The Business Leadership Podcast

You are listening to the Business
Leadership Podcast with Edwin.

Edwin: Good morning, good
afternoon, good evening.

My name's Edwin Frondozo.

I'm the host of the Business
Leadership Podcast, and today we're

recording live at Web Summit Vancouver
2025, where we're exploring how

today's leader shape the future.

Not just through strategy,
but through story.

We believe that a strong point of
view is what inspires communities,

builds movements and cuts through
the noise in uncertain times.

So let's, let's dive
into this conversation.

Today's guest is transforming how
legal work gets done by moving the

entire profession into the future.

Jack Newton is, is the founder and CEO
of Clio, the trailblazing company that

pioneered cloud-based legal technology
and has become the global leader in

client-centered legal practice management.

Under Jack's leadership, Cleo's not
only helping thousands of law firms

run smarter, more efficient, it's
also making legal services more

accessible and equatable for everyone.

Jack is the author of the Client-Centered
Law Firm, the number one bestseller

that's helping lawyers thrive
in an experience-driven world.

And the host of Daily Matters, a
podcast exploring the future of law.

Through conversations with legal
leaders and change makers, he's

been recognized with some of the
highest honors in the business world.

From EYs Entrepreneur of the Year to
Canada's most admired, CEO, and Goldman

Sachs Builder and Innovators, his
company, Cleo, has been celebrated as one

of the Canada's best managed companies
in a tech sector anchor success story.

Welcome to the Business
Leadership Podcast, Jack.

Jack: Thanks for having me.

Oh,

Edwin: thanks for having me.

This is, uh, true story though.

We're, we're, we're sharing a mic here.

So Jack is, uh, playing nice with us
and, uh, it's actually, uh, we're sitting

here in Web Summit Vancouver, first time.

It's been here.

Jack, I just want to just get your
thoughts and insights from being from

Vancouver, Cleo Focus and Gen Vancouver.

What does this mean you personally and
and to the ecosystem and the community?

Jack: Well, look, it's just
phenomenal having web summit,

uh, here in our backyard.

Our vision 17 years ago when we
founded Clio in Vancouver is that

we could help put Vancouver on the
map and, and help build Vancouver

into one of the, the great.

Tech hubs in North America.

And I, I feel really, uh, proud
and excited to see Web Summit,

uh, coming to, to Vancouver.

Uh, my first web summit was going
to Dublin in 2014, and, uh, at that

conference we actually announced that the
fact we were opening our Dublin office and

expanding into emea, uh, 11 years ago now.

So, uh.

11 short years later to be on stage at Web
Summit, uh, delivering a, a keynote on the

main stage to have that web summit hosted
in our own backyard here in Vancouver.

I don't think it was a, a future
either myself or my co-founder

Ryan would've, uh, imagined in,
in our wildest dreams in, in 2014.

So, really cool, really invigorating
and really reinforcing, I think for.

Uh, the Vancouver tech ecosystem to,
to have web Summit here this week.

Edwin: Yeah, and I, I, I'm super
excited and, uh, I mean, I mentioned

this before, we recorded earlier with
Jack 'cause it's just, it's just, I've

been part of the startup ecosystem
as well, globally working, I mean,

nationally and just having the ability
to not only showcase, you know.

Vancouver is the ecosystem and really
celebrate those that are coming out

of here like yourself, Jack and Cleo.

So, so this is great.

So just before we really dive into,
you know, the purpose of this, I'd

love it if you just, just for those
who may never have heard of you

for, you know, the, the 10, 10% of
people haven't heard of you yet.

Um, tell us about Cleo, the problem
that you are solving in the legal

practice, management and technology.

Sure.

So

Jack: Clio is vertical software
as a service for lawyers.

Or vertical SaaS as it's
more affectionately known.

And we, we started out in 2008, uh, before
vertical SaaS really existed as a a term.

But what we saw back then was the
opportunity to go after, uh, rather

than a horizontal approach of tackling,
you know, trying to be all things to

all people with a software application,
getting really tailored and trying to

solve the needs of a specific industry.

And so we.

Uh, me and my co-founder, Ryan
Goro quickly honed in on legal

as, as a industry that we felt
was ripe for transformation.

And in particular, the solo and small
firms segment of the legal market, which

is actually a huge portion of the market.

80% of lawyers practice in
firms of 10 lawyers or less.

50% of all lawyers practices solos.

So it's a, a much more SMB market
than most people appreciate,

and we felt like the cloud was a
uniquely good fit for that market.

So back in 2008, we rolled up our
sleeves and started building the first

cloud-based solution for lawyers.

Launched it later that year and, uh, have
seen a huge amount of success in adoption

over the course of the last 17 years.

And it wasn't, it's
certainly been non-linear.

You know, there's a lot of
education that had to be done.

Uh, back in 2008.

We had a lot of people tell us lawyers
will never store their data in the cloud.

You guys are crazy.

We had lawyers tell us we were, uh.

Irresponsible and encouraging
malpractice to telling lawyers they

should store their data in the cloud.

But we firmly believed back then, and
I think what we saw, you know, as the

future really clearly was everything
is gonna be in the cloud and cut to.

17 years later, 2025.

Clio is 1500 people worldwide.

We're one of the most successful
vertical SaaS companies in the world.

We're over $300 million of annual
recurring revenue, uh, growing quickly,

growing profitably, and uh, onto.

Our next chapter of growth and expansion,
which is oriented, uh, in, in continuing

to both bring cloud technology to
lawyers, but importantly layering AI on

top of that cloud technology and finding
ways of, uh, really unlocking the, the

broader opportunity for, for lawyers
to amplify their impact through ai.

Edwin: Yeah, it, it's been
an amazing journey, Jack.

I, I, I'm a tech entrepreneur
as well, and I, I recognize.

What Clea was doing early, 'cause
I was in the telco space and I,

and it was just so fascinating for
me to see how you built out this

category and really like just went.

Strong on it.

And it was, it was very inspirational
and it, and it's a lot of like

inspiration what we, Paul and I do to
see founders that you who did that.

So I'm curious at the time, and I
know, I know you kind of talked about

a bit, but you know, what was the
unique point of view between you and

the co-founder, you know, that really
thought about, you know, you the one

gonna be solved to solve that problem?

Jack: Well, what we saw really clearly in
2008 was the, i, the, the fact that the

cloud was gonna transform every industry.

And I, I don't think you
necessarily needed to be.

Super prescient to, to
underwrite that bet.

You know, 2008 salesforce.com

was a few years into its growth journey.

We had applications like 37 Signals,
and Basecamp starting to see a lot of

success and we were inspired by this,
this nascent cloud computing industry.

And, and again, I don't even think we
had the term cloud computing to refer

to back in, in oh eight we talked
about web applications and and so on.

But what was really obvious to me
was this is going to be the, the new

dominant form of computing and that.

Every on-premise application was
going to be disrupted by cloud.

So that's what Ryan and I had early
conviction on, and I describe us as

being two hammers looking for a nail.

Back in 2008 where we were hunting
around, this was even 2007, really

hunting around for which industry we
felt would be ripe before transformation.

Uh, and, and again.

Ryan was the IT manager at a, a large
law firm in Canada called Gowings.

And he, he saw all the inefficiency of,
of the on-premise legal tools that the

lawyers that Gowings were using or maybe
better put, weren't using because they

were so hard to use, so inaccessible,
uh, and, and often, you know, not much

more than a, a thin layer of lipstick
on top of a, a database backend.

So we thought we can do better than
this from a user experience perspective.

And that's where the light bulb
moment for, for Clio came from.

And I think what we had.

Deep conviction on in, in 2008 is.

The cloud is going to be the dominant
form of computing for the next several

decades, and legal will eventually
get there and maybe if we're lucky,

we can usher legal into that era
and and be the leader in that space.

And thankfully we got that bet, right?

But we certainly had a lot of
investors tell us we're wrong.

We had a lot of customers tell us, or
prospective customers tell us we're wrong.

But I think that's one of the hallmarks
of a great idea, is you need to have some.

Some folks telling you you're crazy,
because if you're not hearing that,

at least from some people, uh,
it's, it's probably an idea that

somebody else is already executing
because it's, it's too obvious.

So, Jacqueline, what, what about you
made you stick with a crazy idea?

Um, uh.

I've always been entrepreneurial.

I, I've always, you know, back
to my childhood, I was building

computers and selling computers
when I was, you know, 15 years old.

Uh, back, back before the, the
Dells of the world existed.

Uh, I, I ran a.

Snow shoveling business in Edmonton
with my, uh, with my brothers.

Uh, I, uh, had an idea for like a
precursor almost to, to Amazon for

food service delivery to remote
communities in Northern Canada.

So I've just always been somebody that's,
you know, turning over business ideas in,

in my head and trying to find one that.

Uh, that I can really put my weight behind
and that ended up being, being Cleo where,

you know, I, I, I feel like, uh, it's been
a super fun journey and even 17 years,

it, it's obviously a very long time.

I feel like in a lot of ways
Cleo's become my, my life's work,

but it's, it's a new challenge.

Every, every quarter,
every quarter I'm running.

The biggest company I've ever run.

Every quarter I am, you know, running
a bigger team than I've, I've ever run.

I'm tackling a new revenue
challenge that I've never challenge.

I've, I've never experienced.

And, and the technology landscape is
changing where I feel like we're, we're

back at kind of day one with AI and
needing to reinvent ourselves as a company

and to invent on behalf of our customers.

So, you know, I would say I'm,
uh, I'm very tenacious, uh, and.

Ambitious and, uh, love big challenges.

And, and that's exactly what the legal
opportunity has presented me with

for, for the last almost 20 years now.

Paul: And, and so now, um, with, um,
now investing in companies at this

pivotal time where, you know, it's
happening all over again, um, what unique

perspective do you think that your past
17 years provides to the companies you.

Jack: Well, well, one is I, I, I do
invest in a number of, of legal tech

companies and I'm, uh, I've, I've got a,
a unique and deep perspective on all the

opportunity that exists in, in legal.

So it's very easy for me to, to
look at a, a startup and, and

see are they running against an
opportunity that's meaningful and.

One I want to underwrite.

Uh, I also am trying to, uh,
really support a number of diverse

founders in my investments as well.

So both visible minorities and women
and underrepresented folks in the

startup ecosystem, and wanna try to
find a way of paying it forward and,

and making, you know, it is a very
male dominated, uh, uh, and white

male dominated startup ecosystem.

More diverse than it's been historically.

Uh, so I'm, I'm just trying to.

Pay it forward and, and help support,
uh, early founders that I like, that

I believe are tenacious and ambitious
and, and can stick with an idea.

And, and again, I, I know
some of those startups will.

We'll fail and some of them will thrive.

And for me it's a lot less about trying
to generate a, a financial return and

more about trying to put my weight behind
somebody that, uh, I believe in and

doing my best to set them up for success.

Paul: And at this time with, uh, with
how AI is transforming businesses and,

um, you know, how you came in when cloud
was transforming 'em, are, do you, do

you see any sort of, uh, similarities
or patterns that you can apply to.

Jack: Oh, I mean, absolutely.

And you know, as, as Samuel Clemens said,
I, one of my favorite quotes is, history

doesn't repeat itself, but it does rhyme.

And I, I think what we see with the
AI wave is very reminiscent of what

we saw with the, the cloud wave in
the early two thousands with the

mobile wave we saw in the early 2010s.

And, uh, if anything, I,
I think the AI wave is.

Deeply more transformative than what
we saw with the cloud and with mobile.

Uh, and it's, it's reshaping the world
of work in a really profound way.

And I, I think, you know, both
the stakes and the opportunity

are higher than they've ever been.

And in the same way we talked about
cloud first or mobile first, uh, over the

course of the last 20 years, I think any
startup pitch, any, even internally at

Clio, any product discussion we're having.

You know, my question is, where's ai?

AI's gotta be the first word
out of your, your mouth.

The first sense of your product
pitch is how you're weaving

AI into a product capability.

Or, you know, in the keynote I
just gave here at Web Summit,

I talked about Sarah Tves.

Work or her blog post talking about the
idea that you, you need to be selling,

uh, not software, but selling work.

How can you actually be helping automate,
uh, entire roles in companies or how can

you be, uh, unpacking what multiple people
do at, at a law firm or another type of

organization and automate that through
AI or at, at a minimum, dramatically

amplify the, the amount of work somebody's
able to do by leveraging AI into that.

So it's a very exciting
opportunity and for me.

What makes it an exciting and
somewhat ter terrifying opportunities?

Just how fast things are changing.

You know, I feel like the cloud and
mobile, you had breakthroughs like

AWS, you had breakthroughs like
the iPhone, but the way the story

progressed from there was pretty linear.

And at some point you get the iPhone 10
and slightly better than the iPhone nine.

And, but, but with the pace
of change we're seeing in.

Ai, I think even for us that consider
ourselves technologists, it's, it's

shocking, uh, and very hard to keep
up with the pace of change and the

capabilities and, and so what I would
say is, is again, exciting and kind of

terrifying is I feel like the fog of
war almost around how AI is gonna evolve

and how it's gonna impact industries
is, is much harder to penetrate than.

The cloud or mobile.

Again, I, I think if you're a
technologist and you saw the

breakthroughs with the cloud or you
saw the breakthroughs with the mobile,

you, you could see where things would
be in five to 10 years pretty easily.

I don't think anybody, I don't
think anybody including Sam Altman,

uh, or people that are closest to
building this foundational models

can say with any level of conviction.

Where we're gonna be in five
years and certainly not 10 years.

So it's, it's a, it's
interesting time to be alive.

It's an interesting time to be an
entrepreneur and it's, it's, it's, uh,

there's a ton of opportunity and a ton of
disruption happening all at the same time.

Edwin: Yeah.

You, you, you know, what came to mind
as, as you were speaking, and I just,

I'm just curious, you know, where we are.

Um.

With this inflection point with ai, AI
technologies and this being, you know,

speaking about business leadership, I
just want to get your thoughts or your

insights or what's changing as you, as the
leader with, when you're thinking about

ai, and not only for how you're doing it
for your customers, also the philosophy

that's happening internally, like into
your resource, into, into your workforce.

Right?

Yep.

Yeah.

Jack: You know, really the same thing in
the same way that we need to be thinking.

From first principles, how, how do
we reinvent our product and rethink

our, our product for our customers?

Uh, we've been encouraging every
person at Clio to think about

how do they reimagine their role?

How do they reimagine the way their
department works, uh, with, with

AI and leveraging AI to become.

Uh, dramatically more efficient
than they've, they've been in the

past with our engineering team, for
example, they're adopting cursor.

Mm-hmm.

And, and seeing just dramatic
upticks in their productivity

and efficiency, and it's amazing.

Amazing because you see.

Teams that were maybe skeptical about
AI two years ago or even a year ago,

saying, okay, it, it, it's cute and it
does some things to help, but it's not

that impactful to really leaning back and
saying, this profoundly changes how I work

and profoundly amplifies my productivity.

And I think we're, we're just
in the earliest innings, not

just a Clio, but I think mm-hmm.

You know, every, every company in
the world, especially companies that

are in the, the, the knowledge space,
knowledge worker space, are going

through a really profound period
of transformation and, and change.

And, uh, again, I think it's exciting
and terrifying for employees thinking

about, you know, what's my job look like?

How's that changed and how's
that evolve over the course of

the next, the next few years?

Yeah.

And what, what you spent your time
doing, uh, a year ago may not be

something you're spending your time
doing, uh, this year or next year.

And again, I think the overall theme
is, you know, I'm a deep believer

that AI is, is going to be, you know,
an amplifier of, of human impact.

And how do we reorient.

Our humans, you know, our employees on.

The things that humans are best at and
how can we, you know, if we're talking

about our customer support team, for
example, can we leverage AI to automate

away some of the, the drudgery of their
jobs and the drudgery of helping customers

with password resets or, you know, kind
of the the tier one straightforward

support questions and can we help
them move up the value chain and think

about how do I really engage with my.

A customer is a, a strategic partner,
and how can I help them think

about how do I grow my law firm?

How do I grow my revenue?

How do I get better clients in the door?

How do I deploy my marketing spend?

So I think in the same way that I, I
see it again, history doesn't repeat

itself, but it does rhyme to me.

It's very reminiscent of what spreadsheets
did for accounting back in the, the 1970s.

And.

When spreadsheets came to accounting,
there was a lot of gnashing of teeth.

People worried that this was gonna
eliminate the need for accountants,

that it'd be mass unemployment for
accountants because spreadsheets

is, have taken their jobs.

Uh, the way people talk about LLMs, if,
if you read actually quotes of people

talking about VisiCalc, the, the first
spreadsheet, uh, in the seventies and the

way people are talking about LLMs today,
it's actually very similar language.

People talking about the fact
that like, I get a week's work

worth of work done in half a day.

I can go home early.

Mm.

Because the, a spreadsheet back, back
then literally automated what an entire

building full of people were, were doing.

Calculating, you know, basically one
person at one desk was calculating

one cell in that spreadsheet.

And, and that all changed virtually
overnight with, with visit Calc.

But what ended up happening,
I think the lesson from that

spreadsheet and accounting story is.

Uh, there wasn't mass
unemployment for accountants.

Spreadsheets did not replace accountants.

It amplified their productivity.

It allowed them to serve more clients, but
importantly, it helped them move up the

value chain and helped them really be more
in the way of strategic partners to their

clients as opposed to number crunchers.

And I, I think if you look at many, many
roles at companies, different types of

functions, you're gonna see a, a similar
evolution over the next five years.

Edwin: Yeah, I mean it's what, what's for
certain Jack is we're in interesting times

and someone who's a serial entrepreneur.

Uh, always ready to upgrade
your skill in the new challenge.

I think, I think it's right for, for
folks like yourself to take this challenge

and really lead, lead not only the
business, but also the tech, the tech,

tech ecosystem, and business as well.

Um, so before, before we let
you go, I want to present you,

actually, this is a book that
we, me and Paul just co-authored.

It's called Future Narrator.

Jack: Oh, thank you.

Edwin: Um.

You're an inspiration.

I think I've mentioned you from
my, our episode that I had.

Thank you few years ago.

Appreciate it.

Yeah.

Um, and it's, it's all about really
like empowering the founders these days,

the CEOs, because with AI, products
and services come up overnight now it's

about the inspirational leaders, how
they, how they impact community, their

stakeholders and, and their clients.

Right.

So I definitely wanna do that.

You're an inspiration to us and to Canada.

So thank you for joining us on
the Business Leadership Podcast.

Thanks for having me.

Amazing.

Thanks guys.

Good job.

Great stuff guys.

Can we do a, a photo?

Like lets do it.

Just do this, uh, hold
it up and hold, like,

that's good.

Thanks a lot.

Thanks very much guys.

Appreciate, appreciate it having me.

You are listening to the Business
Leadership Podcast with Edwin.