Taylor: [00:00:00] Welcome to Success/ful, where we break down the essential elements of leading customer success strategies. This podcast is all about uncovering blind spots, pushing beyond typical best practices, and tackling those out-of-bounds topics for CS leaders that are key to our success. I'm your host, Taylor Johnston, VP of Customer Success at Vitally. I love connecting with listeners, so find me on LinkedIn and say hello. And we'd also love for you to subscribe on your favorite podcast platform. Today's guest is Lizzy Rosen, Vice President of Customer Success at Vendr. We talk about the first 90 days in a new customer success leadership role. Specifically, how to use that crucial time to build relationships and improve processes across departments. Let's dive in. 

Well, Lizzy, thank you so much for joining us today. I'm excited to talk about all things Customer Success at a new [00:01:00] company, but first congratulations on your first year at Vendr. Before we get into some deeper questions, tell us a bit about your role. 

Lizzy: Sure, and thank you. Yeah. I can't believe it's already been a year. So I lead customer success at Vendr. And what that means is I have reporting to me an account management team, a customer success team, an onboarding team, and I also have a white glove support team that gives kind of a higher tier of service to our customers. Our goal is to provide as much value to our customers as possible, help them meet their goals, and ultimately renew them year over year with Vendr. 

Taylor: Amazing. And a year in, that is no small feat, so are there any major milestones or things you've gotten across the line that you want to share? 

Lizzy: Yeah, I'm, I'm happy we're talking about this because I feel like, you know, people change jobs all the time. When you and I first spoke, you had just joined Vitally. I think I was about six months in. So I think it's a good topic of conversation. It's like, ‘Hey, you're new to our [00:02:00] role. What are you going to do?’ So a year in, we've done a lot. And when I was preparing for this, I was trying to think of all the things we did. And it feels, it feels kind of crazy to list them all out cause it's, it's more than you think, right? So the first thing is we built our customer life cycle. Before I started, there wasn't really a lot of customer segmentation; CSMs were all doing kind of different things, so we really tried to focus on, like, what is the customer journey, how are we providing value to our customers and meeting them in their time of need. 

We implemented Vitally, which has been super successful and helpful in that journey. I also built the account management team, so we previously had customer success managers owning renewals. We decided to build account management and have the commercial conversation be separate from the value conversation, which has been, really, I think, impactful in our overall org structure. And we've done a [00:03:00] ton. We have improved retention, right? That's the number one goal: to improve retention. We've built a digital CS model, which I think is probably the most important. We made a big transition from having more of your traditional customer success model to really needing to be able to scale.

We unveiled a free product this year, and so we are transitioning to PLG. And so with that, we needed to build that one-to-many CS model, and so we've been able to begin work on that. You know, I would like to say it's done. That's never done. You're constantly going to be building out digital CS. But I would say that's the biggest thing that we've done this year. 

Taylor: Incredible. So if you are a CS leader out there thinking there's a lot to do, you are not alone, and it can be done. And, some really cool shifts are happening in the industry and our profession that you've been tackling even in this past year. So [00:04:00] congratulations, you made it to a year. Now I'm going to zoom you back all the way to when you started and today we're going to talk about being a CS leader in a new organization and establishing yourself. So let's talk about those first 30 days, a lot of meetings in those first 30 days, a lot of getting up to speed. How do you, as a leader, ensure that you're getting the most out of those very first conversations with your team? 

Lizzy: Yeah. So, I like to meet with every single person on the team, no matter the level which terrifies people when you first do it, and it's like, I'm a person, I just want to meet with you, I want to understand what your life is like, what your day to day is like. But the key thing I try to ask is I want to know what's not working, and I also want to know what's one thing I should not touch, something that you love, something that's working great for you. Because I think too frequently people come in and they rip up everything all at once, or they try to change everything all at [00:05:00] once, and sometimes forget the stuff that's like the good stuff that people love. So I try to make sure that I understand that. And then I also want to understand people's careers and where they want to go, because while there's a lot to do right now for the organization, there's also a lot to do for the people within the organization and figuring out how we elevate and give them opportunity. And I think through doing that, you also find people who are going to start raising their hands for things like, ‘Hey, I'm building out digital CS. Oh wait, I talked to somebody and that's something that they're really interested in and might want to help on.’ 

So I try to keep those first meetings with the team to be really informal. I want to hear, like, learn about you personally, and I want to know what's, what to fix, what some, like, quick wins might be that we can get, and also what to really just leave ad lib. I also like to meet with people all across the organization. So right, I want to meet with my [00:06:00] direct reports, I want to do skip levels, but I want to meet with the head of products, I want to meet with the head of enablement, I want to meet with everyone, and really just introduce myself, but kind of get a lay of the land, what's going on. 

In every company I've joined, there's friction between CS and some teams. I mean, there is. And let's like, let's be real, they're probably not hiring someone to be the head of CS if there's not a problem to solve, right? And so typically, like, that's a problem that needs to be fixed. , sometimes it's frictionless sales, sometimes it's a frictionless product, and I really try to dig into those and figure out, like, hey, what's, what's not going right so that we can mend this relationship, because, as you know, Taylor, there's, there's no winning with customers unless all of the departments in the organization are focused on the customer, so you have to do it together.

It takes a village. So I try to do, like, those meetings across, the meetings down, and then the other thing I like to spend some time with is getting demos of the product from different people across the [00:07:00] organization. I want to have an onboarding manager give me a demo, a customer support manager, someone from support, and a product person. Everyone does it a 

little bit differently and you learn a little bit more about the positioning, what people are focused on, and why an onboarding manager might do it differently than someone in the product. Like I, I feel like you can find some nuance there, and then I really want to get into the data. I want to look at churn loss reasons. I want to look at are we, you know, contracting more than we're churning? I want to kind of like start getting my head around those numbers and that, that takes some time working with Ops. But it's perfect to do it at the beginning because you don't have any bias yet. You know, I don't have any of the customer stories to justify a loss or any of that. So I can look at it and just kind of slice and dice the data and kind of understand what's going on right now within the business to be able to start making some [00:08:00] decisions on what the strategy is going to be. 

Taylor: That's incredible. And you talked about getting with your peers in other departments. You talked about uncovering some tensions. What else do you look to discover? And in those early meetings, establishing trust and understanding with peers and other departments. 

Lizzy: I want to know what everyone's measured on, what their OKRs are. People are going to be driven by what they're measured on. So, for instance, like if marketing is focused on just net new business, uh, or just leads for net new business, then. Oh, wait, if I'm coming with customer marketing asks, like, maybe that's not going to land that well in marketing. I want to just know those things ahead of time so I can try to understand how I can make sure that not only am I tailoring my message just to the goals that they have, but also that they understand my goals and my team's goals so that we can help one another achieve those. The first thing you really need to know is like, what's [00:09:00] your team focused on right now? What do you care about? , and then I also want, like, what's, what feedback do you have about my team? What are some blind spots I might encounter? I think people will tell you straight at the beginning. They usually want to know, you know, they want someone to come in and help them with these things. So, yeah, I think, I think those are really the two questions that I would focus on. 

Taylor: What about them? I love that. Getting that mutual understanding, but then also offering up that humility and vulnerability. The blind spot question, I think, is such a powerful one, and to your point, folks are willing to be open about it when you ask the question. Are there any other tactics that you use to get to know your team's strengths and weaknesses? Maybe internally, how they operate, but also with customers? 

Lizzy: Listening to phone calls, like. I want to get on customer calls as soon as possible. I want to listen. I'm listening on gong or on whatever recording device you use. I [00:10:00] really just want to understand what's going on with customers and where people are struggling in conveying the value that our product provides to customers. So I think that's a really good way. , I also want to join other team meetings, listen in, how are my directors handling their meetings? I feel like in the beginning you want to be a little bit of a fly on the wall. I think I've made the mistake before. You can probably tell I speak really fast. I move fast. I'm from Boston, like, I just

can't help myself sometimes, but I've made the mistake at some companies of coming in really hot with a ton of ideas, throwing them, like, all on the table at once, and it can cause some, like, panic, some chaos, and so I've really tried as I've matured personally and in my career to just slow down, listen, understand, before prescribing. 

That being said, there are also sometimes some hot fires that just like need to be fixed right away, and so [00:11:00] I try to understand like what those things are and figure out how we can diffuse some of those situations, while also trying to think of like what's going to be the long term strategy for the theme. 

Taylor: Amazing. So you're right. And that 30 days flies by. I mean, just with all those conversations that you're having, listening out for themes and starting to try and untangle, you know, where to start. So let's fast forward to that 60 to 90-day time frame. So you've done a lot of information gathering. This is now the time when you get to start setting the strategy. Any advice on creating clear and concise objectives and prioritizing during that time? 

Lizzy: Yeah. Typically, that's when I'm bringing the team together in person and mapping out, like, what do we want to create for our customers? What is the ideal experience? And I try to do that by saying, like, let's not think about what Vendr needs to deliver to the customer. Let's think about what the customer needs. Like, what are they thinking and what are they feeling? So I typically go through an [00:12:00] exercise that is like, let's do months 1 through 12. And first, we're just doing like, what are the questions customers are asking, right? 

At the beginning they're usually like, oh my gosh, I just bought this thing. It better go well. Oh my gosh, I just asked my VP of finance for money to buy this thing. And like, I've never done that before. I hope it's not a mistake, right? There's a lot of fear in buying, right? So when someone buys your product, they might be feeling those things. And so I try to just break it down into like the human emotion side of it, of where, during the life cycle, what are people, your customers thinking and feeling? Then I try to think about, okay, let's now think about outside of what they're thinking and feeling, what are they trying to achieve? What are maybe the problems that they're having that they need help solving? 

And then how are we going to measure those things? And so by doing that, I find that we can kind of take ourselves out of what Vendr needs and put ourselves into what the customer needs and build a life cycle around that. And so then we're coming up with like, [00:13:00] what are the activities that we're going to do to be able to meet our customer in their time of need? How are we going to measure those things? How are we going to build those things? And so we kind of like to get into that creation mode. It's like, how are we going to build a great life cycle for our customer, something that's going to work for our CSM, something that will scale, and then, after we do that, we go build it, right? 

It's like, we're pulling together groups of people to go build all of this content, build the decks, whatever it may be, the Vitaly playbooks. To go create all of that. And I'm sure your next question is going to be, after that, then what? Roadshow. You got to go on a roadshow. Yeah. Yeah. So, I'm sure you've run into this if you can build a bunch of cool stuff, but if people don't

know about it, they're always going to be confused. What is it that CS is doing over there? And so then I go roadshow. I'm going to the product team meeting. I'm going into all hands. I'm going to all these different things and people on my team and sharing, this is what we're building. This is what we want to accomplish. This is where we need your help. To be super clear about the [00:14:00] changes that we're making, why we're making those changes, and how we're going to measure them over time. 

And I love road shows. It's fun. It's fun to go and, and talk about your team and talk about what you care about. And I find that by doing that you also get this like a united front. everybody really likes, uh, excited about what you're doing but also able to speak about it, uh, in a similar fashion because then that kind of becomes your vernacular in the way that you're going to engage with your customers and internally. 

Taylor: The roadshow, I'm a big fan and again, it's one of those things that you aren't necessarily taught early on the importance of getting the message out and being able to articulate that clearly to the rest of the organization. So you mentioned earlier, this idea of quick wins. Let's talk about, you know, you're setting this long-term strategy, you've got the vision. Now what is the importance of quick wins and how do you figure out what are the one or two things you want to accomplish in a very quick fashion? [00:15:00] 

Lizzy: Yeah. I think the biggest quick win, no matter what company you're at or role, at least for I believe, is quick trust. How do you build trust with your team very quickly? Coming into a new role, like, personally, I don't want to go into a role and just maintain the status quo. I want to go into a role and I want to change things. I want to build things. I want to create things. And you can't do that unless you have trust behind you. That your team members trust you, that the organization trusts you, and is, like, willing to go on that path with you. 

And so, I think that's the first thing that you kind of have to do is build that trust. I think in those one-on-ones, by having them be personal, by sharing about my life, about my family, and being real, I can start to kind of build that trust and then also just being vulnerable that like, ‘Hey, when I started, I didn't know Vendr better than the people on my team.’ They're the experts that I'm learning from. I'm just there to guide [00:16:00] them, to help them with the internal battles, and to take things off of their plate. So I think you can, you can build some of that trust through relationships. And from there, then it's like low-hanging fruit. I find that sometimes there are things that haven't been solved, not because people can't solve them, but because they don't have that outsider perspective of coming in being like, oh, we can fix that. 

Oh, that's like, like, that's just a couple of different things that you maybe need to do that would really just change the life of someone or make something easier for someone. So in those conversations, I'm trying to find those low-hanging fruit. , and, uh, and trying to solve for those as much as I can because if it's like low effort, big impact, you want to get those right off the table.

Taylor: I love that. I mean, to your point, you can create the best vision in the world, but if you don't have that trust, you are not going to get much done after that initial presentation of what you'd like to do. 

Lizzy: So yeah, that's super important early [00:17:00] on. Well, and I just try to think of like, you can think about leaders that you've had before that you've just loved, you've felt inspired by, motivated by. You can probably think about more leaders that you didn't like. So it's like, what are things that I'm going to do that are going to emulate the characteristics of those leaders that I've, you know, been inspired by? And then how do I avoid those things that maybe leaders who didn't inspire me did? And, you know, I think we're all trying to work on what our leadership style is or our methodology all the time. And it's important. I think that's a part of our craft as leaders. 

Taylor: And, you know, you mentioned earlier. In those peer to peer conversations, uncovering where there may be a gap, where there may be some tensions or potential lack of confidence in the function in the organization. And I think also honing in on those as a way to build that trust and some quick wins there, , can help move that along faster too. So it all ties together. 

So in those early days, when you [00:18:00] now, you set your vision, you've got an idea of where you're headed. Maybe in that time frame, some projects come up where you've got specific timelines or maybe you're asking for money. Maybe there's a headcount or a tool that you're looking to bring on board. What advice would you have for leaders in terms of the best way to communicate the potential costs of the plan that you are putting together to more senior leadership? 

Lizzy: Yeah. Always using data. Yeah. Always trying to show the value that it's going to create. I mean, I think One of the first couple of things that you wanna do if it hasn't been built already, is look at a capacity model, and understand, like, what is the capacity of the CS team? Do you need more CSMs, fewer CSMs? Why is A-C-S-M-A one, you know, why is it one to 50 customers versus one to a hundred customers versus one to 10, right? , it really might depend and those might not be accurate yet. , so that's always something to dig into. I think when it comes to purchasing new tools, [00:19:00] You have to create a vision of what the tool is actually going to create for the team. I'm not someone who buys a lot of tools. I typically try to be scrappy before I buy anything, but I think it can be pretty evident when you come in and there is no tool or the team continues to struggle with the same thing over and over again that a tool could easily solve for, it becomes pretty apparent that you may need them. 

It is a little scary making your first purchase. As a new leader on the team, you're spending the company's money, and you want to make sure, right, you're, you're being prudent about that. And so, right, I'm always going through an evaluation period with more than one vendor. I'm using vendors for services when it comes to negotiating, right? You know, got to drink your own champagne, right? , so I, I think when it comes to the justification, it is, it's like building that vision of what this tool or what this additional headcount is going to create, why it's important, what would happen if you didn't have it, like, if [00:20:00] you got to know, what would you go do then and then constantly being, you know, reporting back on, like, the progress of that, right, as a leader, I have to treat the company's money as my own.

Lizzy: And I need to constantly be looking at headcount and understanding, do we have the right amount of people? And then the same thing with the tools, right? Any tools that I'm purchasing are like, is this still providing value? Is this doing what it said it would do? And really just making sure that I have that critical eye. 

Taylor: You know, I think that first 90-day period, it's sort of this, the vulnerable moment as a new person coming in where you both need to understand and learn and get up to speed so fast. And then be willing to make some big asks if the team needs it and be able to do that in a short order. So that's a great way to think about it. So thank you for sharing that. So now that you've got a plan in place, what are some of the KPIs that you use to measure your own success, but also your team's? 

Lizzy: So what I like to do is to have KPIs [00:21:00] related to, like, company performance. , well, not company performance, but team performance that relates to company performance, and company goals, right? So I want to make sure that the team's goals always tie up to like the larger grand picture. But then I like to do individual team KPIs as well. So those KPIs aren't always comp or compensation KPIs. , I think usually they're, you know, usually I try to have some overlap, but what I'm trying to figure out is like, what are the key things to drive within the customer base or the key indicators that drive a higher propensity to renew or a higher propensity to grow. And most companies that I've joined, you don't know those things right away. I think that's right. And those things change, right? So you're constantly trying to figure out what is going to be that one thing that will drive the team to push that's going to drive a higher propensity to renew with my customers. 

And I think at the beginning that that's hard, right? So you want to try to figure out [00:22:00] figure out, I try to first say like, let's drive usage of the product first. Get more people into the product. Right? If that's a problem, we want to get more people in there because I don't think 

anybody can say that a customer is less likely to renew if they use the product a lot, right? So I'm usually measuring things like that, like monthly active usage. I've done weekly active usage. I think it's dependent on the product. Then I'm looking at key-value moments in the product to understand, you know, are our customers who are renewing, are they using those features more than those that aren't renewing or vice versa? 

And then I try to drive some of those things. So for instance, right now, the team found that our SaaS advisory is performing really highly with our customers that are renewing. And so the team is focusing on just driving those. , I want it to be, you know, let's focus on one thing instead of let's focus on 50 things. But in the background, I'm measuring 50 things, right? , so while to the [00:23:00] team it might be one focus area, one campaign, it's important to make sure we still have an eye on all of these different usage indicators to, to understand if we need to change our approach. I feel like I'm jumping around a little bit here, but yeah, I think I would like to summarize it, driving a company metric, so that's typically gross retention, net retention, logo retention, it might be. And then having the team have those indicators as a part of their performance, but then also other indicators that, uh, we're measuring some that are, uh, measuring the background, and then some that are more, like, campaign focused, where the team, that's the only thing that they care about for that quarter.

Taylor: I think that idea of focus, so that we as leaders own, to your point, a lot of metrics happen in the background. It's our responsibility to, like you said it well, keep an eye on those. But to make the team most successful, getting them to focus and rally around something that they have [00:24:00] autonomy to be able to make an impact on game-changing. So, you know, I think you, you honed in on a smart way to do that, especially in a quick order. So you talked about KPIs both in how you measure the team, but also the compensation side of it. So I am curious, when should you evaluate and potentially update compensation plans based on, based on goals? 

Lizzy: It's a tough one. I've had leaders come in and change compensation from day one and I'm like, whoa, whoa, you don't even know anything about my team yet. Right? So I think you do have to wait. You do have to wait. That's everyone is going to get very sensitive around compensation. It's very important. I take it very seriously that this is what people are taking home. You have to be really careful and really thoughtful about it. I waited six months at Vendor, uh, to change compensation. So waited until the new year to reevaluate after having more time in seat, to reevaluate the way that we're compensating in terms of, you know, we were on annual, moving to quarterly, and then also [00:25:00] thinking about, like, how we're going to compensate the team. 

I have worked at organizations where I've come in and they're on a team target, and right, you can't go from a team target to an individual target, like, overnight, and so I've taken the approach of taking a team target, like a global target, and then moving it to, like, a regional target, and then do your specific team target, and then individual target, right? Like, really trying to just, like, narrow it down. So that it isn't as jarring or as shocking and people can get kind of used to it. , the other thing I'll say about making compensation changes is that you need the data to back it up. You need to understand you can't just say we're gonna, you know, push this one thing or we're gonna measure you on this one thing unless we have some evidence or some proof that it does drive a higher propensity to renew. , so I, that's like what I was doing the first six months. It's like how do I figure out what are the right things to measure the team on? And when it comes to compensation goals, right, you want them to be [00:26:00] aggressive, but you want them to also be realistic, and you want them to drive behaviors. 

So when it comes to compensation, I'm always thinking, like, what's the behavior I want to drive? , and then, like, does that align with the metrics associated with it? Because compensation does change behavior, it really does and if I've, you know, if you decide to compensate on one thing and it changes behavior in something completely different than what you thought, you can, you can be in like, that's a really bad culture already. So what we decided to do for this year is we're doing quarterly goals. , with the product shifting, with our focus on PLG, we needed to be able to have the flexibility to change as the product changes. , we have a component of the CSM's compensation based on gross, or yeah, gross retention. And then we have a portion of it based on driving, uh, features. 

We're [00:27:00] driving specific usage. This quarter, it's a feature, SaaS Advisory, like I mentioned, but next quarter we may change the app based on what we're finding, when it comes to user behavior.

Taylor: Well, you have taken us through day one through the first six months. We even got beyond the 90 days, so an incredible amount in a short amount of time. How do you, in that first, you know, we think of the 30, 60, 90 day plan, how do you at the end of 90 days? Reflect and determine how you did. 

Lizzy: So one thing that our CEO had recommended that I do, which I found really helpful, and I actually recommended to someone on my team the other day, is to just headphones in, brain dp. Like, don't care about what it looks like, what it sounds like if it has. But I just associate, just brain dp, just brain do everything that you feel like you've accomplished, everything that's happening in the organization, in the [00:28:00] department, you get it out on a piece of paper. , and the reason why I say that is sometimes I can get a little tripped up with like, how am I going to format it? 

How am I going to position this? How am I going to have the right message? And that can slow someone down from actually just like creating. And so the brain do I think is helpful. , and then obviously doing a look back with the data, working with your ops partner to be able to do that. , 

but I, I take the brain dp and then I try to, like, extrapolate out, like, okay, when I first came in, this is the strategy I created, and then compare it to the brain dp. Did we achieve these goals? , are these, a lot of the times the goals, you're like, okay, that didn't make sense. Like, I said that six months ago, but I didn't know anything at that point. Did I pivot in the right way? , so typically trying to do that. I also do that at the end of every year. I do a year in review where I sit down, I reflect on what I accomplished over the last year just as a [00:29:00] personal exercise, and so I think that's a good point is like doing that when you're into a new job, whether it's at the, you know, end of the year or it's during a six month cycle is, is important also. But yeah, I just try not to worry about what it looks like at first. I can make it pretty later. 

Taylor: Amazing. Well, Lizzie, this has been super insightful. So yes, anyone out there who is Looking for the road map for your first 90 days to six months in the role. This has been incredible. , but before we let you go, we're gonna have a little bit of fun with some quick hit questions. Are you ready? Okay. A little surprise for you here at the end. 

Lizzy: Yes, I'm ready. 

Taylor: rWhat do you wish you could spend some more time on, either in life or at work? 

Lizzy: I've been seeing people needlepoint, and I don't know, for some reason I feel like I would really like doing that, but I'm a reader, so you can't, I can't read and needlepoint at once, and I would always pick reading over needlepointing. But I do think I would like to do that. 

Taylor: There you go. Something new to try out this year. I love [00:30:00] it. Alright, last one. What makes you feel successful? 

Lizzy: The thing that makes me feel most successful and fulfilled at work is speaking with other women who are looking to advance their careers, and who are curious about customer success or tech in general. Just connecting, learning from one another, elevating each other, that's something I spend a lot of time doing, and I just feel like I've had so many people help me

throughout my career. I want to help other people in their careers, and I learn a lot from connecting in that way with people. So just paying it forward in general is, and fostering those connections, is really important. 

Lizzy: Yeah, I think what keeps me doing this over and over and over again makes it fun. 

Taylor: Thank you so much. Big thanks to Lizzie for sharing her insights with us today. And a special thank you to all of you who tuned in. If you enjoyed this episode and found value in our conversation, don't forget to spread the word to your CS friends. Before you go, I'd love to hear your thoughts. Find [00:31:00] me on LinkedIn at Taylor Johnston or linkedin.com/TLJohnston. Leave us a rating and review on your favorite podcast platform and check us out on YouTube. Your feedback means the world to us. See you next time!

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