IT Matters | Tech Solutions and Strategies for Every Industry

This episode of the IT Matters Podcast features a conversation between host Aaron Bock and guest Derek Jones, a longtime technology executive with experience leading IT teams for organizations of more than 350 people. Derek shares lessons from his career, shaped by his “offensive lineman mindset,” a philosophy rooted in team-first leadership. The discussion explores how IT leaders can stay relevant amid rapid technology change, especially the accelerating pressure around AI adoption.

Conversation Highlights:
0:00 Introducing Derek Jones 
[3:10] From Operations to IT Leadership 
[11:03] Leading Enterprise Transformations 
[18:46] Developing Service-Oriented IT Teams 
[40:57] Decisions IT Leaders May Regret

Notable Quotes:
"Especially in this remote world now, where we've got technology leaders everywhere, it's really hard. There's still a value of a handshake, there's still a value of walking that mile in another person's shoes." - Derek Jones [16:26]
"Invest in yourself, invest in your team, and be a team player, and you're gonna win half the battle there." - Derek Jones [45:38]

Connect with Derek Jones on LinkedIn.

Read the transcript: Episode 41

The IT Matters Podcast is about IT matters and matters pertaining to IT. It is produced by Opkalla, a technology advisory firm that helps their clients navigate the confusion in the technology marketplace and choose the solution that is right for their business.

Creators and Guests

AB
Host
Aaron Bock
KH
Host
Keith Hawkey

What is IT Matters | Tech Solutions and Strategies for Every Industry?

Welcome to the Opkalla IT Matters Podcast, where we discuss the important matters within IT as well as the importance of IT across different industries and responsibilities.

About Opkalla:
Opkalla helps their clients navigate the confusion in the technology marketplace and choose the technology solutions that are right for their business. They work alongside IT teams to design, procure, implement and support the most complex IT solutions without an agenda or technology bias. Opkalla was founded around the belief that IT professionals deserve better, and is guided by their core values: trust, transparency and speed. For more information, visit https://opkalla.com/ or follow them on LinkedIn. 

Aaron Bock: Welcome to the IT
Matters podcast, hosted by

Opkalla. We're an IT advisory
firm that makes technology easy

for your business. Our
vendor-neutral technology

advisors work directly with your
team to assess technology needs

and procure the best IT
solutions for your organization.

On this podcast, expect
high-level expertise from our

hosts, plus experience-driven
perspective from the leading

experts on topics like AI,
cybersecurity, industry-focused

IT solutions strategy, and more.
Now let's get into today's

discussion on what matters in
IT.

Welcome back to the IT Matters
podcast. It's nice to be back.

It's been a few months. I know
Keith, my co-host, has been

doing a lot of the episodes
recently, so it feels good to be

back. We're recording this on a
Friday in April here in

Charlotte. We have not had rain
in about three weeks, so

everything is just covered in
pollen, so hopefully where

you're at, you're getting a
little bit more rain, and so

it's not as dry out there, and
luckily I'm recording this

inside, or else I would be
sneezing my ass off. So I hope

that you guys have been doing
well again. Thank you for always

listening to the podcast,
supporting us on whichever

platform you listen. Make sure
to subscribe and leave us a

review. There's been a lot going
on in the world, obviously,

since the beginning of 2026 it
has been busy here at Opkalla.

We're working on a new product
that we're going to be launching

later this year for all of our
customers and folks that we

know. So, we're excited about
that. AI and everything going on

with AI right now is keeping us
busy, and I know a lot of you

busy, so we have a lot to talk
about there. And it's just been

generally busy with the
uncertainty and what's going on

the economy, so very happy to be
taking a break today to record

this episode with a friend and
someone here in Charlotte. So,

without further ado, I'm going
to introduce Derek Jones, who's

here with us today. Welcome,
Derek.

Derek Jones: Welcome. Thank you.

Aaron Bock: Very nice to have
you. So, Derek spent the last

two decades with SYNCREON and DP
World, and he's risen to the

Vice President, Head of
Technology for America's leading

a 350 person IT organization.
He's been in exec leadership

roles, supporting teams across
North and South America, Europe,

Middle East, and Asia, and large
Fortune 500 enterprise global

customers with third-party
logistics and port operations

recently served as executive
vice president of technology

Flow Control, which is a
private, private equity-backed

distribution company. And then
Derek started his career in

operations, and that foundation
still shapes how he leads today

with an offensive lineman
mindset, and he can share a

little bit more about that. It's
a team first grounded in

fundamentals and focused on
execution, while continually

pushing teams to innovate and
raise the bar. Derek and his

family relocated to Charlotte a
couple years ago from Ontario,

Canada, and we are happy to have
him. So, Derek, thanks for

joining the It Matters podcast.
I know I've been excited about

this. We had the pre-call, and
we talked a little bit about

your background, but why don't
you take the first couple

minutes to just share your
background, a little bit more

about yourself with the
listeners.

Derek Jones: Thanks, Aaron,
appreciate the invite, and

excited to be here. Yes, we
relocated into Charlotte a

couple years ago, but long
career so far focused really

around how can it be a service
partner to the business. I was

very fortunate when I started my
career. I came out of college

and started as a materials
analyst, really shaped how I

understand and how I support my
customer, because for the first

several years of my role, I was
the customer I was supporting,

being supported by technology, I
was having to deliver for our

customers or end customers, and
having to understand what it

means when systems are
inefficient, unavailable, or not

adding value, and how does that
translate back to the bottom

line, so it's really been great
for me. I've been very fortunate

to have opportunities to
continue my growth, and then how

do I pay that forward and
continue to develop people along

the way, while still continuing
to innovate and grow the

business? Right, that's
ultimately where the offensive

lineman mindset comes in. We are
one part of a big unit, and you

need to continuously adapt. It
is not always the sexy function

within an operating business,
but ultimately you got to try

and make sure and deliver value,
so that you can show where your

company continues to grow. So
very excited to be here and

share some insights.

Aaron Bock: So before we get
into more of your background, so

we've talked about the offensive
lineman mentality twice, so

maybe share where did you play
offensive linemen and how long

did you play.

Derek Jones: Yeah, so I played
football for 11 years from. From

high school through, and I
played four years in Windsor,

Ontario, Canadian football with
three downs, a wider field, a

bigger ball. It's a little bit
different, but played for what

was at the time the AKO for
Atman, is now Sinclair College,

and I was a center and a guard.
Again, I'm not the tallest. I

was six feet tall and 285 at the
time. You had to win every rep

and make sure that you were not
always going to have a perfect

technique. You're not always
going to have the perfect play

drawn up, but it's about
execution, blocking and tackling

wins football games, and you got
to be able to grind through in

23 years of working, I've missed
a day and a half because there's

no excuse, you have to get the
job done, no matter what.

Aaron Bock: An unsung hero on
the football field and an unsung

hero in companies, as you
mentioned, it before we leave

the football topic, what do you
think of NIL? In a couple

thoughts.

Derek Jones: Yeah, it's a great
opportunity for you to try and

focus on the positive. There's
been a lot of players that have

been only given opportunities at
a smaller school, and now that

there's better opportunities for
them to continue to shine

brighter. Cam Skattebo, a couple
years ago, was, you know,

started off at a junior college
or started off at a small

school, and was able to progress
his way. And again, that's that

doesn't mean that he had to turn
into a first round draft pick,

but he has his brand stock went
up because he had that exposure,

and he became an NFL player, and
we've seen a lot of that in the

last couple years, where it's
not just about the guy that was

a freshman making, you know,
however million dollars. How

about the University of Michigan
that just won the national

championship with a bunch of
transfers from, in many cases,

from smaller schools or had less
opportunity?

Aaron Bock: Yeah, it's a good
perspective, it's, it's

definitely changing the way the
sports and like the recruiting

works, but I do think it
provides a lot more opportunity

for those who are playing, and
then go back, so you know, you

said that you came out, you were
an operational role, and then

you, you know, obviously have
had a lot of success in it, what

drew you to the IT industry, and
being in it, if you will, from

what you started in.

Derek Jones: Yeah, so I went to
school for IT. I went to

Sinclair College, and that was
always.. I took apart my

family's computer when I was
seven, and gradually back in the

day that was always something
interesting, you could build and

create and come up with creative
solutions, and let technology be

an enabler. So that was always
the goal. But when I graduated

from school, I needed something,
and sometimes that's that's the

wherever you start doesn't have
to be where you finish. So

trying to get opportunity has
been a theme throughout my

career, is whether it's for
myself, but more importantly,

for my teams, like it starts
with opportunity and a leader

who believes in you, and
somebody that's going to give

you the chance to shine, and how
do you untap all those

potentials, so the intrigue and
continuing to evolve even across

my IT career, I didn't just
stick in one area. I've led

solutions teams for software,
I've led infrastructure teams.

It's always been around service
delivery back to our internal

customer or supporting external
customers. So, gaining that

perspective across the entire
field of IT has been invaluable

for me.

Aaron Bock: You went to school
for it, you know, not, not in

the last 10 years or whatever,
but you know, get you or you

were intentional about coming
into the IT industry. Do you

think that it's easier or harder
to get into it now? And kind of,

what do you, what would you say
to a recent graduate or a high

school student thinking about
it?

Derek Jones: So, depending on
the space, the challenge that I

have had this conversation with
some high school and recent

college graduates is you can't
expect to walk into the field

necessarily and jump straight
into this mature technology

role. You have to either have a
very technical skill set that

translates well direct in, for
example, the network

engineering, or in a very
technical space where you become

a technical expert, but more
often than not, especially if

you want to grow within the
business you're at, is

understanding the business, and
then how to apply technology

after that. So, there's very
much different tracks. I would

say, if you're going to be a
software developer and you want

to stay in that space, you know,
there's a very technical path to

go that route. If you want to be
a CIO. Or if you want to work in

a space where you're impacting
change and driving

transformation, it's less
important to have had a strictly

technical background. In fact,
that broader background where

you have a lot of different
experiences you can combine

together actually ends up
translating more value.

Aaron Bock: Yeah, and I think
that's true. I mean, I think it

depends on what you want to do.
If you want to be an IT leader,

the business, the broad
experience, managerial

experience, but if you want to
be a very detailed architect,

enterprise architect, network
architect, like that's a

different path. So, agree with
you. You talked about

transformation, we talked about
it in your opening, you just

mentioned it in the last
statement that you made. So,

curious, like, you've been a
part of large, you know, 350

person plus teams doing
enterprise transformations, and

so, you know, what's in it, I
guess, a what's experience

you've had that you can share
that that kind of shapes how you

think about it, leadership, and
just leadership in general from

those transformations?

Derek Jones: The number one
benefit, let's call our number

one intention coming out of a
transformation is being clear

about what's the direction, is
there is there enough

stakeholders that buy into the
message, what are you actually

trying to deliver, and whether
your organization's 50 people,

three 350 people in the IT
department. I've worked in

organizations that had 3000
people or 120,000 people having

a clear vision and intention on
what is the outcome that we're

expecting. What does good look
like at the end of this? And

then let's figure out together
and get the stakeholders bought

in on how to drive that buy-in.
If you can get people bought

into the intention and the end
result, your creative should be

coming out from that space and
getting people to contribute to

those opinions, pull in
information from various

sources, whether that's
experience, new technologies,

and innovations, and then
lessons learned. Right, we've a

lot of these experiences and
transformations will fail

because if we're not, if we're
keeping blinders on and we just

want to see what's in front of
us, you're not going to learn

the lessons of what went wrong.
So, continuing to adapt and

evolve, I think the biggest
thing I've had to learn from

this is it's not always about
the right technical solution. Is

the business ready for it? Is
there enough people bought in?

Is the investment time now, or
can this be phased in where

you're going to see the value?

Aaron Bock: and you mentioned
keeping up and evolving, so I

want to come back to what you
just said in a second, but just

what I mentioned in my opener,
everything's changing. I mean,

every week you read the news,
you read some article, and you

see all these new platforms out,
etc. and a lot of it's AI, but

how is an IT leader? Do you keep
up with the pace of change? And

then maybe the second part to
the question is, it's like, you

know, being focused on the
business and it, there's a

balance, but what happens to an
IT leader if they're not keeping

up and evolving with the pace of
change of technology? Like,

what's your take on it?

Derek Jones: Yeah, well, Well,
if you're not keeping up with

technology and evolving with
your business, you're soon not

going to be in it. The reality
is that any business and the

technology that's changed, even
in the last six months, with

capabilities that have come out
of whether it's AI or just

leveraging new opportunities to
connect products, that's frankly

the where, where I see the
biggest value is if you want to

try and drive true innovation,
trying to drive true change,

it's balancing what is the
capability now, what, how long

do I have to implement it? Can I
continue to iterate and grow

that with the new technologies
ahead? And to answer the

question of how do you stay up
to date, it's very easy to get

distracted every week. There's
going to be something new.

Trying to be balanced and
anchored into what is the

business trying to do? How can I
help drive technologies and

capabilities that support not
only the business as it is

today, but being a strategic
leader, thinking three years,

five years, and then beyond? How
can these technologies, even at

their nascent state, how can
they continue to grow and

support and add value to the
business, and it's working with

partners. Ultimately, it's part
of a team. Everyone's going to

have input, and if you can
present ideas and capabilities

and potentials, getting people
bought into the idea, and then

being comfortable with failing
fast, there are opportunities

out there that are not going to
turn out. But if you commit

yourself to irreversible
decisions, you're going to fail,

and you're not going to have the
opportunity to learn from those

lessons. So, it's making sure
there's balancing. Can you get

80% of the way there? Can you
leave standard 80 and then

variation for 20? If you spend a
lot of time focusing on the 5%

that isn't aligned, you're
likely going to lose the values.

Just try to stay practical as
well, without getting caught up

around the technology,

Aaron Bock: and you've talked a
few times about knowing the

business to be able to make
better technology decisions. So

I'm going to ask you kind of a
situational question, because

I'm sure this has happened,
right, but there are leaders,

and I've seen great leaders in
the IT space who encourage their

folks to go get involved, shadow
business users, shadow like, and

understand the business. But
let's just say that tomorrow

you're going into an enterprise
where you have a four 300 400

person IT team, and you start to
realize, like, hey, some of

these folks don't really
understand the business, and

they don't - it's not that they
don't want to - they just

haven't had the opportunity or
been encouraged to do that. What

are ways that you would try to
start getting those folks to

understand the business to be
able to make that better

decisions? And what are some
successful, like, suggestions

you would give to others that
have to do this.

Derek Jones: Yes, that's that's
a great question. And especially

in this remote world now, where
we've got technology leaders

everywhere, it's really hard.
There's still a value of a

handshake, there's still a value
of walking that mile in another

person's shoes. So, what I've
generally had to do when I've

had to adapt to the new
industries or into new

businesses that companies
acquired is go walk a mile, go

meet people where they're at.
You'd really love for them to

buy into your idea right from
the jump, but that's that's not

realistic. You need to get that
cultural buy-in on where you

want to operate, how you want
the technology to evolve, and

meet people where they're at
now. And how can you provide

some iterative solutions to help
not only gain trust but start to

understand their perspective?
What problems are you dealing

with every day? You can't just
throw money at every problem.

How can we make the solution a
little easier for you to do your

job and deliver value back to
your customer? How can I help,

whether it's an operational
person or the marketing team or

the sales organization? A lot of
times it's just listening and

understanding what problem are
we solving, and then hey, we've

got some experienced people that
can help deliver that value, is

it quality of data, is it
processes that are more

efficient. How can we help again
get let's get 80% value started,

and the rest will continue to
improve and iterate as you get

more experience, and again, if
you're going to only be solving

one problem every day, that's
that's still improvements, 1%

better every day, at least.

Aaron Bock: Even more
specifically than that, you

know. So, say I'm a, I'm a level
two help desk, or I'm some lower

level role in an IT
organization, and you

acknowledge and understand as a
new leader, hey, these folks

don't really understand the
business in order to be

successful. Do you like, have
you set up programs, or have you

seen any programs where it's,
it's successful helping that

level of a person get more
integrated with the business? Is

it, is it, you know, you said
walking a mile in someone's

shoes, is it shadowing, is it
peer group meetings, or, you

know, how do you, how do you
encourage that understanding and

knowledge of the business?

Derek Jones: So it's a bit of
both. When I've worked in the,

in the logistics space, where
we've had, you know, the

customers on the ground at a
warehouse or in an assembly

plant, and they need to see
what's happening with their

eyes, ears, and understand.
Let's go pick parts for a little

bit. Let's go understand the
perspective from the other side.

What happens when they say
something doesn't work? You're

not always going to get a
perfect answer in the way you're

expecting it. So, learning how
to decipher what did they mean

by that. The screen did this,
especially at a level two role,

best case scenario for us was
always finding somebody that was

in level one. Let's progress
them to level two, and then

continue beyond. But having
somebody that has that customer

service focus that can read
between the lines at times, and

then validate. Right, we don't
want to just assume that you

have the answer to every
question, check with the user,

verify, and then if you need to
be physically present somewhere,

if you can't, a picture, a video
says 1000 words, and be

empathetic to the person on the
other end of the line, they have

an emergency, they can't do
their job, even something is.

Simple, as my keyboard doesn't
work, seems trivial, but when

somebody can't work, it's a
major issue. So, something to

the level of understanding how
the service organization is

structured. If you're going to
have that hub and spoke model,

everybody within the link chain
together have to understand the

dependency of each other, but
still remain focused on who is

who is my customer. What are
they trying to do, and how can I

help them?

Aaron Bock: Yeah, you've had a
lot of success over the years,

and so you've built teams,
you've come in and been a part

of teams that were already
built, and then you're changing

them. Let's go, let's just say,
compared to 10, five or 10 years

ago, say you're coming in as the
leader or a leader or top

leader, etc. in it, and you're
building a team in the

enterprise, or you know,
mid-market, etc. How do you

build an IT team in a service
organization today differently

than you did five or 10 years
ago? What's what's changed the

most in from your perspective,
where you, where would you coach

others to say, like, this is how
it's different than it used to

be?

Derek Jones: It's a great
question. Some of the challenge

right now is just because of the
velocity of change, having

people that have the capability
of learning quickly. The old

days of I went to school for
this, and I'm going to target to

do this career for the next 40
years. It's, it's rapidly

evolving, because some of those
roles may not exist. So, if you

can find someone that has
multiple skills, you know, we

call, you know, multiple sport
athletes, they can do a lot of

different things in the
technical technology space. You

want people that have multiple
skill sets, and then

complementing them with
technical expertise, right? So,

you can't just have all
technical experts, you can't

just have all operational-minded
people. There really needs to be

that delicate balance, and then
supplementing that with

technology, whereas years ago it
was finding someone that had an

x number of years experience in
a certain product. Can they

integrate that product across
your existing stack? You can't

rewrite every to every product
that comes out. You can't just

rip and replace. So, how do you
continue to be more multiple,

evolving with what you have, and
then evolving the next

technology spend that you're
going to bring in, let the data

work together, let the
integrations work together to

really get the best value. So
the people side of things is

important, but the ability to
learn first.

Aaron Bock: Yeah, I this, we
didn't talk about this in the

pre-call, but something I've
heard from a lot of IT leaders

over the last couple years is
with the with the rise of AI

tools for resume building and
you know certifications, etc.

Red, when they have a position
open, let's say a more technical

position they need to fill, the
resume pool is so much harder to

go through and really figure
out, does this person have the

experience, or are they using
tools that make them look like

they have the experience, and so
to your point, my opinion from

that, and my, the only, the only
thing that you can do, I think,

is really try to assess the
person in an interview and

assess, do they have the chops
to understand the business? Are

they technical? Do they actually
know how to do the things

they're saying they're doing?
And then do they kind of have it

and want it, and will will work
as a team. So that's from my

perspective. What I see you
changing gears a little bit, but

you just talked about it. We
were saying how things are

moving fast, things are
changing, everything's evolving

in technology. We talked about
this on the pre call a lot, you

know. It leaders are being
forced to make decisions every

day. They have to make more
decisions now than they did

theoretically 10 years ago,
because more things rely on it,

and you can define that however
you want. But how, as a leader,

how has your decision making
changed, knowing that things are

changing faster, and so, like,
traditional frameworks may go

out the window. What are you
doing differently when you're

making decisions, whether it's
on a tech, a person, an

offering, a project, etc.

Derek Jones: So I think that
where we as leaders have to

remain grounded is not to get
too caught up in what the tech

looks like, how do we make sure
that there's value at what

again, what good looks like
starts that process, and what's

the cost of that, but again
every organization should have a

clear understanding of what
their strategy is, and then how

does this decision impact that
strategy? Is this something I've

typically tried to start with?
What's the organizational

strategy? Do we have the people
to execute it? Do we have. A

process that we can support
those people and that strategy,

and where does the technology
come in after that? Because the

reality is there's always going
to be another option. There's so

many different capabilities out
there, whether it's a product

offering or just a methodology
of doing something, and for the

most part it's going to be
similar, right, product to

product, especially in the large
enterprise space. There's a lot

of capabilities that that
they're all going to have, but

which one fits your
organizational strategy? Which

one has the ability to be
adaptable, so that if you do

change something within your
organizational stack, you're not

having to rip and replace, so
doing that extra bit of

research, having the support
from your team, so if the people

that are in your team buy into
whatever it is you're, and

hopefully the suggestions coming
from them, ultimately I want to

be able to say yes or no at the
end, because they've bought into

the strategy and they understand
business needs and they're

bringing together a suggestion,
and that's going to have some

optionality too. It can't be
ever just this is the only

solution, we have to bypass
everything and just go buy it.

What's option A, B, and C?

Aaron Bock: Yeah, well, on that
specifically, like you said,

fail fast earlier, and give you
know, give your teams the

ability to make decisions, and
then you said optionality.

There's there could be
optionality. How do you, as a

leader, empower your team to do
that without creating chaos?

Derek Jones: I think the best
thing, the most important thing

is, do we have a clear
understanding of what was the

objective right at the beginning
of that process, we should,

there should be a clear
alignment, whether that's in a

documented write-up or is its
concepts again. What, what's the

customer asking for? What's the
deliverable look like? And then

having the ability to consider
what those options are, and

which one is the best fit. The
old analogy of, you know, you

get, you get speed, quality, and
price pick too. You don't always

get to have that choice as
easily as you would like, and

it's always going to be a push
pull with the business. So,

while you may have the best
technical decision, it doesn't

fit for the timeline. So, can
your teams and can your

stakeholders, especially, do
they understand where that push

pull needs to take place? Is
there a compromise available

that's the best fit in the short
term? And then can that

optionality kick in later on,
where you are going to grow it.

You may have a critical business
need right now, and you've got

to make the imperfect decision,
but it's the best decision for

what the business needed that
moment. It's a lot more

difficult if that's a decision
that can't be either unlocked or

changed out later on. You're
making a long-term decision

right away, so you'd rather have
something with some options and

be able to at least evolve with
the business, because it's never

a linear path.

Aaron Bock: So we talked about
this, but you're kind of hitting

it, decision making, you may
have to just make decisions and

know where your optionality is
in the future. Right now, you

know, I've mentioned it in my
opening, and just with the pace

of AI, there's a lot of things
changing, and I think a lot of

people feel pressure, and so
from your perspective, like I

see leaders being pressured into
making decisions around AI

because of a board meeting or
conference or whatever, and so

let's talk about AI, maybe a
little bit from your perspective

as an enterprise, like how how
real is the pressure right now

for an IT leader to select AI,
implement AI. Do you think that

it's a real, like, hey, we got
to do this now, or do you think

it's being more of a
manufactured sense of urgency

that's happening?

Derek Jones: It's certainly
real, depending on the type of

business. If you're in a product
space where you're delivering

software or you're selling
something that's

customer-facing, having AI
capabilities is something that

could very easily improve the
product that the customer wants

to buy. When you look at it
from, let's say, the operational

side of things, there are
capabilities that were not there

in the past, the legacy systems
that required a lot of hand

holding and touching and driving
these things forward. The

evolution of AI has allowed some
really incredible things, but

they only will get unlocked when
the people know how to use it.

That there is something
distinctly yours that you can

add value back in. Let me see if
I can rephrase that differently.

Where I think there's a desire
across some of the noise around

AI is that there's got to be an
expectation of immediate return,

and that's not always realistic.
I think understanding how can

you deliver value back to
individuals. Tools, let's call

it a productivity enhancement,
something as simple as, you

know, the co-pilots of the
world, where you're improving

meeting notes and you're
improving summarizing data,

that's great, but that's not the
exclusive piece of AI. It also

doesn't mean that you're
replacing people and replacing

their jobs. You, we need to
augment capabilities and raise

the floor, and there are some
real capabilities that AI,

whether it's in the generative
space, but for in the industry,

especially the power of the
data. If you don't have a good

data governance strategy,
throwing AI at it right now is

not going to be helping you very
much. Now, AI can help cleanse

some of the data, but you need
to have a very structured way of

making sure you have a clean
source data. The genealogy,

where'd that come from? What
does it mean, and how does it

match up as you start
integrating other data sources?

So, there are tremendous
capabilities, but having that

governance structure, having
something that can scale

properly, and you don't need a
one size fits all solution.

There's different horses for
courses. I had a boss used to

tell me that there's a way for
us to try and apply a copilot

and apply a clod. The technology
team may have a different

internal usage than your
marketing department versus the

HR team versus someone that's
running a warehouse, they're all

have usage cases, and making
sure you don't try and one size

fits all all of those different
stakeholders.

Aaron Bock: There's horses for
courses. I love that. I have

never heard that, but I am going
to start using that. I agree

with what you said. I think you
have to look at each thing

individually. I think the tough
thing is that the, you know, and

I shared this with you about
some of the things we're doing.

My pressure as a leader is, are
we making the right decision

because it's changing so fast,
and so you commit to something

that's going to change in three
months, have you already made

the wrong decision? So, curious,
a couple questions on that for

you, because you know an
enterprise or a large

organization can't change as
fast as a small organization. So

take an enterprise organization
that's looking to implement AR

AI, or figuring out how do we
use it, how do you help the

business understand whether they
should even invest in an AI

investment, or like, what's your
methodology for helping a

business leader understand
what's possible? Where, hey,

this is a waste of time.

Derek Jones: Yeah, the reality
is it's still going to start

back at what problem are we
solving? Right, you can throw

money at the problem, and hope
that you're going to get a sexy

new overlay, and hopefully
people are going to buy into it,

but if they don't understand
where's the value, and that can

be something they don't realize
yet, right? The you need to be

able to show them the art of the
possible, and that will start

spurring some of that innovation
on their side, but there are I

think one of the challenges,
especially across enterprise, is

how do you, where do you get
started, and if your first

project that you want to drive
with AI is this gigantic

transformational change, you're
probably going to struggle,

unless you're bringing in a
really good partner, and you

have a really good business
case, and you have some

practical usage cases where
you're going to start getting

some gains quickly. You have to
have both start identifying

through working with
stakeholders where are the pain

points in your organization.
What are some of the

capabilities that AI has done so
far? And then where do we see,

as it leaders, we should be able
to forecast a little bit where

those benefits are trending, but
knowing your business first and

foremost, trying to apply a
technology that doesn't fit is

going to end up wasting
resources, and more importantly,

wasting time, and you can't get
that back, you've got people

every organization is struggling
to do more with less, so if we

can figure out how to augment
the people we have and get more

calories out of what's of that
time and gain and drive

innovation faster, that ends up
again that continued evolution

where we're going to gain more,
that doesn't mean that we can't

have large scale projects. I
believe in driving the

opportunity for scale, and you
need to have interconnecting

pieces. All of your platforms
need to be able to talk with

each other, and if you have
multiple data sets, you're going

to have fragmentation. AI is not
necessarily going to help that.

It needs to start from a clean
base, and that may take some

long-term investment for you to
make that initial investment,

and clean up your data, clean up
your data sources, and

consolidate, but if you don't
have a clear end goal in mind,

you may end up wasting a lot of
time. Time, and money, and not

be, not be around

Aaron Bock: You touched on a
very debated point right now

about fragmentation. I want to
double click on so some people,

there's two sides. Some people
feel we're going to move to

consolidated platform, and
you're going to have AI agents

sit on top of it, and sort of
everything will consolidate, and

you'll have agents that are
running off it. Some people feel

no, you can leave your data in
segmented, fragmented places,

and then the AI agents can be
the connector. Where do you, in

an especially in enterprise, it
like, do you feel that it's tech

is trending towards more
platform-based solutions that

you can then kind of do the
former on, or do you feel like

it's trending towards best of
breed single function systems

and tools that you would then
use AI across like a layer in

between? How do you see it if
you had to guess, or what you

know?

Derek Jones: Yeah, well, I think
from a product perspective, a

lot of the large organizations
want to have integrated

platforms, and that they can
sell, you know, without specific

names. You want to be able to
have that vertical integration.

If you're a product company,
again, How can we get more piece

of the more share of that wallet
from a from a consumer side or

from the business side of
things, where we're buying that

capability and learning and
leveraging it for our business,

the reality is you're always
going to have tech debt as soon

as you, whether you're in an
acquisition side of things or

you're trying to grow your
business, organic growth is only

going to go so far, if you've
got to do some inorganic growth,

you're going to have integral
legacy platforms that some

pieces may be non-negotiable. It
security is an example. You need

to protect your perimeter.
You've got to make sure that you

don't have that leakage. You've
got to make sure that you're

securing any entry points and
protect, protect your core

assets, but you're not
necessarily going to be able to

right away integrate ERPs and
other systems. How can you

leverage some of the AI
capabilities and data

capabilities where you're still
pulling that data in, operating

it through that cleanse,
integrating it into the overall

overlay of your organization,
right? So, creating a platform

that doesn't necessarily need
perfect to operate again. Do you

have a good intention around
what your AI is producing? Do

you have data that can help,
good data that's going to feed

into it, that's going to make it
more valuable? So, I would guess

I would expect that long term
it's always going to be focused

on again around that
optionality. If you don't have a

system that can adapt to where
your business is going, and I

expect AI is going to continue
to drive that, both on the

product side and on the business
too. But you've got to be able

to deliver value.

Aaron Bock: One other question
on that, because you said you

know how AI is going to affect
business, etc. How do you see

like product teams, network
teams, individual teams within

IT organizations? How do you see
that changing over time? Like,

do you do you think we're going
to be talking to a team with an

AI coworker? Like, how do you
see the next five to 10 years

play out?

Derek Jones: Yeah, I mean,
that's that's what we're seeing

right now, where again the life
of the coder is going to evolve.

The reality is that some of
these AI platforms can write

really sophisticated code in a
short amount of time, and if

it's going to write really good
code, then you're not going to

need as much QA. I would hope
that you know if your

organization is going to
continue to scale upwards, you

can automate some of the testing
on the network side of things,

threats identification,
leveraging changes and

deployments across your
ecosystem, those are all things

where you can add a layer of
automation, but as well some of

that intelligent automation to
secure your business. Again, do

more with less. I would expect
the IT person of the future

needs to know how to leverage AI
as a capability tool set, but

it's not I, in my view, you, you
cannot also lose that personal

touch, that understanding of the
business, because at some point

you've got to start somewhere if
you only want to have 20 year

experienced developers and then
a bunch of, you know, AI agents

that sit over top when that
person retires, you're going to

be stuck. So, you've got to
still continue to have the

correct balance of talent,
people power, understanding the

business, and, and then, as
well, you're not going to. Able

to have as many people as you
want, is AI or automation going

to help supplement? Does it
using consultancy or contractor

resources that can help you know
focus on when you have a burst

capacity or you have a specific
knowledge that you don't have in

your team? That's where using a
partner like Opkalla, like

others who can help fill the gap
for you?

Aaron Bock: Yeah, we got to wrap
up here. So, two final

questions, because I think this
has been great, and I think

you've shared a lot of
perspective for anyone

listening. Encourage you to
connect with Derek, just because

he's got the experience. But two
final questions: What's a

decision that UC IT leaders
having to make, or they're going

to be making in the next couple
- we'll call it next year - that

you think they may regret, or
regret not making. What's a

decision that you see that is
going to be a tough one for a

lot of folks?

Derek Jones: Yeah, if you
haven't already made the

investment into the security
side, you're already behind. It

is clear that, as we're seeing
the evolution across these

agents, that there's going to be
a shift very quickly on moving

to more automated agent type
processing, and how those

hardware platforms interface
with AI at the end of the day.

If you're supporting a business,
understanding what they're

trying to do, making sure that
you're staying ahead of the game

with those core principles in
place, good data, good

processes, good people. If you
try and make a decision on

selecting a platform and doing
an all-in-one, whoever your

investment platform, or whoever
your platform you choose is, you

better hope it's one that can
stay involved with the business

too. I think trying to one size
fit all everything ends up being

a challenge, depending on the
scale of the business. In a

smaller business, it makes a lot
of sense, because you may not

have the capability or the
people power to have best in

breed solutions for everything,
but realizing where's your

business headed. What's your
organizational strategy, and do

you have partners along the way?
Invest in those principles and

understand where's the value
going to be. Where's your

organization heading? So core
principles, security, data

governance, get good teams that
that learn that learn quickly

and fail fast, making sure that
you're not over investing into

one platform, you know, even
even storage solutions, a capex

investments going to be a
challenge, knowing where do you

want to invest in something that
has a lifespan, or if you've got

a smaller business, can you
leverage some of these shared

services, or leveraging cloud
wherever it can to help evolve

your business, but modernizing
your stack, because there are a

lot of legacy platforms out
there right now that are going

to quickly start to show their
age when there isn't anyone

supporting them or there's no
platforms that can integrate

with them, so being able to
really have an eye on where's

the future heading and do your
platforms support it and how to

integrate with what's coming.

Aaron Bock: Yeah, I agree with
that. You kind of answered this

already throughout the podcast,
but my last question for you,

Derek, because this has been
great, is what's a piece of

advice you would give someone
younger in their career, or

switching careers, or in IT, and
trying to figure out if they

want to be an IT leader. From
your experience that you've had

over the years, what's a piece
of advice you'd leave for the

listeners.

Derek Jones: I I would, I mean,
if there's an understanding of

where you want to go, I mean,
there's certainly some

industries right now that seem
like they're going to be more

prosperous in the short term,
but just going back to what we

talked about in the beginning.
Ultimately, any individual

person has got to be able to
outwork and set the bar high. If

you don't understand how hard
you have to work to be

successful nowadays, focus on
that. Be the best at your

current job, where there's no
one else that can question where

you're at. If you're at the
management layer, we had this. I

had this conversation with
someone the other day. You're

not always going to get promoted
as quickly as you think you

should. How can you be a
solutions-oriented person and

figure out where can you add
value? Volunteer to do that next

thing. Think whether you're a
young person in the technology

space or an experienced leader,
I still throw my hand up

constantly, trying to offer,
where can I help, what can I do,

where can I learn more, where
can I apply my knowledge, and

where can I pick something up
that otherwise wouldn't have,

wouldn't have seen, so just that
eagerness and that willingness

to do more than other people,
right. You've got to be able to

work and grind your way to
success sometimes. So, no matter

what, it's not always about
being an expert in the specific

tech, but how can you apply it?
So, invest in yourself, invest

in your team, and be a team
player, and you're gonna win

half the battle there.

Aaron Bock: Yeah, I think it's a
great, great lead behind. And if

you didn't learn anything from
Derek on this, connect with him,

because he's a wealth of
knowledge. I learned horses for

courses today, so love, love
that quote. But Derek, thank you

for joining the It Matters
podcast, and for sharing with

us, we always appreciate love
learning from folks like you.

So, thank you for being on. For
those listeners at home, thank

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