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

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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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Episode Transcript

Kevin Metzger (00:05):
Customer success.
Hello and welcome back to theCustomer Success Playbook
podcast.
I'm Kevin Metzger with Mike,co-host Roman Reba.
It's Wednesday and we're joinedby Joe de Grande Again, Roman
Love Wednesdays man.

Roman Trebon (00:23):
Yeah, well, one big question.
We got Joe back, right?
So, uh, we, if you missed ourMonday episode, make sure you go
back.
Joe talks about what a techtouch strategy is and then how
do you implement it.
And he actually gave somefreemium examples, which I
always like the word freemium.
So, uh, some, some low coststrategies that you can actually
implement today, which is, whichis awesome.
So Joe's back for our one bigquestion, but Kev, before we get

(00:46):
into the one big question, youknow, we, we ask these hard
hitting questions up front toget to know our guests a little
bit better.
So, Joe, you ready for thesehard hitting questions up front?
Let's do it.
All right.
So Joe, one place that you'dlike to travel that you've never
been before.

Joe Di Grande (01:02):
Ooh, that's a good question.
I have, I have a few.
I would say two that come top ofmind is Japan.
I would like to go to Japan andalso Australia, so totally
opposite ends of the earth.
But, uh, those are my spotsreally, mainly to go fishing.
You know, I'd be, I've seen alot of videos.
I keep track of those areas andI'm like, yeah, I gotta, I gotta

(01:22):
get out there.

Kevin Metzger (01:23):
That would be awesome.
That'd be awesome.
Besides fishing, what's,

Joe Di Grande (01:26):
uh, what's something else you'd do to
unplug?
It's a good question.
I would say, yeah, outside offishing, I would say it's
definitely like drives, youknow, I'm a car guy myself, so
I'll go on some drives and stufflike that.
I.
And cruises, especially if I'mvisiting up, you know, family up
north, I'll head out to themountains and stuff like that.
So that's always good.
And then tinkering, like if I'malways, uh, like working on the

(01:48):
boat or the car or whatever,that's kind of my way, uh, you
know, therapy, so to speak.

Roman Trebon (01:54):
Yeah.
Good.
That's awesome.
Uh, let's do, uh, a bookrecommendation.
You got a, uh, a business bookor a personal book that you
maybe you've read recently thatyou'd recommend to our audience?

Joe Di Grande (02:03):
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 byNick Meta.
Um, that was a great book.
Um, he did his original books inthe past that I've read, read as
well on Customer Success.
It's a blue cover book as well.
Uh, this one's focused ondigital.
Highly recommended if you arelooking to launch a digital CS

(02:24):
strategy.
Another one, which is, which isalso here behind me, I just
finished, was FanaticalProspecting.
That's just from me, from thestandpoint, not so much Cs, but
I think there's a lot oflearnings from it.
But from a business owner, asI'm prospecting and doing my own
new business strategy, it's uh,super, super, uh, impactful.
Some things are a little, youknow, outdated.
It's about 10, 15 years old now,somewhere in that realm, but

(02:46):
still a lot of things still runring true on that.
So highly recommend those two.

Kevin Metzger (02:51):
Awesome.
Thanks Joel.
Yeah, Joe, thanks for therecommendations.
So our one big question for theday, why do so many companies
end up with bloated CS Techstacks and what can they do to
streamline and fix that problem?

Joe Di Grande (03:06):
Yeah, I think that's a great question.
It actually rings a bell.
I had another conversation aboutthis when they were asking me
about like digital CS Techtouch, you know, and it was
around revolving around toolsand they were like, Hey, you
know, if you were to go to acompany, what's the best company
to get this started?
When should they start thinkingabout this?
And I'm like, honestly, justimmediately, like if you're a

(03:27):
startup, you should be thinkingwith an operations mindset.
And how this ties into it.
Why does it happen as far ashaving a bloated tech stack as
they wait too long and theydon't have an operations team.
They're not thinking systems anddata, 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 withtrying to figure out how to

(03:49):
scale, how to create process foryour CS team as well as
marketing, right?
Marketing still needs data inorder to, you know, to leverage
it for segmentation when they'redoing their, you know, lead
nurturing and et cetera, as wellas new business now.
When we talk about that, right,like now, what happens later,
there's no operations team.
You have these differentdepartments essentially living

(04:10):
in silos, which creates datasilos as well as tech silos.
So they're focusing on theirend, you know, day-to-day goals,
and they'll acquire whateversolution and maybe they're not
communicating with each other,and that's where you might run
into some troubles where they'rebuying stuff that does
duplicative.
Right.
They have the same feature, sametechnology.
Um, so that's something to keepin mind.

(04:32):
I would say.
How to solve that is one, I'vedone this before, develop a
committee.
If you don't have an ops teamthat's broken down by sales,
marketing, cs, and havingsomeone that has this closely
tied to like product, um.
Worst case, have some sort ofcommittees that they connect to
each other.
Someone that's a little bit moreops minded.
How I, honestly, I, this is arecommendation I gave someone

(04:53):
recently.
If they're not sure who thatperson is that has that ops
minded mindset, if there arealready tools, go figure out
what tools that they are using.
Do kind of a tech stackanalysis.
Go talk to that vendor, be like,Hey, who is my top user of that
tool?
And then you're gonna start tofind out.
Okay, great.
You know, Johnny, Sally, whoeverthat is, is a big advocate for

(05:15):
this.
Great.
They might be, you know, be moreops oriented already, and then
that might be your kind ofchampion, so to speak.
Um, but I would say like, tokind of the key takeaway is like
communication is gonna key.
Start thinking about ops as soonas you can.
If you're early startup.
Um, as well as data and thendevelop that committee, get

(05:36):
people talking.
Um, and then that's how you canstart to avoid tech, you know,
tech stack bloat.
Um, and sometimes you're almosteven 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 youto do that.
But those are some tips therethat, um, could be pretty
impactful.

Roman Trebon (05:54):
Yeah.
I, I, I agree.
I was just thinking, Joe, as youwere going through that, I love
the committee idea.
I've seen that work.
It, it, it's great to get peoplethat are using it, real users
on, on what, what's meaningfuland what's not.
I definitely think this isprobably an exercise that's
happening nowadays, probably.
So if you do have a bloated techstack, you're probably being
forced to look at it.
Right.
So, so definitely get thatcommittee up.

(06:15):
So, Joe, let, let's kind of flipit.
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, thatcan lead to that.
What if you were, like, you, youmentioned startups early on
Monday.
Joe, what if you're, you'restarting from scratch.
You had mentioned some freemiumitems.
I, I know you've, you have a lotof experience in the tech stack.
You have your renewal dates, youhave some basic data that you

(06:35):
wanna use.
Where would you start if youwere starting fresh?
Where would you start, Joe, ifyou were building out your tech
stack?

Joe Di Grande (06:42):
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
I'm, I'm my fairy dust of budgetis approved.
Yeah.
All the goodness.
That's, it's tough.
I mean, there are, uh, a wealthof obviously customer success

(07:02):
platforms, sales engagementplatforms.
Um, you know, I'll, I'llrecommend a few.
No particular like preference,just things that come to mind.
Yeah, I would say like, youknow, Salesforce is great.
It is a flexible solution.
HubSpot, you know, is alsosomething I use personally and
it's been great in terms of, youknow, customizing and also
freemium solution as well.

(07:22):
Um, I think you always need aCRM.
Hands down, I think.
Yeah, it's, you know, you needyour, that should be your source
of truth on the front end.
Right.
As far as the data warehouse, interms of preference, out of each
of them, obviously there's tonsout there from Snowflake to
Redshift and you name it.
Right.
That's kind of, again, you knowmore on the data and engineering

(07:44):
side of things, but if you havethat, where that becomes
powerful is that if you everhave to change your, your CRMs
or whatever tools that.
Always stays constant.
And then that way you, youdevelop, transform your
information there and then pipeit out other ways.
Um, as far as just gettingstarted out, I do think you need
a sales engagement platform,tons out there.

(08:06):
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 issuper important.
Um, clay has been a big playerin the space that's been coming
up quite a bit.
Um, as well as Apollo and thenob, obviously you have ZoomInfo,
et cetera.

(08:26):
I think those are very impactfulfor both, obviously new business
as well as, uh, customersuccess.
Um, I think a lot of peopleforget that because if you need
to upsell, you're trying toexpand an account, you need to
find new stakeholders, uh, bebecome multi-threaded.
You need that information.
And then also check out jobchanges, right?
As your key, key decision makerleaving the organization.

(08:46):
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'veseen.
Those be, uh, those be used fortech touch as well as like
digital cs, et cetera.
I think there are some, uh, prosand cons of that though, as

(09:09):
where, because there are moremarketing solution focus metrics
are a little bit different.
Um, and then also you lose alittle bit of that control
where, as opposed to a customersuccess platform in the sales
engagement platform where, youknow, you have either
semi-automated steps fullyautomated, so you have a little
bit more control andflexibility.
And then lastly, you have your,the customer success platforms

(09:31):
and then as well as if you'retracking tickets.
Zendesk or maybe HubSpot,ticketing software, et cetera,
Freshdesk, in order to kind ofbuild that out.
I would say those are kind ofkey and core to get going in a
perfect world.
And then for automation, if youhave an engineer, uh, there's
tons of plug, plug and playsolutions like Zapier makes
another one that's been comingup quite a bit.

(09:52):
I haven't used myselfpersonally, but it's also
another recommended tool.
Yeah, you took that budget foryou, you, you were, you, you
love that, that unlimitedbudget.
Like you weren't, you weren'tscrewing around.
Like,
and listen, I'm a, I'm, I, I'm a big believer in
like I'll chop things, I'll comein.
I've seen it saved organizationsa ton of money.
But at the end of the day,that's like the perfect world
and then have everything feedinginto each other.

(10:15):
But, um.
You know, you can't haveeverything.
So that's, uh, exactly, that'sthe, that's the dream.

Roman Trebon (10:21):
Exactly.
Exactly.
That's awesome.
That's awesome.
Alright Joe, well this is greatstuff.
Uh, thanks for, for talking usthrough bloated tech stacks and
then even if you, you werestarting from scratch.
I, I, I loved, I loved all ofthose 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 anddrive real growth using

(10:43):
artificial intelligence.
So we'll get into AI a littlebit and, uh, for our audience,
make sure you subscribe to theshow, like it, uh, leave a
comment.
You'll receive notifications ifyou subscribe, so you'll know
exactly when our Friday episodecomes out.
As always, Kevin.