December 20, 2025 • 41 mins
In this episode of The Wireless Way, host Chris Whitaker engages in an insightful conversation with Dennis Osha, founder and chairman of Mobile Mentor. The discussion delves into Dennis's journey from working with Nokia in the 1980s to establishing Mobile Mentor in 2004. Dennis shares how his company has become a global leader in modern endpoint management and security, earning multiple Microsoft Partner of the Year recognitions. The episode covers various stages of the company’s evolution, including its pivot during the global financial crisis, partnership with Microsoft, and focus on Intune. Dennis also offers an in-depth analysis of current challenges and future trends in endpoint management, cloud security, and AI integration, underscoring the importance of unlocking the full potential of Microsoft 365 for optimal business outcomes.
00:00 Introduction and Guest Introduction
01:33 Dennis Osha's Background and Mobile Mentor's Origins
03:05 Transition from Engineering to Business Focus
05:21 Challenges and Pivotal Moments
12:14 Evolution of Mobile Mentor and Partnership with Microsoft
16:57 Current Trends and Future Directions
20:54 Challenges in AI Implementation
21:08 Data Security and Initial Findings
21:33 Skillset and Training for AI Tools
21:45 Board's Inquiry and ROI Model
22:31 Types of Companies and AI Adoption
23:35 Future of Device Management and Security Tools
26:33 Proliferation of AI Tools
27:31 Ideal Customer Profile
33:20 Sales Cycle and Marketing Strategies
36:36 Final Thoughts and Reflections
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Episode Transcript
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chris_1_12-19-2025_1311 (00:52):
Welcome to another episode of The
Wireless Way.
I'm your host, Chris Whitaker,and I am so grateful that you're
checking out this episode andI'm equally grateful to, Dennis
Osha, my guest today, and just alittle bit about him.
I met him recently.
Great guy.
He is the founder and chairmanof, mobile Mentor.
We're gonna unpack that.
(01:12):
What does that mean?
it's the global leader in modernendpoint management and security
that helps organizations secureand empower their workforce
across all types of devices.
We're gonna talk a little aboutthat.
he started the company in NewZealand, many moons ago.
And one of the things I thoughtwas really interesting and did
catch my eye was, you know.
During this time at the helm,mobile metor has earned multiple
(01:35):
Microsoft Partner of the Yearrecognitions, and that's no
small feat.
really excited to bring onDennis.
Thanks for making time for ustoday.
how are you doing?
denis-o-shea_1_12-19-202 (01:44):
Great, great.
Thank you.
I'm doing very well, and thankyou for the opportunity to come
on the podcast with you.
I'm excited.
chris_1_12-19-2025_131141 (01:49):
Oh, yes.
I'm always excited, especiallywith new guest people that I've
just met.
I was sharing with you preshow.
selfishly, I'm just excited tohave, I mean, I know how busy
you must be.
you're running a big company, agrowing company, and in an area
that I'm very interested in.
the fact that you're evenwilling to give me this time to
talk about, what you do and howyou do it.
Yeah, I'm equally excited.
(02:10):
So yeah, thanks so much.
so we got this, brief kind ofbio and, of course check the
show notes, folks.
As always, I'll have someinformation and links to, mobile
mentor and how to get ahold ofDennis's team.
what else can you tell us aboutyour journey to getting to where
you are today?
denis-o-shea_1_12-19-2025 (02:25):
Well, I'm looking at that phone on the
shelf behind your head
chris_1_12-19-2025_131141 (02:30):
Yes.
denis-o-shea_1_12-19-2025_1 (02:31):
and that's actually very close to
where I started.
Is that a Nokia or is that aMotorola?
chris_1_12-19-2025_131141 (02:36):
It's an inflatable, probably a Nokia.
denis-o-shea_1_12-19-2025_12 (02:38):
I, okay.
Okay.
So my story Nokia.
my story started in Helsinkiback in the eighties working
with Nokia, and my first mobiledevice was much bigger.
Than the one you've got on theshelf there.
chris_1_12-19-2025_131141 (02:52):
Are you kidding?
denis-o-shea_1_12-19-2025 (02:52):
about the same as a car battery.
chris_1_12-19-2025_131141 (02:54):
Oh Lord.
denis-o-shea_1_12-19-2025_12 (02:55):
it was a colossal thing with
cooling fans.
you could walk around and youheld it in one hand and you had
a curly cable and you'd pick upthe phone and you could do
remote calls, which was anamazing thing in the late
eighties, early nineties.
so I've had a long history inmobile technology and wireless
technology.
spent 15 years at Nokia, workingfor them in different countries
around the world.
eventually I landed in NewZealand and I got an idea from
(03:17):
my time with Nokia and I decidedto leave them, they gave me
their blessing.
They actually gave me somestartup capital and I set up
this company mobile mentor 2004.
I've been running that businessnow for 21 years.
and now I live in Nashville,Tennessee, and I do a ton of
work with Microsoft and someother partners here in the
States.
I'm delighted to be working withyou and your organization and
(03:40):
the TSD community, so it's beena hell of a journey.
chris_1_12-19-2025_131141 (03:43):
I bet, I mean, you've really seen
going from that suitcase, youknow, mobile phone, to what
we're doing today, what ajourney.
I mean, what a so many differentevolutions of, the product.
That's pretty fast.
So were you, even as a child,were you interested in
technology?
I mean, what point in yourdevelopment to a young man did
(04:04):
you like?
I love this technology stuff.
denis-o-shea_1_12-19-2025_121 (04:07):
I never loved technology, to be
honest.
I was interested in engineeringand how things worked.
So I went off and I got anengineering degree.
I got two of them.
I got a master's as well, and Iended up working in a lab doing
research and development forNokia and Finland and I got some
patents and all that.
And through that process Iactually learned that I was not
a great engineer.
(04:28):
I was more of a people person,more of an extrovert.
I found the best engineers inour environment were introverts
and they were able to go deepand stay deep in something for a
long, long time to solve acomplex problem.
I was much more interested inunderstanding what's the end
user going to do with thisproduct and who is the end user
and what are the steps inbetween and how does this
(04:48):
industry work?
I decided to get out of beingthe engineer with the technology
in the lab and get out into theworld.
So when Noia asked me to go toNew Zealand to build the world's
first cellular network.
I said, sure.
When's the flight?
and I moved to New Zealand andthen I went to different places
and I ran Nokia, Switzerland fora few years and ended up back in
(05:08):
New Zealand.
I really followed the growth ofthe industry, but not so much as
an engineer because I didn'tthink I was a good one, but
rather as, somebody who couldunderstand technology and then
help customers unlock the fullpotential of that technology in
a business sense.
chris_1_12-19-2025_13114 (05:24):
that's fantastic.
I can relate to that'cause Igenerally self-describe myself
as a tech enthusiast, but.
denis-o-shea_1_12-19-2025_ (05:31):
Hmm.
chris_1_12-19-2025_131141 (05:31):
as I was listening to you talk, it's
like, you know, I'm really moreinterested in the outcome.
I mean, I'm more interestedlike, Hey, how is this gonna
make my life easier and better?
denis-o-shea_1_12-19-2025 (05:40):
yeah,
chris_1_12-19-2025_131141 (05:40):
years ago I was taught by a mentor
about the idea of beingefficient and effective.
denis-o-shea_1_12-19-2025 (05:46):
yeah,
chris_1_12-19-2025_131141 (05:46):
can have one without the other.
You really want both.
And so I've always lived my lifeof, you know, is this efficient
and is this effective?
And how can we use technology tomake business outcomes, more
efficient and effective?
And then when I talk to businessleaders of all levels, I mean
from SMB to enterprise,efficiency and effectiveness
usually equals profitability.
denis-o-shea_1_12-19-2025 (06:08):
Yeah.
chris_1_12-19-2025_131141 (06:09):
First statement.
denis-o-shea_1_12-19-2025 (06:09):
Yeah.
chris_1_12-19-2025_131141 (06:10):
it's a good return.
denis-o-shea_1_12-19-2025 (06:11):
Yeah.
chris_1_12-19-2025_131141 (06:13):
Yes,
denis-o-shea_1_12-19-2025_1 (06:13):
can I tell you a story that was
quite pivotal in my developmentwas,
chris_1_12-19-2025_1311 (06:16):
please.
denis-o-shea_1_12-19-2025_121 (06:17):
I got my ass kicked, by a customer
around 2003.
I was in Switzerland.
I had found myself in a seniorleadership role, where I was
heavily involved in sales, andwe had just sold a 3G network to
orange, a big, telco in Europe.
That was a big deal, hundreds ofmillions of euros and we were
trying to sell the nextgeneration of technology.
(06:39):
I was in a board meeting.
With the CEO of orange and hebasically, dressed me down said,
why would we buy the nextgeneration of your technology
when our customers are not usingall the stuff we bought from you
over the last few years?
chris_1_12-19-2025_131141 (06:55):
Hmm.
denis-o-shea_1_12-19-2025_1 (06:55):
And I didn't have an answer and I
went.
Back to my, you know, group inHelsinki and we tried to figure
it out and we really struggledbecause what was happening in
the industry was customers aregoing out and buying their first
smartphone, spending roughly athousand dollars on, on this
device.
And guess what they were doing?
They were making phone calls andsending text messages.
That was it.
(07:16):
There was no mobile internet.
there was no app store, therewas no social media.
getting music on your phone wasa nightmare.
Um, because there was only anapp store really back
chris_1_12-19-2025_1311 (07:25):
That's.
denis-o-shea_1_12-19-20 (07:26):
getting email, working with a nightmares
pre Blackberry days, youcouldn't sync your calendar.
so the smartphones were actuallynot that smart and the networks
and the infrastructure wasthere, and these European
carriers are spending, you know,billions on spectrum.
And billions on cell sites andinfrastructure, and billions on,
on all the technology, andpeople are sending text messages
(07:48):
and making phone calls.
it was a very, very, um,intense, uh, situation for a
while.
And, and, you know, we didn'thave an answer and I decided to
leave Nokia and try and dosomething about it.
the idea was to simply sit downwith one business person at a
time and help them configuretheir first smartphone.
(08:10):
it working for one person at atime.
Set up email, get calendarsyncing, transfer their contacts
from their old phone, get theirmusic on it, change all their
numbers with a plus format sothey could go roaming.
get all the basics so that you,Chris, if you had your first
(09:08):
smartphone, would be able tomake you super productive with
it as a business person so youcan spend a day outta the
office, use this device, beproductive, not have to go back
to a desk.
that was the vision.
And so we set up Mobile Mentorto do that, and we ultimately
did that.
We sat down with a millionpeople different countries
around the world, Brazil, China,Australia, New Zealand, Japan,
(09:29):
UK.
We, I think we moved the needlea little bit.
We got a lot of people, youknow, right up to senior
government level, governmentprime ministers and presidents
and company leaders learning howto use, smartphone technology to
the way it was intended to beused, and that then cascaded on
through their organizations.
(09:49):
So it was, and, you know,getting my ass kicked in a
boardroom, was really, I guessthe genesis of the, the idea to
go and do this.
chris_1_12-19-2025_131141 (09:58):
Yeah, that will humble you and, wise
that you took that as a learningmoment instead of, Woe is me
moment.
You know, what was I guythinking?
I mean, it was a great momentfor you.
Yeah.
I love with even the name mobilementor.
I'm a little, I'm kind of sad.
I didn't think of that, I wastelling you earlier, you know,
that's a double entendre,wireless meaning no attached and
(10:19):
no judgment.
The ways, the path, the journey,the adventure.
But, you know, the origin ofthis very show was really about
how to make.
Wireless and mobility, and eveninternet of things to take the
mystery out of it.
You know, we're using thesetechnologies every day.
Even the least technical personof all of us, they know how to
now use their smartphone.
I mean, yeah,
denis-o-shea_1_12-19-202 (10:38):
simple now.
chris_1_12-19-2025_131141 (10:39):
you know, what percentage of people
actually use their smart phonesnow for phone calls and text
versus mostly internet apps likeTikTok and social media and
things like that.
denis-o-shea_1_12-19-2025 (10:52):
Yeah, I'm not sure.
'cause we, we really don't dothat work anymore.
You know, that all changed veryquickly around 2008 when the
iPhone came out and when thecarriers launched.
chris_1_12-19-2025_1311 (11:01):
Mm-hmm.
denis-o-shea_1_12-19-2025_1 (11:02):
and wifi became ubiquitous.
the need for that in initialservice of helping someone set
up their smartphone quicklyevaporated
chris_1_12-19-2025_131141 (11:09):
Yeah.
denis-o-shea_1_12-19-2025_1 (11:09):
the time of the global financial
crisis.
So we pivoted and we became amanaged service provider for
enterprises and governmentdepartments who had a lot of
mobile devices, and they neededhelp to manage them, to secure
them, to build out apps, to doasset management, cost
management.
So our business very quicklyshifted from setting up a
smartphone for one hour.
(11:30):
To then, managing them 24 hoursa day on a long-term basis so
organizations could scale mobileworkforce
chris_1_12-19-2025_131141 (11:39):
You ahead.
denis-o-shea_1_12-19-2025_1 (11:39):
our focus has been mobile workers.
chris_1_12-19-2025_131141 (11:41):
Yeah, you were one of the first ones
to do it, I would imagine.
'cause if you think about theevolution of mobile devices in
the corporate workspace, itdoesn't seem that long ago, I
don't know, call it seven years,maybe, where the only people in
the organization that got aphone was the executives.
You had to be a VP or some, youknow, director.
(12:02):
or, yeah, sales if you're arevenue generator, possibly.
But even my first sales job, Ihad a beeper, you know?
My first sales job, when Igraduated from a beeper to a
Nokia.
I remember being at lunch, myboss, I got my first Nokia and
it was 1999.
and I go to lunch and because,you didn't wanna miss a call, I
took my Nokia set in the middleof the table, and I.
(12:24):
Pull the antenna up because Iwouldn't want everyone to know
I'm somebody.
I got a cell phone.
denis-o-shea_1_12-19-2025_ (12:30):
now.
chris_1_12-19-2025_131141 (12:30):
You don't have a cell phone.
I got a cell phone and of courseI didn't wanna miss that call.
denis-o-shea_1_12-19-2025 (12:35):
Yeah.
chris_1_12-19-2025_131141 (12:35):
it was all, when my phone rang, it
was always the money line.
I just heard, Ching ching.
You know, it was a great, agreat time.
But another funny story, asyou're talking about, when Smart
phones came on, I was talking toa friend of mine that worked at
Blackberry and they were at anall hands meeting that year, and
someone raised a hand when theywere doing the Q and a with the
CEO.
He said, Hey, what are we gonna,how are we gonna respond to the
(12:59):
app store?
Apple has this app store, youknow, what's our answer to that?
He says, that's just a fad.
People business people onlywanna make phone calls and
receive emails.
We have that market corneredthat's, don't worry about that.
she said, you could hear acollective sigh across the room.
'cause everyone knew, oh mygosh, we're in trouble.
(13:20):
That's a problem.
And of course, they were right.
It was a problem for them, whichis shame because you're right.
Even, you know, during theheyday b Blackberry, man, they,
they owned the market too.
denis-o-shea_1_12-19-2025_ (13:29):
they did for about five minutes.
And so it did PalmPilot forabout five minutes.
chris_1_12-19-2025_13114 (13:33):
That's correct.
denis-o-shea_1_12-19-2025_ (13:34):
they
chris_1_12-19-2025_131141 (13:34):
Yep.
denis-o-shea_1_12-19-2025_1 (13:35):
and Nokia owned it for a while and
Blackberry owned it for a while.
it's extraordinary to see howbusinesses have made fortunes
and lost fortunes very rapidly,over the years in this industry.
It's really, really interesting.
chris_1_12-19-2025_131141 (13:48):
so you talked about how you started
out with the goal of just beingthat mobile mentor, helping
people set up phones.
What did you see in the marketor the industry that prompted
you to, expand, more into,Modern endpoint management and
cloud security.
denis-o-shea_1_12-19-2025 (14:04):
Well, first we contracted.
Because the global financialcrisis changed our business
model and we hit to shift, wehit about 250 people at the
start of the global financialcrisis, and we had to do a rapid
downsizing and retrenchmentfrom, from our operations in
China and Brazil in particular.
So we retrenched, we pivoted, webecame a managed service
provider in the mobile space.
(14:24):
From there, we started building,mobile apps.
So we built a softwaredevelopment practice, which we
actually spun out as a separatecompany.
Later we got into mobilesecurity.
We partnered with AirWatchfirst.
still super proud.
One of my guys who chose them asa partner back around 2010 or
11, and they turned out to bethe global leader in mobile
device management and mobilesecurity.
(14:45):
So we worked with them for along time and Citrix and Mobile
arm and.
And then we had a fascinatingthing happen around 2015.
We were doing really well, youknow, able to basically go into
any enterprise and help themfigure out what's the right
platform to manage all theirmobile devices and secure them
with either AirWatch, mobileIron or Citrix.
Microsoft came to us and theysaid, the first thing they said
(15:09):
to me, first conversation I everhad with Microsoft was, you are
really annoying us.
They said, we're seeing you onall our accounts and we know
you're just laughing at ourproduct Intune, because it was a
very immature product backaround 2015.
they said, you know, we wouldlike mobile mentor to consider,
becoming a Microsoft partner,helping us to take Intune to
(15:31):
market, stop laughing at us, butactually work with us and help
us take this immature product tomarket and help us win some
market share, and become apartner.
And I told my engineers aboutthis conversation and they all
said, no way.
No way.
It's a dog you don't wanna touchinto.
And it's totally immature.
No, no.
That would be a huge stepbackwards.
And so I went and said yes toMicrosoft because of the power
(15:53):
of the partnership.
Not, not the technology, but thepower of the partnership.
chris_1_12-19-2025_13114 (15:57):
right.
denis-o-shea_1_12-19-202 (15:57):
'cause I had been given different
advice from other people aboutwhen you form.
A constructive partnership withMicrosoft, totally change your
business.
So we decided to set ourselves aNorth Star, and we said, what if
we aim to become the best in theworld at designing and deploying
Microsoft Intune?
As a platform to manage all thedevices because it won't just be
(16:18):
smartphones, it'll be thetablets and it'll be windows,
and ultimately it'll be MacBooksand virtual machines as well,
and then servers.
So we kind of had this vision.
We thought, you know, let's beaudacious here.
What if we aim to try and becomethe best in the world at one
narrow thing build a greatpartnership with Microsoft?
we had also been schooled at thetime with a very sobering number
(16:39):
that Microsoft had 400,000partners.
None of them get any attentionfrom Microsoft unless you find a
way to stand out.
So that really motivated us tofigure out, how do we become the
best in the world at one narrowthing so that they want to bring
us into all their top accountsand position us and introduce us
as their premium partner ortheir best partner for that one
(17:01):
thing.
So we spent 10 years working onthat, and then we won Global
Partner of the Year It kind ofplayed out as we hope, you know,
they have brought us into thelargest accounts in the world.
One of our accounts now has overa million devices on Intune.
We've got some hugely complexinteresting and diverse accounts
where, we're now managingmillions and millions devices,
(17:22):
and Microsoft has turned out tobe an amazing partner.
I've been invited onto theadvisory board for the Intune
product line.
engineers are part ofMicrosoft's elite engineering
team, so they get insights intowhat's coming and they have a
voice at the table, you know, toshare customer concerns,
customer frustrations.
But also to, to help withprioritization of future
(17:43):
products and features So that'sbeen a remarkable journey from
being a competitor to Microsoftand clearly annoying them so
much that they came to us andsaid, Hey, let's be friends.
to then winning their respectand now being able to work with
them and, these amazing accountsaround the world.
It's, been one of the greathighlights of my career
actually.
chris_1_12-19-2025_131141 (18:03):
I can only imagine to have one of the
largest, biggest softwarecompanies in the world say
you're annoying.
I mean that.
denis-o-shea_1_12-19-2025_ (18:09):
Hmm.
chris_1_12-19-2025_131141 (18:10):
You had to feel pretty.
Yeah.
That was a pretty proud moment.
I imagine they even knew who youwere.
Right?
I mean, of all the companiesyou, when you annoy eight pound
gorilla like that, I mean, youmust be doing something right?
Yeah.
denis-o-shea_1_12-19-2025_1 (18:21):
And remember we were in New Zealand,
right?
So we were in the second lastRock before you step off the
edge of the planet.
and for them to notice us atthat distance was, was pretty
cool.
chris_1_12-19-2025_131141 (18:31):
Oh my gosh.
So all of this, decades plusexperience with working with
enterprises and mobile devices.
There's really two questions Iwanna say.
first of all, the problems youwere solving 10, 15, 20 years
ago.
Are they still existing today?
They're gone, right?
So it's new problems.
They've been solved, got newproblems.
denis-o-shea_1_12-19-2025_1 (18:52):
new problems.
chris_1_12-19-2025_131141 (18:53):
Yeah.
give the listeners some idea,what's a common trend when your
team, has a new engagement oreven existing customer?
are you seeing trends of, issuesthat companies are maybe not
giving attention to?
some people just accept thingsfor the way they are because
they don't know there's a betterway.
what are you guys seeing?
denis-o-shea_1_12-19 (19:12):
Overseeing primarily is people not.
Able to unlock the fullpotential of what they're
spending with Microsoft.
So Gartner predicted about 10years ago that 95% of all
organizations in the world willend up using Microsoft 3, 6, 5.
Gartner was spot on with that.
Absolutely spot on.
'cause everyone, everyone has anaccount with Microsoft,
chris_1_12-19-2025_131141 (19:33):
Yes.
denis-o-shea_1_12-19-202 (19:34):
Apple, even Amazon, even Google, you
know, everyone uses Microsoftproducts to a certain extent and
most people end up usingMicrosoft 3 6 5 because it's the
bundle.
It's where the value lies and wedo a ton of assessments and what
we find is customers on averageare only using 44% of what
they've paid for.
So the work we then end up doingis helping them do more with the
(19:55):
licenses they've got.
we'll often say Stop buying newstuff, if you're only using 44%
of Microsoft, it probably meansyou're only using 44% of all the
other overlapping things youmight have as well.
All the security tools andmanagement tools and identity
tools and AI tools.
So the approach we tend to takeis, you know, let's help you
(20:16):
extract as much value aspossible.
From Microsoft as a strategicplatform, starting with
Microsoft 3, 6, 5, and veryoften starting with Intune
because we know we can use thatto manage all your devices and
you can probably retire two orthree other products.
if you're using Jam for yourMax, if you're using your watch
for your mobiles, if you'reusing SCCM for your windows,
(20:37):
let's collapse all those into inJune.
you're using Okta for identityor CrowdStrike for security or.
Proofpoint or whatever we can,we can collapse all of those
into Microsoft.
So now you get a lot more valuefrom one platform.
But as we think about the futureand AI in our businesses now, we
give ourselves the opportunityto allow AI to reason over all
(21:00):
that information.
'cause it's all inside a singletenant.
if we're using lots and lots ofdifferent products, AI can't
possibly reach that data andreason over it.
to answer your question, most ofthe work we do now is unlocking
the full potential of Microsoft3 6, 5.
And now what's rapidly shiftingis Microsoft co-pilot
(21:22):
organizations wanting to getco-pilot and not knowing how to
extract value from it in a waythat they can report up to their
board and give them data andsay, here's the ROI we're
getting based on the way we havedeployed it.
Here's how we're doing itsecurely, and here are the
agents we're building and here'swhy it's a sustainable strategy.
chris_1_12-19-2025_131141 (21:43):
are.
denis-o-shea_1_12-19-2025_ (21:43):
gone from mobile devices to all
devices to Microsoft 3, 6, 5,and now into the Microsoft
copilot space.
chris_1_12-19-2025_131141 (21:50):
So if I heard you right, are you now
kind of the copilot mentor?
I mean, you're, you're helpingcompanies, optimize and leverage
that.
That's pretty fascinating.
You know, I mean, because you'reright that is app and you see it
all the time.
Just like every day there's anarticle about how people or
companies are using AIincorrectly or not to this
fullest extent.
denis-o-shea_1_12-19-2025_12 (22:10):
to the fullest extent.
And, and also in a way justjumping into it, like we see
this all the time.
We did this, like, I'll admit wedid this.
So as a Microsoft partner, wedived into copilot.
We gave it to a lot of people.
And at one stage I had a come toJesus moment with our leadership
team because we realized wehadn't actually defined our use
cases.
We didn't know who we shouldhave given it to.
(22:31):
we hadn't really analyzed theway we worked to figure out
which roles and which types ofwork would benefit most from ai.
We hadn't done the groundwork.
We hadn't done our data securitywork.
So when we did the first scan,you won't believe this, but
we're a small organization,right?
Just under a hundred people.
We hit 33,000 sensitivedocuments that were overshared
(22:52):
overprivileged over permissioned33,000 on the.
And then we figured out that,you know, we could all use
copilot in the browser.
That that's easy.
But trying to use it well insideExcel, our word, our PowerPoint,
totally different.
You need a different skillsetset.
You need to be able to writeprompts in a different way.
We didn't know how to do that.
And when it came to developingAI agents to do, you know,
(23:15):
autonomous work, we didn't knowwhere to start.
We really were clueless.
Then, you know, when the boardasked me, how's the, how's the
AI initiative going?
Are we getting a return on that?
I couldn't answer the question.
I didn't know whether I shouldturn it all off tomorrow and
say, this is a waste of time.
Or whether I should say yes,give it to everybody.
It's amazing.
I had no data, so we had to goand solve those five problems
(23:38):
for ourselves to the use cases,secure the data, train ourselves
on how to use this and learn howto do good prompts.
Build some agents, get theplumbing in, place all the APIs
and build those agents and thenbuild an ROI model so we can
actually see what's working andwhat's not, who we should pull
licenses away from, and who weshould assign licenses to.
(23:59):
So we had to do all that spadework before we could then take
it out and actually helpcustomers do something similar
for themselves.
chris_1_12-19-2025_131141 (24:05):
Yeah.
You know, I gotta believe, yeah,there's probably two types of
company, one's that aredeploying it, not really knowing
how to measure our OI and how todo it the way you described.
And then there's some that arelike, you know what?
we don't know this, we don'tunderstand it.
We're just not gonna do it.
we're a blocking, no copilot, noai.
I've heard a couple otherpolicies that don't put anything
in chat GPT ever on yourcompany.
(24:26):
Work computer.
You know, there's like, youknow, the fear factor, you know,
if you don't know, it's easierto just ignore it, it seems.
denis-o-shea_1_12-19-2025 (24:33):
Those companies will, We'll have to
figure it out.
chris_1_12-19-2025_131141 (24:36):
Left behind.
denis-o-shea_1_12-19-2025_ (24:37):
It's not a, yeah, not doing AI is not
a sustainable strategy.
Just like not doing the internetwould not have been a great
strategy, 25 years ago Embracingmobile technology or wireless
technology would not have been agreat strategy.
it's a matter of time andfiguring these things out and
right sizing it for your ownbusiness,
chris_1_12-19-2025_131141 (24:54):
So it sounds like you have a knack,
you know, for kind of, 20 yearsago leaving Nokia, having this
vision and, then, running intoMicrosoft of, how you could
help, businesses going forward,from today what do you see for
2026 and beyond?
denis-o-shea_1_12-19-2025_121 (25:10):
A couple of things.
I see.
You know, where we started withthinking about device
technology, mobile devicemanagement, mobile security
products, I think that market'sgonna disappear.
I honestly think it's gonnacollapse.
Intune is going to be such adominant product all the legacy
products will almost becomeirrelevant.
(25:30):
probably end up with a small.
Set of use cases that, so OTIwill still do well for supply
chain inventory management,stuff like that.
Air Watch will carve out a smallniche jam full, hang around for
a while, but I think Intune willjust mop up the market.
Microsoft will dominate thecategory in the same way.
Microsoft dominates so manyother categories.
chris_1_12-19-2025_131141 (25:51):
Look at teams.
denis-o-shea_1_12-19-2025_12 (25:51):
is really, no,
chris_1_12-19-2025_131141 (25:53):
Yeah, teams.
Teams.
I remember a time when teamsfirst came on the market, like
nobody was using it.
It was glitchy.
denis-o-shea_1_12-19-2025_12 (25:59):
It was glitchy.
chris_1_12-19-2025_131141 (26:00):
I mean, see more teams than
anything it seems like,
denis-o-shea_1_12-19-2025_12 (26:03):
Oh yeah, and Teams probably isn't
even the best example becausethey have a very strong
competitor with Zoom and
chris_1_12-19-2025_13114 (26:08):
right,
denis-o-shea_1_12-19-2025_12 (26:09):
is not included in the bundle in
some markets, but Intune isincluded in the bundle in every
market.
chris_1_12-19-2025_131141 (26:15):
I hear that a lot.
denis-o-shea_1_12-19-2025_12 (26:15):
if you think it's free as opposed
to paying Jam or AirWatch orManage Engine or UL Alteris or
whoever else, eventually the CFOis gonna say, why are we not
using the free one everyone elseis?
And so that's the first thing.
We think Intune will justeventually be the default
product for all endpointmanagement, and the excitement
will go out of that marketbecause it'll essentially be a
(26:38):
single product market, just likeWindows is the dominant always
across.
Microsoft would just dominatethat space.
That's not interesting.
but I think it's inevitable.
What I think is superinteresting is the proliferation
of security tools that we'veseen over the last 15 years.
(26:58):
we know now mid-sizeorganizations have an average 52
security tools.
large organizations, reallylarge enterprises have 70 to 80
security tools.
And, I believe that's happenedbecause we've been operating
with a defensive mindset.
We've been under attack from badactors,
chris_1_12-19-2025_13114 (27:19):
Right.
denis-o-shea_1_12-19-2025_12 (27:20):
to think about it.
You know, if you were to findout how many drone launch
systems do you think Ukraine hasright now, or how many different
missile defense systems havethey got right now?
I bet you they've got lots.
They'll basically buy missiledefense from anyone who turns up
with a credible product that'swilling to sell it to them.
over the last 10 or 50 yearswe've been under attack.
(27:40):
So we've been trying to protectourselves and we've ended up
with 52 different tools.
Now what I'm seeing is a shiftin CIO mindset and CSO mindset
to say, instead of having 52point solutions, let's think
about.
Consolidating down to a smallernumber of strategic platforms
that have more integration, moreautomation, more AI going on
(28:02):
and, and so I think we're gonnasee a big consolidation in
security tooling over the nextfew years.
But when we look out into thefuture, I think we're gonna have
exactly the same scenario playout with ai.
I'm predicting, and some peoplewill hate me for this, but I'm
predicting that largeorganizations will end up with
52 different AI tools.
(28:23):
Not because of fear, because youknow, we armed ourselves at 52
security tools'cause we wereunder attack.
It was, it was one kind of fear.
Now it's different kind of fear.
It's fear of missing out, it'sfomo,
chris_1_12-19-2025_131141 (28:34):
Yeah.
denis-o-shea_1_12-19-2025_ (28:35):
it's organizations and led from the
CEO in many cases saying we needto get AI in our business.
We need to learn how to workbetter, faster, cheaper,
smarter, et cetera.
Uh,'cause our competitors aredoing it.
And because there'sopportunities.
I believe organizations will endup with a huge number of AI
tools across their business.
(28:55):
It'll become a very complexfabric we get to a point where
we can even think about tryingto consolidate on a smaller
number of strategic platforms.
chris_1_12-19-2025_13114 (29:06):
What's an ideal customer look like for
you?
denis-o-shea_1_12-19-2025 (29:12):
there are Microsoft shop.
We would be useless if they'rean AWS shop or a Google shop.
So we're, we're work exclusivelyin the Microsoft space.
Now they have workforce.
People in different countries ordifferent offices, different
geographies, some working fromhome, some working in offices.
they've got a lot of knowledgeworkers.
(29:32):
They've got a need to be able towork on many different devices
throughout the day.
They are partway through thejourney.
Of embracing ai, and theyideally are in some kind of
regulated industry wheresecurity is mandatory, they're,
(29:53):
they're subject to some kind offederal mandate to protect data,
financial data, student data,patient data.
So they have to take securityseriously.
know they need to embrace ai,they want to do it with
Microsoft.
They don't have all the skillsin-house and they want a partner
(30:15):
to come in and work with them,them deploy the technology with
best practice, them automate allthe manual processes and do lots
of knowledge transfer.
know, the word mentor our nameis there for a very good reason.
We still do a lot of knowledgetransfer.
It's a very large part of how wework.
And helping people become theexperts on the technology stack
(30:38):
they've chosen so they canextract maximum value from it.
chris_1_12-19-2025_131141 (30:42):
Gosh.
denis-o-shea_1_12-19- (30:43):
hopefully that describes the ideal
customer.
chris_1_12-19-2025_131141 (30:44):
No, that does.
I love, healthcare,
denis-o-shea_1_12-19-2025 (30:47):
Yeah,
chris_1_12-19-2025_13114 (30:47):
higher education.
denis-o-shea_1_12-19-2025_12 (30:49):
of our business
chris_1_12-19-2025_1 (30:49):
Insurance.
How, how
denis-o-shea_1_12-19-2025_1 (30:52):
it.
chris_1_12-19-2025_131141 (30:52):
even, governments, I mean, state,
local, federal,
denis-o-shea_1_12-19-2025_12 (30:55):
Oh Yeah.
And, and federal, you know, wemanage, we manage all the it and
all the mobile devices for some,large defense organizations
chris_1_12-19-2025_131141 (31:03):
very good.
denis-o-shea_1_12-19-2025_1 (31:03):
and highly secure government
organizations.
a lot of the work we do in othermarkets as well.
chris_1_12-19-2025_131141 (31:10):
Gosh.
where'd it go from there?
That, that's a lot of goodinformation and definitely has
the gears turning.
'cause I, I agree with you.
My, I didn't know the last 10years was so focused on mobility
and wireless and all thesedevices.
the one thing that almost alwayscomes up, if you mention
copilot, ugh.
That's complicated.
I can't figure it out.
Or we, or I love askingcustomers.
So what's your MDM strategy?
(31:31):
Oh, we use copilot.
Oh, that's great.
How, how's that going?
Long pause.
Well actually, John set it upfour years ago and, and he left,
you know, two years ago and Idon't think anyone's really
managing it.
denis-o-shea_1_12-19-2025_1 (31:43):
Oh.
Oh, you're right.
I mean, up until last week,Intune had 10,000 unique
settings.
It was a big product.
And then with the announcementslast week when Microsoft added
five new products into Intune,all included in the, Microsoft
3, 6 5 license.
I don't know the exact number,but we're getting closer to
20,000 unique settings just inone product.
(32:04):
you know how many years it takesto get an engineer to expert
level on Intune and be really,really good at just Windows or
Mac or iOS, or deep in theAndroid area?
It's a beast.
Intune is a colossal product.
chris_1_12-19-2025_131141 (32:18):
Wow.
Do you have any insight ontowhat that's gonna look like
going forward?
I mean, will it always requiresomeone like you and an
engineering staff to configureit properly and then, regularly
maintain it?
denis-o-shea_1_12-19-2025_1 (32:32):
Yes and no.
You will be able to do basicconfiguration with best
practices, very easily out ofthe box, properly.
Have an AI agent.
Set up some policies to alignwith your favorite regulatory
framework.
You know, if you're a CIS,whatever, there will be ways of
doing that easily with smarttech, but.
(32:56):
That will leave a gap inunderstanding.
And so if you need to dosomething custom or something
breaks, or there's a policyconflict between what you've got
in entre with your identity oryour conditional access policies
and the way you've set up yourdevices, if users are getting
locked out or timeoutshappening, wrong times and all
that, that's where there wouldbe a skills gap.
(33:17):
getting started, easy scalingsustainably a bit harder.
chris_1_12-19-2025_131141 (33:23):
Yeah.
denis-o-shea_1_12-19-2025 (33:24):
liken it to pickleball, right?
I'm a huge pickleball, fan, easysport to get into and start, and
you're just having so much funvery quickly, but a difficult
sport to master and really playat a high level and,
chris_1_12-19-2025_131141 (33:38):
If you're not careful, you'll trip
and break your ankle or yourwrist
denis-o-shea_1_12-19-2025_121 (33:42):
I broke my partner's nose.
chris_1_12-19-2025_131141 (33:44):
I'll put a muscle in my calf, my calf
muscle last year.
And, you know, because again, ifyou're not warming up, I mean,
just like everything, if youdon't prepare properly and you
don't have the right training,you're gonna hurt something or
somebody's gonna get hurt.
It's the same way with
denis-o-shea_1_12-19-2025 (33:57):
yeah,
chris_1_12-19-2025_131141 (33:57):
like, if, if you're, if you're not, if
know, learning fromprofessionals, caring properly,
yeah.
You're, you're in for a world ofhurt.
denis-o-shea_1_12-19-2025 (34:05):
Yeah.
point, you know, we come acrossa lot of clients where they say,
oh yeah, Jimmy set up in Junefour years ago, and he's gone.
and now we're not sure what it'sdoing or where we're at.
chris_1_12-19-2025_131141 (34:15):
Like, what's the point,
denis-o-shea_1_12-19-2025_1 (34:16):
set and forget.
chris_1_12-19-2025_13114 (34:17):
right?
Yeah.
denis-o-shea_1_12-19-2025_1 (34:18):
No, no.
chris_1_12-19-2025_131141 (34:19):
but that's, you know, I, feel like
there's a slow trend that I'venoticed just in my limited, view
of this space of, companies arelike, yeah, we're gonna make
Intune work.
You know, I'd want to payanother subscription for, you
know, pick one.
Um, I already have this, youknow, Microsoft is a reputable
company.
They clearly know aboutsoftware.
we're just gotta figure it out,you know, type thing.
But, back to the point, unlessyou have someone on staff that's
(34:41):
a specialist in that area.
denis-o-shea_1_12-19-2025 (34:43):
Yeah.
chris_1_12-19-2025_131141 (34:43):
how long are you gonna fill around
in the dark till you figure itout?
Why, you know, just go to youguys on that note.
So your team identifies acustomer that needs your help.
what does that sales cycle looklike?
I gotta believe there must be alot of due diligence and, a lot
of information gathering beforeyou can even begin to configure
a proper deployment.
(35:04):
is that fair?
denis-o-shea_1_12-19-202 (35:05):
That's a great question.
Our sales cycle has just gotshorter and shorter over the
years, which is reallyconvenient actually as a
business owner.
And, and that is, yeah, andthat's happened for a couple of
reasons.
we got great advice from amarketing company in Canada
about five or six years agocalled, Neural impact.
they said, as a small companytrying to establish ourselves,
(35:27):
the more we share, the moretransparent we are, the faster
we'll be able to establishtrust.
So their advice was put yourprices on your website, share
your customer logos, producelots of videos, share your ip,
write blogs, write white papers.
Give it all away.
And establish trust quickly.
So when people come to yourwebsite, they get to see, well,
(35:49):
this is what you charge andthese are the people you work
with, and here's some stuff yourengineers have published and
here's a white paper from yourarchitect.
And the customer will veryquickly self qualify.
They'll either say, no, you'retoo expensive, or they'll say,
your prices are reasonable.
Clearly you know what you'redoing.
You've worked with my peers.
I recognize the logos on yourwebsite.
(36:09):
I like the way you describedthis thing, or the way you
articulated, an approach, I'mgonna hire you.
chris_1_12-19-2025_131141 (36:15):
Yeah.
denis-o-shea_1_12-19-2025_ (36:15):
that helps enormously to break down
barriers and get to trustquickly.
The second thing that helps iswhen Microsoft introduces us.
says, mobile mentor is our toppartner, and they're the guys
who do the most complex work andthe biggest work and the biggest
rollouts.
And know, for some of thebiggest healthcare providers,
biggest defense organizations,biggest retailers, that's how
(36:37):
they introduce us.
And so those customers just go,okay, that's great.
Thank you.
We don't have to do an RFP.
don't need to spend three monthsscanning the market.
We're talking to the people who.
Done it before many times, andwe can get into it.
You know, we can immediatelydrop into a very nuanced
conversation about theirspecific use cases and
(36:57):
scenarios.
Even if they don't buy from us,they're gonna learn.
chris_1_12-19-2025_131141 (37:01):
That.
denis-o-shea_1_12-19-20 (37:01):
They're gonna learn a ton about how to
approach it.
chris_1_12-19-2025_131141 (37:04):
You mentioned that marketing firm in
Canada, all the great advicethey gave you.
I'm just curious, did theymention that you need to come on
this podcast by chance, that youshould work at the wireless way?
I mean, we need to, we, I needto get with that marketing firm
recommending that should havebeen the first advice you Hey,
call Chris and get on hispodcast.
A great conversation, Dennis, II do have one last question
(37:26):
that's kind of, tongue in cheek,but, so it, I, there's a rumor
that you, you moved to Nashville'cause you're gonna start a, if
this mobile mentor didn't workout, you're gonna become a
country western singer.
Is, is there any truth to that?
denis-o-shea_1_12-19-20 (37:37):
There's no truth.
Sadly.
I wish there was.
I wish there was, but I'll tellyou a funny story.
When I moved here, we were stilldoing a lot of app development.
mobile app development.
and, you know, very quicklyrealized Nashville is in the
buckle of the Bible belt here inthe south.
And we were thinking aboutsetting up the app development
practice here, we thought maybe,we'll, maybe we'll call it, John
(38:00):
the Aptist.
We didn't,
chris_1_12-19-2025_131141 (38:06):
I was.
denis-o-shea_1_12-19-2025_12 (38:06):
we had a good laugh at that, John
the Baptist.
chris_1_12-19-2025_131141 (38:10):
Well that is.
Is there any last words,anything as we wrap up, is there
anything we didn't hit on thatyou wanna mention or a favorite
quote or a book?
Anything you can share with us?
denis-o-shea_1_12-19-2 (38:19):
Favorite quote is, future we see is the
future we get.
It's been my favorite quote foryears
chris_1_12-19-2025_131141 (38:24):
The future we see
denis-o-shea_1_12-19-2025_1 (38:25):
it.
chris_1_12-19-2025_131141 (38:26):
the future.
denis-o-shea_1_12-19-2025_12 (38:26):
we see is the future we get.
I believe it's all in the mind'seye.
know how we visualize and like Itell my team, you know, we set
that vision, let's you know,what would it look like to
become the best in the world ifwe just get up every day and
think about that for 10 years?
What happens?
chris_1_12-19-2025_131141 (38:41):
I,
denis-o-shea_1_12-19-2025_12 (38:42):
we
chris_1_12-19-2025_1311 (38:42):
support that.
denis-o-shea_1_12-19-2025_ (38:42):
get.
chris_1_12-19-2025_131141 (38:43):
Some people call it law of
attraction.
Some people call it positivethinking, whatever you call it.
It does work.
I mean, I can speak
denis-o-shea_1_12-19-2025 (38:50):
yeah.
chris_1_12-19-2025_131141 (38:50):
that my whole life, everything well
in my life, other than being amatter of prayer and, my belief
in God.
but, you know, I also have avery positive attitude.
You know, I believe if someoneelse can do it, I can do it.
I mean.
denis-o-shea_1_12-19-2025 (39:02):
Yeah.
chris_1_12-19-2025_131141 (39:02):
if you have a position of,
pessimism, don't be surprisedwhen you're just not successful
in life.
'cause you won't be.
You have to be, we have to bewilling to learn.
You have to be open-minded, butyou have to be positive What a
great way to end thisconversation.
denis-o-shea_1_12-19-2025_1 (39:15):
and that's not my quote Chris.
I read it somewhere.
but I latched onto it
chris_1_12-19-2025_13114 (39:21):
That's right.
denis-o-shea_1_12-19-20 (39:21):
latched onto me,
chris_1_12-19-2025_1311 (39:23):
Whoever said it, you know,
denis-o-shea_1_12-19-2025_121 (39:24):
a wise man
chris_1_12-19-2025_13114 (39:25):
that's right.
denis-o-shea_1_12-19-202 (39:25):
woman.
chris_1_12-19-2025_131 (39:26):
probably from the stoics or something.
I see.
Marcus or, or, saying somethinglike that.
Dennis, I really appreciate yourtime.
I've enjoyed this conversation.
I've learned a lot.
please check the show notes andyou'll, and I'll have more
information there.
But, thanks again for makingtime for us.
denis-o-shea_1_12-19-2025 (39:41):
Thank you Chris.
I'm delighted to be part of yourcommunity.
chris_1_12-19-2025_131141 (39:44):
Thank you so much.
and thank you for listening tothis, episode of The Wireless
Way.
And as always, if, any of thisresonated, if it hit home, you
thought about a customer, youthought about a colleague, share
this episode with them.
go to the wireless way.net.
There's a contact us button ifyou like more information.
Of course there'll beinformation in the show notes
and links to, mobile mentor and,learn a little bit more about
(40:06):
Dennis, as well.
So we'll see you next time onthe Wireless Way.
Welcome to another episode of The
Wireless Way.
I'm your host, Chris Whitaker,and I am so grateful that you're
checking out this episode andI'm equally grateful to, Dennis
Osha, my guest today, and just alittle bit about him.
I met him recently.
Great guy.
He is the founder and chairmanof, mobile Mentor.
We're gonna unpack that.
(01:12):
What does that mean?
it's the global leader in modernendpoint management and security
that helps organizations secureand empower their workforce
across all types of devices.
We're gonna talk a little aboutthat.
he started the company in NewZealand, many moons ago.
And one of the things I thoughtwas really interesting and did
catch my eye was, you know.
During this time at the helm,mobile metor has earned multiple
(01:35):
Microsoft Partner of the Yearrecognitions, and that's no
small feat.
really excited to bring onDennis.
Thanks for making time for ustoday.
how are you doing?
denis-o-shea_1_12-19-202 (01:44):
Great, great.
Thank you.
I'm doing very well, and thankyou for the opportunity to come
on the podcast with you.
I'm excited.
chris_1_12-19-2025_131141 (01:49):
Oh, yes.
I'm always excited, especiallywith new guest people that I've
just met.
I was sharing with you preshow.
selfishly, I'm just excited tohave, I mean, I know how busy
you must be.
you're running a big company, agrowing company, and in an area
that I'm very interested in.
the fact that you're evenwilling to give me this time to
talk about, what you do and howyou do it.
Yeah, I'm equally excited.
(02:10):
So yeah, thanks so much.
so we got this, brief kind ofbio and, of course check the
show notes, folks.
As always, I'll have someinformation and links to, mobile
mentor and how to get ahold ofDennis's team.
what else can you tell us aboutyour journey to getting to where
you are today?
denis-o-shea_1_12-19-2025 (02:25):
Well, I'm looking at that phone on the
shelf behind your head
chris_1_12-19-2025_131141 (02:30):
Yes.
denis-o-shea_1_12-19-2025_1 (02:31):
and that's actually very close to
where I started.
Is that a Nokia or is that aMotorola?
chris_1_12-19-2025_131141 (02:36):
It's an inflatable, probably a Nokia.
denis-o-shea_1_12-19-2025_12 (02:38):
I, okay.
Okay.
So my story Nokia.
my story started in Helsinkiback in the eighties working
with Nokia, and my first mobiledevice was much bigger.
Than the one you've got on theshelf there.
chris_1_12-19-2025_131141 (02:52):
Are you kidding?
denis-o-shea_1_12-19-2025 (02:52):
about the same as a car battery.
chris_1_12-19-2025_131141 (02:54):
Oh Lord.
denis-o-shea_1_12-19-2025_12 (02:55):
it was a colossal thing with
cooling fans.
you could walk around and youheld it in one hand and you had
a curly cable and you'd pick upthe phone and you could do
remote calls, which was anamazing thing in the late
eighties, early nineties.
so I've had a long history inmobile technology and wireless
technology.
spent 15 years at Nokia, workingfor them in different countries
around the world.
eventually I landed in NewZealand and I got an idea from
(03:17):
my time with Nokia and I decidedto leave them, they gave me
their blessing.
They actually gave me somestartup capital and I set up
this company mobile mentor 2004.
I've been running that businessnow for 21 years.
and now I live in Nashville,Tennessee, and I do a ton of
work with Microsoft and someother partners here in the
States.
I'm delighted to be working withyou and your organization and
(03:40):
the TSD community, so it's beena hell of a journey.
chris_1_12-19-2025_131141 (03:43):
I bet, I mean, you've really seen
going from that suitcase, youknow, mobile phone, to what
we're doing today, what ajourney.
I mean, what a so many differentevolutions of, the product.
That's pretty fast.
So were you, even as a child,were you interested in
technology?
I mean, what point in yourdevelopment to a young man did
(04:04):
you like?
I love this technology stuff.
denis-o-shea_1_12-19-2025_121 (04:07):
I never loved technology, to be
honest.
I was interested in engineeringand how things worked.
So I went off and I got anengineering degree.
I got two of them.
I got a master's as well, and Iended up working in a lab doing
research and development forNokia and Finland and I got some
patents and all that.
And through that process Iactually learned that I was not
a great engineer.
(04:28):
I was more of a people person,more of an extrovert.
I found the best engineers inour environment were introverts
and they were able to go deepand stay deep in something for a
long, long time to solve acomplex problem.
I was much more interested inunderstanding what's the end
user going to do with thisproduct and who is the end user
and what are the steps inbetween and how does this
(04:48):
industry work?
I decided to get out of beingthe engineer with the technology
in the lab and get out into theworld.
So when Noia asked me to go toNew Zealand to build the world's
first cellular network.
I said, sure.
When's the flight?
and I moved to New Zealand andthen I went to different places
and I ran Nokia, Switzerland fora few years and ended up back in
(05:08):
New Zealand.
I really followed the growth ofthe industry, but not so much as
an engineer because I didn'tthink I was a good one, but
rather as, somebody who couldunderstand technology and then
help customers unlock the fullpotential of that technology in
a business sense.
chris_1_12-19-2025_13114 (05:24):
that's fantastic.
I can relate to that'cause Igenerally self-describe myself
as a tech enthusiast, but.
denis-o-shea_1_12-19-2025_ (05:31):
Hmm.
chris_1_12-19-2025_131141 (05:31):
as I was listening to you talk, it's
like, you know, I'm really moreinterested in the outcome.
I mean, I'm more interestedlike, Hey, how is this gonna
make my life easier and better?
denis-o-shea_1_12-19-2025 (05:40):
yeah,
chris_1_12-19-2025_131141 (05:40):
years ago I was taught by a mentor
about the idea of beingefficient and effective.
denis-o-shea_1_12-19-2025 (05:46):
yeah,
chris_1_12-19-2025_131141 (05:46):
can have one without the other.
You really want both.
And so I've always lived my lifeof, you know, is this efficient
and is this effective?
And how can we use technology tomake business outcomes, more
efficient and effective?
And then when I talk to businessleaders of all levels, I mean
from SMB to enterprise,efficiency and effectiveness
usually equals profitability.
denis-o-shea_1_12-19-2025 (06:08):
Yeah.
chris_1_12-19-2025_131141 (06:09):
First statement.
denis-o-shea_1_12-19-2025 (06:09):
Yeah.
chris_1_12-19-2025_131141 (06:10):
it's a good return.
denis-o-shea_1_12-19-2025 (06:11):
Yeah.
chris_1_12-19-2025_131141 (06:13):
Yes,
denis-o-shea_1_12-19-2025_1 (06:13):
can I tell you a story that was
quite pivotal in my developmentwas,
chris_1_12-19-2025_1311 (06:16):
please.
denis-o-shea_1_12-19-2025_121 (06:17):
I got my ass kicked, by a customer
around 2003.
I was in Switzerland.
I had found myself in a seniorleadership role, where I was
heavily involved in sales, andwe had just sold a 3G network to
orange, a big, telco in Europe.
That was a big deal, hundreds ofmillions of euros and we were
trying to sell the nextgeneration of technology.
(06:39):
I was in a board meeting.
With the CEO of orange and hebasically, dressed me down said,
why would we buy the nextgeneration of your technology
when our customers are not usingall the stuff we bought from you
over the last few years?
chris_1_12-19-2025_131141 (06:55):
Hmm.
denis-o-shea_1_12-19-2025_1 (06:55):
And I didn't have an answer and I
went.
Back to my, you know, group inHelsinki and we tried to figure
it out and we really struggledbecause what was happening in
the industry was customers aregoing out and buying their first
smartphone, spending roughly athousand dollars on, on this
device.
And guess what they were doing?
They were making phone calls andsending text messages.
That was it.
(07:16):
There was no mobile internet.
there was no app store, therewas no social media.
getting music on your phone wasa nightmare.
Um, because there was only anapp store really back
chris_1_12-19-2025_1311 (07:25):
That's.
denis-o-shea_1_12-19-20 (07:26):
getting email, working with a nightmares
pre Blackberry days, youcouldn't sync your calendar.
so the smartphones were actuallynot that smart and the networks
and the infrastructure wasthere, and these European
carriers are spending, you know,billions on spectrum.
And billions on cell sites andinfrastructure, and billions on,
on all the technology, andpeople are sending text messages
(07:48):
and making phone calls.
it was a very, very, um,intense, uh, situation for a
while.
And, and, you know, we didn'thave an answer and I decided to
leave Nokia and try and dosomething about it.
the idea was to simply sit downwith one business person at a
time and help them configuretheir first smartphone.
(08:10):
it working for one person at atime.
Set up email, get calendarsyncing, transfer their contacts
from their old phone, get theirmusic on it, change all their
numbers with a plus format sothey could go roaming.
get all the basics so that you,Chris, if you had your first
(09:08):
smartphone, would be able tomake you super productive with
it as a business person so youcan spend a day outta the
office, use this device, beproductive, not have to go back
to a desk.
that was the vision.
And so we set up Mobile Mentorto do that, and we ultimately
did that.
We sat down with a millionpeople different countries
around the world, Brazil, China,Australia, New Zealand, Japan,
(09:29):
UK.
We, I think we moved the needlea little bit.
We got a lot of people, youknow, right up to senior
government level, governmentprime ministers and presidents
and company leaders learning howto use, smartphone technology to
the way it was intended to beused, and that then cascaded on
through their organizations.
(09:49):
So it was, and, you know,getting my ass kicked in a
boardroom, was really, I guessthe genesis of the, the idea to
go and do this.
chris_1_12-19-2025_131141 (09:58):
Yeah, that will humble you and, wise
that you took that as a learningmoment instead of, Woe is me
moment.
You know, what was I guythinking?
I mean, it was a great momentfor you.
Yeah.
I love with even the name mobilementor.
I'm a little, I'm kind of sad.
I didn't think of that, I wastelling you earlier, you know,
that's a double entendre,wireless meaning no attached and
(10:19):
no judgment.
The ways, the path, the journey,the adventure.
But, you know, the origin ofthis very show was really about
how to make.
Wireless and mobility, and eveninternet of things to take the
mystery out of it.
You know, we're using thesetechnologies every day.
Even the least technical personof all of us, they know how to
now use their smartphone.
I mean, yeah,
denis-o-shea_1_12-19-202 (10:38):
simple now.
chris_1_12-19-2025_131141 (10:39):
you know, what percentage of people
actually use their smart phonesnow for phone calls and text
versus mostly internet apps likeTikTok and social media and
things like that.
denis-o-shea_1_12-19-2025 (10:52):
Yeah, I'm not sure.
'cause we, we really don't dothat work anymore.
You know, that all changed veryquickly around 2008 when the
iPhone came out and when thecarriers launched.
chris_1_12-19-2025_1311 (11:01):
Mm-hmm.
denis-o-shea_1_12-19-2025_1 (11:02):
and wifi became ubiquitous.
the need for that in initialservice of helping someone set
up their smartphone quicklyevaporated
chris_1_12-19-2025_131141 (11:09):
Yeah.
denis-o-shea_1_12-19-2025_1 (11:09):
the time of the global financial
crisis.
So we pivoted and we became amanaged service provider for
enterprises and governmentdepartments who had a lot of
mobile devices, and they neededhelp to manage them, to secure
them, to build out apps, to doasset management, cost
management.
So our business very quicklyshifted from setting up a
smartphone for one hour.
(11:30):
To then, managing them 24 hoursa day on a long-term basis so
organizations could scale mobileworkforce
chris_1_12-19-2025_131141 (11:39):
You ahead.
denis-o-shea_1_12-19-2025_1 (11:39):
our focus has been mobile workers.
chris_1_12-19-2025_131141 (11:41):
Yeah, you were one of the first ones
to do it, I would imagine.
'cause if you think about theevolution of mobile devices in
the corporate workspace, itdoesn't seem that long ago, I
don't know, call it seven years,maybe, where the only people in
the organization that got aphone was the executives.
You had to be a VP or some, youknow, director.
(12:02):
or, yeah, sales if you're arevenue generator, possibly.
But even my first sales job, Ihad a beeper, you know?
My first sales job, when Igraduated from a beeper to a
Nokia.
I remember being at lunch, myboss, I got my first Nokia and
it was 1999.
and I go to lunch and because,you didn't wanna miss a call, I
took my Nokia set in the middleof the table, and I.
(12:24):
Pull the antenna up because Iwouldn't want everyone to know
I'm somebody.
I got a cell phone.
denis-o-shea_1_12-19-2025_ (12:30):
now.
chris_1_12-19-2025_131141 (12:30):
You don't have a cell phone.
I got a cell phone and of courseI didn't wanna miss that call.
denis-o-shea_1_12-19-2025 (12:35):
Yeah.
chris_1_12-19-2025_131141 (12:35):
it was all, when my phone rang, it
was always the money line.
I just heard, Ching ching.
You know, it was a great, agreat time.
But another funny story, asyou're talking about, when Smart
phones came on, I was talking toa friend of mine that worked at
Blackberry and they were at anall hands meeting that year, and
someone raised a hand when theywere doing the Q and a with the
CEO.
He said, Hey, what are we gonna,how are we gonna respond to the
(12:59):
app store?
Apple has this app store, youknow, what's our answer to that?
He says, that's just a fad.
People business people onlywanna make phone calls and
receive emails.
We have that market corneredthat's, don't worry about that.
she said, you could hear acollective sigh across the room.
'cause everyone knew, oh mygosh, we're in trouble.
(13:20):
That's a problem.
And of course, they were right.
It was a problem for them, whichis shame because you're right.
Even, you know, during theheyday b Blackberry, man, they,
they owned the market too.
denis-o-shea_1_12-19-2025_ (13:29):
they did for about five minutes.
And so it did PalmPilot forabout five minutes.
chris_1_12-19-2025_13114 (13:33):
That's correct.
denis-o-shea_1_12-19-2025_ (13:34):
they
chris_1_12-19-2025_131141 (13:34):
Yep.
denis-o-shea_1_12-19-2025_1 (13:35):
and Nokia owned it for a while and
Blackberry owned it for a while.
it's extraordinary to see howbusinesses have made fortunes
and lost fortunes very rapidly,over the years in this industry.
It's really, really interesting.
chris_1_12-19-2025_131141 (13:48):
so you talked about how you started
out with the goal of just beingthat mobile mentor, helping
people set up phones.
What did you see in the marketor the industry that prompted
you to, expand, more into,Modern endpoint management and
cloud security.
denis-o-shea_1_12-19-2025 (14:04):
Well, first we contracted.
Because the global financialcrisis changed our business
model and we hit to shift, wehit about 250 people at the
start of the global financialcrisis, and we had to do a rapid
downsizing and retrenchmentfrom, from our operations in
China and Brazil in particular.
So we retrenched, we pivoted, webecame a managed service
provider in the mobile space.
(14:24):
From there, we started building,mobile apps.
So we built a softwaredevelopment practice, which we
actually spun out as a separatecompany.
Later we got into mobilesecurity.
We partnered with AirWatchfirst.
still super proud.
One of my guys who chose them asa partner back around 2010 or
11, and they turned out to bethe global leader in mobile
device management and mobilesecurity.
(14:45):
So we worked with them for along time and Citrix and Mobile
arm and.
And then we had a fascinatingthing happen around 2015.
We were doing really well, youknow, able to basically go into
any enterprise and help themfigure out what's the right
platform to manage all theirmobile devices and secure them
with either AirWatch, mobileIron or Citrix.
Microsoft came to us and theysaid, the first thing they said
(15:09):
to me, first conversation I everhad with Microsoft was, you are
really annoying us.
They said, we're seeing you onall our accounts and we know
you're just laughing at ourproduct Intune, because it was a
very immature product backaround 2015.
they said, you know, we wouldlike mobile mentor to consider,
becoming a Microsoft partner,helping us to take Intune to
(15:31):
market, stop laughing at us, butactually work with us and help
us take this immature product tomarket and help us win some
market share, and become apartner.
And I told my engineers aboutthis conversation and they all
said, no way.
No way.
It's a dog you don't wanna touchinto.
And it's totally immature.
No, no.
That would be a huge stepbackwards.
And so I went and said yes toMicrosoft because of the power
(15:53):
of the partnership.
Not, not the technology, but thepower of the partnership.
chris_1_12-19-2025_13114 (15:57):
right.
denis-o-shea_1_12-19-202 (15:57):
'cause I had been given different
advice from other people aboutwhen you form.
A constructive partnership withMicrosoft, totally change your
business.
So we decided to set ourselves aNorth Star, and we said, what if
we aim to become the best in theworld at designing and deploying
Microsoft Intune?
As a platform to manage all thedevices because it won't just be
(16:18):
smartphones, it'll be thetablets and it'll be windows,
and ultimately it'll be MacBooksand virtual machines as well,
and then servers.
So we kind of had this vision.
We thought, you know, let's beaudacious here.
What if we aim to try and becomethe best in the world at one
narrow thing build a greatpartnership with Microsoft?
we had also been schooled at thetime with a very sobering number
(16:39):
that Microsoft had 400,000partners.
None of them get any attentionfrom Microsoft unless you find a
way to stand out.
So that really motivated us tofigure out, how do we become the
best in the world at one narrowthing so that they want to bring
us into all their top accountsand position us and introduce us
as their premium partner ortheir best partner for that one
(17:01):
thing.
So we spent 10 years working onthat, and then we won Global
Partner of the Year It kind ofplayed out as we hope, you know,
they have brought us into thelargest accounts in the world.
One of our accounts now has overa million devices on Intune.
We've got some hugely complexinteresting and diverse accounts
where, we're now managingmillions and millions devices,
(17:22):
and Microsoft has turned out tobe an amazing partner.
I've been invited onto theadvisory board for the Intune
product line.
engineers are part ofMicrosoft's elite engineering
team, so they get insights intowhat's coming and they have a
voice at the table, you know, toshare customer concerns,
customer frustrations.
But also to, to help withprioritization of future
(17:43):
products and features So that'sbeen a remarkable journey from
being a competitor to Microsoftand clearly annoying them so
much that they came to us andsaid, Hey, let's be friends.
to then winning their respectand now being able to work with
them and, these amazing accountsaround the world.
It's, been one of the greathighlights of my career
actually.
chris_1_12-19-2025_131141 (18:03):
I can only imagine to have one of the
largest, biggest softwarecompanies in the world say
you're annoying.
I mean that.
denis-o-shea_1_12-19-2025_ (18:09):
Hmm.
chris_1_12-19-2025_131141 (18:10):
You had to feel pretty.
Yeah.
That was a pretty proud moment.
I imagine they even knew who youwere.
Right?
I mean, of all the companiesyou, when you annoy eight pound
gorilla like that, I mean, youmust be doing something right?
Yeah.
denis-o-shea_1_12-19-2025_1 (18:21):
And remember we were in New Zealand,
right?
So we were in the second lastRock before you step off the
edge of the planet.
and for them to notice us atthat distance was, was pretty
cool.
chris_1_12-19-2025_131141 (18:31):
Oh my gosh.
So all of this, decades plusexperience with working with
enterprises and mobile devices.
There's really two questions Iwanna say.
first of all, the problems youwere solving 10, 15, 20 years
ago.
Are they still existing today?
They're gone, right?
So it's new problems.
They've been solved, got newproblems.
denis-o-shea_1_12-19-2025_1 (18:52):
new problems.
chris_1_12-19-2025_131141 (18:53):
Yeah.
give the listeners some idea,what's a common trend when your
team, has a new engagement oreven existing customer?
are you seeing trends of, issuesthat companies are maybe not
giving attention to?
some people just accept thingsfor the way they are because
they don't know there's a betterway.
what are you guys seeing?
denis-o-shea_1_12-19 (19:12):
Overseeing primarily is people not.
Able to unlock the fullpotential of what they're
spending with Microsoft.
So Gartner predicted about 10years ago that 95% of all
organizations in the world willend up using Microsoft 3, 6, 5.
Gartner was spot on with that.
Absolutely spot on.
'cause everyone, everyone has anaccount with Microsoft,
chris_1_12-19-2025_131141 (19:33):
Yes.
denis-o-shea_1_12-19-202 (19:34):
Apple, even Amazon, even Google, you
know, everyone uses Microsoftproducts to a certain extent and
most people end up usingMicrosoft 3 6 5 because it's the
bundle.
It's where the value lies and wedo a ton of assessments and what
we find is customers on averageare only using 44% of what
they've paid for.
So the work we then end up doingis helping them do more with the
(19:55):
licenses they've got.
we'll often say Stop buying newstuff, if you're only using 44%
of Microsoft, it probably meansyou're only using 44% of all the
other overlapping things youmight have as well.
All the security tools andmanagement tools and identity
tools and AI tools.
So the approach we tend to takeis, you know, let's help you
(20:16):
extract as much value aspossible.
From Microsoft as a strategicplatform, starting with
Microsoft 3, 6, 5, and veryoften starting with Intune
because we know we can use thatto manage all your devices and
you can probably retire two orthree other products.
if you're using Jam for yourMax, if you're using your watch
for your mobiles, if you'reusing SCCM for your windows,
(20:37):
let's collapse all those into inJune.
you're using Okta for identityor CrowdStrike for security or.
Proofpoint or whatever we can,we can collapse all of those
into Microsoft.
So now you get a lot more valuefrom one platform.
But as we think about the futureand AI in our businesses now, we
give ourselves the opportunityto allow AI to reason over all
(21:00):
that information.
'cause it's all inside a singletenant.
if we're using lots and lots ofdifferent products, AI can't
possibly reach that data andreason over it.
to answer your question, most ofthe work we do now is unlocking
the full potential of Microsoft3 6, 5.
And now what's rapidly shiftingis Microsoft co-pilot
(21:22):
organizations wanting to getco-pilot and not knowing how to
extract value from it in a waythat they can report up to their
board and give them data andsay, here's the ROI we're
getting based on the way we havedeployed it.
Here's how we're doing itsecurely, and here are the
agents we're building and here'swhy it's a sustainable strategy.
chris_1_12-19-2025_131141 (21:43):
are.
denis-o-shea_1_12-19-2025_ (21:43):
gone from mobile devices to all
devices to Microsoft 3, 6, 5,and now into the Microsoft
copilot space.
chris_1_12-19-2025_131141 (21:50):
So if I heard you right, are you now
kind of the copilot mentor?
I mean, you're, you're helpingcompanies, optimize and leverage
that.
That's pretty fascinating.
You know, I mean, because you'reright that is app and you see it
all the time.
Just like every day there's anarticle about how people or
companies are using AIincorrectly or not to this
fullest extent.
denis-o-shea_1_12-19-2025_12 (22:10):
to the fullest extent.
And, and also in a way justjumping into it, like we see
this all the time.
We did this, like, I'll admit wedid this.
So as a Microsoft partner, wedived into copilot.
We gave it to a lot of people.
And at one stage I had a come toJesus moment with our leadership
team because we realized wehadn't actually defined our use
cases.
We didn't know who we shouldhave given it to.
(22:31):
we hadn't really analyzed theway we worked to figure out
which roles and which types ofwork would benefit most from ai.
We hadn't done the groundwork.
We hadn't done our data securitywork.
So when we did the first scan,you won't believe this, but
we're a small organization,right?
Just under a hundred people.
We hit 33,000 sensitivedocuments that were overshared
(22:52):
overprivileged over permissioned33,000 on the.
And then we figured out that,you know, we could all use
copilot in the browser.
That that's easy.
But trying to use it well insideExcel, our word, our PowerPoint,
totally different.
You need a different skillsetset.
You need to be able to writeprompts in a different way.
We didn't know how to do that.
And when it came to developingAI agents to do, you know,
(23:15):
autonomous work, we didn't knowwhere to start.
We really were clueless.
Then, you know, when the boardasked me, how's the, how's the
AI initiative going?
Are we getting a return on that?
I couldn't answer the question.
I didn't know whether I shouldturn it all off tomorrow and
say, this is a waste of time.
Or whether I should say yes,give it to everybody.
It's amazing.
I had no data, so we had to goand solve those five problems
(23:38):
for ourselves to the use cases,secure the data, train ourselves
on how to use this and learn howto do good prompts.
Build some agents, get theplumbing in, place all the APIs
and build those agents and thenbuild an ROI model so we can
actually see what's working andwhat's not, who we should pull
licenses away from, and who weshould assign licenses to.
(23:59):
So we had to do all that spadework before we could then take
it out and actually helpcustomers do something similar
for themselves.
chris_1_12-19-2025_131141 (24:05):
Yeah.
You know, I gotta believe, yeah,there's probably two types of
company, one's that aredeploying it, not really knowing
how to measure our OI and how todo it the way you described.
And then there's some that arelike, you know what?
we don't know this, we don'tunderstand it.
We're just not gonna do it.
we're a blocking, no copilot, noai.
I've heard a couple otherpolicies that don't put anything
in chat GPT ever on yourcompany.
(24:26):
Work computer.
You know, there's like, youknow, the fear factor, you know,
if you don't know, it's easierto just ignore it, it seems.
denis-o-shea_1_12-19-2025 (24:33):
Those companies will, We'll have to
figure it out.
chris_1_12-19-2025_131141 (24:36):
Left behind.
denis-o-shea_1_12-19-2025_ (24:37):
It's not a, yeah, not doing AI is not
a sustainable strategy.
Just like not doing the internetwould not have been a great
strategy, 25 years ago Embracingmobile technology or wireless
technology would not have been agreat strategy.
it's a matter of time andfiguring these things out and
right sizing it for your ownbusiness,
chris_1_12-19-2025_131141 (24:54):
So it sounds like you have a knack,
you know, for kind of, 20 yearsago leaving Nokia, having this
vision and, then, running intoMicrosoft of, how you could
help, businesses going forward,from today what do you see for
2026 and beyond?
denis-o-shea_1_12-19-2025_121 (25:10):
A couple of things.
I see.
You know, where we started withthinking about device
technology, mobile devicemanagement, mobile security
products, I think that market'sgonna disappear.
I honestly think it's gonnacollapse.
Intune is going to be such adominant product all the legacy
products will almost becomeirrelevant.
(25:30):
probably end up with a small.
Set of use cases that, so OTIwill still do well for supply
chain inventory management,stuff like that.
Air Watch will carve out a smallniche jam full, hang around for
a while, but I think Intune willjust mop up the market.
Microsoft will dominate thecategory in the same way.
Microsoft dominates so manyother categories.
chris_1_12-19-2025_131141 (25:51):
Look at teams.
denis-o-shea_1_12-19-2025_12 (25:51):
is really, no,
chris_1_12-19-2025_131141 (25:53):
Yeah, teams.
Teams.
I remember a time when teamsfirst came on the market, like
nobody was using it.
It was glitchy.
denis-o-shea_1_12-19-2025_12 (25:59):
It was glitchy.
chris_1_12-19-2025_131141 (26:00):
I mean, see more teams than
anything it seems like,
denis-o-shea_1_12-19-2025_12 (26:03):
Oh yeah, and Teams probably isn't
even the best example becausethey have a very strong
competitor with Zoom and
chris_1_12-19-2025_13114 (26:08):
right,
denis-o-shea_1_12-19-2025_12 (26:09):
is not included in the bundle in
some markets, but Intune isincluded in the bundle in every
market.
chris_1_12-19-2025_131141 (26:15):
I hear that a lot.
denis-o-shea_1_12-19-2025_12 (26:15):
if you think it's free as opposed
to paying Jam or AirWatch orManage Engine or UL Alteris or
whoever else, eventually the CFOis gonna say, why are we not
using the free one everyone elseis?
And so that's the first thing.
We think Intune will justeventually be the default
product for all endpointmanagement, and the excitement
will go out of that marketbecause it'll essentially be a
(26:38):
single product market, just likeWindows is the dominant always
across.
Microsoft would just dominatethat space.
That's not interesting.
but I think it's inevitable.
What I think is superinteresting is the proliferation
of security tools that we'veseen over the last 15 years.
(26:58):
we know now mid-sizeorganizations have an average 52
security tools.
large organizations, reallylarge enterprises have 70 to 80
security tools.
And, I believe that's happenedbecause we've been operating
with a defensive mindset.
We've been under attack from badactors,
chris_1_12-19-2025_13114 (27:19):
Right.
denis-o-shea_1_12-19-2025_12 (27:20):
to think about it.
You know, if you were to findout how many drone launch
systems do you think Ukraine hasright now, or how many different
missile defense systems havethey got right now?
I bet you they've got lots.
They'll basically buy missiledefense from anyone who turns up
with a credible product that'swilling to sell it to them.
over the last 10 or 50 yearswe've been under attack.
(27:40):
So we've been trying to protectourselves and we've ended up
with 52 different tools.
Now what I'm seeing is a shiftin CIO mindset and CSO mindset
to say, instead of having 52point solutions, let's think
about.
Consolidating down to a smallernumber of strategic platforms
that have more integration, moreautomation, more AI going on
(28:02):
and, and so I think we're gonnasee a big consolidation in
security tooling over the nextfew years.
But when we look out into thefuture, I think we're gonna have
exactly the same scenario playout with ai.
I'm predicting, and some peoplewill hate me for this, but I'm
predicting that largeorganizations will end up with
52 different AI tools.
(28:23):
Not because of fear, because youknow, we armed ourselves at 52
security tools'cause we wereunder attack.
It was, it was one kind of fear.
Now it's different kind of fear.
It's fear of missing out, it'sfomo,
chris_1_12-19-2025_131141 (28:34):
Yeah.
denis-o-shea_1_12-19-2025_ (28:35):
it's organizations and led from the
CEO in many cases saying we needto get AI in our business.
We need to learn how to workbetter, faster, cheaper,
smarter, et cetera.
Uh,'cause our competitors aredoing it.
And because there'sopportunities.
I believe organizations will endup with a huge number of AI
tools across their business.
(28:55):
It'll become a very complexfabric we get to a point where
we can even think about tryingto consolidate on a smaller
number of strategic platforms.
chris_1_12-19-2025_13114 (29:06):
What's an ideal customer look like for
you?
denis-o-shea_1_12-19-2025 (29:12):
there are Microsoft shop.
We would be useless if they'rean AWS shop or a Google shop.
So we're, we're work exclusivelyin the Microsoft space.
Now they have workforce.
People in different countries ordifferent offices, different
geographies, some working fromhome, some working in offices.
they've got a lot of knowledgeworkers.
(29:32):
They've got a need to be able towork on many different devices
throughout the day.
They are partway through thejourney.
Of embracing ai, and theyideally are in some kind of
regulated industry wheresecurity is mandatory, they're,
(29:53):
they're subject to some kind offederal mandate to protect data,
financial data, student data,patient data.
So they have to take securityseriously.
know they need to embrace ai,they want to do it with
Microsoft.
They don't have all the skillsin-house and they want a partner
(30:15):
to come in and work with them,them deploy the technology with
best practice, them automate allthe manual processes and do lots
of knowledge transfer.
know, the word mentor our nameis there for a very good reason.
We still do a lot of knowledgetransfer.
It's a very large part of how wework.
And helping people become theexperts on the technology stack
(30:38):
they've chosen so they canextract maximum value from it.
chris_1_12-19-2025_131141 (30:42):
Gosh.
denis-o-shea_1_12-19- (30:43):
hopefully that describes the ideal
customer.
chris_1_12-19-2025_131141 (30:44):
No, that does.
I love, healthcare,
denis-o-shea_1_12-19-2025 (30:47):
Yeah,
chris_1_12-19-2025_13114 (30:47):
higher education.
denis-o-shea_1_12-19-2025_12 (30:49):
of our business
chris_1_12-19-2025_1 (30:49):
Insurance.
How, how
denis-o-shea_1_12-19-2025_1 (30:52):
it.
chris_1_12-19-2025_131141 (30:52):
even, governments, I mean, state,
local, federal,
denis-o-shea_1_12-19-2025_12 (30:55):
Oh Yeah.
And, and federal, you know, wemanage, we manage all the it and
all the mobile devices for some,large defense organizations
chris_1_12-19-2025_131141 (31:03):
very good.
denis-o-shea_1_12-19-2025_1 (31:03):
and highly secure government
organizations.
a lot of the work we do in othermarkets as well.
chris_1_12-19-2025_131141 (31:10):
Gosh.
where'd it go from there?
That, that's a lot of goodinformation and definitely has
the gears turning.
'cause I, I agree with you.
My, I didn't know the last 10years was so focused on mobility
and wireless and all thesedevices.
the one thing that almost alwayscomes up, if you mention
copilot, ugh.
That's complicated.
I can't figure it out.
Or we, or I love askingcustomers.
So what's your MDM strategy?
(31:31):
Oh, we use copilot.
Oh, that's great.
How, how's that going?
Long pause.
Well actually, John set it upfour years ago and, and he left,
you know, two years ago and Idon't think anyone's really
managing it.
denis-o-shea_1_12-19-2025_1 (31:43):
Oh.
Oh, you're right.
I mean, up until last week,Intune had 10,000 unique
settings.
It was a big product.
And then with the announcementslast week when Microsoft added
five new products into Intune,all included in the, Microsoft
3, 6 5 license.
I don't know the exact number,but we're getting closer to
20,000 unique settings just inone product.
(32:04):
you know how many years it takesto get an engineer to expert
level on Intune and be really,really good at just Windows or
Mac or iOS, or deep in theAndroid area?
It's a beast.
Intune is a colossal product.
chris_1_12-19-2025_131141 (32:18):
Wow.
Do you have any insight ontowhat that's gonna look like
going forward?
I mean, will it always requiresomeone like you and an
engineering staff to configureit properly and then, regularly
maintain it?
denis-o-shea_1_12-19-2025_1 (32:32):
Yes and no.
You will be able to do basicconfiguration with best
practices, very easily out ofthe box, properly.
Have an AI agent.
Set up some policies to alignwith your favorite regulatory
framework.
You know, if you're a CIS,whatever, there will be ways of
doing that easily with smarttech, but.
(32:56):
That will leave a gap inunderstanding.
And so if you need to dosomething custom or something
breaks, or there's a policyconflict between what you've got
in entre with your identity oryour conditional access policies
and the way you've set up yourdevices, if users are getting
locked out or timeoutshappening, wrong times and all
that, that's where there wouldbe a skills gap.
(33:17):
getting started, easy scalingsustainably a bit harder.
chris_1_12-19-2025_131141 (33:23):
Yeah.
denis-o-shea_1_12-19-2025 (33:24):
liken it to pickleball, right?
I'm a huge pickleball, fan, easysport to get into and start, and
you're just having so much funvery quickly, but a difficult
sport to master and really playat a high level and,
chris_1_12-19-2025_131141 (33:38):
If you're not careful, you'll trip
and break your ankle or yourwrist
denis-o-shea_1_12-19-2025_121 (33:42):
I broke my partner's nose.
chris_1_12-19-2025_131141 (33:44):
I'll put a muscle in my calf, my calf
muscle last year.
And, you know, because again, ifyou're not warming up, I mean,
just like everything, if youdon't prepare properly and you
don't have the right training,you're gonna hurt something or
somebody's gonna get hurt.
It's the same way with
denis-o-shea_1_12-19-2025 (33:57):
yeah,
chris_1_12-19-2025_131141 (33:57):
like, if, if you're, if you're not, if
know, learning fromprofessionals, caring properly,
yeah.
You're, you're in for a world ofhurt.
denis-o-shea_1_12-19-2025 (34:05):
Yeah.
point, you know, we come acrossa lot of clients where they say,
oh yeah, Jimmy set up in Junefour years ago, and he's gone.
and now we're not sure what it'sdoing or where we're at.
chris_1_12-19-2025_131141 (34:15):
Like, what's the point,
denis-o-shea_1_12-19-2025_1 (34:16):
set and forget.
chris_1_12-19-2025_13114 (34:17):
right?
Yeah.
denis-o-shea_1_12-19-2025_1 (34:18):
No, no.
chris_1_12-19-2025_131141 (34:19):
but that's, you know, I, feel like
there's a slow trend that I'venoticed just in my limited, view
of this space of, companies arelike, yeah, we're gonna make
Intune work.
You know, I'd want to payanother subscription for, you
know, pick one.
Um, I already have this, youknow, Microsoft is a reputable
company.
They clearly know aboutsoftware.
we're just gotta figure it out,you know, type thing.
But, back to the point, unlessyou have someone on staff that's
(34:41):
a specialist in that area.
denis-o-shea_1_12-19-2025 (34:43):
Yeah.
chris_1_12-19-2025_131141 (34:43):
how long are you gonna fill around
in the dark till you figure itout?
Why, you know, just go to youguys on that note.
So your team identifies acustomer that needs your help.
what does that sales cycle looklike?
I gotta believe there must be alot of due diligence and, a lot
of information gathering beforeyou can even begin to configure
a proper deployment.
(35:04):
is that fair?
denis-o-shea_1_12-19-202 (35:05):
That's a great question.
Our sales cycle has just gotshorter and shorter over the
years, which is reallyconvenient actually as a
business owner.
And, and that is, yeah, andthat's happened for a couple of
reasons.
we got great advice from amarketing company in Canada
about five or six years agocalled, Neural impact.
they said, as a small companytrying to establish ourselves,
(35:27):
the more we share, the moretransparent we are, the faster
we'll be able to establishtrust.
So their advice was put yourprices on your website, share
your customer logos, producelots of videos, share your ip,
write blogs, write white papers.
Give it all away.
And establish trust quickly.
So when people come to yourwebsite, they get to see, well,
(35:49):
this is what you charge andthese are the people you work
with, and here's some stuff yourengineers have published and
here's a white paper from yourarchitect.
And the customer will veryquickly self qualify.
They'll either say, no, you'retoo expensive, or they'll say,
your prices are reasonable.
Clearly you know what you'redoing.
You've worked with my peers.
I recognize the logos on yourwebsite.
(36:09):
I like the way you describedthis thing, or the way you
articulated, an approach, I'mgonna hire you.
chris_1_12-19-2025_131141 (36:15):
Yeah.
denis-o-shea_1_12-19-2025_ (36:15):
that helps enormously to break down
barriers and get to trustquickly.
The second thing that helps iswhen Microsoft introduces us.
says, mobile mentor is our toppartner, and they're the guys
who do the most complex work andthe biggest work and the biggest
rollouts.
And know, for some of thebiggest healthcare providers,
biggest defense organizations,biggest retailers, that's how
(36:37):
they introduce us.
And so those customers just go,okay, that's great.
Thank you.
We don't have to do an RFP.
don't need to spend three monthsscanning the market.
We're talking to the people who.
Done it before many times, andwe can get into it.
You know, we can immediatelydrop into a very nuanced
conversation about theirspecific use cases and
(36:57):
scenarios.
Even if they don't buy from us,they're gonna learn.
chris_1_12-19-2025_131141 (37:01):
That.
denis-o-shea_1_12-19-20 (37:01):
They're gonna learn a ton about how to
approach it.
chris_1_12-19-2025_131141 (37:04):
You mentioned that marketing firm in
Canada, all the great advicethey gave you.
I'm just curious, did theymention that you need to come on
this podcast by chance, that youshould work at the wireless way?
I mean, we need to, we, I needto get with that marketing firm
recommending that should havebeen the first advice you Hey,
call Chris and get on hispodcast.
A great conversation, Dennis, II do have one last question
(37:26):
that's kind of, tongue in cheek,but, so it, I, there's a rumor
that you, you moved to Nashville'cause you're gonna start a, if
this mobile mentor didn't workout, you're gonna become a
country western singer.
Is, is there any truth to that?
denis-o-shea_1_12-19-20 (37:37):
There's no truth.
Sadly.
I wish there was.
I wish there was, but I'll tellyou a funny story.
When I moved here, we were stilldoing a lot of app development.
mobile app development.
and, you know, very quicklyrealized Nashville is in the
buckle of the Bible belt here inthe south.
And we were thinking aboutsetting up the app development
practice here, we thought maybe,we'll, maybe we'll call it, John
(38:00):
the Aptist.
We didn't,
chris_1_12-19-2025_131141 (38:06):
I was.
denis-o-shea_1_12-19-2025_12 (38:06):
we had a good laugh at that, John
the Baptist.
chris_1_12-19-2025_131141 (38:10):
Well that is.
Is there any last words,anything as we wrap up, is there
anything we didn't hit on thatyou wanna mention or a favorite
quote or a book?
Anything you can share with us?
denis-o-shea_1_12-19-2 (38:19):
Favorite quote is, future we see is the
future we get.
It's been my favorite quote foryears
chris_1_12-19-2025_131141 (38:24):
The future we see
denis-o-shea_1_12-19-2025_1 (38:25):
it.
chris_1_12-19-2025_131141 (38:26):
the future.
denis-o-shea_1_12-19-2025_12 (38:26):
we see is the future we get.
I believe it's all in the mind'seye.
know how we visualize and like Itell my team, you know, we set
that vision, let's you know,what would it look like to
become the best in the world ifwe just get up every day and
think about that for 10 years?
What happens?
chris_1_12-19-2025_131141 (38:41):
I,
denis-o-shea_1_12-19-2025_12 (38:42):
we
chris_1_12-19-2025_1311 (38:42):
support that.
denis-o-shea_1_12-19-2025_ (38:42):
get.
chris_1_12-19-2025_131141 (38:43):
Some people call it law of
attraction.
Some people call it positivethinking, whatever you call it.
It does work.
I mean, I can speak
denis-o-shea_1_12-19-2025 (38:50):
yeah.
chris_1_12-19-2025_131141 (38:50):
that my whole life, everything well
in my life, other than being amatter of prayer and, my belief
in God.
but, you know, I also have avery positive attitude.
You know, I believe if someoneelse can do it, I can do it.
I mean.
denis-o-shea_1_12-19-2025 (39:02):
Yeah.
chris_1_12-19-2025_131141 (39:02):
if you have a position of,
pessimism, don't be surprisedwhen you're just not successful
in life.
'cause you won't be.
You have to be, we have to bewilling to learn.
You have to be open-minded, butyou have to be positive What a
great way to end thisconversation.
denis-o-shea_1_12-19-2025_1 (39:15):
and that's not my quote Chris.
I read it somewhere.
but I latched onto it
chris_1_12-19-2025_13114 (39:21):
That's right.
denis-o-shea_1_12-19-20 (39:21):
latched onto me,
chris_1_12-19-2025_1311 (39:23):
Whoever said it, you know,
denis-o-shea_1_12-19-2025_121 (39:24):
a wise man
chris_1_12-19-2025_13114 (39:25):
that's right.
denis-o-shea_1_12-19-202 (39:25):
woman.
chris_1_12-19-2025_131 (39:26):
probably from the stoics or something.
I see.
Marcus or, or, saying somethinglike that.
Dennis, I really appreciate yourtime.
I've enjoyed this conversation.
I've learned a lot.
please check the show notes andyou'll, and I'll have more
information there.
But, thanks again for makingtime for us.
denis-o-shea_1_12-19-2025 (39:41):
Thank you Chris.
I'm delighted to be part of yourcommunity.
chris_1_12-19-2025_131141 (39:44):
Thank you so much.
and thank you for listening tothis, episode of The Wireless
Way.
And as always, if, any of thisresonated, if it hit home, you
thought about a customer, youthought about a colleague, share
this episode with them.
go to the wireless way.net.
There's a contact us button ifyou like more information.
Of course there'll beinformation in the show notes
and links to, mobile mentor and,learn a little bit more about
(40:06):
Dennis, as well.
So we'll see you next time onthe Wireless Way.
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