see movement on them in that first ninety-day period. And so I want you to be thinking about what metrics can move in the next ninety days, right? Those are gonna be leading indicators.

They're gonna be much more actionable in the short term for those quick wins, those pilot projects that will then lead into the broader, more overarching initiatives. So some examples, things like time to first value, right? If you're making a few tweaks to your onboarding process, did time to first value change?

Did your customers get onboarded quicker and not just onboarded in the way you mean, "Yep, we checked the boxes," right? But did your customers start to use the system in the way that they want to be using it faster? Did that happen sooner, right? That's a great example, something that can move relatively quickly.

Sometimes I see adoption or product usage moving really quickly, right? This could be true in an example like, let's say there was a new-ish key feature that was rolled out or updated or changed in your product. And before you came in, CSMs just were not seeing their customers really using it or using it properly or using it in a way that worked with their customers' workflows.

So maybe you added some training on that. Maybe you added some slides to your CSMs, excuse me, to your CSMs' QBR decks or regular check-in cadence call decks about that specific product feature. And maybe you're starting to see adoption of that feature increase, right?

Things like that, again, can change relatively quickly. It's a good leading indicator. We know product usage is not the end-all, be-all customer success metric, but it is a good leading indicator. What are they using? And then you can get to, are they finding value from it? Execution velocity is a huge one, right?

This is about what can your team get done. Are they moving faster? Are they able to hold more QBRs, more strategic meetings because you've freed up some manual tedious tasks from their plate, right? Maybe that's in evaluating what CSMs are handling versus what goes to support. Maybe that's in automating some data collection or capture that they were handling manually.

Maybe that is a new template for some of their decks, their presentations, so they don't have to build from scratch. Is your team getting to stuff faster? Have you freed up time in their day for them to have more strategic customer conversations? That execution velocity is a really good one early on to show some quick wins.

And then this one can be hard to see in the first ninety days. But I put it in here because it is possible, right? You can start to see impacts in things like movement of renewal risk pretty early, right? Even if you're just putting into place, hey, CSMs used to be inconsistent about how far ahead of the renewal they were reaching out to customers, right?

CSMs were afraid to bring up the renewal. They were waiting for the customer to bring it up. I've heard that from a lot of CSMs, by the way. They get scared. And you're coming in, and you're saying, "Hey, guys, we're not going to be afraid of talking about renewal anymore, and here's why." You can show them the data, right?

Talking about the renewal way ahead of renewal, I'm talking like six months before, is actually the thing that's going to, number one, give you the best accuracy in predicting retention or churn. And number two, it's gonna give you time for your CS team to do something about it if there is risk to the renewal.

So you can start to see some broader business metrics, like renewal risk, move relatively quickly. Not as fast as maybe the first three. But I included that one on there 'cause you can start to stretch out a little further as you think about these early leading metrics. And there are many other examples, too.

You don't have to use these categories. Just some examples of things I've seen work well as early leading metrics.

What Good Looks Like After 90 Days in Customer Success Leadership

Marley: Okay. Thinking about what good looks like by the end of that first ninety days, right? We all—I think ninety days in our minds, whenever we start a new role, kind of sticks out as okay, by ninety days, like I should be onboarded, right? I should be up and running. I should be in my normal flow into this role.

And that's a great goal. Reminder that might not always happen, and it's okay if it doesn't. It's okay if there are things you're still learning and people you're still meeting and things you're still trying to understand, particularly if you're working for a large multi-product, highly complex or highly technical company, right?

So it's okay if you don't know everything by that ninety-day mark, but it's great to have that as a goal, right? You want to feel settled into your new role in ninety days. I think that's a great goal. In order to do that, number one, you want to have trust in both directions. You want to have earned people's trust as you're coming in and being the new person.

And then you want to feel like you can trust the people around you that you've stepped into as well. You want to have that clarity about what customer success is optimizing for. What have you been tasked with in accepting this role of doing with the customer success organization? You want to start to have some momentum on some of those early wins, quick wins, and starting with some of those broader, larger projects.

And then you want to think about what's next, right? You want to have that roadmap that we talked about. What's coming up in the next ninety days, and looking out past this time frame as well, right? Ninety days, you're definitely not done. You're nowhere near done. It's not a finish line. I think about it as a launch pad, right?

You are getting to the point where, hey, the next quarter and the next year looks a lot more clear. So think about it as that launch pad. And quickly, I see a question in the chat here about copies of the presentation and the webinar. And yes, our friends at ChurnZero will be sending out a recording and the slides.

Everything will be in your inbox tomorrow. Yeah. Thanks, Ravi.

Avoiding Change Fatigue and Customer Success Leadership Pitfalls

Marley: Awesome. So as we're coming to the end here, I want to point out a few common pitfalls, I'm gonna call it turbulence here, that you wanna try to avoid in this first 90 days. These things are easy to fall into, and so I wanna call 'em out for you. I want to make sure that you can proactively avoid stepping into these traps.

Number one, changing too soon. Unless you are going to work for a brand-new startup that literally just started and you're a founding member of the team, this is not a blank canvas that you're walking into, right? Every other company has some sort of history, some sort of context. And so if you come in and change immediately without understanding that context, odds are high you're gonna make a mistake. So we want to try to avoid that, right?

Number two, we don't want to try to fix everything. We can't do everything all at once, right? A giant list is not a strategy. You have to be able to prioritize that list, understand what's the most important now and what can wait. Knowing that in many businesses, those things that you say can wait, guess what?

The priorities might change, and they might wait for a really long time, right? And that's sometimes something we just have to live with. So focusing on what you can fix now and what is the most important to fix. Fix the right things, not everything. Number three, I don't want you to confuse activity with impact.

Just because your team is busy does not mean that they're necessarily creating outcomes, right? And I know that we could go into a longer conversation about that as it relates to some of the sort of team speed metrics that we talked about, right? There's some nuance there, and that's okay. But don't confuse activity with impact, right?

Just because your team is like, "Oh, I'm so swamped, I'm so busy, I'm talking to customers all the time, I'm doing all this stuff," blah, blah, blah. It doesn't necessarily mean that it's making the impact on the things that you have been tasked with changing or improving or holding onto, right? Maybe your NRR is great when you're stepping into a new role, right?

And your mandate is to keep it there. Fantastic. Doesn't mean you can't improve things. And the last one here I want you to try to avoid is skipping the alignment work. This one can be so easy to skip, right? You can often find yourself going straight from assess to act and skip over alignment with those cross-functional folks, with your team underneath you, with your executives above you.

But again, the path later will slow down, even if you're running really fast right now. By skipping that alignment, I can guarantee at a certain point you will find yourself slowed down significantly if you skip that alignment work. So please take the time to do it. Get to know your cross-functional peers.

Make sure you're all rowing in the same direction. My boss uses that analogy. We're all rowing in the same direction. We have found a lot of funny canoe GIFs from that one. So those are four really common pitfalls. Again, turbulence, right? Bumps in the road to try to avoid as you're going through this process.

So circling back to this question that I asked at the beginning. After listening to me talk, and I'm sorry, I know a webinar with one person talking for forty-five minutes is not the most fun use of your time, but I hope you learned something. What's your instinct now? What do you do first? Again, you should do all these things, but what do you—has your instinct changed? Feel free to put in the chat again, and if it's different than what you thought in the first place.

I know a lot of folks already said listen and learn, which is also what I would choose. But curious if anyone has thoughts and if their thoughts have changed.

And while you're typing in the chat your new answer here, I see a really good question from Rayhan. Thank you for asking this. When a business is already navigating significant change, what should we be careful not to introduce in order to avoid creating additional friction or change fatigue?

Yes, such a good question. I think, number one, want to acknowledge that this is common, right? Oftentimes, customer success leaders are brought on as part of broader changes. And so you want to really be super aware of that in your assess and your align, right? And so maybe it is, "Hey, we really can only pilot one thing right now in addition to the other changes that are going on that I don't own and I'm not driving, but I know the team is experiencing," right?

And so sometimes that means, yes, needing to move even a little bit slower on your own initiatives. Sometimes that means taking some extra time in the assess phase. If you were brought on as part of a total company reorg, and there's a big shift in company structure or strategy, assess might take longer than thirty days, right?

So acknowledging that there's nuance in this thirty/sixty/ninety, I think, is also important there. I would also avoid too many process changes for individual contributors at one given time, right? And there's no—I can't give you, like, a two is too many 'cause it depends, right? Five, you might be able to do five in a two-week span.

It might just be one. It depends on the size and the scale and how big the change is. How long the team has been there and been doing it the same way. All those things add a bunch of nuance. But in general, as you're rolling out changes, be, number one, observing and gauging how your team is reacting to those changes.

Are they seeming more overwhelmed? And then ask them directly, "Hey, I know there's a lot of change going on here. Tell me about how you're feeling. How are you doing with it?" And there are things you can put in place to be measuring, hey, if we're changing—I used the onboarding example earlier.

If we're changing from five training sessions to now four working sessions, do you have a way in either your CS platform, your CRM, or even just like your meeting tool, your Zoom or what have you, do you have a way to track, hey, is the team doing this new thing, right? Can I see that, okay, they're having these four working sessions instead of those five training or whatever it is.

So thinking through, hey, how can I actually measure team adherence to the changes is another good way to gauge. But yeah, just being super aware of individual contributor-specific change fatigue on their day-to-day, what they have to do every day, that's the biggest thing to avoid there when there are other big changes going on.

And I, again, I've been there. It's hard. It's a really hard environment to navigate.

Another question in the chat. How would you advise someone joining an early-stage startup where there's no CS org, the existing team has no CS experience, and you will need to act both as a player coach and a strategist builder?

Oh, man. Number one, I think being a player coach is the hardest job ever. So kudos to you if that's the kind of role that you're taking. I think it's very difficult for me personally, and in general, I think it's difficult for humans to switch in and out of those mindsets. That being said, you may be one of the few who actually is stepping into a clean-ish slate, right?

Where there isn't a ton of history, there isn't a ton of, "This is how we've always done this." And to your point, there's no CS org, there's no CSMs today. So one of the benefits there is that theoretically you do get to design relatively from scratch. That being said, I would still go through this same process.

Just some of the questions you're asking are gonna maybe look a little bit different. They're gonna be potentially a little bit more goal-oriented as opposed to historic context-gathering oriented, right? The context of the questions just might be slightly different as you're thinking about going through the assess, align, act.

But I would still follow the same process. Awesome.

AI in Customer Success Leadership: Where It Helps

Ravi: Marley, thank you. Yeah. This was great. I do have a few more questions since we have a little bit more time if we want to go through them. Curious about the role that AI would play in this. Not only today but as we kinda go into the future since it is changing so, so many things.

Marley: It is, absolutely, and I think, number one, I would say don't start with AI, right? Particularly in assess and align, start with humans. Because a big part of those two things is the human connection, right? It's building that trust, building those relationships. Now, that doesn't mean that if your company has an AI product attached to your SharePoint or your Google Drive or whatever, that you can't ask the AI, "Hey, give me an overview of this thing," after someone told you about it, right?

Certainly, use AI to support your investigation, to support your assessment. Definitely use AI for things like tracking patterns or common themes across conversations, right? Throw all your notes into AI and say, "Hey, give me the top themes and patterns. Tell me who said them and in what context," right?

Absolutely. Use AI for pulling together your thoughts and pulling together a lot of that roadmap and prioritization. I would say that's a big area where AI can be extremely helpful. As you're moving from that align into act in particular, that's the period where I would lean super heavy into AI.

Again, in assess, I would try to keep it mostly human. And align, I would try to keep it mostly human. But as you're starting to prepare to move into act, I think there's a ton of really useful ways that you can use AI, particularly, again, if you have some sort of access to ChatGPT or Claude or an internal AI tool that is connected to all your existing data and content and all of that.

It can definitely help speed up a lot. And we didn't talk a ton about this, but I mentioned it briefly. AI can really help in you understanding your product that your company sells. 'Cause we know product training can take a really long time depending on the complexity. So lean into using AI for that in particular.

And then a lot of the rest of it depends on what your AI tech stack is like internally. What tools do you have available to you? And think through maybe one of the pilots that you're testing is, "Hey, I want to build this AI agent for the team to use to do this manual task that's taking them 10 hours a week."

God, I hope no manual task is taking your team 10 hours a week. That was very dramatic of me. But maybe that's one of your pilots as well, right? As we're thinking about, to your point, Ravi, moving forward in the world of AI, it is important to be thinking about, "Hey, how do I incorporate AI into what my team is doing every day, into how we scale faster, into those pilots I'm testing and those larger projects ahead?"

Building Strategic Influence for Customer Success

Ravi: Cool. We got one more in the chat since we have three more minutes here. It's when customer success lacks formal authority or organizational influence, how do you earn credibility and align other functions around customer outcomes? And how can customer success become a strategic partner rather than just a support function?

Marley: Oh, man. We could have a whole webinar about this question. Number one, make sure that you, as the customer success leader, understand all of your business metrics, all of your financial metrics, all of your financial goals. Become best friends with your finance leader, right? Ask your CFO or whoever runs finance at your company for 30 minutes of their time and be like, "Hey, I want to make sure I'm really understanding our goals as a business."

They will be thrilled to walk you through it. And do your research, do your prep, right? Access what you can access on your own, and if you're publicly traded, watch your earnings call. If you're not, what metrics are reported out that everyone can see? But I would really encourage you to put time on your CFO's calendar.

Most CFOs are really excited to talk, to teach people about financial metrics. And I would say that's the place to start to understand how the business as a whole thinks about metrics like retention, right? Again, like I said earlier, typically your existing customer base in a SaaS model is your biggest portion of revenue.

Unless you're having some insane growth curve, that's gonna be true. And so being able to understand how the business thinks about the retention of that revenue will help you think through, "Hey, how do I then make a proposal back that will resonate on how we can impact that metric?" There's also tangential questions about who owns upsell, cross-sell, who owns the renewal.

Like, all of those are tangential questions that you're gonna have to go down and evaluate. I would guess that CS does not own those things if you're seen as more of a support function, but may or may not be true. Yeah, that's a really good question, and one I don't have a short answer for other than start with your CFO and understand your business metrics.

Ravi: Thanks, Marley. We really appreciate this. This was a great discussion. And going back to that question and that point at the outset, we did mention that retention, growth, advocacy, relationships are now board-level metrics, right?

Yeah. Really understanding those metrics from the get-go is the best way to start gaining that credibility.

Marley: Absolutely.

Ravi: Everyone, this was awesome. As we mentioned during the webinar, we will be sending out a follow-up tomorrow, so keep an eye out for that. But thank you all for attending, and everyone give thanks to Marley. She did a great job today.

Marley: Thank you all so much. Thanks for joining. Everyone, please feel free to find me on LinkedIn. I always love connecting with other CS leaders. Have a great day.