Hijacking the AI Hype: Why Your "Automated" CS Strategy is a Trap

Speaker A: Are you feeling disruptive? All right, rebels, we are back in the studio today with fellow North Carolinian Tim Van Leeuw. Tim, thanks for hanging out with us today.

Speaker B: Thanks so much for having me. I know we've been chatting quite a bit and it's been a long time coming. Super excited to be here.

Speaker A: Yes. So you may have seen Tim around, he shares so much as far as content strategy, really kind of the orchestration that happens behind whatever the buzzword is today around digital sort of CS function and, or like scaling success because I think everyone's trying to do it with AI. Uh, anyway, Tim is out doing wonderful things with, with Plan Hat and I won't belabor more of that, but just to say we're so excited Tim, because I know we, you see it on the ground, like what people, what's working, what's not.

Speaker B: Yeah, I see it every single day. And uh, you know, I've had a, a career path that keeps pushing me back to CS and working with CS people. So it's super meta and it's, it's been a, I mean it's been interesting because it's a, uh, it's a space that's had to fight for itself for so long. You think about sales and sales ops and rev ops and all of this and I feel like for lack of better term, it's the redheaded stepchild sometimes and doesn't get the uh, the attention it deserves when that's the set, that's the organization or the functional group managing all of the revenue of the company. So there's great companies out there that put a lot of thought and strategy into post sale management, customer outcomes and all that. And there's some that just don't, just don't do enough. So trying to fight that good fight.

Speaker A: Yeah, no, uh, absolutely. So, you know, I think it's really cool just to hear about people like you who really have lived and worked inside of this organization, built teams, global teams of people that do this. Like, where did all this start? Tell us about, you know, you and how you got to North Carolina. What are you into? What do you do when you're not working? Right. I know that's hard, but yeah, I

Speaker B: mean, so born and raised, you know, 90 minutes north of New York City, went to school in Boston, started work at Oracle in sales. And then I realized I really liked the value extraction, value side of things, use cases. And then I found what customer success is. I didn't know that term. Uh, you know, it was a small town, farm town in New York, not huge tech community there. Yeah, Spent. Spent a lot of time in Boston on the tech hub there, which was really awesome. And then wanted to, uh. Covid happened and was. It was a great time to reassess where do I live, values, all that stuff. And I had some friends that lived down in Charlotte and the, uh, the outskirts and spent some time down here. And I was like, man, it's super reasonable, really great people down here. Uh, people complain about the airport, but I love it. I've never had an issue.

Speaker A: I mean, it's so funny because for. I love, I love. The thing that I love about it is there's. I call it the land of a thousand chairs. There's so many rocking chairs in Charlotte airport.

Speaker B: Oh, yeah.

Speaker A: Like flying in and out declines. It's like, oh, yeah, I'm gonna go rock for a while. But hey, it's fine, right? To your point, it's a pretty decent airport.

Speaker B: Yeah, I think it's perfectly fine. And like, it's also nice because coming down here is a little bit of a reminder of my hometown. It's, uh, my hometown Dutchess county, the Hudson Valley of New York, which is mountains and hills and lush greenery and all that. It's, it's down here. It's that plus the, uh, most ridiculous humidity you could ever feel. So it's not, it's not, not all that different. Except for that. But. But yeah, I mean, spending time outdoors, bodybuilding, uh, is a passion of mine. So I'm actually an amateur bodybuilder and did a show, my first show ever, about a year ago, and next year we'll be doing my second. That's exciting. So excited about that. I think it's. I always say this about it. It's, uh, when you work in software, just work anywhere, there's so much uncertainty. You don't know if your boss is going to be happy or sad or on that day or how they're going to treat you. You don't know how the stock's going to do on that day. But with bodybuilding, it's interesting because it's, It's. You get 100% out of what you put in. So if you track every calorie, if you track all of your cardio, if you track your weights and your movements and things like that. So it's kind of an area of grounding yourself, uh, which I like at the end of the day that I can control something because I can't control much outside of that.

Speaker A: Wow. No. Spoken so truly. And for someone that touches as many customers at the level of customer that you work with, as well as just growing people and then things you share in the community, like control. I think one thing, and I'm sure you can relate to this, it's like control is actually an illusion.

Speaker B: Yes, for sure. And I think that lends itself to the whole AI world right now. Um, and, um, control, I think it is an illusion because, I mean, one, a lot of folks don't put the governance they need in place first. But two, even when the governance is in place, I mean, just yesterday, you know, there's another announcement of Feda and their bot hacking something else. And there's all the people, the tin foil hat people saying it's just a PR play and it could be, but, uh, I really think these things are just out of control and people don't know how to harness the power of them.

Speaker A: So. True. Uh, no, I agree, I agree. And it's like things are happening literally so quickly. Being able to catch up to a place where, you know, it's kind of like, I think about the genie in the bottle, you know, and it's out. And like, that's one of those things where it's like, do we. And one of the things I love about some of the things that I see and that you talk about is like, we have to control that and drive the accountability in that narrative. Right?

Speaker B: Uh, yeah, I think a really good version of this that I saw early on. I was working at a company called Locallytics Startup in Boston and we did mobile app marketing and analytics. So we work with companies like Macy's, the Weather Channel, espn. Really cool stuff. And with that came like push messages. So the messages you get on your phone in app interstitials that you get set of calls to actions and stuff like that. But with the power that came with all of that, it's like with a click of a button, I could send a message to all of my users. I'm just gonna blast them and they're gonna open the app and do great things. And then people realized, oh, they don't like that. They'll uninstall the app, they'll turn off push notifications. So like, being, you know, being direct in the way that you deliver these messages is a hell of a lot more important than your audience size. I think there's parallels to AI right now. I wrote a piece recently about like these, this efficiency illusion or like efficiency is the vanity metric with AI. Like, uh, it was so like five years ago or more. Every single Deck that you saw in CS or go to market was we need to become more customer centric. Customer centricity is the key. And all of this. And the microscope was on the customer. And now that, uh, microscope is just on your internal operations and headcount and efficiency and all of this, no one's measuring are we being more efficient at getting the wrong outcome or having the wrong experience for the customer.

Speaker A: So is the customer now it's getting good? Uh, yes.

Speaker B: Right, yeah. It's like, are we accelerating a poor experience faster but we save more money? You know, like, we reduce headcount by 10% or so? I mean, I think that that's, that's what I'm pushing a lot of people towards is like, efficiency is a great metric, but you need to look beyond that and understand, like ticket closures. Does that mean actual problem resolution or you. Because I've been on the other side of that too. You know, I've been a CS leader for years and I would log tickets and it would close and I'm like, what? Nothing's solved? Like, and then I open another one, I'm like, what happened to the other? So it's a bit of a vanity metric. You know, Seth Godin and these other people would always talk about vanity metrics and things that look good. So if you can't, if you can increase a, uh, metric without increasing experience for the customer or outcomes for the customer, that's an issue because that's showing internally. Hey, we, we massaged some way to do something to make it look good here, but customers aren't benefiting. So I think that's really an introspective look that a lot of CS leaders need to do right now. And I will say, like the last point on this, like, with AI, with Claude, like, it's so easy to get captured and captivated by, uh, immediate output of, like, my dream dashboard is now realized. Or like, this is the coolest, uh, you know, graphic for my marketing team to share. But like, you need to, on the dashboard point, you need to understand, like, there's a lot more underneath that. So people that are building these tools in Claude or doing that type of work, there's a ton of governance, there's security. Now you're your own support team. Automation engines are impossible to build security of. Like, I'm trying to build a portal where my customers can engage. Good luck with that. And then when you build these agents, like you see it, uh, with these frontier models, they're just escaping and doing random things. So like, CS Leaders are not it people nor should they be. So there's a bit of, I used to call it shadow CFS back in like 2018 when people in CSMs would be like creating their own workflows and stuff. But like it's exploded and it's dangerous. But it's also exciting about how do I harness this and how do I get more value for the customer?

Speaker A: Mhm. No, I couldn't agree more. And I think it's, it's so important right to um, to be able to have a reasonable idea about what you want to see outcomes wise and then be able to do that in a non vanity way that scales. And it's interesting because you know, and I'm going to be real because that's the only way I know how to be. Right. Like I've had fully functioning CSPs that were, that were that I inherited. Okay. I also inherited a boss in this case scenario. Company will go unnamed gig. Not necessarily so relevant. But the point, the point feeds into exactly what you said. If the boss doesn't let the orchestrator roll and actually build this in a way that, that works and, or there's not sort of this organizational alignment around like what we're going to show which has to be sold I think somewhat by the orchestrator. Right. But like to your point then it goes nowhere and so then there's this beautiful fantastic technology that's just sitting there and it's doing nothing because there's a person like I still think there has to be a partnership with somebody like almost doing exactly what you're doing from a consultative standpoint say hey look this is working. Maybe this not what does this customer want? What are they not. Let's talk about this from a vertical perspective like somebody who's actually driving that. Right?

Speaker B: Yeah. And that's the fun part of me not having any true sales experience and now being a sales rep for enterprise deals. It's like uh, my whole thing is being a consultant or uh, you know, a high performing CSM or VP of cs. And I think that's what I bring, you know, different to these types of. This uh, type of role is heavily consultative because like I've been in their shoes, I've been, I've done evals, I've run teams where I'm like this is a nightmare and this is causing customer. And uh, you know I think people, people like that, uh, for the most part the where I. Right. I wouldn't, I wouldn't say where I get in trouble but where I Need to pull back is like trying to be too direct and be like don't do that, that's a terrible idea. And massage it in the right way. You know like when someone says they're going to build all of their post sale tools in, in Claude and they have no, you know, no resources from an engineering perspective and it's some csops person who used to be a CSP admin. I'm um, like oh, you're going to burn a lot of money. And the interesting thing too on that, just to give you some more examples because I've been beating the drum about like the build versus buy thing. It's been here forever, you know, Salesforce, build versus Buy, you know, plan hat bills, build versus buy. But there was a company that I worked with, I won the RFP, I won the RFP on 2, 2 prospects. Both of them then got top down mandates to try to build it in Claude and figure it out themselves. One of them I just talked to recently, they're five and a half months in, they still can't write back to Salesforce. They don't have an automation engine. They have about a quarter of the team actually adopting it. There's serious governance issues, there's no usage, um, tracking so they can't actually see how things are performing. And then the other one, the other company man, it was kind of sad. He like it really opened up to me, this guy who's on the op side and he was saying like you know, they don't know what they're getting into. There's a lot of headaches. Uh, right now um, his life is hell trying to figure all of this out because he doesn't know how to do it. And now their leadership is turning over and it's a nightmare. And I'm like, you know, I feel like here's my whole thesis. I think this year is going to be the year of everyone tries to build and figures it out. Small companies are going to do great. You can, you can clog code your, your CS, uh, CSP or CRM. If you're 50, maybe a hundred people I'm sure you could do that and you grow into something. But enterprises that are starting to do some of this stuff, I think there's going to be a big realization from uh, uh, from, from what they're doing right now that it's burning a lot of money, it's not helping customers and instead that efficiency illusion, uh, and the control illusion are going to be at the forefront.

Speaker A: Understood. I'm curious because again you're on the front lines of this, this conversation. Right. Do you think that that's the, the vanity metrics and is it that we're reporting on the wrong thing or is there something else gap wise that we need to kind of solve for as we're trying to bring like say you know, Sally C. Sally. Sally, head of cs uh, at uh, X Organization. I know it's going to depend somewhat on product and size.

Speaker B: Sure.

Speaker A: But where does, where does Sally like not screw up? I know that sounds like a basic question but I know somebody like you knows like what does Sally avoid?

Speaker B: As a csm?

Speaker A: No, as like somebody who's trying to build somebody who's trying to make the tool work for them. Like whether they're going to like say they actually. Let's say in this case she gets to go and vet, let's say it's a magical world and she can go choose a uh, CSP and she's got the technology behind it to feed it and it works. Right. She can push and pull data she needs to tech stacks. Magic things work. Like where do you think she really starts to dig in? It sounds kind of rudimentary but where does she kind of dig in to start, you know, so that she's not wasting five and a half months basically of time.

Speaker B: Yeah, I mean I hate to say it and go back to the um, original thing we were talking about. It's like customer outcomes. What is what you're going to do in a CSP or whatever you build what is going to get that customer to value faster, renew them faster, expand them faster. And if you aren't doing those things you don't have much to stand on unless you're just figuring out a way to be more efficient and get the vanity metric. I think I used to run this accelerator, uh, program for CS leaders and I had them do this capstone project, uh, which I thought was great and it was so simple that anyone, literally anyone could do it. And it's a, this comes from Gainsight, it's the opsp, the one page strategic plan. And it's something that I, I love. And every company should do it, every organization should do it. And on the top you have your, your objectives. What are your objectives? Why does CS exist? Kind of just like your theoretical high level, like what are you trying to get done? But then there's three boxes and I always read it right to left. So on the right is your lag outcomes, your lag indicators. That's your classic grr, your nrr. All of that, yes. Then in the middle is your lead indicators, you know, what are the proxies that you can read on a daily or weekly basis that should fuel. It's a hypothesis, right? It should fuel your lag outcomes. And then all the way to the left of the activities, what on a daily basis is everyone doing to make sure uh, that that lag outcome comes to fruition? And this is all a hypothesis. And this is where I get, you know, one of my pet peeves is like working with companies and they're like, oh, we just want to know the best practices. We want to know, we want to start here and like, tell me what works best. I'm like, best practice. Everyone would be doing great if there was just a common best practice for everything. They need to be manipulated a little bit and massaged for your organization. Uh, so I had all of these leaders come together and like create their one page strategic plan and then on the last session would go and present it back to everyone else. And it was so cool because so many people, so many questions like, oh, why do you measure this? How do you measure this? Has that worked for you? Like, like these kind of like group meetups and things, uh, you know, whether they're events, uh, you know, like Gainsight Pulse or, or plan had open that we do. You know, these things are really great areas to bounce those ideas off of because there's hypotheses that people haven't tried, uh, that might actually work for you. And it's not just banging the phone or you know, having a million meetings or anything like that. You need to find the things that are valuable, uh, and measure those. So like, if you're creating, if you're looking to buy a tool, you need to have a plan and a hypothesis. If you don't have a hypothesis, you have nothing. You have a hope and a prayer and a checkbook and that's it.

Speaker A: Mhm, that's right. Yeah. That was so true though. And then, you know, what's interesting to me is, you know, obviously from a customer success standpoint, we have to, I would, I would say my hypothesis. Right. And I'm not sure, uh, it'll be some time to test it. We'll have to talk again about it. But like, I think over time that's where the redheaded stepchild and we have to work just that much harder to your point to be able to show those things. And I think this one pager and what you were doing, I love the idea because it's such an awesome way to get People thinking about fundamentals. Right. And back to that part, back to where we were talking the very beginning, you know, smart orchestration toward outcomes and not just hey, I've got a tool. Fantastic. And then with that 250k customer, which isn't, you know, in your world, I get it, it's probably not fantastically huge customer, but it's pretty significant that customer rolls. And then you know, you're getting a random message from your ball saying oh well, your health model missed this. Yeah, but that's because health models grow and change.

Speaker B: Yes. Oh man, don't get me started. Health models. Sherry. Sherry will be listening to this and she'll be. She, uh, yeah, I can't agree more with her on health models. Cause that's like with the. Oh man, that. I mean that is like the crux of every software that dies is when it doesn't change with the times. And, and that's when I hate when people point to the vendor and say this isn't working anymore. It's like, yeah, well have you seen what happened in the past three years with AI and you haven't changed anything in your tracking or your system to reflect this type of stuff. So yeah, I mean like people need to start and I think uh, we're seeing a really good change on post sales organizations and CS in general. Because when I started in CS there wasn't a huge variable component to compensation. Uh, and I think the real maturity indicator of CS organizations is looking and seeing if they have a variable comp and what that's tied to. There are so many CS orgs now that are still flat salary and it's strange to be. Even if they're not, even if they're not owning like a quota for renewal or expansion or anything like that, there needs to be some sort of incentive for expansion identification or outcome tracking. So like value logging, value extraction. So you have that type of information. But we're seeing a lot more quote carrying CSMs. Uh, and I think that's great. You know, I see it depends on several things. Right. I think like the way we used to describe it is like you had two by two of looking at like product complexity and like how horizontal you are in the organization. So like sprawl, like the spread of what you're doing at that org. It's like if you are up and to the right on that, you need help from a commercial perspective because there's a lot of different use cases and if it's a technical product, unless you have the tam. So like that's the one size doesn't fit all thing here. So if you have a tam, an uh, account manager and a csm, you might need that because it might be a million dollar contract and you're working through sales, marketing success and a bunch of different things.

Speaker A: That's right.

Speaker B: If you're a company that's like more of these like born in the AI era, productized connectors, really fast ramp time, like yeah, CS genome expansion, own the renewal, things like that and you can incrementally get there. You can have a team metric that's grr related or nrr and then you could start rolling out quota paths. But I think that's something where everything is starting to mature. And something I loved about joining Plan hat was that like when we have like when I sell a deal, there's certain deals where we can hold on to them when there's certain expansion. Expansion versus upsell. Right. So the csm, the upsell. But if there's expansion into a different organization, product group, geo, that's where sales can come in. So I uh, like how those are kind of like lines in the sand because everyone understands it and it's easy to measure those things that are, you know, if you can't measure it, you can't manage to it. That was, you know, a classic quote. But like that's, that's so true. But that doesn't mean things are easy to measure, to talk about like outcomes and things, you know, it's not an excuse.

Speaker A: Yeah, no, I love that. And you know, okay, so uh, I know the chat is, is, is getting lit and I love everything that you're sharing because I think honestly if you've only walked in and led like one type of organization, or if you've only worked in one size portfolio, or if you're still trying to break into success and figure out how to be a success manager in 2026. Because I see and talk to a lot of people that do that too. I just think it's important that the learning, the sharing, the community piece of this. You've said that so much. You've mentioned several awesome events. You know, I've actually never been to the plan event, which is crazy. But I, I love, I love Pulse. Like it's. I love to go to Pulse. In fact, I have a puppy of Pulse floating around here. Cali can. Yeah, that's uh, right. Yeah.

Speaker B: There's also CS Week, which they're now calling Moment. I think they've rebranded from Customer Success Collective. So yeah, that's coming in October, like, so if you're a CS leader or if you're a csm, like, a lot of these things have CSM tracks or like csm, you know, learnings or things like that. I find those things so helpful. You know, I'm a salesperson right now, but, like, I think the best thing that you could be. I, uh, think I wrote a post on this a while ago, like, as a CSM or a sales rep, like, if you want to be genuine and not feel like you have an agenda, you have to be genuinely curious. Like, if you are just curious about. Oh, interesting. Like, you're. You're looking to do a scaled program, like, what's causing that? Like, I want to know, like, is there a board number metric? Is. Are you trying to move out of SMB and go into enterprise? So what's the motivation behind some of these questions or some of these strategies? Because that way you don't have to have your, your list of discovery questions and run them through the pain funnel, as they say in sales and all that stuff. But if you're genuinely curious, it also shows to them that it's like, this person's trustworthy and they're not just trying to push me through their process.

Speaker A: Yes. Because I always say it's the use. And again, like I say, avoid the used car salesman sort of pitch and mentality because nobody wants to be pitched by that gal or guy with the fake orange tan who's like, oh, yeah, you know what I mean? It's the same. And. And I think any CIO worth their salt, you know, or, you know, in, in our case, there could be CCO all sorts of different EDs. Right. But, like, I think that so many wonderful technologies are getting pitched right now. If somebody's worth their salt, it. It gets lost in the noise, if it's cheap, if it's not real. So I love that authentic curiosity part.

Speaker B: Yeah. And it's funny, what we're seeing right now, what everyone's seeing is like the AI label slapped on everything.

Speaker A: Yeah, yeah.

Speaker B: And myself and I know you, you know, Christy Falterusso really well. We talked about this specifically, and I was doing research on it because I knew it was coming up all the time and I didn't realize it, but Gartner has a name for it, and it's called Agent Washing. Isn't it actually something that coined, uh, so they labeled it because they're like, we see this all the time. We need to call it out. Um, but that's really cool. But it's A marketing tactic obviously. Uh, so like you need to know the right questions to understand is this agentic AI, is this generative AI, like what type of AI do you have? Or is it workflow automation? And I don't say workflow automation with a bad tone behind it because a lot of people, a lot of people just need workflow automation right now. And I think owning up to that is like one of the most humble things you can do as a CS leader. Especially if you're in a bit of an archaic, not archaic company, but archaic processes to jump something that's like extremely manual to like completely agentic. It's not shathambable. So like uh, there have been so many studies and reports of people who have gone on site and done all these things and like 90% of what they do is just automation. And that's fine. You uh, know like, okay, now you have an automated process. The next step is figuring out how do you layer AI into this or how do you optimize that with AI? Like you remove steps, do you add steps that make it more value add with AI on top. So I think people need to be honest with themselves about, about that because there's a lot of noise on LinkedIn about hey, I've, I've go to my CSP this past weekend, it's great and everyone loves it and like everyone's like oh my God, this is amazing. Now I have to think about it now you go to that person's LinkedIn profile and they work for a 55 person startup and you work for a 10,000 person company with a uh, 500 person CS org. It doesn't match.

Speaker A: Different, you're so right.

Speaker B: Yeah, different. Yeah, but that's, that's the LinkedIn is a marketing tool at the end of the day like it's a popularity contest trigger, you know, like hook lines and all that stuff. Luckily there's great people on there, but some of the noisiest ones are these ones. So I think people just need to root themselves into their own maturity and start there. Like there's, I'll tell you this, when, when we sell plan hat we want to have several AI use cases, you know, handful of AI use cases and that could be something as simple as summarizing a transcript, but like the one kind of like a bit of agentic, a bit of summarization, action oriented. The most popular one is the sales to CS handoff. So sales has a bunch of conversations. I have dozens of conversations over six months with the company, multiple stakeholders talking about Tech stack and outcomes and all of this. And it was funny when I closed my deal in December of last year, my first deal, I closed the deal. I'm like, oh man, I had so much information here. Now I need to type it all up. But like, I went into Plan Hat. Plan Hat created the document for me already with everything lined out because it had a. A prompt behind it that was prompting the perfect document for a sales handoff that the CSM needs. So I didn't need to prep that at all. That is like one of the key use cases everyone should start with because it, it's low friction. It's something that requires a bunch of different data connectivity. So there's a lot of summarization and it's something that doesn't take a lot of change management to implement. So if you're starting with agent, agentic or AI processes, I think those are the criteria you need to think about. Change management is still the hardest part of anything. And I think I used to run a change management session at uh, a previous company. And my. The best quote ever is people hate two things, change and the way things are. And that is. But I would start my session with that and then instantly everyone's like, yeah, you're right. So it's like so disarming.

Speaker A: Okay, so it's. I don't know how because I've, I've been having so much fun. But we are actually at the half hour already, so that's fun. Tell us a few things. Tell us about, you know, do you think positive rebellion is a good thing in tech and SAS and cs? Uh, like, is that a good thing? If so, why, uh, if so, why not? And then how do we find all things you. Because, you know, obviously your and Christie's most recent talk was just, you know, I think that's a really great one where however and whenever here you want to share floor is yours there?

Speaker B: Yeah, I mean like any type of. I, uh, did an enneagram test a long time ago at a company and I think that's my favorite of the personality tests. And my personality is the challenger. And I think that. I think that looks great.

Speaker A: Totally love that and see that. By the way.

Speaker B: I think that's the curiosity we need nowadays to understand like, like to think about constructive disruption. Because if we look, I mean we looked at all of these m. The famous MIT study of everyone trying to launch things and 95% of things fail. Okay. So when you get that mandate about, uh, using AI from the top, from the board from C level, push back on that. What are the metrics? How does this impact our customers? So like, you know, I'm very, I'm very bullish on AI, but bullish for the people that actually have the governance in place and the metrics in place to do this. Because I see it in small pockets where it's absolutely mind blowing. So I ab. I love that and I think people just need that curiosity and the pushback because I think some people are a little afraid to do it sometimes when there's a company mandate, some people ask questions and are, uh, shunned a little bit. But it all comes down to the company culture. So are those ideas embraced? So I mean, I think that's, I think that's the rebellion aspect. I think it's perfectly fine. Yeah. To find me, uh, LinkedIn, Tim Van Leeu. You can read my stuff, you can argue with me. Some people do. I really like that. It gives me more stuff to write about. And if you want to talk customer success, if you want to talk about go to market. Uh, you know, I ran product marketing teams, advocacy teams. Advocacy is one of the most favorite projects I've ever done in my life. Your customers are your biggest sellers and they always will be. Yeah. Reach out to me. I'm happy to talk with any of this stuff.

Speaker A: Mhm. Well, thank you so much for joining us and thanks for having me, Dan. It's been so much fun and rebels. Until next time, do it big and do it different. Thanks again and bye for now. Sam.