Scaling Customer Success from Scratch with Calendly Head of Customer Success, Katie Christian

this going. We've got Charlotte with Tanner, Amsterdam, Salt Lake, London, Chicago, Russia. Nice. Brisbane. That's early in Brisbane. Thank you for joining. Cali, Atlanta. All right. ATL reppin' here. We got Oregon. Nice. Good stuff. Well, I am pumped to be able to connect with everyone today. I'm here in Atlanta, Georgia, and really just excited to share my lessons learned from scaling customer success teams over the past 10 years. And so, um, I am Katie Christian. You can certainly follow me on Twitter or on LinkedIn. The information's down below. Um, but my experience really comes from scaling hypergrowth customer success teams, really from $200K in revenue at Salesloft to $35 million, and then here at Calendly from $36 million to almost $70 million just this year alone. And so when you talk about hypergrowth environments, needing to make quick pivots and really just solid investments in a short amount of time, that's really what my go-to is. And so today I'm so excited to be able to share with you some of my tricks of the trade, if you will, and what I've learned across the years. And so, um, as Caitlin said in the housekeeping, if you have questions, feel free to unmute yourself. I'd love for this to be as interactive as possible. We also have breakout sessions later on. So that way, we can dive into some of the learnings from today as well. So with that, let's go. The number one question that I get from new CS leaders is, Katie, where do I start? And one of the most frustrating answers that I could give them is start where you are. Like, what does that even mean? Right? And I had a mentor say that to me when I first started my customer success organization. And so Today, I will say start where you are towards the end, because I'll help you identify where you are in your process. But more so, we're going to give some really tactical tips to helping you launch your customer success endeavor. And so in the chat, let's take a quick second here. Who has a customer success team already in motion? Who's thinking about launching a new initiative in 2021? Share some insights so that way I know where everyone is. So starting from scratch, give me a 1. Have a current team, give me a 2. Here just for the kicks, give me a 3. All right, we've got 1s, a few 2s. So people learning, looking to learn some best practices, a lot of folks starting. Whoa, okay, awesome. So good mix of everything here. Just for fun, thanks, I'm here too. We'll make it work, hopefully. Um, we go, but lots of 1s. Okay, everyone really trying to figure out how they're going to start their initiative, and so With that, here are my 5 phases to launching CS. And the first is become a data whisperer. Each of these areas we're going to talk through, and I'm going to give you some tactical tips and lessons learned as we go through. So first, become a data whisperer. Data has never been more important to what we do and how we operate. The second is we're going to use that to define our strategy and get incredibly specific about what we're looking to prove and the outcomes we're looking to attain. Then we're going to talk about how we start scrappy. A majority of us start our CX endeavors in smaller startups where there's not a lot of budget, and, and we're really just trying to have some quick wins. And so I'll give you some tips on how I've started scrappy, and we'll even have a dedicated breakout session towards it so we can really get some good ideas for you to go back and bring to your teams. The fourth is we've got to keep it real. Is it actually working, all these efforts that we're putting towards it? And so I give you some questions to ask. And some ideas on how to pivot if it isn't. And then finally, I talk about scaling it. And so with that, let's dive into each of these. The first is becoming a data whisperer. And so each of us have had some type of compelling reason to launch customer success within our organizations. And so that, that compelling event could be, okay, do we have too much churn happening, or we don't have the right amount of adoption within our current customer accounts, and we're fearful that it may lead to churn or contraction down the road. And so whatever that compelling event is, make sure you're truly understanding that and asking your executive team, why now? Why this pressing moment? And ask them what data they're leading their decisions with. And so ask them for those data samples. A lot of us start out— I don't know about you, but I've been in many positions where I start and there's no data. There's just hunches and guesses as to what we need to fix and where we need to begin with customer success. So the first thing is really dig into those data insights. The second, as much as we want to rely on the data, we need both quantitative and qualitative data. So those voice of customer sentiments have never been more important. Everyone hears VOC thrown around in a majority of conversations across businesses today, but really data whisperer part is blending the quantitative and the qualitative together. And so those customer interviews, once you have your hunches off of that data, so maybe there are specific churn areas, whether it's product or it is onboarding, and people aren't actually able to launch. Once you have those hunches, validate them with those customer interviews. So that way, when you bring it back to the customer, or the executive team, you know, how you're driving those conversations, and you can share some really concrete examples. Then with that, also create two different types of profiles. More often than not, when customer success teams, we typically create that risk profile, the red accounts, we all know about them, and everyone wants to move as quickly as we can to green, but more often than not, we don't take a moment to define what does that success profile look like. And as our teams grow in scale, they know they're so focused on risk, but they don't know how to get a customer or what the characteristics are of a successful customer other than expansion or renewal. But what are the factors that make up that successful customer? And in this, so here are some examples. For risk, some of the things that I found in my past is, you know, if we have churn More often than not, churn is that outcome, but the leading indicator is potentially a failure to launch. They can't actually get up and running with the software. And so we're identifying customers in our risk segment here by, by them experiencing these onboarding challenges, whether it's a failure to get set up and implement a platform, or, you know, monthly active users, whatever your metrics are internally. On the flip side, for the success profiles, It could be something not even related to the product, like a strong technical admin, or the particular use case was extremely clear and the customer knew exactly how they wanted to implement it. We've seen a wide array of, of risk characteristics as well as success characteristics at Calendly over the past year. And as far as the success go, some of our most successful customers have no knowledge of our product, but they come in with an incredibly clear plan and how they want to prove ROI. And there's a strong technical admin who can do all of the work on the backend with a little bit of coaching from the CSM. And so as you look into your customer base here, from a Data Whisperer standpoint, identify two types of profiles, risk and success, and have your frontline teams, if you have them, maybe you don't have a CS team right away, maybe you have some support folks, ask them to identify what they believe those characteristics of that profile are. So that way, as you dive in, you know what you're guiding away from and towards on the Data Whisperer front. All right, any questions here, feel free to pop them into chat. I am checking from time to time, looking over to my right. And so once we become Data Whisperers, we're going to move it along. And really why we become Data Whisperers is because we We all know CSMs are the unicorn wranglers, the rainbow makers, the sorter of all the broken things. But with that, ultimately what we really need to do is tie down that strategy. So we need to take all that data and compile it into really clear initiatives of what we're going to do. And typically as a CS leader in your first 90 days, everyone is looking at you to define your strategy as quickly as possible. And so I've learned over the years that I can go pretty big. And so I've got Alicia Roberts here who is a manager on my customer success team. And so she keeps me grounded. So she's a source of truth, but sometimes I can be a little too visionary. And I've learned over the years that when I'm starting in a new CS endeavor, it's really important to focus on one key area, improve ROI and outcomes in that to max. And so I challenge us to see us leaders, instead of trying to solve all of the things, really focus on one key outcome and start with the end in mind. So what is that outcome we're thinking— we're seeking? So let's focus specifically around churn. If we're looking to decrease churn, what do we want that to be? Answer: How will we know if it's working? And with churn, That's a pretty specific conversation, but it could mean different things. Are we looking to reduce logo churn? Are we looking to reduce revenue churn? Or is it both? And sometimes our executive team will say all of the above, right? We've all been there. I can see some smiles across the team. Yeah. And so as they say all of the above, ask the clarifying question, if you had to prioritize one, which would be first? And really seek that clarification to help you define your strategy. And know not only the outcomes that we're driving towards, but really the metrics that we need to track to ensure that our initiatives and engagement are going well. And so here I've outlined just some very specific examples of activity reporting. So if our efforts are going to be emails, calls, webinar, whatever that may be, we need to know how often and when we're doing those. We need to know the engagements from those, so email open rates or call dispositions or webinar attendance. We need to be tracking that the entire way so that way we can clearly understand what's leading to the increased outcomes or decrease in churn if that's the case. And so at Calmee in the past year, we've literally embodied this and led with, here are the outcomes that we're trying to, increase, and it really was monthly active users. So this isn't a, this isn't a made-up example. We've really focused on that, and we did that through a series of calls, emails, and webinars, and we tracked everything. And what we're able to do is really understand some emails were terrible, and we absolutely stopped them after a couple of weeks, but others were really thriving. And so we innovated there. And so with this, by tracking each step of the way, you really get a good understanding of what's working and what's not. But you have to think with the end in mind and define these outcomes and these steps prior to diving in, so that way you have the data set up and reporting set up in advance to track them. And so we go back to this question: where do we start? And I always say start scrappy, and people get really annoyed with me, but I had no budget for my first, so 10 years ago with Salesloft, I had no budget. And Kyle said, start where you are, the CEO. I was like, what the heck does that mean? Right. Start where I am. So I started where I was and I started scrappy. And so I thought, what is the minimum viable experience? What, what is the one thing that I could do today to make an impact towards outcome X? And I really set up SMART goals to align by that. And so if I have 90 days to prove that we can drive traction towards this one initiative, what is that going to be? And knowing that you probably don't have a budget— if you do, you're incredibly lucky, use it wisely— but with this, execute with what you have. And so for some people, if you have a team, Ask them what they would do. Focus on outcome-driven engagement. So when I started at Calendly, we had a customer success team of 3. We've now grown that to 10. Um, but I started with those initial 3 CSNs and I said, hey, if you could change one thing today, what would that be? And how would you do it? And I got 3 very different answers from the team. They've been at the company for anywhere from, I think at that point in time it was a year to 5 years. And so they had amazing context that I quickly ramped with, but I asked them all the questions. And so really utilize your team if you have them. Remember, as leaders, we have to be facilitators. We don't always have to come up with the brilliant idea. And sometimes we put some stress on ourselves to have that golden idea come to us, but really utilize that team that you have. And even if it's not your direct team, I often will go to support or product teams. Even the sales teams. Um, so really just make sure you're building those internal bonds, but focus on those outcome-driven engagements. And so what does that mean? We created email cadences. We recorded trainings for customers because not everybody wanted to join live calls. They wanted short tidbit videos in their inbox. So we did that. And for others who did want to join live calls, we did live Q&As. And so you don't need, you know, a lot of people think for a live webinar, gosh, we need this really robust webinar platform, needs to have all these capabilities. Look what we're on here today. We're on Zoom. I can see all of your faces. We have a chat option. So you can start webinars with Zoom in no time. And so we actually do this with our customers today. We do live Q&As. We keep it down to about 20 customers where they can join. Daily and come and talk with us. And I'd say we probably have about 50% attendance, but the customers that come in have really powerful questions, and we then turn that into blog posts, into knowledge-based articles, and things of that nature to drive further engagement. But whatever your outcome-driven engagements are, make sure you're tracking them so you can see those stats. And of course, those stats typically are going to be stored in a spreadsheet. So spreadsheets initially are your friend. You might not always be able to track things in a CRM, and so it's really about keeping it scrappy, keeping it organized, but starting small. And then once you start small and you get things going, this was me probably about a month into Calendly. We're starting to work on our adoption focus, trying to drive and increase our monthly active users. Ultimately, I did a step back and said, alright, gut check time. Is what we're doing actually working? And in some cases, we all have those wins, right? Is the V1 strategy working? No, it's not. We're like Ross. We're yelling pivot. We feel the weight of the world on us. Maybe we're not holding the couch, but we feel that weight. And so when it comes to that, we want to not stress. We want to step back, reflect on the data because we've set ourselves up for success with some key indicating metrics. Reflect, look back on them and say, okay, what do we need to pivot? What's working and what's not? And think about your engagement strategy. But in other cases, it does work. And if it is working, you absolutely want to keep moving. And you want to innovate based on those learnings. And so it's just once you get to that probably about 30 to 60 day timeline of implementing that new strategy, you've really got to take a step back and ask, okay, I'm about halfway through. Do we need to pivot this? And it's okay if you do, but think about those next steps wisely. And so to give a concrete example here, as we were working on our monthly active users, we realized that a certain subset of customers did not engage with email well at all. And so we thought, okay, how do we engage with them? What does that look like? And we went down this rabbit hole. And ultimately, we ended up deciding we have so much happening with another segment of customers where we're being so successful, we're actually going to pause our efforts here right now. We're going to focus on what's going well. And so sometimes you may decide to pause on a specific customer segment because there's success in other areas and you want to explore that fully over the 90-day cycle or whatever your cycle is. So just little things to think about where you always— you don't always have to have a a next step. Sometimes it's okay to pause and shift to a, to a different segment. That's happened a few times throughout my career. We do end up going back to it, but ultimately, if you have success, you want to fully explore that. So the last part here is scale it. And so when you do have that success, you really want to focus on sharing those insights back to the business and really create a 6-month strategy. And what I can tell you is that, that 6-month strategy is just to showcase to the business that you have a vision and why you're not creating a 1-year vision is because your current business is going to change and evolve so much that in 6 months, you know, your plan is just, it's not even going to be really realistic. And so we want to showcase to our executive team, hey, we have a 6-month vision. We understand the business is going to change. And as it does, we will evolve. We've done the 90-day, we're ready to double it. This helps us gain internal buy-in and alignment. You'll have a lot of executives nodding their head because they know the business is going to change quite rapidly. So now that you've proven success, and you have those initial key indicators of where you know you've been successful, it's the time to make your asks. And so is that hiring and investing in your team? Or is it resources? You, you know your business best. You know what it needs best. Just be mindful in those requests and make sure it's not too lavish, that it's still within reason, because we're still trying to vet out the process. And I always get asked this, but Katie, why is the customer success platform last on your list of recommendations? So just to give context, I started in February at Calendly and we are now just in December. Starting to evaluate our tech stack. And so it's last on my list because the CS platform is not a solution. It enforces a process and strategy that's already been validated. And so as CS leaders, we need to roll up our sleeves, put the work in, and validate the process and the strategy that we have, showcase initial ROI back to the business before we make an ask for a large dollar value customer success platform that may take anywhere from 30 to 90 days to implement. And so I'm all about doing the work upfront, rolling up my sleeves, connecting with the team, connecting with customers. And then once I have those wins under our belt, those learnings under our belt, and knowing how we can truly serve our customers, then I make the ask for a customer success platform, showing how we can elevate our experience and our efforts to maturing, you know, our customer strategy. And so with that, what I'm going to do now is break us up into 2 breakout rooms. And so we've got the first is Defining Strategy. So for those of you who clicked number 1 earlier, where you're creating your team from scratch and maybe you're trying to figure out your strategy and your focus, I highly recommend number 1. That's where I'll be. And then number 2 is Starting Scrappy. So for those of you who are, um, You know, in the trenches right now, and you're actively creating engagement strategies, I highly suggest number 2. And so identify where you are. We'll head into the breakout. I think Caitlin will help us there, and you'll have Alicia Roberts guiding number 2. I'll be in number 1, and then we'll all come back here and we'll share some of those learnings that we, we connected with in the breakout sections. Thank you, Katie. I'm going to open the rooms and you guys can pick like she said, or I will assign you to one if you linger a little bit. But we'll spend some time in there, and I will open them now. Cool. Can you guys see them? I cannot. You cannot? But humor me in the chat if you can't see them as well. Maybe I'm just Flying solo here. I see some people picked them, so— No, can't see them. Okay, we're all in the same boat. Let's hang tight. Oh, that's weird. Some people are picking, so I will assign people as they go in, um, and hopefully we can still get some conversation going from there. Okay. Looks like we've got certain folks putting in the chat which breakout room they want to be in. So we'll see how that goes. Alicia's where she needs to be. I want to make sure, Katie, you get where you need to be. Yeah. Nothing changed on my end, so maybe— so everyone who's still with me, are you wanting to be in the first breakout room? Give me a nod, some of you a video. Cool. Michael, I got you. Thank you. All right. Well, all right, we got thumbs up. Okay, I'm going to assume whoever is here with me that we're ready to rock and we're ready to talk some strategy. Give me some context, I guess, on, on where, where you are. Do you have a defined strategy today? Are you working on building it? Anybody feel free to speak up. I'd love to get some conversation started.

Hi there. Can you hear me?

Great.

So I lead client engagement, customer success for a SaaS tool that is financial-focused. So it's actually a pretty technical tool. And my team right now, I have a team of 3 under me. We are involved. We're still early stage. We're involved in kind of like pretty much everything. I just got it. Wait, I just got a pop-up saying the host is inviting you to join breakout rooms defining strategy. Are we all going to get kicked out, do you think?

You're good. Okay. All right.

Okay. I'm going to just exit out of that. All right, cool.

Sorry, I wasn't sure if I was going to get kicked out.

Okay, cool. So we're right now, we're actually kind of participating through everything from like assisting sales and like sales engineer capacity through to doing onboarding through to very white glove, I guess, service and success. And we're trying to— I have to focus on, as you know, we scale the business, we're going to try to meaningfully scale over the next couple of years, like how do I try to build the team up in a way that's