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

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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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Episode Transcript

Kevin Metzger (00:05):
Customer success.

Roman Trebon (00:10):
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 theweek and we're wrapping up our
conversation with Joe de Grandeon talking all things tech,
touch strategies, CS tools, etcetera.

(00:31):
It's been a fun week with Joe.
Uh, we've been talking how toavoid a bloated CX tech stack,
how to build simple data-drivenprocesses, how to enable a tech
touch strategy.
It's been, it's been greatthroughout.
So if you've missed any of thoseepisodes.
Make sure and go back to check,uh, check those out.
Today we will look at how AI canamplify or undermine those

(00:55):
efforts that we talked about.
Kev, you excited for today'sepisode?

Kevin Metzger (00:58):
I always love AI Friday, get to learn new things
about AI and how it's beingused.
So, Joe, welcome back and we're,let's, let's get into the AI
discussion from automatingcustomer engagement to
predictive analytics.
AI promises a lot of big wins.
How can you, how can productmarketing and CS teams use AI
wisely without falling into thesame tech stack below, or

(01:21):
looking at the, you know, newshiny.
New shiny thing, which is reallyone of the big problems in, in
product selection anyway, so

Joe Di Grande (01:30):
Yeah, no, a hundred percent I get it right
now.
I, I think we're really in aplace where there's this shiny
object syndrome, especially withai.
Um, I mean, I was just scrollingon y Combina the other day, and
when we're talking about likethe number of companies, I feel
like we're in the.com boom whereeverything is just ai.
It's, it's honestly a bitoverwhelming.

(01:51):
So there's tons of solutions outthere that you can do to solve
whatever the use case is.
Analyzing data, you know,automating customer outreach,
documentation.
I would honestly say first andforemost, right, it kind of goes
back to what we talked about inprevious episodes, is under
understanding the goal first andwhat are you trying to do?
Obviously ai, the biggest KPI inmy, in my eyes is first cutting

(02:15):
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, isthat how quickly can I get
whatever it is that I need toget done?
Whether that's analyzing data,whether that's creating content.
So that's number one.
So try to figure out what thattime savings is and then kind of
go back, you know, potentiallyto leadership.

(02:37):
Like, hey, here's where we couldrefocus those efforts.
Um, you know, and then we couldfocus on account expansion, so
on and so forth.
Um, obviously there's.
You know, the signals that arestarting to, um, come up, like
churn signals as well asexpansion signals.
I was just looking at a productthe other day.
It was, I believe it was churnchurn.io.
Um, interesting solution.

(02:57):
It's another customer successplatform with a heavy emphasis
on AI being able to, you know,distill your information and
your data.
Obviously centralizing it, butof course coming up with some
predictive analytics.
There are tons of othersolutions too.
Personally, I've actually evencreated my own chat, GBT bot.
Um, happy to share it with theaudience as well as you guys
here.

(03:17):
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 forcustomer journey workflows.
And the reason why, when I putit into a bot, it starts to
understand the business, what,you know, who I'm working with.
It'll actually go and createflow charts for me if, if I
instructed to do so.

(03:38):
And it does a pretty good job.
Um.
In addition to that, uh,content, in addition to content
creation and then creating thoseworkflows, 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 acompany with x.
Number of employees, here's whatthey're paying, hypothetically,

(03:59):
this is the space that they'rein.
The users are broken down todifferent personas, you know,
based on what we're able totrack.
So I put all that informationand obviously within reason
everybody out there, right?
Ai, it's a very scary thing withcertain organizations where
they're a little iffy on whatyou plug in.
But, um, once you go and dothat, it'll spit out a
recommendation.

(04:19):
The one thing I will say, andthere 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'lleither have typos, just make up
stuff if it just doesn't knowand you have to kind of double
check.
So I don't know if we're in ayet, in a place yet to fully
rely on it, but it's definitelychanging the space.

(04:42):
Um.
One in particular that reallycaught my eye, uh, cast app, uh,
that I believe the founder'sname is, uh, Dickie.
He's out in in Dick Dickie?
Yeah.
San Francisco.
We had

Roman Trebon (04:52):
him on the show.
Former guest.
Former guest.
Dickie.
Yeah.

Joe Di Grande (04:56):
Awesome app.
Like I had a conversation thatwas 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 aboutAI taking our jobs and so on.
It's, it's pretty scary, youknow, especially even now.
Churn zero.
Um, you know, something I'veused in the past, they didn't
have this at the time, but theyjust partnered with syn, uh, I

(05:19):
can't even pronounce it.
Synthesia, I believe it is.
I, I not recognize their logo.
They're big on like the avatarAI space, you know, and, you
know, for training videos, etcetera.
Now you could create your ownavatar and, you know, introduce
yourself as a CSM or a salesrep.
That way you could do it atscale.
Pretty crazy stuff.
But it goes back to, to kind ofwrap it all up again.

(05:40):
See, I'm even having this shinyobject 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 onCSPs and CRMs and I'll use like
tango, uh, AI to create myenablement documentation.

(06:00):
And that's helps me so that wayit tracks my steps.
That's fully ai and then Idownload the PDF or the video or
whatever, you know, thedeliverable 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, butat least I could get the point
across to Mike.

Kevin Metzger (06:16):
Yeah.
Uh, I mean, I think one of thethings that, um, I've actually
had this conversation a fewtimes lately is when you are
considering ai, there was adocument.
A couple years ago by McKessonon how to evaluate AI projects.
And one of the, to me, what waspretty interesting about it, and

(06:37):
I I, I said this at a, uh,networking meeting.
The other guy day that I thoughtit was an interesting document,
guy pointed out to me, he islike, well, you thought it was
interesting.
Me, I.
But, but the truth is, is whenyou're looking at AI projects,
it's not all that different,right?
From looking at any otherproject.
It's, you've gotta look at whatare you trying to achieve.

(07:00):
You should be looking at whatthe value that they're bringing
is.
And then how you, how youimplement 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 towhether or not a project's
feasible and whether you'reusing, whether you're using AI

(07:23):
or not.
It's the same, same evaluationcriteria.
Um, but.
I mean, yeah, I think that was a2022 McKesson document that, uh,
um, that got circulated.
And it's just, it's aninteresting thought process.
Right.
So really it doesn't matter whatthe AI app is, it matters how

(07:44):
you're gonna use it and whereit's gonna bring value.
Exactly.
Yeah.

Roman Trebon (07:48):
Shout out to episode 46 when we had Dickie on
the show toss talking about castapp.
So make sure you go check thatout.
Little shout out there.
Joe, you mentioned tango too.
Like I, I think that's some ofthe stuff, like that's an
amazing tool.
Like there's so many tools thatI 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'mnot a tech person.

(08:10):
I've told everyone this.
Like, if you can't unplug it andplug it back in, you've
overextended my, my technicalability.
I can go into tango and build anentire process, document
enablement.
Click, click, click, click,click, you're done.
You can see who, I mean, it'samazing how quick and, and these
tools are out there, like, uh,and so use'em, right?

(08:30):
Like that's a great suggestion,Joe.
There's stuff, there's so manythings that I think people hear
AI and they get so spun up intolike, it has to be some super
elaborate thing.
It, it's, no, just, just.
Get some of these tools we'retalking about, go in, play
around a little bit and Iguarantee you'll get some value,
right?
It's, there's tons out there.
Alright, well we have got Joe tothe end of the week.

(08:52):
Thank you for joining us allweek.
You've lasted three shows withus, us three shows with us, so
thanks for putting up with us,uh, that long.
Really appreciate it.
Joe, where can our audience findmore about, uh, yourself?
I know you're on LinkedIn, butwhere else can they find out
what you, what, what you havegoing on?

Joe Di Grande (09:08):
No, definitely.
You can find me on, uh, Joe doestech 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 abouta podcast, you know, in the
works, and it'll be announced inthat newsletter as well.
It's about all about theunsuccessful things in customer
success.
It didn't go like, yeah, we'lltalk more about that.
Um, I think it's gonna becustomer unsuccess and um, you

(09:32):
know, that's something that'llbe launched as well.
But if you subscribe to thatnewsletter, I'll shoot you guys
the link.
Um, you'll find out all aboutthat as well as kind of your
guide of, whether it's tech,touch, sales, operations,
customer success operations.
They'll be providing tips, youknow, and reaching out to people
you know, in that newsletter.
So that's where you can find me.
Awesome.
Awesome.

Roman Trebon (09:49):
That's great.
Sign up for check out Joe onLinkedIn.
Check out his website.
Sign up for the newsletter.
Right.
I love that podcast idea.
I know you and I had talkedabout that when I met you in
Atlanta.
I think that's an awesome, funidea and.
Uh, I probably have a, I'm, I'msure we all know a few people,
myself included, that we couldprobably share a story or of
unsuccessful, uh, uh, customerendeavor.
So that, that'll be a greatshow.

(10:10):
Alright, to our audience, uh,thank you as always for
listening.
That's the end of our threeparts series.
You can find Joe on LinkedIn.
You can find Kevin and myself onLinkedIn as well at Roman Trevon
and at Kevin Metzker.
If you found these episodesvaluable, please subscribe and
share'em with your team and, andyour colleagues.
We'll be back next week withmore strategies for your

(10:33):
customer success playbook.
We appreciate you listening.
As always, until next time,Kevin, keep on.