Customer Success Playbook PS3 E50 - Joe Di Grande - Your CS Tech Stack

Gear up for an energizing discussion on tech stacks and smart scaling! In this midweek episode of the Customer Success Playbook, Kevin Metzger and Roman Trebon welcome Joe Di Grande back to tackle a pressing issue: bloated CS tech stacks. Joe shares why so many organizations fall into this trap and delivers actionable advice on how to avoid or fix it. From building cross-functional committees to starting tech ops planning early, Joe's wisdom is essential for anyone striving to build a lean, mean customer success machine.

Detailed Analysis: Joe Di Grande's return to the Customer Success Playbook is like having your favorite professor hand you the cheat sheet to a passing grade. In this session, he unpacks why bloated tech stacks happen: a lack of operational foresight, siloed decision-making, and the absence of data-first strategies. Acquisition fever might keep the lights on, but without systems thinking, organizations find themselves in a tangled mess of redundant tools.

Joe highlights a proactive cure: form a cross-functional committee that includes sales, marketing, CS, and product voices. Bonus points if you find your "ops-minded" champions by tapping the power users of existing tools! His approach is practical, tactical, and refreshingly unpretentious.

For those starting from scratch (aka "dream budget approved!" scenarios), Joe delivers a fantasy list of tech essentials: a reliable CRM, a centralized data warehouse, sales engagement tools, data enrichment platforms, marketing automation solutions, and customer success platforms—all strategically selected to foster scalability and transparency.

Joe’s core advice? Think operations early, communicate often, and let your data be the thread tying it all together. It's a masterclass in balancing ambition with operational excellence for any customer success playbook.

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Transcript

Kevin Metzger: 0:05

Customer success. Hello and welcome back to the Customer Success Playbook podcast. I'm Kevin Metzger with Mike, co-host Roman Reba. It's Wednesday and we're joined by Joe de Grande Again, Roman Love Wednesdays man.

Roman Trebon: 0:23

Yeah, well, one big question. We got Joe back, right? So, uh, we, if you missed our Monday episode, make sure you go back. Joe talks about what a tech touch strategy is and then how do you implement it. And he actually gave some freemium examples, which I always like the word freemium. So, uh, some, some low cost strategies that you can actually implement today, which is, which is awesome. So Joe's back for our one big question, but Kev, before we get into the one big question, you know, we, we ask these hard hitting questions up front to get to know our guests a little bit better. So, Joe, you ready for these hard hitting questions up front? Let's do it. All right. So Joe, one place that you'd like to travel that you've never been before.

Joe Di Grande: 1:02

Ooh, that's a good question. I have, I have a few. I would say two that come top of mind is Japan. I would like to go to Japan and also Australia, so totally opposite ends of the earth. But, uh, those are my spots really, mainly to go fishing. You know, I'd be, I've seen a lot of videos. I keep track of those areas and I'm like, yeah, I gotta, I gotta get out there.

Kevin Metzger: 1:23

That would be awesome. That'd be awesome. Besides fishing, what's,

Joe Di Grande: 1:26

uh, what's something else you'd do to unplug? It's a good question. I would say, yeah, outside of fishing, I would say it's definitely like drives, you know, I'm a car guy myself, so I'll go on some drives and stuff like that. I. And cruises, especially if I'm visiting up, you know, family up north, I'll head out to the mountains and stuff like that. So that's always good. And then tinkering, like if I'm always, uh, like working on the boat or the car or whatever, that's kind of my way, uh, you know, therapy, so to speak.

Roman Trebon: 1:54

Yeah. Good. That's awesome. Uh, let's do, uh, a book recommendation. You got a, uh, a business book or a personal book that you maybe you've read recently that you'd recommend to our audience?

Joe Di Grande: 2:03

Yeah, I act ironically enough. I have a few behind me. One that was pretty recent, um, was actually the Digital Customer Success, uh, book by Nick Meta. Um, that was a great book. Um, he did his original books in the past that I've read, read as well on Customer Success. It's a blue cover book as well. Uh, this one's focused on digital. Highly recommended if you are looking to launch a digital CS strategy. Another one, which is, which is also here behind me, I just finished, was Fanatical Prospecting. That's just from me, from the standpoint, not so much Cs, but I think there's a lot of learnings from it. But from a business owner, as I'm prospecting and doing my own new business strategy, it's uh, super, super, uh, impactful. Some things are a little, you know, outdated. It's about 10, 15 years old now, somewhere in that realm, but still a lot of things still run ring true on that. So highly recommend those two.

Kevin Metzger: 2:51

Awesome. Thanks Joel. Yeah, Joe, thanks for the recommendations. So our one big question for the day, why do so many companies end up with bloated CS Tech stacks and what can they do to streamline and fix that problem?

Joe Di Grande: 3:06

Yeah, I think that's a great question. It actually rings a bell. I had another conversation about this when they were asking me about like digital CS Tech touch, you know, and it was around revolving around tools and they were like, Hey, you know, if you were to go to a company, what's the best company to get this started? When should they start thinking about this? And I'm like, honestly, just immediately, like if you're a startup, you should be thinking with an operations mindset. And how this ties into it. Why does it happen as far as having a bloated tech stack as they wait too long and they don't have an operations team. They're not thinking systems and data, you know, oriented first. They're focused on acquisition, which is great, right? That keeps the lights on. Well understood. But down the line, I. You're gonna have trouble with trying to figure out how to scale, how to create process for your CS team as well as marketing, right? Marketing still needs data in order to, you know, to leverage it for segmentation when they're doing their, you know, lead nurturing and et cetera, as well as new business now. When we talk about that, right, like now, what happens later, there's no operations team. You have these different departments essentially living in silos, which creates data silos as well as tech silos. So they're focusing on their end, you know, day-to-day goals, and they'll acquire whatever solution and maybe they're not communicating with each other, and that's where you might run into some troubles where they're buying stuff that does duplicative. Right. They have the same feature, same technology. Um, so that's something to keep in mind. I would say. How to solve that is one, I've done this before, develop a committee. If you don't have an ops team that's broken down by sales, marketing, cs, and having someone that has this closely tied to like product, um. Worst case, have some sort of committees that they connect to each other. Someone that's a little bit more ops minded. How I, honestly, I, this is a recommendation I gave someone recently. If they're not sure who that person is that has that ops minded mindset, if there are already tools, go figure out what tools that they are using. Do kind of a tech stack analysis. Go talk to that vendor, be like, Hey, who is my top user of that tool? And then you're gonna start to find out. Okay, great. You know, Johnny, Sally, whoever that is, is a big advocate for this. Great. They might be, you know, be more ops oriented already, and then that might be your kind of champion, so to speak. Um, but I would say like, to kind of the key takeaway is like communication is gonna key. Start thinking about ops as soon as you can. If you're early startup. Um, as well as data and then develop that committee, get people talking. Um, and then that's how you can start to avoid tech, you know, tech stack bloat. Um, and sometimes you're almost even forced to it too when budgets start to get slashed, which is obviously probably a little bit more common nowadays. Um, so it'll kind of force you to do that. But those are some tips there that, um, could be pretty impactful.

Roman Trebon: 7:21

Yeah. I, I, I agree. I was just thinking, Joe, as you were going through that, I love the committee idea. I've seen that work. It, it, it's great to get people that are using it, real users on, on what, what's meaningful and what's not. I definitely think this is probably an exercise that's happening nowadays, probably. So if you do have a bloated tech stack, you're probably being forced to look at it. Right. So, so definitely get that committee up. So, Joe, let, let's kind of flip it. I'll go complete reverse here, right? You have a bloated tech stack. That's one end of the spectrum, and I think you mentioned acquisitions and all that, that can lead to that. What if you were, like, you, you mentioned startups early on Monday. Joe, what if you're, you're starting from scratch. You had mentioned some freemium items. I, I know you've, you have a lot of experience in the tech stack. You have your renewal dates, you have some basic data that you wanna use. Where would you start if you were starting fresh? Where would you start, Joe, if you were building out your tech stack?

Joe Di Grande: 8:09

Oof. That was starting from scratch. If I had to be, if I had to be, like, if I were to go spend the money. Right. If I had budget. Um, definitely need, yeah. That's like

8:20

I'm, I'm my fairy dust of budget is approved. Yeah. All the goodness.

Joe Di Grande: 8:24

That's, it's tough. I mean, there are, uh, a wealth of obviously customer success platforms, sales engagement platforms. Um, you know, I'll, I'll recommend a few. No particular like preference, just things that come to mind. Yeah, I would say like, you know, Salesforce is great. It is a flexible solution. HubSpot, you know, is also something I use personally and it's been great in terms of, you know, customizing and also freemium solution as well. Um, I think you always need a CRM. Hands down, I think. Yeah, it's, you know, you need your, that should be your source of truth on the front end. Right. As far as the data warehouse, in terms of preference, out of each of them, obviously there's tons out there from Snowflake to Redshift and you name it. Right. That's kind of, again, you know more on the data and engineering side of things, but if you have that, where that becomes powerful is that if you ever have to change your, your CRMs or whatever tools that. Always stays constant. And then that way you, you develop, transform your information there and then pipe it out other ways. Um, as far as just getting started out, I do think you need a sales engagement platform, tons out there. Sales, SalesLoft, outreach.io, apollo.io, um, those are even the top three. Um, you know, even, uh, something from like a, a data enrichment standpoint I think is super important. Um, clay has been a big player in the space that's been coming up quite a bit. Um, as well as Apollo and then ob, obviously you have ZoomInfo, et cetera. I think those are very impactful for both, obviously new business as well as, uh, customer success. Um, I think a lot of people forget that because if you need to upsell, you're trying to expand an account, you need to find new stakeholders, uh, be become multi-threaded. You need that information. And then also check out job changes, right? As your key, key decision maker leaving the organization. Obviously that's a churn risk. Marketing solutions, I mean. Turns out there as well. You have Marketo, you have, uh, Iterable, Klaviyo. Um, again, that's something I've seen. Those be, uh, those be used for tech touch as well as like digital cs, et cetera. I think there are some, uh, pros and cons of that though, as where, because there are more marketing solution focus metrics are a little bit different. Um, and then also you lose a little bit of that control where, as opposed to a customer success platform in the sales engagement platform where, you know, you have either semi-automated steps fully automated, so you have a little bit more control and flexibility. And then lastly, you have your, the customer success platforms and then as well as if you're tracking tickets. Zendesk or maybe HubSpot, ticketing software, et cetera, Freshdesk, in order to kind of build that out. I would say those are kind of key and core to get going in a perfect world. And then for automation, if you have an engineer, uh, there's tons of plug, plug and play solutions like Zapier makes another one that's been coming up quite a bit. I haven't used myself personally, but it's also another recommended tool.

11:23

Yeah, you took that budget for you, you, you were, you, you love that, that unlimited budget. Like you weren't, you weren't screwing around. Like,

Joe Di Grande: 11:29

and listen, I'm a, I'm, I, I'm a big believer in like I'll chop things, I'll come in. I've seen it saved organizations a ton of money. But at the end of the day, that's like the perfect world and then have everything feeding into each other. But, um. You know, you can't have everything. So that's, uh, exactly, that's the, that's the dream.

Roman Trebon: 11:48

Exactly. Exactly. That's awesome. That's awesome. Alright Joe, well this is great stuff. Uh, thanks for, for talking us through bloated tech stacks and then even if you, you were starting from scratch. I, I, I loved, I loved all of those recommendations. It was terrific. So you're coming back on Friday, we're gonna explore, uh, tech touch, and. How, uh, you can scale CS and drive real growth using artificial intelligence. So we'll get into AI a little bit and, uh, for our audience, make sure you subscribe to the show, like it, uh, leave a comment. You'll receive notifications if you subscribe, so you'll know exactly when our Friday episode comes out. As always, Kevin.