Customer Success Playbook S3 E51 - Joe Di Grande - Understand the Goal

Close out the week with a power-packed episode of the Customer Success Playbook, as Roman Trebon and Kevin Metzger welcome Joe Di Grande for a lively Friday discussion on AI in customer success! Joe shares an honest look at how AI can supercharge your customer success playbook—but only if deployed with clarity and purpose. Learn how to avoid the common pitfall of chasing shiny AI tools without aligning them to your actual goals. From automation to predictive analytics, this episode is a must-listen for forward-thinking CS and product marketing teams.

Detailed Analysis: In a world where every scroll brings a new "game-changing" AI app, Joe Di Grande brings much-needed sanity to the conversation. Returning to the Customer Success Playbook, Joe shares practical ways AI can drive serious gains—faster customer engagement, smarter predictive analytics, better documentation—but not without a word of caution: it's not about the tool, it's about the goal.

Joe lays out a clear decision framework: start by asking what business problem you're solving, measure the potential time savings, and always weigh the cost versus value, much like any traditional tech investment. He shares examples from his own consulting work, including custom GPT bots, clever workflow automation with tools like Tango, and AI-driven stakeholder management.

Kevin and Roman add extra layers of wisdom, emphasizing that AI project evaluation is not fundamentally different from any other project: start with objectives, measure value, manage implementation smartly. Along the way, they give a shoutout to innovative tools like Cast.app and discuss how to stay grounded when AI hype is everywhere.

If you want to integrate AI into your customer success playbook—without losing focus or budget—this episode delivers practical, optimistic, and realistic strategies.

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Check out https://funnelstory.ai/ for more details about Funnelstory. You can also check out our full video review of the product on YouTube at https://youtu.be/4jChYZBVz2Y.

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Transcript

Kevin Metzger: 0:05

Customer success.

Roman Trebon: 0:10

Welcome back to the Customer Success Playbook podcast. I'm your host, Roman Trevon. Joined by, uh, joined. By my cohost Kevin Metzker. Kevin, it's Friday. Congratulations. We've gotten to the end of the week and we're wrapping up our conversation with Joe de Grande on talking all things tech, touch strategies, CS tools, et cetera. It's been a fun week with Joe. Uh, we've been talking how to avoid a bloated CX tech stack, how to build simple data-driven processes, how to enable a tech touch strategy. It's been, it's been great throughout. So if you've missed any of those episodes. Make sure and go back to check, uh, check those out. Today we will look at how AI can amplify or undermine those efforts that we talked about. Kev, you excited for today's episode?

Kevin Metzger: 0:58

I always love AI Friday, get to learn new things about AI and how it's being used. So, Joe, welcome back and we're, let's, let's get into the AI discussion from automating customer engagement to predictive analytics. AI promises a lot of big wins. How can you, how can product marketing and CS teams use AI wisely without falling into the same tech stack below, or looking at the, you know, new shiny. New shiny thing, which is really one of the big problems in, in product selection anyway, so

Joe Di Grande: 1:30

Yeah, no, a hundred percent I get it right now. I, I think we're really in a place where there's this shiny object syndrome, especially with ai. Um, I mean, I was just scrolling on y Combina the other day, and when we're talking about like the number of companies, I feel like we're in the.com boom where everything is just ai. It's, it's honestly a bit overwhelming. So there's tons of solutions out there that you can do to solve whatever the use case is. Analyzing data, you know, automating customer outreach, documentation. I would honestly say first and foremost, right, it kind of goes back to what we talked about in previous episodes, is under understanding the goal first and what are you trying to do? Obviously ai, the biggest KPI in my, in my eyes is first cutting back time, right? Like a lot of the things that. You're starting to see with ai, especially like chatt is like the most glaring example, is that how quickly can I get whatever it is that I need to get done? Whether that's analyzing data, whether that's creating content. So that's number one. So try to figure out what that time savings is and then kind of go back, you know, potentially to leadership. Like, hey, here's where we could refocus those efforts. Um, you know, and then we could focus on account expansion, so on and so forth. Um, obviously there's. You know, the signals that are starting to, um, come up, like churn signals as well as expansion signals. I was just looking at a product the other day. It was, I believe it was churn churn.io. Um, interesting solution. It's another customer success platform with a heavy emphasis on AI being able to, you know, distill your information and your data. Obviously centralizing it, but of course coming up with some predictive analytics. There are tons of other solutions too. Personally, I've actually even created my own chat, GBT bot. Um, happy to share it with the audience as well as you guys here. And I use that obviously the, the content creation's gonna be key. I think that's not, you know, not anything new that we've heard, I've even created for customer journey workflows. And the reason why, when I put it into a bot, it starts to understand the business, what, you know, who I'm working with. It'll actually go and create flow charts for me if, if I instructed to do so. And it does a pretty good job. Um. In addition to that, uh, content, in addition to content creation and then creating those workflows, it also does, it'll do the sequencing for me too. So I'll be like, all right, hey, I'll give the information where it's like, alright, here's a company with x. Number of employees, here's what they're paying, hypothetically, this is the space that they're in. The users are broken down to different personas, you know, based on what we're able to track. So I put all that information and obviously within reason everybody out there, right? Ai, it's a very scary thing with certain organizations where they're a little iffy on what you plug in. But, um, once you go and do that, it'll spit out a recommendation. The one thing I will say, and there are a couple other tools I wanna bring up, but. It does still hallucinate. And that's not just chat GPT, that's a lot of other solutions that are out there that'll either have typos, just make up stuff if it just doesn't know and you have to kind of double check. So I don't know if we're in a yet, in a place yet to fully rely on it, but it's definitely changing the space. Um. One in particular that really caught my eye, uh, cast app, uh, that I believe the founder's name is, uh, Dickie. He's out in in Dick Dickie? Yeah. San Francisco. We had

Roman Trebon: 6:19

him on the show. Former guest. Former guest. Dickie. Yeah.

Joe Di Grande: 6:23

Awesome app. Like I had a conversation that was blown away and I'm like, this is, this is the future. I mean, hate to sound so cliche. It's like, okay, we talk about AI taking our jobs and so on. It's, it's pretty scary, you know, especially even now. Churn zero. Um, you know, something I've used in the past, they didn't have this at the time, but they just partnered with syn, uh, I can't even pronounce it. Synthesia, I believe it is. I, I not recognize their logo. They're big on like the avatar AI space, you know, and, you know, for training videos, et cetera. Now you could create your own avatar and, you know, introduce yourself as a CSM or a sales rep. That way you could do it at scale. Pretty crazy stuff. But it goes back to, to kind of wrap it all up again. See, I'm even having this shiny object syndrome. Um, what's, what's the goal, right? Like, what is the goal? What am I gaining from it? What's the time, you know? And then some of them are like, I'll even use it for my business now again, I'm consulting on CSPs and CRMs and I'll use like tango, uh, AI to create my enablement documentation. And that's helps me so that way it tracks my steps. That's fully ai and then I download the PDF or the video or whatever, you know, the deliverable is, and then I send it off. And that saves hours for me. I'm not a graphics guy. I'm not great at that stuff, but at least I could get the point across to Mike.

Kevin Metzger: 7:43

Yeah. Uh, I mean, I think one of the things that, um, I've actually had this conversation a few times lately is when you are considering ai, there was a document. A couple years ago by McKesson on how to evaluate AI projects. And one of the, to me, what was pretty interesting about it, and I I, I said this at a, uh, networking meeting. The other guy day that I thought it was an interesting document, guy pointed out to me, he is like, well, you thought it was interesting. Me, I. But, but the truth is, is when you're looking at AI projects, it's not all that different, right? From looking at any other project. It's, you've gotta look at what are you trying to achieve. You should be looking at what the value that they're bringing is. And then how you, how you implement is just like any other projects you, you implement, right? So. What, what's the objective? What's the return on the value? And then look at the cost. And now you've got an idea as to whether or not a project's feasible and whether you're using, whether you're using AI or not. It's the same, same evaluation criteria. Um, but. I mean, yeah, I think that was a 2022 McKesson document that, uh, um, that got circulated. And it's just, it's an interesting thought process. Right. So really it doesn't matter what the AI app is, it matters how you're gonna use it and where it's gonna bring value. Exactly. Yeah.

Roman Trebon: 9:15

Shout out to episode 46 when we had Dickie on the show toss talking about cast app. So make sure you go check that out. Little shout out there. Joe, you mentioned tango too. Like I, I think that's some of the stuff, like that's an amazing tool. Like there's so many tools that I think if you just go out and try'em and start to use them. You'll start to see real value. Like I'm not you, you know, I'm not a tech person. I've told everyone this. Like, if you can't unplug it and plug it back in, you've overextended my, my technical ability. I can go into tango and build an entire process, document enablement. Click, click, click, click, click, you're done. You can see who, I mean, it's amazing how quick and, and these tools are out there, like, uh, and so use'em, right? Like that's a great suggestion, Joe. There's stuff, there's so many things that I think people hear AI and they get so spun up into like, it has to be some super elaborate thing. It, it's, no, just, just. Get some of these tools we're talking about, go in, play around a little bit and I guarantee you'll get some value, right? It's, there's tons out there. Alright, well we have got Joe to the end of the week. Thank you for joining us all week. You've lasted three shows with us, us three shows with us, so thanks for putting up with us, uh, that long. Really appreciate it. Joe, where can our audience find more about, uh, yourself? I know you're on LinkedIn, but where else can they find out what you, what, what you have going on?

Joe Di Grande: 10:35

No, definitely. You can find me on, uh, Joe does tech touch.com. You can find me on LinkedIn. Um, I'll send it to you guys, but I do have a newsletter as well. Um, and also nice thinking about a podcast, you know, in the works, and it'll be announced in that newsletter as well. It's about all about the unsuccessful things in customer success. It didn't go like, yeah, we'll talk more about that. Um, I think it's gonna be customer unsuccess and um, you know, that's something that'll be launched as well. But if you subscribe to that newsletter, I'll shoot you guys the link. Um, you'll find out all about that as well as kind of your guide of, whether it's tech, touch, sales, operations, customer success operations. They'll be providing tips, you know, and reaching out to people you know, in that newsletter. So that's where you can find me. Awesome. Awesome.

Roman Trebon: 11:16

That's great. Sign up for check out Joe on LinkedIn. Check out his website. Sign up for the newsletter. Right. I love that podcast idea. I know you and I had talked about that when I met you in Atlanta. I think that's an awesome, fun idea and. Uh, I probably have a, I'm, I'm sure we all know a few people, myself included, that we could probably share a story or of unsuccessful, uh, uh, customer endeavor. So that, that'll be a great show. Alright, to our audience, uh, thank you as always for listening. That's the end of our three parts series. You can find Joe on LinkedIn. You can find Kevin and myself on LinkedIn as well at Roman Trevon and at Kevin Metzker. If you found these episodes valuable, please subscribe and share'em with your team and, and your colleagues. We'll be back next week with more strategies for your customer success playbook. We appreciate you listening. As always, until next time, Kevin, keep on.