September 26, 2025 • 41 mins
Technology has transformed from a necessary evil to a strategic business driver, and nowhere is this more evident than in the managed IT services industry. In this candid conversation with Kathleen Shoop, Chief Revenue Officer at Digital Boardwalk, we explore the dramatic evolution of IT sales over the past decade.
Remember when selling managed IT services meant convincing skeptical business owners that paying a monthly fee for technology support made sense? Kathleen takes us back to those early days when the value proposition centered primarily around help desk support and predictable billing. The contrast with today's landscape couldn't be more striking.
Cybersecurity emerges as the turning point in our discussion. Between 2017 and 2020, major incidents like WannaCry ransomware fundamentally changed how businesses approached technology protection. We debunk the dangerous myth that small businesses are "too insignificant" to be targeted, revealing how modern attackers use automation to scan for vulnerabilities indiscriminately. This new reality transformed cybersecurity from an optional add-on to a non-negotiable core service.
The most fascinating shift has been in client expectations. Today's businesses approach IT providers looking to scale through technology—seeking efficiency, automation, and strategic guidance. Through real-world examples, Kathleen illustrates how the right technology partnership can completely transform operations, turning week-long processes into same-day completions. As we look to the future, automation and zero-trust security frameworks represent the next frontier in this continuing evolution.
What technology partnerships have transformed your business? Subscribe to Nerds on Tap for more insights at the intersection of technology and business strategy, and join our community of curious, forward-thinking professionals.
Sponsor of this episode: Digital Boardwalk
Digital Boardwalk is one of the top 10 Managed IT Service Providers in the United States. If you are seeking to outsource your IT Management, or if your IT Team could use some help with projects or asset management, give Digital Boardwalk a call today! They offer a FREE IT Maturity Assessment on their website. If you want to see how your business's IT scores against industry standards, go to GoModernOffice.com now.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:09):
Hey everybody, welcome back to Nerds on Tap,
the podcast where tech meetstenacity.
I'm your host, tim Shoup, andtoday we're diving into the
world of managed IT services howit's evolved, what's changed
and why it's more relevant thanever.
Joining me is someone who'sbeen at the forefront of this
transformation, kathleen Shoup,chief Revenue Officer at Digital
(00:33):
Boardwalk since 2013.
Kathleen leads the Sales andCustomer Service Department in
Pensacola, florida, and has beeninstrumental in shaping how
businesses adopt and scaletechnology to stay competitive.
She also happens to be my bossafter 5 pm, so welcome to the
show, kathleen.
Speaker 2 (00:53):
Thank you for having me.
Speaker 1 (00:56):
So today we are going to talk about.
The title for today's episodeis very unique From Cold Calls
to Cloud Control Selling IT in aNew Era.
We're going to talk about thetransformation of selling IT way
back when you started atDigital Boardwalk versus now and
(01:20):
how it's changed.
And we're going to get into afew things today, like
cybersecurity and how that kindof tied into all of it and a few
other things.
So again, welcome to the show.
Now you've seen the show before, kathleen.
What do we normally do first?
Speaker 2 (01:38):
Drink beer.
Speaker 1 (01:39):
Drink beer.
We're going to drink beer today.
Speaker 2 (01:41):
I don't see any beer.
Speaker 1 (01:43):
Did you want beer?
Speaker 2 (01:45):
Why should I be treated differently?
Speaker 1 (01:48):
Well, we were going to do a dry episode because I
figured you didn't want to drinkanything today.
Speaker 2 (01:52):
It's dry September.
Speaker 1 (01:54):
I don't know.
We can pull out the beers andstart over.
Speaker 2 (01:58):
Maybe All right, see you All right, well, let's do it
.
Speaker 1 (02:01):
You want to go get some beer?
All right, we'll do a dryepisode then.
So let's talk about selling ITbefore subscriptions.
I like to call this the WildWest era for a lot of reasons,
but let's rewind the clock,shall we?
Before subscription models andcloud platforms, selling managed
(02:25):
IT was a whole different beast.
So my question to you to kickoff this first segment is what
was the biggest hurdle you facedwhen trying to sell managed IT
services before subscriptionmodels were common?
Speaker 2 (02:43):
I mean, that's really it In a nutshell subscription
models weren't common.
I mean, that's really it In anutshell subscription models
weren't common.
And educating people that youknow IT wasn't set it and forget
it was difficult.
I mean, you even have a betterstory when you met with, you
know, one of your break fixcustomers and he said that it
(03:04):
was going to be a terrible ideaand no one was going to pay us
for IT.
That summed it up in a nutshell.
So it was a totally newapproach, especially here in
Pensacola, to charge a monthlyfee for IT.
Speaker 1 (03:18):
I think anywhere.
It was a challenge for anyoneto sell subscription-based IT
services and I'll get into mystory in a little bit because
we're going to get into anothertopic that I think kind of leads
into it but I think also tryingto find the right balance,
because I was also selling backthen and trying to find the
(03:40):
right balance between offeringgood, solid coverage while
trying to find that perfectpricing fit, and we'll talk
about that.
But it was a challenge becauseit was so new.
It was a new concept.
People weren't used to it andwhat did we have like three
layers of cybersecurity backthen.
Speaker 2 (03:59):
Like malware and antivirus.
Speaker 1 (04:01):
Yeah, antivirus, a firewall and spam filtering,
email threat protection, whichwasn't really referred to as
email threat protection backthen.
So how did you explain thevalue of proactive IT support to
skeptical clients?
Think back to a client you mayhave met with a decade ago or
(04:25):
more and you know how did youget into the value prop for
selling IT support to them?
Speaker 2 (04:34):
I think back then the help desk piece was probably
the most important to customersand having them understand that
you know you may call and youhave one problem and it could
cost you $150.
Speaker 1 (04:48):
Right.
Speaker 2 (04:48):
But you know, if you pay us a subscription amount per
month and you have, we willanswer unlimited questions or
solve unlimited problems.
I think that spoke to peoplethe most back then.
Um, cybersecurity wasn't as bigof a thing at that point, you
know, like you mentioned,because we only had just a
(05:09):
handful of protections in place.
So I think the biggest thingback then was customer service
and responding and accuratelyfixing things and that was kind
of the big push and what gotpeople interested and that was
kind of the big push and whatgot people interested.
Speaker 1 (05:25):
I think my biggest tagline back then was you can
call the IT guy when somethingbreaks or you can just pay me to
keep it working in the firstplace.
Now that adage, it's differentnow.
Yeah Right, it's so complex.
Now I think you I haven't usedthat tagline in probably seven
or eight years at least.
Speaker 2 (05:46):
Sometimes, when I'm presenting like that's all, like
the help desk, part of it isalmost an afterthought After we
talk about the importance ofpatching and updating and all
the 20 some odd layers we have.
And oh, by the way you know allof your trouble tickets will be
covered under this agreement.
So it's like a total flip flop.
Speaker 1 (06:06):
Can you share a memorable story from one of your
early sales pitches?
If you can think back to maybea sales pitch 10 years ago,
think of a customer that yousold to pitch.
I'll tell you what I got abetter idea.
Speaker 2 (06:22):
I think our producer is laughing in the background,
because I'm kind of puttingwhich I'll tell you what I got a
better idea.
Speaker 1 (06:25):
No, I think our producer is laughing in the
background because I'm kind ofputting Kathleen on the spot and
he knows it.
But here's the thing you knowhow to sell IT now we know how
to sell it and we're going toget into that.
It's a totally differentballgame now because it's
acceptable.
People know what we do.
They need our services.
(06:47):
But 10, 15 years ago we startedwhat.
16 years ago you came on 13 or14 years ago Sitting down with a
customer and pitching thatvalue prop.
Pretend I'm the customer andpitch me on IT services.
Back then, not now.
Speaker 2 (07:05):
Back then you know, you forget that I had a
two-year-old and a zero.
Speaker 1 (07:12):
Oh, I I don't, I don't, I don't forget that I
don't remember what I honestlydon't remember.
Speaker 2 (07:19):
you know what the pitch was.
Um, you know and I have to justgo back to you know people
weren't able to resolve thingsquickly and efficiently back
then and people were so used togetting these massive bills when
they had a problem and I guessthat might've been part of it is
(07:41):
predictable billing.
You know being able to projectwhat your expenses will be
because all of your issues wouldbe handled.
And you know that monthly fee.
I think that was a big thingBecause back then you never know
Somebody, your internet wasn'tworking and your tech would roll
(08:02):
in and they'd spend 10, 15, 20hours on it.
And then you got a thousanddollar bill Like that was kind
of like we don't want to have.
We don't want you, mr Potentialcustomer, to have those kinds
of.
Speaker 1 (08:14):
I can't tell you back when I was in the break fix
arena.
I mean, I was one of thosebreak fix guys 20, 30 years ago
and having that billingconversation when I would have
to hit a customer with a $2,000bill when they were used to
paying me maybe 100 bucks orwhatever it was and explaining
(08:34):
to them well, I just spent 20hours in your server closet
because you needed X, y and Zdone and they never wanted to
pay it.
They wanted me to cut the billin half.
So from a sustainabilityviewpoint, from the IT
business's perspective, it'sjust not sustainable.
Right, and that was one of mypitches is break fix isn't a
(08:58):
sustainable industry and inorder to be able to hire good
engineers and put them on staff,we need a more sustainable
model.
And that was the billingconcept behind it.
And I want to stay on thistopic for a minute, because we
talk about this all the time.
(09:20):
Times say, oh, mr Prospect,you're currently using ABC
company.
Well, that's a break-fixcompany, right?
Well, no, he'll say no, they'renot a break-fix company.
They're selling me managedservices, I'll go.
Well, they started as abreak-fix company and they're
(09:42):
still fixing iPad displays andthings like that, which takes a
lot of time.
So technically they're notselling you managed services at
the core.
All they're doing is sellingyou a different billing model
for break-fix services.
Speaker 2 (09:56):
Yeah.
Speaker 1 (09:56):
Right, and that there's the rub yeah Right, so
that's good.
Do you have anything else toadd to that, or?
Speaker 2 (10:04):
Right, so that's good .
Do you have anything else toadd to that or no?
I think it's interesting,though, when you talk about that
and you know ABC company whodoesn't have managed services at
the core.
So they've got phones, they'vegot printers, they've got
websites, they've got, you know,like you said, screen fixes
like jack of all trades, masterof none sort of thing.
Speaker 1 (10:25):
Exactly.
But boy, they're Johnny on thespot.
Right, yeah, johnny on the spot, but your data is not
necessarily protected.
Speaker 2 (10:34):
No.
Speaker 1 (10:34):
Because they don't have the time to make sure all
that stuff's always working andit does break, and we might talk
about that in a little bit.
So what pricing strategies didwe use?
Do you remember back in the daybefore recurring revenue became
the norm, when we startedgetting into pricing out managed
services?
Do you remember how much of ahurricane it felt like Because
(10:56):
we tried so many different waysto try to price it because
customers just didn't want it?
Speaker 2 (11:03):
Yeah, yeah.
Things that looking back orjust so silly, like trying to
find a service level.
That was just the bare bonesthat somebody's going to bite,
and then maybe we can upsellthem and then selling a few of
those and regretting it at somepoint down the road.
Speaker 1 (11:24):
Remember, we sold annual contracts, yeah.
Then we switched to monthlybecause competitors were selling
monthly.
Boy, that was a mistake, wasn'tit?
Speaker 2 (11:32):
And block time.
Speaker 1 (11:33):
Yeah, and only because competitors were doing
it.
We don't do that anymore.
Instead of following trends,we're the innovators and they're
trying to catch up with us now.
Speaker 2 (11:44):
And I think that it's .
Also it feels good when you youknow, now that we've grown and
we're out meeting with otherMSPs and going to conferences
and they're talking aboutpricing structure and they're
talking about, you know,bundling in your cyber with the
support piece and things that wegot to through our gut and
(12:05):
understanding you know whatcustomer needs and what also
worked best for us.
It's kind of a warm fuzzy whenyou you've realized that you're
you know you're doing the rightthing and you have your gut
instinct was right in you knowstructuring things as they
become.
Speaker 1 (12:22):
So, um.
So when we look back again,right now we're stepping back.
This first segment's all aboutstepping back.
What do you think helped youbuild trust with clients in that
era?
I mean, let's not talk abouthow we do it now, let's talk
about how we had to do it then.
Speaker 2 (12:42):
It was all about.
It was really all about thequality of the clients that we
had, their willingness to vouchfor us.
And then, you know, back in theday, I got a lot of from you
too, got a lot of our leads froma group called BNI, and it was
(13:03):
a quality group and qualitypeople, and those people were
referring us yeah and there wassomething to be said.
When you know, this person said,hey, I've got a lead for you,
like this is warm and I vouchfor you, and so that that, I
think, was a big piece of it.
(13:23):
Everything was based on areputation, I mean it still is,
but we've got kind of a widerreach.
But everything, our reputation,was everything at the time and
it still is.
Speaker 1 (13:32):
Yeah.
Speaker 2 (13:32):
But that's how we got it.
Speaker 1 (13:35):
And we were the only ones scaling a help desk here
locally, so we were able torespond within minutes, remotely
, instead of and that's what Iheard a lot when we would bring
on a new customer.
They had to wait hours or days,and with us they switched and
it was minutes Now, granted, yousaid earlier yes, help desk is
(13:55):
part of it, but we don't lead inwith that.
That is expected, I think, butback then it wasn't no.
So let's get in, let's fastforward.
Okay, all right, and I knowit's better to.
Speaker 2 (14:08):
It's easier to think in the now than in history,
especially now To have a littleeffect that goes yeah, Woo, woo,
woo, woo, woo, woo, woo woo.
Speaker 1 (14:15):
Okay, Fast forward to today.
Cybersecurity is no longeroptional right, it is a
necessity.
So what major cybersecurityevent do you think was a turning
point for the industry?
Speaker 2 (14:31):
I can't pinpoint one.
There are just so many.
It's so commonplace now,unfortunately.
Speaker 1 (14:38):
Do you remember when our industry really started to
scale and grow 2017.
Do you remember 2017 to COVID?
We started to see a huge uptick, right, and before that it was
just randoms, right.
That was when the WannaCryransomware event happened and it
(14:58):
was huge.
It was global seismic shift inhow organizations viewed
cybersecurity, because everybodywas scared.
All of a sudden it affectedover 200,000 computers, which
was big back then, and now we'reseeing more scale, but across
150 countries.
So it kind of set the precedent.
(15:20):
But remember the Target creditcard attack when data was
starting to get leaked?
I think that was in what, 2013?
Data was starting to get leaked.
I think that was in what 2013?
And then there were other knownvulnerabilities with patching
and Windows, and I think theWannaCry affected a lot of that.
(15:42):
The Edward Snowden leaks westarted to see whistleblowers
and leaks like that.
So people were starting to getspooked, but businesses weren't
necessarily changing theirmindset yet, but it was setting
the stage.
Speaker 2 (15:59):
And I think too the government started with HIPAA
and electronic medical recordsand that sort of thing.
That started becoming a buzzwordyeah and you know we did a lot
with medical, so of course thatwas a big deal for us.
And then you know inklings ofnist, which became cmmc like
(16:20):
that was kind of happening too.
So there was a lot of that.
And then you mentioned covid.
That was huge, was huge becausewe've always been built on
doing everything remotely andthen all of a sudden every
business in the world needed todo something remotely.
So it was just, it was sosmooth, like fitting into that
need because we were built thatway from the get-go.
Speaker 1 (16:45):
Yeah.
Speaker 2 (16:45):
And setting it up for other companies was nothing.
Speaker 1 (16:47):
Do you remember how easy that was for us?
Speaker 2 (16:49):
It was just like gravy.
I would have four or five leadscome in a week and we would
close four or five of them.
It was just from asalesperson's perspective.
I was an order taker at thatpoint.
I mean we could hardly keep upwith the amount of stuff that we
had coming in.
Yeah, I mean we could hardlykeep up with the amount of stuff
that we had coming in.
Yeah, that was.
(17:09):
I mean, I was much of a crappytime as it was.
That was a bright spot.
Speaker 1 (17:14):
Yeah.
Speaker 2 (17:15):
From a sales perspective, Because a lot of
businesses couldn't handle thatand we were just a.
It fit like a glove.
Speaker 1 (17:22):
Not to mention COVID is, I think, when I started
drinking beer, and that's howthe show was born.
Speaker 2 (17:27):
Oh, really Well, I didn't.
Speaker 1 (17:28):
Was I drinking beer before that?
Speaker 2 (17:30):
I think so yeah.
Speaker 1 (17:31):
Well, 10 years ago, many clients viewed
cybersecurity as a technicalafterthought, something to
address only after a breach or asystem failure.
So today, clients expectcontinuous monitoring, threat
protection, detection andincident response plans as part
of their IT services.
And that is, I mean, that'swhere the stage is now and we'll
(17:56):
talk about where it's goinghere in a few minutes, but it
definitely cybersecurity has.
Definitely the ones that wereat the forefront of it like us.
It gave us a huge competitiveadvantage Because I know MSPs
out there.
I meet them all the time atconferences.
They're still playing catch up.
Yeah, we're not all created thesame, no.
(18:17):
So what role does?
You were talking aboutcompliance and I kind of want to
dig into that.
What role does compliance playin shaping IT service offerings
today?
How does it fit in?
Speaker 2 (18:31):
Well, I think that for me, as a salesperson
targeting companies, I know thatthe best targets are those that
have some sort of regulatorycompliance that they need to
adhere to.
It's a much easier conversationbecause they're familiar most
times with what they need to do.
Speaker 1 (18:49):
So it's easy.
But how do you educate themwithout overwhelming them?
I mean, how is that?
It's a much easier conversationbecause they're familiar most
times with what they need to do,so it's easy.
But how do you educate themwithout overwhelming them?
I mean, how?
Speaker 2 (19:04):
is that?
I mean I know because we canget into the weeds with it, with
them, but do you kind of, doyou go ahead?
I mean I would imagine youlisten and then kind of, oh yeah
, oh yeah.
I mean 90% of what I do islistening in a discovery meeting
(19:25):
what the pain points are, whatcompliance issues they may,
meeting and going through theentire offering and associating
the different line items withrequirements that I know they
might have.
And they might know too, or itmight be news to them, you know,
so usually I save that for.
Hey, you know you're going to,you're dealing with sensitive
(19:47):
data and CUI or PHI, and so thisencryption tool would be great
for you.
Speaker 1 (19:55):
Is it an option?
Speaker 2 (19:56):
That is an option.
Speaker 1 (19:58):
Is cybersecurity an option?
Speaker 2 (19:59):
No, no, and that's something we changed years ago
is just knowing that.
You know.
It just was a stickyconversation and this is kind of
part of, at this point, thesales pitch you know it just was
a sticky conversation and thisis kind of part of, at this
point, the sales pitch, you know, because I can show, you know,
this big section full of allthese, you know, cyber security
(20:19):
related things, and I lost mytrain of thought, I lost my
train of thought.
Speaker 1 (20:27):
Well, I mean, I would say that it would line up with
what we were talking aboutearlier.
Sometime between 2017 and 2020is when cybersecurity became the
norm.
Speaker 2 (20:40):
Oh, you said it's not an option.
Speaker 1 (20:41):
So it's not an option .
And was that about the time?
I think that was about the timewe changed it around 2017.
Speaker 2 (20:47):
Yeah, we just kept having these weird conversations
when somebody would say opt outof email threat protection, and
then something came throughthrough an email and somebody
clicked on something.
And they're like well, youdidn't protect me.
And then we had to say well, youknow, when you accepted the
quote, you didn't want this, soyou weren't protected.
So it just became kind of a painto have those conversations and
(21:08):
you know, we just had to take ahard line of we want to be a
company that does things by thebook and by best practices and
if you want to do business withus you're going to have to take
on, you know, these sorts ofprotections, because it, you
know, from a business standpoint, you don't want your engineers
chasing down all these thingsthat you could have easily
(21:31):
invented by selling somethingthat costs two bucks per user.
It just didn't make any sense.
So when we were able to figureout you know how to price it, so
that, and I think when we gotto a certain volume or we were
able to kind of negotiate withour vendors and come up with a
pricing strategy that wouldallow us to include it, you know
(21:52):
that was a big thing too.
You know, just having thetiming so we could kind of take
a hard line on hey, if you wantto work with us, you got to do
this, and you know you want todo it anyway.
Yeah, so that but, and wedidn't really have a lot of
pushback when we did that?
No, we didn't really have a lotof pushback when we did that.
Speaker 1 (22:09):
No, we didn't At all and you know, just kind of step
back.
It's okay if you lose yourtrain of thought next to me,
because every time I sit next toyou I lose my train of thought
Because you know our producer'slaughing behind the scenes.
Ladies and gentlemen, he grewup in his trap.
Oh, come on now.
So what's one cyber securitymyth?
(22:30):
You wish more business ownersunderstood, and I I I know where
I want to take this questionwhy don't you take it?
well, tell me what you think isthe one cyber security myth.
Speaker 2 (22:44):
So put yourself when I ran into the other day okay,
good, oh, my goodness so I metwith this potential prospect.
Um, and they were just.
The contract was a big stickingpoint for them and kind of
educated them on why a contractwas important for both sides and
(23:05):
they agreed with that.
Speaker 1 (23:06):
Mm-hmm.
Speaker 2 (23:07):
But they were so fixated on this one certain
point, which was how do wekeep—this is them talking—how do
we keep your engineers fromstealing our data?
Yeah, and then me, I think,trying to explain to them that
you know, we background checkand we do all these things and
(23:30):
we're not going to have accessto certain things, but what you
really need to be worried aboutare your people.
Speaker 1 (23:36):
Yeah, exactly.
Speaker 2 (23:37):
That was a difficult conversation.
Speaker 1 (23:39):
We don't look at customers' data.
We see metrics, we see tickets.
I mean that's the world we livein.
Electrics.
We see tickets.
I mean that's the world we livein, and but an employee I mean
our, our, our people aren'tgoing to get disgruntled.
I mean we signed a contractyeah, it's built into the
culture of digital boardwalk,right, but we're not actually
(23:59):
looking at their data anyway no,I mean you want to say, and
it's encrypted, many things todo exactly.
Speaker 2 (24:05):
Then worry about stealing your data or somebody
doing that.
Speaker 1 (24:10):
I would say the big myth is well, ms Kathleen, my
business is too small to beattacked.
Why would they care about me?
They're not going to come afterme, they're going to go after
Target.
They're going to go afterMicrosoft.
They're going to go afterMicrosoft.
Well, microsoft lives in yourorganization too, mr Prospect,
(24:33):
because all those machinessitting on your desks are
Microsoft.
What I like to say to them ifyou're online, you're a target.
Speaker 2 (24:42):
And most bad actors know that the smaller guys
aren't going to have theprotections in place, so it's
easy pickings to go after thesmaller people yeah.
Speaker 1 (24:52):
I mean, and they don't discriminate because they
use botnets now, and I mean it'sall automated.
They're using AI and they'reusing bot networks to scan
computers across the globe.
Until it finds an opening, itcreates a ticket for them.
They're sitting in a cubiclejust like an employee.
(25:12):
They're clocking in the bad Bobthat we do.
If anybody ever wants to tuneinto that, you can find it at
Digital Boardwalk TV on YouTube.
But we did a whole series onwhat we called Bad Bob and it's
the bad actor that goes to work,says goodbye to his wife and
kids every day, goes to work,but he's sitting at a cubicle to
(25:33):
attack American businesses, andthat's what's going on.
Speaker 2 (25:36):
And they have great customer service oh my God, yeah
.
Speaker 1 (25:40):
So let's jump into segment three because, time
permitting, this is going to becalled scaling through tech, so
we'll talk about scaling whyclients now come to us instead
of us looking for them.
I mean, our phones ring all thetime.
Today, businesses are coming toIT providers with a clear goal
(26:03):
scale through technology.
So, kathleen, what's thebiggest difference in how
clients approach you todayversus 10 years ago?
I told you we were going to getinto the today, so when they
come to you today as opposed to10 years ago, what's that
polarizing difference?
Speaker 2 (26:22):
I think they're.
Now they're looking to be moreefficient, like with Office 365
and SharePoint and all of that.
I think that they're lookingfor ways.
They're looking for ways toautomate, they're looking for
ways to utilize the technologythat they have to better their
process and better theirbusiness.
Speaker 1 (26:45):
Yeah, it's more seen as a growth enabler now.
I'd say 10 years ago it moreseen as a growth enabler now,
I'd say 10 years ago it was seenas a cost center.
It was just something on thedebit side, on the expense side
of their books, that they didn'tnecessarily want to pay for,
but every now and then they knewthey needed.
(27:05):
Now it's a necessity.
Speaker 2 (27:08):
I had a meeting earlier and this exact thing
came up.
It was with an existingcustomer and they said hey, I'm
looking for a I couldn'tremember what he called it, but
basically they were looking forkind of a way to approve
purchases.
And James was on the call withme James Todd, our CIO, and he
(27:31):
said well, you can go at it twoways.
You can buy an application thatsits on the server that's going
to be very, very in-depth andyou'll be able to tweak it
exactly the way you want it, oryou can use SharePoint.
Speaker 1 (27:44):
Yeah.
Speaker 2 (27:45):
And there's an approval process that you can
build into SharePoint and itcosts you nothing.
Speaker 1 (27:50):
It's a game changer.
Speaker 2 (27:52):
It's just so versatile and there's so many
things that you can do with it,and I think that companies are
just now seeing thepossibilities with SharePoint.
Speaker 1 (28:04):
Well, and not just that, but I mean we had a really
large customer lean on usrecently for a.
They wanted more efficiency onhow the communication and the
ticketing between theirticketing system and our
ticketing system and and their,their, their other main CRM, you
(28:26):
know, and and they wanted itall to talk together.
So our AI coding team atDigital Boardwalk went ahead and
I mean it took a while.
Right, I want to say that wholeproject we probably spent
somewhere between four and sixmonths on, I mean with testing
and everything because it had tobe foolproof.
(28:46):
On I mean with testing andeverything because it had to be
foolproof.
We developed integrationbetween all those platforms and
we got raving reviews and wewere able to make them more
efficient in the way all thatworkflow happens.
So it's basically roboticprocess automation and being
able to have one trigger have anif-then effect.
(29:13):
So if this happens, then thisis going to happen.
Speaker 2 (29:16):
So how do you that says a lot too, though.
We have an AI department.
Speaker 1 (29:19):
I know.
Speaker 2 (29:20):
Like that's new.
Speaker 1 (29:21):
Well and think about it, we had a cybersecurity
department before.
Cybersecurity was really beenpushed by a lot of MSPs.
Speaker 2 (29:34):
Now we have an AI department, because that is the
next huge evolution of what wedo.
And I think the coolest part iswhen we talked to Brian, who
was Brian Wilkie, who was ourCOO, and you know, just ask the
question like, how manyautomated hours did we have this
?
Speaker 1 (29:45):
Yeah, no-transcript.
Speaker 2 (29:46):
Oh, we had 5,000.
It's just kind of crazy whenyou think about how much
automation we have in place, andwhen you equate that to staff,
it's nuts.
Speaker 1 (29:58):
Yeah, I think we would have.
At least, if we didn't have anyof it in place, we would have
at least 12 to 15 more employeesthan we do now.
Yeah, which I mean.
There's good and bad to that,right, right, but I think the
good that comes out of it is wecan lower our customers' costs
and do more.
Speaker 2 (30:16):
And be more accurate.
Speaker 1 (30:17):
So how do you help clients identify the right
technologies to scale theirbusiness?
And I promise we've only got acouple more questions left, so I
mean we have to work within thetools that we have.
Right.
Speaker 2 (30:33):
Again, we're not trying to be, like I mentioned
before, a jack of all trade.
So if it can be done withinSharehouse, we do have partners
who can consult and find, youknow, the right match for their
(30:55):
need.
Speaker 1 (30:57):
So what's a?
Give me one example Now.
I know you've been doing a lotof case studies on this show
today.
I mean, we've talked about acouple of different customers
and I'm going to ask one more.
Give me an example of a companythat transformed through
managed IT services by DigitalBoardwalk without naming names,
obviously.
(31:18):
Can you give me a case study?
Speaker 2 (31:19):
And this was a case study done several years ago.
But we had an HVAC company andwe completely transformed their
business through iPad andSharePoint.
Speaker 1 (31:30):
Yeah.
Speaker 2 (31:30):
Like they would go out, they, they would send their
I don't know measure out.
No, it was.
It was a floor company or HVAC,I can't remember.
I maybe it was a flooringcompany.
They would send somebody out,they would measure, they would
take those measurements back,they would walk it over to
whoever did the pricing.
That person would do all theirnumbers and send it back to that
(31:53):
person, who would get it to thesalesperson, who would go so
inefficient, yeah, yeah so weended up working with them and
figuring out a way thatbasically everything could
happen all at once on sitethrough a tablet First meeting,
you know, assessment of you knowwhat materials and space and
(32:13):
all that stuff Price generatedthere, and a signature as well,
right, which is huge, you know.
So what may have taken a weekor so happened in one visit.
Speaker 1 (32:24):
So you talked earlier about you know how.
Help Desk is one of ourservices, obviously, but we
don't lead in with that, that'sa known thing.
So how do you position yourteam as strategic, our team,
sorry as strategic partnersversus just a tech support arm?
(32:45):
You know, if you will, you know, I mean, I can think of a
couple things off the top of myhead.
I mean, strategic planning isobvious, Continuous improvement.
Speaker 2 (32:56):
Right.
Speaker 1 (32:56):
We talked about that yeah.
Speaker 2 (32:58):
Well, you know, there's always got to be
communication between us and thecustomer, because everything,
things are constantly changing,whether it's a new threat or a
new capability within SharePointor-.
Speaker 1 (33:12):
So knowledge training , yeah Right.
Speaker 2 (33:14):
There's always something that we need to be or
something's end of life.
Right now, we're in the middleof the Windows 10 to Windows 11
transition.
Speaker 1 (33:22):
Yeah, that's been keeping us busy.
Speaker 2 (33:25):
And we're constantly trying to be proactive in all
ways.
So when we bring on a customer,you know we offer that.
This is what we want to be.
We want to be a partner to youand we explain all the ways we
can.
Some people take advantage ofit, some people don't, but you
(33:46):
know a lot of them do.
And we have our virtual CIOmeetings and that's where a lot
of this can be discussed, and wetry to meet with our customers
twice a year to talk about wherewe are, where we've been and
where do you want to go.
And here's what we see that youmight need to think about and
here's a non-negotiable thatwe've got to deal with.
Speaker 1 (34:05):
And then listen, listen, yeah, and then build a
strategic plan around it and goto strategy with it.
So the big final loadedquestion and I love this
question because we talked aboutit briefly earlier, so this
should be easy as pie.
Speaker 2 (34:21):
I hope so.
Speaker 1 (34:24):
What trends do you see shaping the future of IT
management and clientrelationships?
Speaker 2 (34:32):
We talked about the automation.
I mean that's the biggest thing.
Speaker 1 (34:35):
About zero trust.
Speaker 2 (34:38):
Zero trust is huge.
Speaker 1 (34:39):
Yeah.
Speaker 2 (34:40):
We didn't get into specifics of that.
I mean, there are lots of neatcybersecurity tools that we're
seeing and that we'reimplementing we're already
automating patching yeah, andwe've all.
We've done that since day onethreat detection's automated.
Speaker 1 (34:55):
Now backups are automated um.
Speaker 2 (34:59):
We've automated the pen pen test scans we got a
really cool tool that we justrolled out that automates PC
setups, which is huge.
Speaker 1 (35:10):
Yeah.
Speaker 2 (35:10):
I mean, that's just a massive time saver, especially
right now when we've gotthousands, literally thousands,
of replacements that we'rehaving to do.
Speaker 1 (35:19):
And I think trust and privacy is huge.
I mean, that's where the zerotrust that I was talking about
comes in.
I mean those customers that arereally worried about those
types of things.
That's when you want to lean onzero trust, because there's
more data and touch pointshappening now, so I mean it's
(35:40):
complicated.
Yeah, so zero trust meanseverything has to be verified
before they can do it.
Everything has to be verifiedbefore they can do it, and I
mean you can't get into yourbank on your phone without face
detection or whatever.
Speaker 2 (35:55):
I think that's one that we're really going to have
to.
That's one that's hard toeducate on and hard to get
people to buy in.
There is a cost to it, but it'sthe way things are going.
Speaker 1 (36:08):
You know Absolutely Well.
Why are you giving me that?
Look, cause you don't know whatI'm about to hit you with.
Speaker 2 (36:14):
I thought that was it .
Speaker 1 (36:15):
We're going to hit you with the rapid fire
questions.
You can give me one, one wordto one sentence answers on these
.
So I'm going to keep it fastand we're going to go fast.
First thing that pops in yourhead, give me an answer.
Don't look at me, look straightat that camera.
Your camera's over there, yourcamera's right there.
Speaker 2 (36:37):
Oh, okay.
Speaker 1 (36:38):
All right, caleb I mean Jared get Kathleen zoomed
in.
Here we go.
Are you ready, kathleen?
Speaker 2 (36:48):
I guess so.
Speaker 1 (36:50):
Mac or PC.
Speaker 2 (36:52):
PC.
Speaker 1 (36:53):
Favorite tech tool right now.
Speaker 2 (36:56):
Gosh my watch.
I mean that's a tech tool,right.
I mean, find my is my favoritebutton on this thing.
Speaker 1 (37:03):
That's more than one word or one sentence.
I'm just kidding.
First job in tech.
Speaker 2 (37:13):
I was a technical recruiter for a company called
interim.
I found help desk people fordell and round rock awesome
biggest sales win oh gosh, therehave been a lot most underrated
it service.
Speaker 1 (37:27):
You can think about this one for a second.
Speaker 2 (37:29):
Don't take too long, yeah, underrated.
Most underrated it service Idon't know we don't underrate
any, it All right.
Speaker 1 (37:40):
Good, good answer Coffee or tea?
During client calls Coffee.
One word to describecybersecurity today.
Necessity, necessity dreamclient industry dream client
industry yeah, who is your dreamclient?
What?
What industry do they come from?
They'd have to be like law okay, best pensacola lunch spot for
(38:05):
business meetings I'm just asucker for cactus flower, social
or business.
Hey, there's a plug for cactusflower on 12th Avenue in
Pensacola, right next to DeNovoSalon.
Speaker 2 (38:17):
Yes, Palanzo, though for breakfast, Ah yeah, they got
good breakfast.
Speaker 1 (38:21):
Yeah.
What's one thing people mightnot know about your journey to
becoming chief revenue officerat Digital Boardwalk?
One thing they might not knowabout your journey to becoming
chief revenue officer at DigitalBoardwalk One thing they might
not know?
Speaker 2 (38:32):
I don't know, it's probably a lot, they don't know.
Speaker 1 (38:37):
Okay, you can't name one thing.
Speaker 2 (38:39):
One thing what was the question?
Speaker 1 (38:42):
One thing people might not know about your
journey to becoming the CRO atDigital Boardwalk.
So what got you here?
Oh, that's right.
Speaker 2 (38:51):
Oh, don't even.
Speaker 1 (38:52):
I'm kidding.
Speaker 2 (38:54):
I think that is not a one-word answer, so if you've
got time I'll tell you.
Speaker 1 (38:58):
Well, we'll skip it.
What's your favorite way tounwind after a long day of
client meetings?
Speaker 2 (39:04):
Gosh watering my plants.
Speaker 1 (39:07):
Yeah, that's good, they're everywhere they are.
It's like a jungle out there.
Speaker 2 (39:10):
It is.
Speaker 1 (39:12):
And all the leaves get in our pool.
Speaker 2 (39:14):
No, it's because I'm not watering enough.
Speaker 1 (39:18):
Anyway, Kathleen, thank you so much for joining me
today.
I know it was kind of shortnotice.
I'm glad that you finally cameon.
Speaker 2 (39:27):
Make me look good.
Speaker 1 (39:28):
You didn't get any beer, though, and I think you
were might might've been lookingforward to that.
We'll have you on again andwe'll do beer.
Speaker 2 (39:33):
Yeah.
Speaker 1 (39:34):
Okay, I just figured.
We had client meetings todayand you didn't want to show up
10 minutes.
You didn't want to show up allsauce, that's true?
Yeah, so I see I was takingcare of you, ladies and
gentlemen.
Ladies and gentlemen, thank youfor listening to another
episode of Nerds on Tap, wherewe had Kathleen Shoup on today.
And again, just a quick shoutout to our sponsor, digital
(39:57):
Boardwalk, and hey, have a nerdyday, cheers my fellow nerds and
beer lovers.
Speaker 3 (40:06):
Stay tuned for more Nerds on Tap.
Oh, and one more thing Help usspread the nerdy love and the
love for grape brews by sharingthis podcast with your friends,
colleagues and fellow beerenthusiasts.
Let's build a community thatembraces curiosity, innovation
(40:28):
and the enjoyment of a cold one.
Hey everybody, welcome back to Nerds on Tap,
the podcast where tech meetstenacity.
I'm your host, tim Shoup, andtoday we're diving into the
world of managed IT services howit's evolved, what's changed
and why it's more relevant thanever.
Joining me is someone who'sbeen at the forefront of this
transformation, kathleen Shoup,chief Revenue Officer at Digital
(00:33):
Boardwalk since 2013.
Kathleen leads the Sales andCustomer Service Department in
Pensacola, florida, and has beeninstrumental in shaping how
businesses adopt and scaletechnology to stay competitive.
She also happens to be my bossafter 5 pm, so welcome to the
show, kathleen.
Speaker 2 (00:53):
Thank you for having me.
Speaker 1 (00:56):
So today we are going to talk about.
The title for today's episodeis very unique From Cold Calls
to Cloud Control Selling IT in aNew Era.
We're going to talk about thetransformation of selling IT way
back when you started atDigital Boardwalk versus now and
(01:20):
how it's changed.
And we're going to get into afew things today, like
cybersecurity and how that kindof tied into all of it and a few
other things.
So again, welcome to the show.
Now you've seen the show before, kathleen.
What do we normally do first?
Speaker 2 (01:38):
Drink beer.
Speaker 1 (01:39):
Drink beer.
We're going to drink beer today.
Speaker 2 (01:41):
I don't see any beer.
Speaker 1 (01:43):
Did you want beer?
Speaker 2 (01:45):
Why should I be treated differently?
Speaker 1 (01:48):
Well, we were going to do a dry episode because I
figured you didn't want to drinkanything today.
Speaker 2 (01:52):
It's dry September.
Speaker 1 (01:54):
I don't know.
We can pull out the beers andstart over.
Speaker 2 (01:58):
Maybe All right, see you All right, well, let's do it
.
Speaker 1 (02:01):
You want to go get some beer?
All right, we'll do a dryepisode then.
So let's talk about selling ITbefore subscriptions.
I like to call this the WildWest era for a lot of reasons,
but let's rewind the clock,shall we?
Before subscription models andcloud platforms, selling managed
(02:25):
IT was a whole different beast.
So my question to you to kickoff this first segment is what
was the biggest hurdle you facedwhen trying to sell managed IT
services before subscriptionmodels were common?
Speaker 2 (02:43):
I mean, that's really it In a nutshell subscription
models weren't common.
I mean, that's really it In anutshell subscription models
weren't common.
And educating people that youknow IT wasn't set it and forget
it was difficult.
I mean, you even have a betterstory when you met with, you
know, one of your break fixcustomers and he said that it
(03:04):
was going to be a terrible ideaand no one was going to pay us
for IT.
That summed it up in a nutshell.
So it was a totally newapproach, especially here in
Pensacola, to charge a monthlyfee for IT.
Speaker 1 (03:18):
I think anywhere.
It was a challenge for anyoneto sell subscription-based IT
services and I'll get into mystory in a little bit because
we're going to get into anothertopic that I think kind of leads
into it but I think also tryingto find the right balance,
because I was also selling backthen and trying to find the
(03:40):
right balance between offeringgood, solid coverage while
trying to find that perfectpricing fit, and we'll talk
about that.
But it was a challenge becauseit was so new.
It was a new concept.
People weren't used to it andwhat did we have like three
layers of cybersecurity backthen.
Speaker 2 (03:59):
Like malware and antivirus.
Speaker 1 (04:01):
Yeah, antivirus, a firewall and spam filtering,
email threat protection, whichwasn't really referred to as
email threat protection backthen.
So how did you explain thevalue of proactive IT support to
skeptical clients?
Think back to a client you mayhave met with a decade ago or
(04:25):
more and you know how did youget into the value prop for
selling IT support to them?
Speaker 2 (04:34):
I think back then the help desk piece was probably
the most important to customersand having them understand that
you know you may call and youhave one problem and it could
cost you $150.
Speaker 1 (04:48):
Right.
Speaker 2 (04:48):
But you know, if you pay us a subscription amount per
month and you have, we willanswer unlimited questions or
solve unlimited problems.
I think that spoke to peoplethe most back then.
Um, cybersecurity wasn't as bigof a thing at that point, you
know, like you mentioned,because we only had just a
(05:09):
handful of protections in place.
So I think the biggest thingback then was customer service
and responding and accuratelyfixing things and that was kind
of the big push and what gotpeople interested and that was
kind of the big push and whatgot people interested.
Speaker 1 (05:25):
I think my biggest tagline back then was you can
call the IT guy when somethingbreaks or you can just pay me to
keep it working in the firstplace.
Now that adage, it's differentnow.
Yeah Right, it's so complex.
Now I think you I haven't usedthat tagline in probably seven
or eight years at least.
Speaker 2 (05:46):
Sometimes, when I'm presenting like that's all, like
the help desk, part of it isalmost an afterthought After we
talk about the importance ofpatching and updating and all
the 20 some odd layers we have.
And oh, by the way you know allof your trouble tickets will be
covered under this agreement.
So it's like a total flip flop.
Speaker 1 (06:06):
Can you share a memorable story from one of your
early sales pitches?
If you can think back to maybea sales pitch 10 years ago,
think of a customer that yousold to pitch.
I'll tell you what I got abetter idea.
Speaker 2 (06:22):
I think our producer is laughing in the background,
because I'm kind of puttingwhich I'll tell you what I got a
better idea.
Speaker 1 (06:25):
No, I think our producer is laughing in the
background because I'm kind ofputting Kathleen on the spot and
he knows it.
But here's the thing you knowhow to sell IT now we know how
to sell it and we're going toget into that.
It's a totally differentballgame now because it's
acceptable.
People know what we do.
They need our services.
(06:47):
But 10, 15 years ago we startedwhat.
16 years ago you came on 13 or14 years ago Sitting down with a
customer and pitching thatvalue prop.
Pretend I'm the customer andpitch me on IT services.
Back then, not now.
Speaker 2 (07:05):
Back then you know, you forget that I had a
two-year-old and a zero.
Speaker 1 (07:12):
Oh, I I don't, I don't, I don't forget that I
don't remember what I honestlydon't remember.
Speaker 2 (07:19):
you know what the pitch was.
Um, you know and I have to justgo back to you know people
weren't able to resolve thingsquickly and efficiently back
then and people were so used togetting these massive bills when
they had a problem and I guessthat might've been part of it is
(07:41):
predictable billing.
You know being able to projectwhat your expenses will be
because all of your issues wouldbe handled.
And you know that monthly fee.
I think that was a big thingBecause back then you never know
Somebody, your internet wasn'tworking and your tech would roll
(08:02):
in and they'd spend 10, 15, 20hours on it.
And then you got a thousanddollar bill Like that was kind
of like we don't want to have.
We don't want you, mr Potentialcustomer, to have those kinds
of.
Speaker 1 (08:14):
I can't tell you back when I was in the break fix
arena.
I mean, I was one of thosebreak fix guys 20, 30 years ago
and having that billingconversation when I would have
to hit a customer with a $2,000bill when they were used to
paying me maybe 100 bucks orwhatever it was and explaining
(08:34):
to them well, I just spent 20hours in your server closet
because you needed X, y and Zdone and they never wanted to
pay it.
They wanted me to cut the billin half.
So from a sustainabilityviewpoint, from the IT
business's perspective, it'sjust not sustainable.
Right, and that was one of mypitches is break fix isn't a
(08:58):
sustainable industry and inorder to be able to hire good
engineers and put them on staff,we need a more sustainable
model.
And that was the billingconcept behind it.
And I want to stay on thistopic for a minute, because we
talk about this all the time.
(09:20):
Times say, oh, mr Prospect,you're currently using ABC
company.
Well, that's a break-fixcompany, right?
Well, no, he'll say no, they'renot a break-fix company.
They're selling me managedservices, I'll go.
Well, they started as abreak-fix company and they're
(09:42):
still fixing iPad displays andthings like that, which takes a
lot of time.
So technically they're notselling you managed services at
the core.
All they're doing is sellingyou a different billing model
for break-fix services.
Speaker 2 (09:56):
Yeah.
Speaker 1 (09:56):
Right, and that there's the rub yeah Right, so
that's good.
Do you have anything else toadd to that, or?
Speaker 2 (10:04):
Right, so that's good .
Do you have anything else toadd to that or no?
I think it's interesting,though, when you talk about that
and you know ABC company whodoesn't have managed services at
the core.
So they've got phones, they'vegot printers, they've got
websites, they've got, you know,like you said, screen fixes
like jack of all trades, masterof none sort of thing.
Speaker 1 (10:25):
Exactly.
But boy, they're Johnny on thespot.
Right, yeah, johnny on the spot, but your data is not
necessarily protected.
Speaker 2 (10:34):
No.
Speaker 1 (10:34):
Because they don't have the time to make sure all
that stuff's always working andit does break, and we might talk
about that in a little bit.
So what pricing strategies didwe use?
Do you remember back in the daybefore recurring revenue became
the norm, when we startedgetting into pricing out managed
services?
Do you remember how much of ahurricane it felt like Because
(10:56):
we tried so many different waysto try to price it because
customers just didn't want it?
Speaker 2 (11:03):
Yeah, yeah.
Things that looking back orjust so silly, like trying to
find a service level.
That was just the bare bonesthat somebody's going to bite,
and then maybe we can upsellthem and then selling a few of
those and regretting it at somepoint down the road.
Speaker 1 (11:24):
Remember, we sold annual contracts, yeah.
Then we switched to monthlybecause competitors were selling
monthly.
Boy, that was a mistake, wasn'tit?
Speaker 2 (11:32):
And block time.
Speaker 1 (11:33):
Yeah, and only because competitors were doing
it.
We don't do that anymore.
Instead of following trends,we're the innovators and they're
trying to catch up with us now.
Speaker 2 (11:44):
And I think that it's .
Also it feels good when you youknow, now that we've grown and
we're out meeting with otherMSPs and going to conferences
and they're talking aboutpricing structure and they're
talking about, you know,bundling in your cyber with the
support piece and things that wegot to through our gut and
(12:05):
understanding you know whatcustomer needs and what also
worked best for us.
It's kind of a warm fuzzy whenyou you've realized that you're
you know you're doing the rightthing and you have your gut
instinct was right in you knowstructuring things as they
become.
Speaker 1 (12:22):
So, um.
So when we look back again,right now we're stepping back.
This first segment's all aboutstepping back.
What do you think helped youbuild trust with clients in that
era?
I mean, let's not talk abouthow we do it now, let's talk
about how we had to do it then.
Speaker 2 (12:42):
It was all about.
It was really all about thequality of the clients that we
had, their willingness to vouchfor us.
And then, you know, back in theday, I got a lot of from you
too, got a lot of our leads froma group called BNI, and it was
(13:03):
a quality group and qualitypeople, and those people were
referring us yeah and there wassomething to be said.
When you know, this person said,hey, I've got a lead for you,
like this is warm and I vouchfor you, and so that that, I
think, was a big piece of it.
(13:23):
Everything was based on areputation, I mean it still is,
but we've got kind of a widerreach.
But everything, our reputation,was everything at the time and
it still is.
Speaker 1 (13:32):
Yeah.
Speaker 2 (13:32):
But that's how we got it.
Speaker 1 (13:35):
And we were the only ones scaling a help desk here
locally, so we were able torespond within minutes, remotely
, instead of and that's what Iheard a lot when we would bring
on a new customer.
They had to wait hours or days,and with us they switched and
it was minutes Now, granted, yousaid earlier yes, help desk is
(13:55):
part of it, but we don't lead inwith that.
That is expected, I think, butback then it wasn't no.
So let's get in, let's fastforward.
Okay, all right, and I knowit's better to.
Speaker 2 (14:08):
It's easier to think in the now than in history,
especially now To have a littleeffect that goes yeah, Woo, woo,
woo, woo, woo, woo, woo woo.
Speaker 1 (14:15):
Okay, Fast forward to today.
Cybersecurity is no longeroptional right, it is a
necessity.
So what major cybersecurityevent do you think was a turning
point for the industry?
Speaker 2 (14:31):
I can't pinpoint one.
There are just so many.
It's so commonplace now,unfortunately.
Speaker 1 (14:38):
Do you remember when our industry really started to
scale and grow 2017.
Do you remember 2017 to COVID?
We started to see a huge uptick, right, and before that it was
just randoms, right.
That was when the WannaCryransomware event happened and it
(14:58):
was huge.
It was global seismic shift inhow organizations viewed
cybersecurity, because everybodywas scared.
All of a sudden it affectedover 200,000 computers, which
was big back then, and now we'reseeing more scale, but across
150 countries.
So it kind of set the precedent.
(15:20):
But remember the Target creditcard attack when data was
starting to get leaked?
I think that was in what, 2013?
Data was starting to get leaked.
I think that was in what 2013?
And then there were other knownvulnerabilities with patching
and Windows, and I think theWannaCry affected a lot of that.
(15:42):
The Edward Snowden leaks westarted to see whistleblowers
and leaks like that.
So people were starting to getspooked, but businesses weren't
necessarily changing theirmindset yet, but it was setting
the stage.
Speaker 2 (15:59):
And I think too the government started with HIPAA
and electronic medical recordsand that sort of thing.
That started becoming a buzzwordyeah and you know we did a lot
with medical, so of course thatwas a big deal for us.
And then you know inklings ofnist, which became cmmc like
(16:20):
that was kind of happening too.
So there was a lot of that.
And then you mentioned covid.
That was huge, was huge becausewe've always been built on
doing everything remotely andthen all of a sudden every
business in the world needed todo something remotely.
So it was just, it was sosmooth, like fitting into that
need because we were built thatway from the get-go.
Speaker 1 (16:45):
Yeah.
Speaker 2 (16:45):
And setting it up for other companies was nothing.
Speaker 1 (16:47):
Do you remember how easy that was for us?
Speaker 2 (16:49):
It was just like gravy.
I would have four or five leadscome in a week and we would
close four or five of them.
It was just from asalesperson's perspective.
I was an order taker at thatpoint.
I mean we could hardly keep upwith the amount of stuff that we
had coming in.
Yeah, I mean we could hardlykeep up with the amount of stuff
that we had coming in.
Yeah, that was.
(17:09):
I mean, I was much of a crappytime as it was.
That was a bright spot.
Speaker 1 (17:14):
Yeah.
Speaker 2 (17:15):
From a sales perspective, Because a lot of
businesses couldn't handle thatand we were just a.
It fit like a glove.
Speaker 1 (17:22):
Not to mention COVID is, I think, when I started
drinking beer, and that's howthe show was born.
Speaker 2 (17:27):
Oh, really Well, I didn't.
Speaker 1 (17:28):
Was I drinking beer before that?
Speaker 2 (17:30):
I think so yeah.
Speaker 1 (17:31):
Well, 10 years ago, many clients viewed
cybersecurity as a technicalafterthought, something to
address only after a breach or asystem failure.
So today, clients expectcontinuous monitoring, threat
protection, detection andincident response plans as part
of their IT services.
And that is, I mean, that'swhere the stage is now and we'll
(17:56):
talk about where it's goinghere in a few minutes, but it
definitely cybersecurity has.
Definitely the ones that wereat the forefront of it like us.
It gave us a huge competitiveadvantage Because I know MSPs
out there.
I meet them all the time atconferences.
They're still playing catch up.
Yeah, we're not all created thesame, no.
(18:17):
So what role does?
You were talking aboutcompliance and I kind of want to
dig into that.
What role does compliance playin shaping IT service offerings
today?
How does it fit in?
Speaker 2 (18:31):
Well, I think that for me, as a salesperson
targeting companies, I know thatthe best targets are those that
have some sort of regulatorycompliance that they need to
adhere to.
It's a much easier conversationbecause they're familiar most
times with what they need to do.
Speaker 1 (18:49):
So it's easy.
But how do you educate themwithout overwhelming them?
I mean, how is that?
It's a much easier conversationbecause they're familiar most
times with what they need to do,so it's easy.
But how do you educate themwithout overwhelming them?
I mean, how?
Speaker 2 (19:04):
is that?
I mean I know because we canget into the weeds with it, with
them, but do you kind of, doyou go ahead?
I mean I would imagine youlisten and then kind of, oh yeah
, oh yeah.
I mean 90% of what I do islistening in a discovery meeting
(19:25):
what the pain points are, whatcompliance issues they may,
meeting and going through theentire offering and associating
the different line items withrequirements that I know they
might have.
And they might know too, or itmight be news to them, you know,
so usually I save that for.
Hey, you know you're going to,you're dealing with sensitive
(19:47):
data and CUI or PHI, and so thisencryption tool would be great
for you.
Speaker 1 (19:55):
Is it an option?
Speaker 2 (19:56):
That is an option.
Speaker 1 (19:58):
Is cybersecurity an option?
Speaker 2 (19:59):
No, no, and that's something we changed years ago
is just knowing that.
You know.
It just was a stickyconversation and this is kind of
part of, at this point, thesales pitch you know it just was
a sticky conversation and thisis kind of part of, at this
point, the sales pitch, you know, because I can show, you know,
this big section full of allthese, you know, cyber security
(20:19):
related things, and I lost mytrain of thought, I lost my
train of thought.
Speaker 1 (20:27):
Well, I mean, I would say that it would line up with
what we were talking aboutearlier.
Sometime between 2017 and 2020is when cybersecurity became the
norm.
Speaker 2 (20:40):
Oh, you said it's not an option.
Speaker 1 (20:41):
So it's not an option .
And was that about the time?
I think that was about the timewe changed it around 2017.
Speaker 2 (20:47):
Yeah, we just kept having these weird conversations
when somebody would say opt outof email threat protection, and
then something came throughthrough an email and somebody
clicked on something.
And they're like well, youdidn't protect me.
And then we had to say well, youknow, when you accepted the
quote, you didn't want this, soyou weren't protected.
So it just became kind of a painto have those conversations and
(21:08):
you know, we just had to take ahard line of we want to be a
company that does things by thebook and by best practices and
if you want to do business withus you're going to have to take
on, you know, these sorts ofprotections, because it, you
know, from a business standpoint, you don't want your engineers
chasing down all these thingsthat you could have easily
(21:31):
invented by selling somethingthat costs two bucks per user.
It just didn't make any sense.
So when we were able to figureout you know how to price it, so
that, and I think when we gotto a certain volume or we were
able to kind of negotiate withour vendors and come up with a
pricing strategy that wouldallow us to include it, you know
(21:52):
that was a big thing too.
You know, just having thetiming so we could kind of take
a hard line on hey, if you wantto work with us, you got to do
this, and you know you want todo it anyway.
Yeah, so that but, and wedidn't really have a lot of
pushback when we did that?
No, we didn't really have a lotof pushback when we did that.
Speaker 1 (22:09):
No, we didn't At all and you know, just kind of step
back.
It's okay if you lose yourtrain of thought next to me,
because every time I sit next toyou I lose my train of thought
Because you know our producer'slaughing behind the scenes.
Ladies and gentlemen, he grewup in his trap.
Oh, come on now.
So what's one cyber securitymyth?
(22:30):
You wish more business ownersunderstood, and I I I know where
I want to take this questionwhy don't you take it?
well, tell me what you think isthe one cyber security myth.
Speaker 2 (22:44):
So put yourself when I ran into the other day okay,
good, oh, my goodness so I metwith this potential prospect.
Um, and they were just.
The contract was a big stickingpoint for them and kind of
educated them on why a contractwas important for both sides and
(23:05):
they agreed with that.
Speaker 1 (23:06):
Mm-hmm.
Speaker 2 (23:07):
But they were so fixated on this one certain
point, which was how do wekeep—this is them talking—how do
we keep your engineers fromstealing our data?
Yeah, and then me, I think,trying to explain to them that
you know, we background checkand we do all these things and
(23:30):
we're not going to have accessto certain things, but what you
really need to be worried aboutare your people.
Speaker 1 (23:36):
Yeah, exactly.
Speaker 2 (23:37):
That was a difficult conversation.
Speaker 1 (23:39):
We don't look at customers' data.
We see metrics, we see tickets.
I mean that's the world we livein.
Electrics.
We see tickets.
I mean that's the world we livein, and but an employee I mean
our, our, our people aren'tgoing to get disgruntled.
I mean we signed a contractyeah, it's built into the
culture of digital boardwalk,right, but we're not actually
(23:59):
looking at their data anyway no,I mean you want to say, and
it's encrypted, many things todo exactly.
Speaker 2 (24:05):
Then worry about stealing your data or somebody
doing that.
Speaker 1 (24:10):
I would say the big myth is well, ms Kathleen, my
business is too small to beattacked.
Why would they care about me?
They're not going to come afterme, they're going to go after
Target.
They're going to go afterMicrosoft.
They're going to go afterMicrosoft.
Well, microsoft lives in yourorganization too, mr Prospect,
(24:33):
because all those machinessitting on your desks are
Microsoft.
What I like to say to them ifyou're online, you're a target.
Speaker 2 (24:42):
And most bad actors know that the smaller guys
aren't going to have theprotections in place, so it's
easy pickings to go after thesmaller people yeah.
Speaker 1 (24:52):
I mean, and they don't discriminate because they
use botnets now, and I mean it'sall automated.
They're using AI and they'reusing bot networks to scan
computers across the globe.
Until it finds an opening, itcreates a ticket for them.
They're sitting in a cubiclejust like an employee.
(25:12):
They're clocking in the bad Bobthat we do.
If anybody ever wants to tuneinto that, you can find it at
Digital Boardwalk TV on YouTube.
But we did a whole series onwhat we called Bad Bob and it's
the bad actor that goes to work,says goodbye to his wife and
kids every day, goes to work,but he's sitting at a cubicle to
(25:33):
attack American businesses, andthat's what's going on.
Speaker 2 (25:36):
And they have great customer service oh my God, yeah
.
Speaker 1 (25:40):
So let's jump into segment three because, time
permitting, this is going to becalled scaling through tech, so
we'll talk about scaling whyclients now come to us instead
of us looking for them.
I mean, our phones ring all thetime.
Today, businesses are coming toIT providers with a clear goal
(26:03):
scale through technology.
So, kathleen, what's thebiggest difference in how
clients approach you todayversus 10 years ago?
I told you we were going to getinto the today, so when they
come to you today as opposed to10 years ago, what's that
polarizing difference?
Speaker 2 (26:22):
I think they're.
Now they're looking to be moreefficient, like with Office 365
and SharePoint and all of that.
I think that they're lookingfor ways.
They're looking for ways toautomate, they're looking for
ways to utilize the technologythat they have to better their
process and better theirbusiness.
Speaker 1 (26:45):
Yeah, it's more seen as a growth enabler now.
I'd say 10 years ago it moreseen as a growth enabler now,
I'd say 10 years ago it was seenas a cost center.
It was just something on thedebit side, on the expense side
of their books, that they didn'tnecessarily want to pay for,
but every now and then they knewthey needed.
(27:05):
Now it's a necessity.
Speaker 2 (27:08):
I had a meeting earlier and this exact thing
came up.
It was with an existingcustomer and they said hey, I'm
looking for a I couldn'tremember what he called it, but
basically they were looking forkind of a way to approve
purchases.
And James was on the call withme James Todd, our CIO, and he
(27:31):
said well, you can go at it twoways.
You can buy an application thatsits on the server that's going
to be very, very in-depth andyou'll be able to tweak it
exactly the way you want it, oryou can use SharePoint.
Speaker 1 (27:44):
Yeah.
Speaker 2 (27:45):
And there's an approval process that you can
build into SharePoint and itcosts you nothing.
Speaker 1 (27:50):
It's a game changer.
Speaker 2 (27:52):
It's just so versatile and there's so many
things that you can do with it,and I think that companies are
just now seeing thepossibilities with SharePoint.
Speaker 1 (28:04):
Well, and not just that, but I mean we had a really
large customer lean on usrecently for a.
They wanted more efficiency onhow the communication and the
ticketing between theirticketing system and our
ticketing system and and their,their, their other main CRM, you
(28:26):
know, and and they wanted itall to talk together.
So our AI coding team atDigital Boardwalk went ahead and
I mean it took a while.
Right, I want to say that wholeproject we probably spent
somewhere between four and sixmonths on, I mean with testing
and everything because it had tobe foolproof.
(28:46):
On I mean with testing andeverything because it had to be
foolproof.
We developed integrationbetween all those platforms and
we got raving reviews and wewere able to make them more
efficient in the way all thatworkflow happens.
So it's basically roboticprocess automation and being
able to have one trigger have anif-then effect.
(29:13):
So if this happens, then thisis going to happen.
Speaker 2 (29:16):
So how do you that says a lot too, though.
We have an AI department.
Speaker 1 (29:19):
I know.
Speaker 2 (29:20):
Like that's new.
Speaker 1 (29:21):
Well and think about it, we had a cybersecurity
department before.
Cybersecurity was really beenpushed by a lot of MSPs.
Speaker 2 (29:34):
Now we have an AI department, because that is the
next huge evolution of what wedo.
And I think the coolest part iswhen we talked to Brian, who
was Brian Wilkie, who was ourCOO, and you know, just ask the
question like, how manyautomated hours did we have this
?
Speaker 1 (29:45):
Yeah, no-transcript.
Speaker 2 (29:46):
Oh, we had 5,000.
It's just kind of crazy whenyou think about how much
automation we have in place, andwhen you equate that to staff,
it's nuts.
Speaker 1 (29:58):
Yeah, I think we would have.
At least, if we didn't have anyof it in place, we would have
at least 12 to 15 more employeesthan we do now.
Yeah, which I mean.
There's good and bad to that,right, right, but I think the
good that comes out of it is wecan lower our customers' costs
and do more.
Speaker 2 (30:16):
And be more accurate.
Speaker 1 (30:17):
So how do you help clients identify the right
technologies to scale theirbusiness?
And I promise we've only got acouple more questions left, so I
mean we have to work within thetools that we have.
Right.
Speaker 2 (30:33):
Again, we're not trying to be, like I mentioned
before, a jack of all trade.
So if it can be done withinSharehouse, we do have partners
who can consult and find, youknow, the right match for their
(30:55):
need.
Speaker 1 (30:57):
So what's a?
Give me one example Now.
I know you've been doing a lotof case studies on this show
today.
I mean, we've talked about acouple of different customers
and I'm going to ask one more.
Give me an example of a companythat transformed through
managed IT services by DigitalBoardwalk without naming names,
obviously.
(31:18):
Can you give me a case study?
Speaker 2 (31:19):
And this was a case study done several years ago.
But we had an HVAC company andwe completely transformed their
business through iPad andSharePoint.
Speaker 1 (31:30):
Yeah.
Speaker 2 (31:30):
Like they would go out, they, they would send their
I don't know measure out.
No, it was.
It was a floor company or HVAC,I can't remember.
I maybe it was a flooringcompany.
They would send somebody out,they would measure, they would
take those measurements back,they would walk it over to
whoever did the pricing.
That person would do all theirnumbers and send it back to that
(31:53):
person, who would get it to thesalesperson, who would go so
inefficient, yeah, yeah so weended up working with them and
figuring out a way thatbasically everything could
happen all at once on sitethrough a tablet First meeting,
you know, assessment of you knowwhat materials and space and
(32:13):
all that stuff Price generatedthere, and a signature as well,
right, which is huge, you know.
So what may have taken a weekor so happened in one visit.
Speaker 1 (32:24):
So you talked earlier about you know how.
Help Desk is one of ourservices, obviously, but we
don't lead in with that, that'sa known thing.
So how do you position yourteam as strategic, our team,
sorry as strategic partnersversus just a tech support arm?
(32:45):
You know, if you will, you know, I mean, I can think of a
couple things off the top of myhead.
I mean, strategic planning isobvious, Continuous improvement.
Speaker 2 (32:56):
Right.
Speaker 1 (32:56):
We talked about that yeah.
Speaker 2 (32:58):
Well, you know, there's always got to be
communication between us and thecustomer, because everything,
things are constantly changing,whether it's a new threat or a
new capability within SharePointor-.
Speaker 1 (33:12):
So knowledge training , yeah Right.
Speaker 2 (33:14):
There's always something that we need to be or
something's end of life.
Right now, we're in the middleof the Windows 10 to Windows 11
transition.
Speaker 1 (33:22):
Yeah, that's been keeping us busy.
Speaker 2 (33:25):
And we're constantly trying to be proactive in all
ways.
So when we bring on a customer,you know we offer that.
This is what we want to be.
We want to be a partner to youand we explain all the ways we
can.
Some people take advantage ofit, some people don't, but you
(33:46):
know a lot of them do.
And we have our virtual CIOmeetings and that's where a lot
of this can be discussed, and wetry to meet with our customers
twice a year to talk about wherewe are, where we've been and
where do you want to go.
And here's what we see that youmight need to think about and
here's a non-negotiable thatwe've got to deal with.
Speaker 1 (34:05):
And then listen, listen, yeah, and then build a
strategic plan around it and goto strategy with it.
So the big final loadedquestion and I love this
question because we talked aboutit briefly earlier, so this
should be easy as pie.
Speaker 2 (34:21):
I hope so.
Speaker 1 (34:24):
What trends do you see shaping the future of IT
management and clientrelationships?
Speaker 2 (34:32):
We talked about the automation.
I mean that's the biggest thing.
Speaker 1 (34:35):
About zero trust.
Speaker 2 (34:38):
Zero trust is huge.
Speaker 1 (34:39):
Yeah.
Speaker 2 (34:40):
We didn't get into specifics of that.
I mean, there are lots of neatcybersecurity tools that we're
seeing and that we'reimplementing we're already
automating patching yeah, andwe've all.
We've done that since day onethreat detection's automated.
Speaker 1 (34:55):
Now backups are automated um.
Speaker 2 (34:59):
We've automated the pen pen test scans we got a
really cool tool that we justrolled out that automates PC
setups, which is huge.
Speaker 1 (35:10):
Yeah.
Speaker 2 (35:10):
I mean, that's just a massive time saver, especially
right now when we've gotthousands, literally thousands,
of replacements that we'rehaving to do.
Speaker 1 (35:19):
And I think trust and privacy is huge.
I mean, that's where the zerotrust that I was talking about
comes in.
I mean those customers that arereally worried about those
types of things.
That's when you want to lean onzero trust, because there's
more data and touch pointshappening now, so I mean it's
(35:40):
complicated.
Yeah, so zero trust meanseverything has to be verified
before they can do it.
Everything has to be verifiedbefore they can do it, and I
mean you can't get into yourbank on your phone without face
detection or whatever.
Speaker 2 (35:55):
I think that's one that we're really going to have
to.
That's one that's hard toeducate on and hard to get
people to buy in.
There is a cost to it, but it'sthe way things are going.
Speaker 1 (36:08):
You know Absolutely Well.
Why are you giving me that?
Look, cause you don't know whatI'm about to hit you with.
Speaker 2 (36:14):
I thought that was it .
Speaker 1 (36:15):
We're going to hit you with the rapid fire
questions.
You can give me one, one wordto one sentence answers on these
.
So I'm going to keep it fastand we're going to go fast.
First thing that pops in yourhead, give me an answer.
Don't look at me, look straightat that camera.
Your camera's over there, yourcamera's right there.
Speaker 2 (36:37):
Oh, okay.
Speaker 1 (36:38):
All right, caleb I mean Jared get Kathleen zoomed
in.
Here we go.
Are you ready, kathleen?
Speaker 2 (36:48):
I guess so.
Speaker 1 (36:50):
Mac or PC.
Speaker 2 (36:52):
PC.
Speaker 1 (36:53):
Favorite tech tool right now.
Speaker 2 (36:56):
Gosh my watch.
I mean that's a tech tool,right.
I mean, find my is my favoritebutton on this thing.
Speaker 1 (37:03):
That's more than one word or one sentence.
I'm just kidding.
First job in tech.
Speaker 2 (37:13):
I was a technical recruiter for a company called
interim.
I found help desk people fordell and round rock awesome
biggest sales win oh gosh, therehave been a lot most underrated
it service.
Speaker 1 (37:27):
You can think about this one for a second.
Speaker 2 (37:29):
Don't take too long, yeah, underrated.
Most underrated it service Idon't know we don't underrate
any, it All right.
Speaker 1 (37:40):
Good, good answer Coffee or tea?
During client calls Coffee.
One word to describecybersecurity today.
Necessity, necessity dreamclient industry dream client
industry yeah, who is your dreamclient?
What?
What industry do they come from?
They'd have to be like law okay, best pensacola lunch spot for
(38:05):
business meetings I'm just asucker for cactus flower, social
or business.
Hey, there's a plug for cactusflower on 12th Avenue in
Pensacola, right next to DeNovoSalon.
Speaker 2 (38:17):
Yes, Palanzo, though for breakfast, Ah yeah, they got
good breakfast.
Speaker 1 (38:21):
Yeah.
What's one thing people mightnot know about your journey to
becoming chief revenue officerat Digital Boardwalk?
One thing they might not knowabout your journey to becoming
chief revenue officer at DigitalBoardwalk One thing they might
not know?
Speaker 2 (38:32):
I don't know, it's probably a lot, they don't know.
Speaker 1 (38:37):
Okay, you can't name one thing.
Speaker 2 (38:39):
One thing what was the question?
Speaker 1 (38:42):
One thing people might not know about your
journey to becoming the CRO atDigital Boardwalk.
So what got you here?
Oh, that's right.
Speaker 2 (38:51):
Oh, don't even.
Speaker 1 (38:52):
I'm kidding.
Speaker 2 (38:54):
I think that is not a one-word answer, so if you've
got time I'll tell you.
Speaker 1 (38:58):
Well, we'll skip it.
What's your favorite way tounwind after a long day of
client meetings?
Speaker 2 (39:04):
Gosh watering my plants.
Speaker 1 (39:07):
Yeah, that's good, they're everywhere they are.
It's like a jungle out there.
Speaker 2 (39:10):
It is.
Speaker 1 (39:12):
And all the leaves get in our pool.
Speaker 2 (39:14):
No, it's because I'm not watering enough.
Speaker 1 (39:18):
Anyway, Kathleen, thank you so much for joining me
today.
I know it was kind of shortnotice.
I'm glad that you finally cameon.
Speaker 2 (39:27):
Make me look good.
Speaker 1 (39:28):
You didn't get any beer, though, and I think you
were might might've been lookingforward to that.
We'll have you on again andwe'll do beer.
Speaker 2 (39:33):
Yeah.
Speaker 1 (39:34):
Okay, I just figured.
We had client meetings todayand you didn't want to show up
10 minutes.
You didn't want to show up allsauce, that's true?
Yeah, so I see I was takingcare of you, ladies and
gentlemen.
Ladies and gentlemen, thank youfor listening to another
episode of Nerds on Tap, wherewe had Kathleen Shoup on today.
And again, just a quick shoutout to our sponsor, digital
(39:57):
Boardwalk, and hey, have a nerdyday, cheers my fellow nerds and
beer lovers.
Speaker 3 (40:06):
Stay tuned for more Nerds on Tap.
Oh, and one more thing Help usspread the nerdy love and the
love for grape brews by sharingthis podcast with your friends,
colleagues and fellow beerenthusiasts.
Let's build a community thatembraces curiosity, innovation
(40:28):
and the enjoyment of a cold one.
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I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!
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