184. Ironclad’s CCO Reveals How AI Actually Predicts Churn ft. Rob Edmondson (Ironclad)

And that in fact there was like getting some of the fundamental data structures right first as part of like their onboarding were important before they started trying to apply the AI features to it.

Josh Schachter [Host]:
Oh, that’s really interesting.

Rob Edmondson:
Yeah, yeah. And so we walked away. We’re like, all right, we have a better understanding now of what our customers are like and we can use that to help us be smarter about where we might intervene.

Josh Schachter [Host]:
You’re listening to Unchurned, brought to you by the Gainsight podcast network. Before Rob Edmondson became chief customer officer at Ironclad, he was a second lieutenant in the U.S. army. He carried one idea out of that mission. First people, always. And years later, answering support tickets, running CS teams, building a cco Org at a legal tech company in the middle of an AI transformation. That idea is still the thread today. Rob talks about what it actually takes to build a post sales team that measures outcomes, not just activity.

Josh Schachter [Host]:
And what happens when you build a churn prediction model and it tells you something you didn’t expect to hear. I’m Josh Schachter. This is Unchurned. 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 everybody. Welcome to this week’s episode of Unchurned. I’m Josh Schacter, senior vice president of strategy and go to market development at Gainsight and host of Unchurned.

Josh Schachter [Host]:
One of the products we use Ironclad for our contract management. And so I am very happy to have joining me today, Rob Edmondson. Rob is the chief customer officer of Ironclad. Rob, thanks so much for being here.

Rob Edmondson:
Thank you, Josh. It’s my pleasure. And I was just talking to Caitlin, your AGC yesterday about how she was using Ironclad. So appreciate you as a customer for sure.

Josh Schachter [Host]:
How’s she using Ironclad? Let’s just go straight into the plug.

Rob Edmondson:
Yeah, well, I mean she, your sales team is using it to get contracts done. And so we’re a contract lifecycle management solution, very much powered by AI, but it lets you take the process of getting contracts done, makes it faster, more efficient, and gets you good clean data in A database of what we call repository of contracts.

Josh Schachter [Host]:
Yeah, yeah. And very much benefiting from AI transformation in these days. You’re very much in the thick of it.

Rob Edmondson:
The legal tech space is ripe with AI use cases and it’s really exciting time honestly, in that space, what does

Josh Schachter [Host]:
your org look like? And then I want to talk about you and then go back to your org. So what is your remit at Ironclad and what’s the orc orchestration of your organization?

Rob Edmondson:
Yeah, so I’m the chief customer officer. My team, we is known internally as customer Outcomes. And so our goal is really to make sure we’re solutioning the right solution for a customer, implementing make sure they get value all the way through renewal. And so what that means is I’ve got our solution engineering team in pre sales. We also have a team called technical Services that kind of sits on some of the more integration type approaches. My professional services, a scaled customer experience team and a support team. So we pretty much cover the full life cycle of the customer.

Josh Schachter [Host]:
Was it always customer outcomes or is that like a new AI?

Rob Edmondson:
Yeah, we did that about a year and a half ago. When I first joined I was running professional services and I’ve been fortunate to take on like a broader scope here. But it really, I think I’ve seen other organizations move in instruction too because if you think about the big thing now is the outcomes based pricing. And really our goal is if you think about a future where people are just paying for a discrete piece of value that you get out of your software, our goal is to make sure we’re solutioning that the right way and then allowing customers to attain that. And really I think it puts the customer first. This type of work structure.

Josh Schachter [Host]:
You’ve had a rich background in, in sas, but prior to that if we go all the way back, you’re, you’re a military guy, you’re a West Point guy.

Rob Edmondson:
Yes.

Josh Schachter [Host]:
Yeah. Tell how, how did you go? How’d you make the leap from the, the bridge over into tech?

Rob Edmondson:
Yeah, I mean when I, I had an engineering degree from West Point, I spent five years active duty. And I think what I would say I took away from that, it was a great experience, but really was at a young age professionally a leadership focus and understanding, you know what that means and making a lot of mistakes early in your career that you can learn from. When I got out of the army, it was a good time in the economy. I was able to get into a technology company that was actually computer aided design software because my degree was in Mechanical engineering a long time ago. And I was a support agent, like taking calls from customers. And so that honestly was like the best way you can imagine, like an entrance into a future CCO is just like picking up the phone or, or an email from a customer that’s trying to get value from the software and hitting the, hitting the obstacle.

Josh Schachter [Host]:
You know, for some reason I’m having trouble thinking of somebody going from like military experience, like you had to, to support.

Rob Edmondson:
Yeah, it was a big, it was a big transition. But, and, but, but, but truthfully, like the, the thing I’ve carried through, like I think we talked about this earlier was like this idea of, of mission first people always is a motto that you have, you kind of learn in the military or in the army. And so regardless of like what role you’re in, I think like, it’s a really a good mantra in the sense, like as a leader, whether you’re officially a leader of a team, whether you’re working collaboratively with customers or with peers, like understanding the human element, and that’s something of the dynamics, but also having a clear view of what are we trying to accomplish in whatever team we’re on and what are our clear goals and making sure everyone understands that and then not losing that human, the human element of working together.

Josh Schachter [Host]:
People first, mission always.

Rob Edmondson:
Mission first, people always. You could do it either way, honestly, but I think you could argue maybe one goes in one direction or another. But the idea is like, you have to have that mix that view on both sides. And I’m really proud of the team we have here and that we are able to get, we’ve given people opportunities as we’ve grown as a company to grow professionally and, but also getting the job done at the same time.

Josh Schachter [Host]:
So this is a total non sequitur that I was not prepared to talk to you about or audience about today. But I was like up all night last night trying to think about potentially a new title for a book that I’m writing, Founders who Build really Strong Relationships. And I’ve been calling it the Relational Founder. And then I was talking to a guy who’s going to help advise me on writing the book.

Rob Edmondson:
Okay.

Josh Schachter [Host]:
And, and he kind of poo pooed that. And I’m like struggling with it a little. He, he had good reasons for it. He’s like, you know, who’s not a relational founder? You gotta be like, where’s the tension there? Where’s the point of view? Right? And, and as I heard you say that, and so it was probably like this you know, Freudian slip or whatever. People first mission always I’m like, oh yeah, there’s a title.

Rob Edmondson:
Yeah, that would be a good title. The other thing, we did our sales kickoff a couple like a month ago. They allowed me to get on stage for a few minutes. And one of the things I was talking about is, and I always talk about as a theme since I’ve been here is a customer love. Like how do we make sure our customers know we care? And one of the things I was talking about this year was you can connect to somebody’s brain or you can connect to their heart. And I think like you have to do both to really make sure, like they, you can do a business case, for example, an ROI and say we’re going to save you this much money. And that’s like the brain. But unless you can like tell stories, unless you can really help them understand how at the human level what it’s going to mean for them that like you really miss out on opportunity to connect with customers.

Rob Edmondson:
And so like, I don’t know if

Josh Schachter [Host]:
that’s, it’s more important in your experience, the brain or the. I thought you were going somewhere else. I thought you were going to say you can, can do either or, but I think you were suggesting you do both. But which, which do you think is the more critical piece?

Rob Edmondson:
Well, yeah, I think it’s the human element because. And that goes for selling, it goes for customer success, whatever. Like people when they make buying decisions, when they make decisions about renewal or expansion or just how they show up. I still fundamentally believe like we’re in a people business and if you don’t get that right, then you’re just kind of like at the whim of the elements to see can you keep this customer or not? If you can connect at a human level with someone, I think it really is like a multiplier. That’s my particular. I guess it depends too. I hate to like sometimes you see people say this is always true and it’s like at least it’s true. I think in our business, particularly when you’re trying to move into the enterprise and have complex relationships with customers at a different.

Rob Edmondson:
If you’re in a B2C business, that’s a different scale. It’s probably you would think about it differently, I would say. But like for me most of my experience has been selling to mid size or enterprise customers and I think it’s really true there.

Josh Schachter [Host]:
Is there anything that you do with your teams to help enable them, train them, make them really that people first mindset.

Rob Edmondson:
Yeah. I wouldn’t say there’s anything specific. The. I try to model that I think in my approach, you know, I have a standing office hours on my calendar that anyone can just book, you know, and I encourage my team to just. I love it. I wish they would do it more, you know, and just. I’m like, you can come tell me about what you’re up to. I think I, I blocked this time to just hear what’s going on.

Rob Edmondson:
And I try to, like, I try to know, I would say. And it’s hard to do sometimes, but like, I try to know my team at a human level and understand as a person what they’re like. I mean, we’re still. It’s a job, it’s, you know, we’re not. I’m not. Yeah, there’s boundaries there, but I think that’s. And I, And I would say too, just trying to have a leadership team that takes that same approach. It helps.

Josh Schachter [Host]:
So it all, I mean, the culture stems from the top always. Right. So it got to. Example, how’s AI changing the game for you guys? For, you know, not, not commercially, but. Well, not as far as the product, but. Right. Like with, with how you operate.

Rob Edmondson:
So I mean, I can answer this from a couple angles. One, and I think it’s good to acknowledge just how much disruption it’s causing in terms of just. People have established business models, operating systems, and it’s all changing and it’s in it. It’s changing so fast that you really can’t predict three months or six months out what might be true.

Josh Schachter [Host]:
Yeah.

Rob Edmondson:
And so I think that’s just one thing to understand. And like, I’ve been talking a lot with my team about like, we have, we. We don’t. We are going to have incomplete information about what the future is going to look like. We have to make some good assumptions. We have to give ourselves permission to like, do the best we can and try to adapt. Right. And so I think that’s just one thing.

Rob Edmondson:
And I think we see it everywhere and with our customers, we see it the. Internally, we’ve had some real wins with AI in terms of some things we can do for our customers to help them and also understand our customers better. And I can talk about that a little bit.

Josh Schachter [Host]:
Go talk about that a little bit.

Rob Edmondson:
So one area we’ve used, it’s been super interesting. And one of the things I’ve talked about too with other people is like, sometimes you get these sort of surprises when you use AI. Like the things that you don’t expect but one was around predicting churn for our customers. And so we have a pretty robust view on from a data standpoint, both like product usage but all the data that everybody has within their business about customer interactions. And we did a project with a vendor to say what can we do to build a model for six months out? What if this customer would turn or not. And what we found it was a, it was a very data intensive thing as you can imagine. But now we have a model that.

Josh Schachter [Host]:
Can you say the vendor? I don’t know. I mean I’m gainsight here but I like to be open Kimono.

Rob Edmondson:
It’s one of your competitors I would say.

Josh Schachter [Host]:
Oh, so then yeah, we’re not going to say that. Forget that I don’t want to keep going.

Rob Edmondson:
Keep going.

Josh Schachter [Host]:
Rob.

Rob Edmondson:
There’s a lot. But even so there’s a lot of interesting solutions in this space. Like I’m not, I’m not here to talk about the one vendor but the. So what was interesting is one is we learned a lot about what our the digital signature of our customers looks like especially on a happy path or on a not a happy path to keep it simple. And what was surprising was the things that sometimes you might assume were, were indicators of, of a successful renewal or sexual use. Successful use weren’t always true. So in and the other thing we learned was like our upmarket profile was different than our down market. We could segment and say above this many employee company we see a certain type of behavior and below a different one.

Rob Edmondson:
So upmarket what we saw was it wasn’t actually consistent usage like every day that indicated a successful renewal, but there were these patterns of renewal. And if you think about contracting it’s a very cyclical process within business. And so digitally we could see like if they’re following this pattern it was a really good sign for us. And then just like an interesting finding down market was for AI features within our product. If they tried to adopt them too soon, it actually didn’t correlate well to a good outcome. And that in fact there was like getting some of the fundamental data structures right first as part of like their onboarding were important before they started trying to apply the AI features to it.

Josh Schachter [Host]:
Oh, that’s really interesting.

Rob Edmondson:
Yeah yeah. And so we walked away. We’re like all right, we have a better understanding now of what our customers are like and we can use that to, to help us be smarter about where we might intervene.

Josh Schachter [Host]:
How, how many users usually are engaged with ironclad. I mean you’re working with large companies, but you know how many. I know legal teams aren’t often so huge.

Rob Edmondson:
Yeah, it’s like the legal teams could be small, it could be one person or a team of like legal operations. But then there’s a lot of the, the sales team would be interacting, you know, either via salesforce integration or directly within the tool. And you could have thousands of people requesting contracts, for example.

Josh Schachter [Host]:
Okay. Okay. Join me at Pulse this May in Las Vegas. I’d love to meet our listeners. Come say hi. And your daiquiri in that tall fluorescent cup is on me. Seriously. Use code unchurned for a special rate@gainsightpulse.com you guys went through a maturity model assessment or is that what you were just describing?

Rob Edmondson:
Yeah, well the interesting goes then that actually helped us build a very robust, we call journey stages, but essentially like a four stage process where we know like you if you hit these six benchmarks within product usage, you go from what we call foundational adoption to advanced adoption to a maintenance or like a mature phase. And then the first would be like during implementation. But we now have signals we know we can watch for either upmarket or down market customers, what that progression should look like. And then it helps us intervene more quickly when we see them not on track. And then also we’ve partnered with our account management team for what we call like an early warning system where we can intervene if we don’t see value signals early on and we can make sure we’re talking to the customer and making sure they’re getting what they need.

Josh Schachter [Host]:
Yeah. Tell me more about, I mean once you were able to establish those milestones, that life cycle, what were the next steps that you took or maybe still are taking to, you know, to, to make sure that they are passing through those stage gates as customers.

Rob Edmondson:
Yeah. So it’s one thing we’ve done is taught we, as we went through our planning process, we’ve tied some KPIs for the team. So our CSMs actually have targets for their book of business to say on a given quarter. I want to, I want to see them advance their book of business a certain number of percent of customers from one stage to the next. And so it’s given us a really clear like I’m actually quite excited about it. Cause it gives like a really clear mandate to a CSM of like how we can measure progress. And it’s not just you know, did we do a qbr? Did we talk to the customer so many times we can see like in actual adoption metrics are they improving or going down the path?

Josh Schachter [Host]:
It’s funnel analysis almost, in some sense.

Rob Edmondson:
Yeah, yeah. And so it’s, it’s the challenge with it. It’s data intensive. So we have like, we have a reliance on our data team. If there’s something goes wrong on the data side and suddenly those metrics aren’t working one day everybody’s like, wait a minute, what’s, what is this going on? But that’s the, like, if you think about just AI in general, that’s the world we’re going to where it’s all about quality data and having that robust set of data.

Josh Schachter [Host]:
How are you going back to AI? What is the vibe, and I don’t mean that term as a pun though it is of how your team is perceiving AI right now and what are you doing as far as putting it directly in their hands for, for building out their own tools or playing around with all the different options that are out there these days?

Rob Edmondson:
Yeah, I mean it’s, I’m sure it’s very similar to anybody listening to this podcast in a similar boat. But, you know, we have a lot of options. I would say is the first challenge is like, okay, we’ve got Glean internally we use, which I’ve been a big fan of, because it has access and respect permissions across to the data that you have access to. You know, we’ve got, we’re, we’re, you know, we’re using Claude in some parts of our organization and there’s all the, you know, it’s a little overwhelming.

Josh Schachter [Host]:
Yeah.

Rob Edmondson:
People, there’s this. What, what I would say we actually just did. My, actually my boss just did a AI usage survey internally and it, the fi. He published the finding just the other day. And it’s like really interesting. The, the biggest balance or challenge we’re having is like the governance of IT versus giving people freedom to experiment. I think we probably are a little bit too high on the governance process right now, but there’s good reasons for having governance of how much you put in place. But what we are working on is we do have a set of agents that we’re defining to do specific tasks in the customer journey.

Rob Edmondson:
So one example would be actually in pre sales we have a solution fit score and summary. We do as a solution engineer will do for an opportunity. And we now have an agent that will help the SE write that, but also help recommend the solution fit. And so it’s taking something that could take an hour today into five minutes and letting them update it into Salesforce. So it’s a classic efficiency gain use case.

Josh Schachter [Host]:
And everybody has. You said Claude, everybody’s got their portals, their accounts that they can tinker with or you’re still kind of working on that rollout.

Rob Edmondson:
Yeah, I think in Claude, our engineering team is using it more right now, I think, than we have the GDP GTM team. But we’re evaluating, we’re trying to figure out like, what does the future look like and is it like, does everybody get one of everything and they figure out, you know, what works best for them? Again, it’s that governance thing. And I think because I have a lot of ideas on where we can use it and so does my team. But figuring out it’s one thing to have an agent that one or two people use, but then like I’ve got 140 people in my organization or somewhere in that range and so like are all of them using the same tools in the same way and is that even. Does it even matter? Right. Or is it like, you know, is there a balance there?

Josh Schachter [Host]:
Now? The reason I’m not trying to put you in the hot speed, hot seat, I just, I have this conversation all the times with, all the time these days with leaders and everybody’s trying to figure it out. You know, we at Gainsight came out with our MCP that we’re super stoked about. And one of the reasons that we’re really excited about that is because we’ve recently become huge on Claude.

Rob Edmondson:
Yeah.

Josh Schachter [Host]:
You know, and. But also trying to, you know, distribute it to everybody, which, which we’ve done. Chuck has just kind of like just trailblazed and made sure that that that productivity tool is accessible to the whole organization. But then we have to do that in a very safe way. Right. Obviously as well. So like it’s, it’s a very kind of thing, complicated thing to finesse and.

Rob Edmondson:
Yeah, I’m not supposed to ask you the question, but like, the question in my mind is like, how do you enable everybody in a way that, that helps them? But also. Yeah, like, we’re not man, we can’t mandate and say you have to do your job with this tool. Right. Like, like you give people a little bit of freedom to still do what they need.

Josh Schachter [Host]:
So I don’t know, can you mandate it? Yeah, you can’t. Yeah, I don’t know. You can’t mandate it to the exact. Like. But like, do you need a CRM if you’re in sales? Do you need to use that? Well, maybe, maybe sellers would say no.

Rob Edmondson:
Here’s what I’VE said like to my team is that like 12 months from now, like if you’re a CSM or a consultant or an SEO whatever and you’re not, you don’t know how to use AI tools as daily part of your job, it’s going to be really hard to be very good at your job. And so like figure it out what works for you. But, but yeah, ultimately like it’s clear that that’s. People have to, to own it themselves a little bit of like and adapt it.

Josh Schachter [Host]:
So yeah, they do. I mean we rolled out Claude to the whole org, I believe at least to the whole field. Right. Go to Market Motion. We had rko, you know, our sales kickoff about a month ago and held open session for, you know, with one of the citizen builders, this guy Brady Bloom. He comes on the program a lot, but he, he just took it upon himself to just, just learn everything about Claude over the past year. And he’s just such a guru and he just, he held court and showed us all how to do it, built skills for us. So like we’re all kind of in it together.

Josh Schachter [Host]:
You got the slack channels, the office hours.

Rob Edmondson:
Yeah.

Josh Schachter [Host]:
You know, our CEO Chuck is sending emails on the weekend about what he. He vibe coded and, and so it’s interesting. But then again, right then you’ve got legal and IT that are coming up with the guardrails and making sure that we’re doing this in a very secure way, which is critical. So you know, and then there’s the whole build versus buy debate that I have, you know, with, with a conversation I should say I have with folks.

Rob Edmondson:
And you know, I’ll tell you one thing I, I am doing. We’re like. Because we’re actually working on a roadmap too right now. An AI roadmap for my team of like what are the. How are we going to prioritize certain tools? But what I, what I’ve asked is like let’s tie it to. We have. We use an OKR model but let, let’s tie. If we’re going to build an agent, let’s tie it to an OKR so we know it’s, it’s moving a needle somewhere because I think it’s easy.

Rob Edmondson:
The problem is it’s easy to start you. It’s like you’re a kid in Candyland and just having time and you’ve gotta. We’re still obviously have a business to run. So like I’m trying to make sure we are focused in the right areas.

Josh Schachter [Host]:
Yeah, yeah, no, that’s that’s, that’s part of the responsibility as well. So when you think about those okrs and you think about annual planning goals for this year, what are the biggest rocks that you’re trying to affect this year?

Rob Edmondson:
So, so one of them is like incre. One of the metrics we have is essentially a time to value metric. So like the time, the day a customer signs to, to going back to that, that model we talked about, like, we know there’s like a, a point where we’re like, all right, they’re putting contracts live through production and we, we like use that as a, a proxy for. They’re getting value. It’s. It’s not like, it’s not a perfect thing, but at least it’s a, it’s a really clear indicator or milestone. So, so we measure that and we can measure that across segments, across verticals and that kind of stuff. And one of our okrs is like, how do we reduce that time? And so we’re looking, you know, we’re doing time studies, process studies to figure out what can we do to be more efficient to get there.

Rob Edmondson:
There’s also gives us a good partnership with our product organization to say what are things you could do in the product that would. That what are the biggest rocks that are causing us to not get there faster? And so that’s one kind of interesting focus.

Josh Schachter [Host]:
Can AI help you with that? Is that something you guys are thinking through yet?

Rob Edmondson:
Or. I mean, AI can help us with like if we identify maybe there’s certain parts that take a long time. Like how do we get maybe do that faster? I don’t. The team is actually due to like proposed to me like some findings there this week. So I’m curious to see how they did it. But yeah, that’s like one area we’re really focused on. We’re also then once that initial milestone, we also have metrics for the CSM team of like, how quickly can we progress them through those stages of the life cycle to what we would call like a mature stage? And so that’s one of our OKRs. And then the other.

Rob Edmondson:
That is interesting. Like, I think it’s very, it’s like elegantly simple, which is like what percent of our customers are using AI in the contracting process? And we have, we have a couple. There’s different features we use today. We want, it’s like that number is. Isn’t where we want it. It’s not bad. But like we, we know we want that to be better. And so we’re really focused on hey, we’re, we’re releasing new agents, we’re releasing these capabilities.

Rob Edmondson:
It gives a really good incentive for our account managers or CSMs to say, hey, like this, this is something you can use, here’s why it’s important. And then it’ll be a good proxy. Then at the end of the year we can show that that’s improved quite a bit.

Josh Schachter [Host]:
So that’s, that’s about customer communications, just getting the word out, letting people know the well and driving adoption too.

Rob Edmondson:
Like, like we’re, we’re releasing a new agent that helps you do X as part of the contract and lifecycle. It’s a new capability. We’ve got to make sure customers are enabled to go use that thing. And so that’s the team we have today is very, like, my team is very focused on adoption. So it gives us a really simple way to say, are we helping customers adopt new capabilities as they come out?

Josh Schachter [Host]:
From what I’ve heard, from what you said, that’s what I love about the way you guys are operating is that it’s very metrics driven, it’s very product usage driven. I’m a former product manager. Right. So that’s kind of music to my ears. Um, because, yeah, like, I, I love the idea that you can treat, treat the different stages and funnel and, and observe that across your, across your entire customer base.

Rob Edmondson:
It’s really cool that, you know, I, I, I’m, I’m, I’m proud of what we’ve done there. I think it gives us a really good, you know, framework. It’s not perfect, but it’s, if you think about even just like a few years ago, the view we had on our customer was very, it was, we had some data, but it wasn’t nearly as robust.

Josh Schachter [Host]:
So, yeah, Rob, this was great. Yeah, yeah, we’ll wrap it up here. Thank you so much. Wishing you the best of luck for the rest of this year. And I’d love for you to come back maybe later, towards the end of the year and tell us how things ended up.

Rob Edmondson:
I would love that. And I’ll just say thanks for being a customer.

Josh Schachter [Host]:
So you’re very welcome. Thanks a lot. Rob Edmondson, CCO of Ironclad.