191. The Retention Killer Hiding in Your Product Demos ft. Kellie Snyder (LinkSquares)

Right. We have some customers that don’t want to talk to us and they renew and they’re happy and as long as they get what they need. But that’s up to them, right? A lot of customers I find that with the whole digital first we kind of, you know, we over rotated in the wrong direction a little bit and so now we’re bringing that back.

Josh Schachter [Host]:
You’re listening to Unchurned, brought to you by the Gainsight podcast network. Linksquare spent two years rebuilding their product around AI agents. Then they brought it to people whose entire job is caution, lawyers and general counsels. Kellie Snyder runs everything post sales there and she found something the data made clear. When you show a careful buyer everything at once, you don’t win them over, you overwhelmed them. So she rebuilt the entire approach around meeting customers where they actually are today, how you earn trust when your product moves faster than the people you serve. I’m Josh Schachter. This is Unchurned.

Josh Schachter [Host]:
Subscribe to our substack@ Unchurned.Gainsight.com where we go deep on every episode. Like how one post sales team at cloudbeds built over 150 AI agents. That story and more at unchurned.gainsight.com hey everybody. Welcome to this episode of Unchurned. I’m your host, Josh Schachter, senior vice president of strategy and go to market development at Gainsight. And I’m thrilled to be here today with Kellie Snyder. Kellie is the chief customer officer at LinkSquares. Kellie, welcome so much to the program.

Kellie Snyder :
Hi Josh, thanks for having me. It’s a pleasure to be here.

Josh Schachter [Host]:
Pleasure to have you. Tell us about Linksquare as you guys are going through your own transformation. We’re what is Link Squares? And then let’s talk about you.

Kellie Snyder :
Sure. So Link Squares, we’re in the contract lifecycle management space and very excited after a huge two year investment that we just launched our new platform on Tuesday, which is a truly fully agentic contract management tool. And in a nutshell, what that means is instead of traditionally just thinking about managing files and workflows around all of that, we agentic piece actually does the work for you. So if you, based on your, you know, your contract assets that you have, you can ask our agent to do anything for you from creating a new template for a certain kind of doc to creating playbooks, you know, term term libraries, all kinds of things that would have taken customers hours and hours and hours before and put that power out into the, the business as well so that the lawyers, you know, can do focus on what they want to do and that’s making sure that they protect the company.

Josh Schachter [Host]:
Is that your ICP is you’re selling into the council and the legal firms and legal departments of enterprise.

Kellie Snyder :
Yeah, for the most part, you know, procurement, sales, it you know, gets mixed in there a little bit. But yes, a lot of our customers are the lawyers and the general counsels.

Josh Schachter [Host]:
Yeah. What’s your remit as cco? Give us a little bit of a sense of the company. I think you guys are around 200 people worldwide. We um, you know, who, who sits under you and what does CCO look like at link squares?

Kellie Snyder :
Sure. So the easiest way to say it is I, I own everything post sales. So once, once a customer buys they get to work with my team. So everything from professional services and onboarding to tech support, customer success and then also our account management and renewals team as well as customer education which I know we’ll talk a little bit about that later on.

Josh Schachter [Host]:
Yeah. Yes we will. Many things. So I want to lead here a little bit with a, with a human first, you know, story your husband Rob. Sadly my condolences passed away about a year ago and you’ve he suffered from, from some of the things around long Covid and you’ve started a scholarship in his name to remember him. And I want to give you the opportunity to share with our listeners a little, a little bit about Rob and about the scholarship and because I know it’s timely right now with what’s going on with that.

Kellie Snyder :
Oh thanks so much. I really appreciate the opportunity to take a moment on this. Rob was passionate about golf. It was a big part of his life and that was the way that I could find to really continue on his legacy. Not only do you love to golf, you love to teach and you love to teach kids. And so what I did was create a scholarship fund that focuses just on that. And so the one year anniversary is coming up on July 19th and so we’ll be awarding the first three scholarships at that time. So really excited.

Kellie Snyder :
The, the response has been huge. The contribution. We’re already multiple years into this beyond this year and so far we’ve had 52 applications. So all kids in high school that aspire to go on to college and play in their golf programs there. And as we all know, college is not a cheap thing, so want to try to help them out so that they can get there and continue their passion. So I know it’s something that RA Would be extremely thrilled with. As far as how well it’s gone so far.

Josh Schachter [Host]:
That’s wonderful. Congratulations to you for going through that, taking that initiative, and having such a special impact in the community. It feels like golf is also one of those sports that’s able to. To. To do that. You see a lot about, like, the grassroots golf engaging with the community. So that’s wonderful. What was.

Josh Schachter [Host]:
What was Rob’s handicap?

Kellie Snyder :
Well, you. You don’t really track that when you’re a PGA player, but somewhere in the realm of like a plus eight.

Josh Schachter [Host]:
Yeah. Yeah. Wonderful.

Kellie Snyder :
So those who know golf go, ooh.

Josh Schachter [Host]:
Yeah. Yeah.

Kellie Snyder :
Okay. Don’t worry about it.

Josh Schachter [Host]:
He was good.

Kellie Snyder :
Yeah.

Josh Schachter [Host]:
Yeah, he was good. He was good. Okay, let’s go back to. To the professional setting in the world of post sales, owning post sales, you guys are going through as a product. You know, you’ve just launch, replatformed, rebuilt, you know, gone through this full transformation commercially and as a product. And I want to talk about that. Let’s start out by talking about what you’re doing as far as AI transformation and enablement internally for your teams to help them perform better and do all the things. What’s going on right now at Link Squares?

Kellie Snyder :
Sure. So we’re very much AI first in, you know, every opportunity we can to. To get better. So from the product side of things, that’s largely supported through Claude. So we’re a big Claude shop, and just about everybody who needs one has a license of that right now. So one of the things that I think is really interesting, though, is to try to not go so rogue with that, but to really capture the places where you can have impact across the organization. So with all my different teams, the goal has always been to break down silos, you know, get teams working together. And so a big piece for us is really around looking at our customers holistically.

Kellie Snyder :
Right. So we call it our customer360, you know, common term out there, but it really, you know, it takes on a whole new meaning, I think, because of what you can harness now if you have the data, which we do, and then you apply the tools to it to figure out things that are really humanly impossible otherwise a lot of times. So some of the insights that you can get really can impact your decisioning significantly.

Josh Schachter [Host]:
You’ve Got. I mean, I have my notes here from our last call. You’re consolidating like nine systems into one. You’re putting things through Snowflake. Can you describe some of the specific. Using Claude, describe some of the specifics of what you’re stitching together these days for that customer? 360, yeah.

Kellie Snyder :
So again, since the data, you can handle data differently these days, we’re really looking at more the front end of the tools and what’s the consumption side of it for the team and how can we bring more of the whole picture to them? So they’re very conversant in what they do and what they’re responsible for and that impact and engagement with the customer, but they don’t necessarily know what’s going on all around them. So how do we bring that to the table? So we just purchased one tool where we think we’re going to be able to depict a really nice picture of that full customer journey. Everything from the specific licensing that’s happened over time with us, you know, so not just initially, but if they buy more, if they down, you know, if they downgrade anything that happens, good or bad, any of the services, you know, not just initial implementation and onboarding, but any other services we help with them over time. And then I think most importantly, customer success, as they spend the most time with the customer, you know, in that whole journey, what are the things that they’re doing? Right, and where are the. The successes and challenges come from there? And, and basically, you know, the transparency. Right. Making that available to the whole team and then really working with them to understand how they best, you know, leverage all of that knowledge to do what they do.

Josh Schachter [Host]:
Yeah. How have you, as a leader personally gotten the most out of Claude and. And this tooling over the past, let’s say, I mean, things move so quickly over the past quarter.

Kellie Snyder :
Really digging in on that data set to figure out, you know, where the customer problems are and why, you know, we all are trying to create, you know, higher retention. Right. So where do we focus? And certainly, as. As you can imagine, like, we’ve seen things on the product side since we have been talking about, you know, the new product coming for a long time. But the other thing is engagement, which is interesting. Right. So in a world where, you know, everybody’s trying to go digital first, I think there’s huge value and there’s going to be a ton that still comes there over time as far as where, you know how you do that successfully. But I guess the way I look at it, Is how do you, you know, how do you use tools like AI to do all of those basic things that just take up time.

Kellie Snyder :
Right. So yeah, like we talked about gong before, like bringing that can that can, you know, enter a lot of the data fields that you have in a lot of your systems of just capturing did this meeting happen? What did the customer say? Are they happy? Are they not happy? All of that, like taking that all off the table and really putting a lot more focus on what the human contribution, the most important things to be doing there. Right. So that’s, you know, again, over time I would say like a CSM leveraging all of that to say here’s the next 12 things I got to talk to the customer about right over my next several different, you know, meetings and how do I optimize that time frame to do those things and let the systems do everything else? And so that’s, you know, at the highest level I think that’s really what we’re trying to achieve.

Josh Schachter [Host]:
Are you, are you CSM sharing skills in Claude and passing around, you know, what’s working for them the best internally?

Kellie Snyder :
Yeah, we’re starting to do that. We haven’t, we haven’t had everybody on the team on Claude until like really recently. We’re starting to hand out those expensive, it’s expensive.

Josh Schachter [Host]:
Those, those license add up.

Kellie Snyder :
It is and you know the, the, the commonality for me is, is capturing those wins and creating consistency out of it. Right. Because you can give people tools and then your best do some of the most interesting things and other people are going to be scared. Right. And you don’t want that. So that’s what I think about is how do we turn that around into more of our standard that you know, here’s what the agents are doing for us and everybody needs to know that, leverage that and that’s part of their how they work on a day to day basis.

Josh Schachter [Host]:
What’s been one speed bump that you hit or headwind or learning from challenge of, of, of, you know, creating this more AI native type of environment for your team.

Kellie Snyder :
I think it’s similar for our customers as it is in our own team. Everybody’s at a different place. And so I do think that there’s more training and more education that’s going to be needed to help make sure we get out of it what we need to. Some people just go on their own and teach themselves up unafraid, I think to just play with it. Other people don’t even know how to write a good prompt. Right. And so there’s just, I think that’s probably one of the things to like I, I, I guess I’m on the spectrum of I’ll try anything right in AI and so, but I’ve encouraged folks on my team like I’m like do, do you ever run your emails through you know, like basic, really basic stuff. And so I think that’s the speed bump is kind of getting everybody excited and on board with that.

Kellie Snyder :
Certainly our product’s going to help because I think when you look at something new like that in a world, you know. Right. Because they’ve known the product really well. I’m hoping that that kind of pairs to get to help, you know, work on some of that. I think stress and anxiety that exists out there because again people, and some people aren’t going to admit it either.

Josh Schachter [Host]:
Right. Yeah. It’s so funny. You talk about everybody’s a different place and everybody’s trying to learn and we actually skilljar our product runs the education product education for anthropic and we’ve seen like this massive supernova of activity in, in Anthropics, you know, self service product education through, through our platform because that’s it. Like everybody is just trying to learn how to keep up, how to, you know, things are moving so quickly. But yeah, it’s one of those times right now where it feels like you just really need to hang in there and keep up with it. I will tell you my favorite resource for keeping up on AI because you asked is the AI Daily Brief. It’s a podcast.

Josh Schachter [Host]:
It’s like a 25 minute podcast every morning that I listen to and I know by listening to that podcast that I am not missing out on the latest news and trends and things like that. With an AI now the next step is actually then sitting down and blocking out time for my calendar to practice it and tinker and stuff like that. That’s a separate issue but to actually get to the knowledge piece and then you’ve got this replatforming of link squares. So I want to talk about that story, tell us the story of that. Where you guys came from, where you are now, you’re in the first inning of that. I mean not even you get the first person at bat right from a, and the impact of that from a post sales perspective for you with your remit underneath you.

Kellie Snyder :
So yeah, it took, it was quite a wind up into the launch on Tuesday. But the story is that this is Tuesday.

Josh Schachter [Host]:
We’re going to film this is going to air a little. This is like May what? May 5th. May 5th, May 5th. You launched. Okay.

Kellie Snyder :
So well before my time at Link Squares, because I’ve been at Link Squares about eight months now. They made the tough decision, right, which a lot of tech companies have a struggle with, or they wait way too long, that they needed to replatform, they really needed to rethink the solution space for contract management. So they made that. They made that decision. They made that bet. And the team’s been working on it for an extremely, you know, long time in. In development years nowadays. Right? Two years is a really long time.

Kellie Snyder :
And so now we finally launched, it’s, you know, certainly a lot more to come. There’s quite a product roadmap for the rest of the year as far as what’s coming with the platform. But even internally, it’s been, you know, a bit of a change management piece where we had, you know, test fests and all kinds of different sessions to try to get the team on board, which was super helpful because it is such a dynamic shift. And then with some of our early access with key customers, we even saw a spectrum of, you know, most of them were super excited. And I want this, you know, where, where’s the order form? We have all these amazing quotes from those efforts, but a couple that were like, this is a lot. I feel overwhelmed. Am I going to lose control of my system? You know, maybe, yes, AI is everywhere. But do I need this thing right now? Which is kind of a very laggard statement, but we got that too.

Kellie Snyder :
So the one thing I think that hasn’t changed is you’re going to have that maturity model right out in the marketplace with this. As far as, like, and we have this, we have, you know, customers who are all over us, right, that want it. We’ve actually already launched the first customer upgrade that happened before the launch on Tuesday. So that, that’s big. And then you have other ones that I know we’re going to be chasing. Right. You know, a year from now, I’m sure my CEO is going to be like, hey, are we end of life in yet? And I’m going to be like, well, let’s look at the numbers. I’m not sure, you know, that that’s where we are yet.

Kellie Snyder :
And that’s, that’s kind of the world we live in. So, you know, to translate that into my challenge, I’ve got everything from, you know, a couple leaders on my team focused on getting those new customers onboarded as fast as possible, redefining time to value, taking advantage of all those opportunities. Speed, speed, speed. And then, you know, I’ve got other, other leaders focused on, you know, the existing customers and how do we get them upgraded because there’s a little bit more to that. And that’s where I think a lot of, a lot more of the education is going to come in. You know, because new customers kind of, they don’t know anything else. So we can just take them on the journey from the beginning of this version of the platform and the existing customers. I think there’s going to be some challenges there.

Kellie Snyder :
Right. Because they’re going to have their reference of the old and it’s going to be a little scary. Right, to go into the new for some of them. And so we’ve invested, you know, I mentioned education. So the one place we’ve invested from a human perspective with this is on the customer education side just knowing that we need to produce not so much, you know, instructor led, but just a lot more online courses pairing knowledge base with, you know, key snippet videos of the how to side of it and just really build up a lot more in the, like, even the thought leadership side of it with why AI and why is this good for you? And what our LLM means separate from like a chat GPT. Right. There’s, there’s all of that kind of knowledge, I guess that gets wrapped around this as well. And, and then obviously, because a lot

Josh Schachter [Host]:
of your customer base, I mean your icps and your end users are not necessarily the most AI native. I mean there certainly, I’m sure, are AI enthusiasts. But it’s not like you’re talking to, not like you’re selling to AES and BDRs that are, you know, using these tools day in, day out.

Kellie Snyder :
Yeah, and it’s often not it either who, you know, is driving that mandate for the corp, you know, for the company. It’s, you know, the legal teams that, you know, want to make it easier for the business, want to be better partners, may have never implemented software before. In some cases we still get some of that.

Josh Schachter [Host]:
Yeah. So migration is going to be a big part of your role for the next five years. Five months. Five months. By end of year, you’re done with it. Yeah, that’s my crystal ball for you is by December 31st you’ve done every single migration of every customer. We’ll see but for the new logos, for new bookings and maybe it’s too early, but so if it’s too early, maybe you can just predict how do you think that will change the way that your team operates Yeah, I think

Kellie Snyder :
the time to value for sure is going to be different. And so I think what, what we’re really trying to push with this too is it’s less of a one size fits all than we tried to make it in the past. Which sounds very cliche from a product perspective. Yeah, because it does so much Right. So like we’re trying to take the feedback of the overwhelming aspect of things and say well new customers could be that way. Like so a smaller, like an SMB company that’s trying to cover the basics and wants to wrap AI around it like just very fundamentally is something different than, because we, we have the spectrum, we go all the way up to, I’d say like lower enterprise and those are very different customers. So, so where do we start? That’s a big focus. That’s different.

Kellie Snyder :
Right. So how do we diagnose through what happened in the sales process and then that very early engagement to say how far do we want to go with this customer? Right. To get them launched doesn’t mean they can’t keep going and can’t keep growing later. I think we tried to just show em everything all the time before and we see in again some of the analysis we’ve been able to do with Claude that we scared some of those customers. Right. And that was part of, you know, part of our retention problem is it was just too much for them. It was more than what they needed. So we’re, that’s, I think one of the biggest things we’ve identified that we’re now trying to you know, factor that into the model and the approach.

Kellie Snyder :
So for professional services that’s a big change for them.

Josh Schachter [Host]:
Yeah. You mentioned investing in customer education. It sounds like a big heap of that investment is in the actual content production, creation and thought leadership. Is that fair to say?

Kellie Snyder :
Yes.

Josh Schachter [Host]:
So what, what did you do there? What, what specifically? How, how specifically did you invest in that?

Kellie Snyder :
Um, well we put, we made the team bigger. Uh, it was very small. Uh, not that we wanted to be huge, it’s not huge. Um, but really to one, we wanted to separate education a little bit more even in that initial onboarding because our PS team was technically doing a lot of that. So you know, bring that out, make it higher quality, let the, you know, the services people focus on their expertise in the product itself, marry that with the education and then hopefully from the beginning get customers more on board with like the con, the structure that we have. So knowledge base, get more self serve, get excited about what’s out there, watch more videos that Just, you know, are easier for you to consume because they all, they all have other jobs, most of them. Right. That they’re doing all day long.

Kellie Snyder :
So there’s that time finding the time issue. And you know, we also, you know, do a lot with webinars. You know, we haven’t. You’re, you’re, you made me think a lot about podcasts leading up to this for sure, because we don’t do a lot of that. So just, you know, how can you make it easier for the customer to get what they need? And then like I said, when we need to engage from a human perspective, we want to be there at that time. And that’s the challenge. Right? That’s the whole challenge that we have is you can’t engage with every customer all the time, but you can use the data, the digital engagement and all the things that you’re doing to then identify, hey, now it’s time we should, you know, step in and make, you know, take, you know, remove a block, a blocker or take a next step with them and then, then they can be back on their, their merry way.

Josh Schachter [Host]:
I wish I could say this podcast was reaching all of our long tail customers and accounts, but I’m not sure that, that our numbers justify that or warrant that. Um, but, but yeah, podcasts could be a thing for you. Value realization. You mentioned that already. So how do you guys go about quantifying the value that you’re delivering to customers day in, day out?

Kellie Snyder :
Now we do it a little differently. So we really try to start in the pre sales and identifying what the customer’s business outcomes are. Right. And so tie that through the whole way and do those checkpoints. So, you know, onboarding are we, you know, are we actually implementing them to, to realize those outcomes? And of course they shift over time as well. And so with a lot of our existing customers, we want to revisit that and say, hey, the outcomes, we shouldn’t assume that they’re going to be the same. Right. So what are they now? And then that can certainly guide that again, that initial scope.

Kellie Snyder :
And where do we start with them? The, you know, I think we still do all of the, you know, the typical things with like customer sat stat you know, pulsing and things like that. But to me, I think what it really comes down to is like when you wrap all of this capability, right, Systems, data, AI, all of this stuff around what we do, it’s really still trying to figure out what that right. Human engagement model should be to be successful and you know, does an entirely Digital first really work sometimes. Right. But that’s dictated by the customer I find. Right. We have some customers that don’t want to talk to us and they renew and they’re happy and as long as they get what they need, but that’s up to them. Right.

Kellie Snyder :
A lot of customers I find that with the whole digital first we kind of, you know, we over rotated in the wrong direction a little bit and so now we’re, we’re bringing that back using the opportunity with the new, new platform to create the engagement that kind of fell by the wayside a little bit. And again that’s a lot of, that’s with that long tail group of customers and bring them back on board and get them excited about what we’re doing. And we’re starting, it’s taken a, it’s taken a minute but we’re starting to see some success and they are, they are responding.

Josh Schachter [Host]:
You’re in your first year in this role. It’s a great role. What is something, I’m going to throw you a curveball here. We didn’t even prep for. What’s something you thought you would be further along with by now. That’s taken maybe longer than expected.

Kellie Snyder :
Well, the, the, the timing on the launch wasn’t clear to me even when I started.

Josh Schachter [Host]:
So that, okay, that’s might be out of your control, but I, that, yeah,

Kellie Snyder :
that’s been one thing. So that, that definitely threw some curveballs into timing and some of the focus. I think I thought we’d be a little bit further along on the overall customer journey in some respects. I think with the diversity of our customer base and the approach we were taking and like as I mentioned, being a little bit too much, one size fits all, it’s taken quite a bit to unwind that. But the good side of this launch, even though I didn’t know the timing is that gives us a great opportunity. It’s just a human thing too to say, hey, it’s a great time to reset. And for whatever reason that just opens, you know, opens it up a lot more to say hey, you know, how can we do this better? And let’s, let’s do it this way now. And that change comes a lot easier I think than just trying to convince people to change old habits.

Josh Schachter [Host]:
Looking at your organization one year from now. So just finishing up Q2 inside of Q2, Q3 for 2027. What does success look like for you guys?

Kellie Snyder :
Well, certainly growth. You know, we want this product to be successful so that we see the growth that we’d like to see which is always difficult these days, these last many years. Certainly the sentiment on the product should be wildly positive, you know, because I feel like we’ve held a lot of our customers at bay for a while. So now they’re, you know, continue the excitement that we’re seeing initially. You know, we’ll have a very well developed product at that point based on where the roadmap is. And so I think we’ll, you know, some of the bumpiness I think we’ll experience in the initial, you know, selling and, and migrating will have smoothed out. And I do know we’ll be talking about how do we start end of lifing the first platform by then.

Josh Schachter [Host]:
Oh, gosh, that’ll be fun. That’ll be. Yeah, that sounds like a fun 2027 project for you. Yeah. What’s one thing you’d like to learn from other post sales leaders and CCOs, maybe that I could ask other leaders on this show?

Kellie Snyder :
I think very relevant. Right. What are. And I think you’ve done this, I think you’ve done this on one or two of your podcasts. I did watch some of the other ones.

Josh Schachter [Host]:
Thank you.

Kellie Snyder :
What, you know, what are the key learnings that you’re finding, especially using a tool like AI? As, you know, you’ve talked about data on some of the other ones. Like we did a lot on data when I first got here. I feel a lot better about that. There’s always work to do in data, I think, but like, as you continue to interrogate and you have more and richer data, like, what are those key findings? What are the things that you found that, you know, maybe I think back to, I think back to my days at Adobe with a B testing, right. We used to get in front of customers, we do QBRs and we would walk them through a test and show them how the human mind doesn’t anticipate or make the right decisions, you know, based on the data. Those used to be some of my, you know, most fun, you know, meetings that I would have and, you know, customers would be very surprised. Right. Because you think you can logic your way to anything.

Kellie Snyder :
And so I kind of equate that similarly with AI. Like, you know, I still get surprised sometimes where it connects dots that I never would have thought of. And so like from, from a delivery and from what good customer success looks like, good customer engagement, you know, what are the things that are working?

Josh Schachter [Host]:
Yeah. Yeah. Okay. Well, we’ll, we’ll keep trying to extract that out from other leaders. Kelly Snyder, Chief Customer Officer at Link Squares. You’ve got. You’ve got a lot going on right now. Congratulations so much on.

Josh Schachter [Host]:
On the new re platforming. It sounds like really exciting times ahead for Link Squares. Congratulations on the momentum that you have for Rob’s fund and the scholarship and wishing you nothing but success. Head through the rest of this year.

Kellie Snyder :
Oh, thanks very much, Josh, and thanks for having me.

Josh Schachter [Host]:
Of course,