A Conversation With Curt Sigfstead (Video) – Corporate and Company Law

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Mark Longo: Hello to all of our viewers. My
name is Mark Longo. I’m the Co-Chair of the Emerging and High
Growth Companies group at Osler, Hoskin & Harcourt, and I’m
the Managing Partner of the Vancouver office of Osler.

I’m very pleased to welcome Curt Sigfstead, Chief Financial
Officer of Clio. Prior to joining Clio, Curt was the head of West
Coast Technology Investment Banking at JP Morgan, based in San
Francisco. He has advised on some of the tech sector’s largest
M&A deals and has raised billions of dollars across public and
private debt and equity markets. With over two decades of
technology financing experience, Curt has held senior finance
leadership roles at several companies, including Clearco. He sits
on multiple nonprofit boards, including C100, which supports
Canadian technology entrepreneurs through investment and
mentorship. He is also a member of several leadership and
investment communities, such as Bain Capital Ventures’ CFO
Advisory Board, The Circle by Founders Circle Capital and the Brown
University Angel Group. As Cleo’s CFO, Curt oversees all
finance functions, including accounting, treasury, financial
planning and analysis, legal and corporate development. His track
record includes major financing events such as mergers and
acquisitions, IPOs and private and public equity and debt
financings.

Great to chat with you today, Curt.

Curt Sigfstead: Great to be here, Mark, and
thanks for all the work that Osler does for us all the time, and
particularly recently with the Series F, which I know we’re
going to get into.

Can you give an overview of Clio?

Mark Longo: Absolutely a pleasure. To kick it
off, can you give our audience a brief overview of Clio?

Curt Sigfstead: Absolutely. So Clio
fundamentally is the world’s leading cloud-based legal tech
platform. And why we define it as a platform is because really,
we’re providing the operating system for the law firm, which
includes comprehensive practice management, CRM, legal content
solutions and a payments, billing and invoicing platform. But
we’re more than that in the sense that we also, really, our
mission here at Clio is to transform the legal experience for all.
And we do that by, obviously, our technology platform, but
we’re also very much an industry leader with Clio Con and
bringing together the legal professionals from around the world,
across the United States, to talk about all the pressing issues in
terms of operating a law firm and ensuring that they’re ahead
of the trends in terms of operating their business.

We’re committed to that education and we’re committed to
that aspect of improving the experience for the entire legal
community. Fundamentally, what Clio does with its platform is it
streamlines the operations and improves client communications and
accelerates revenue for law firms, which is obviously a very
compelling value proposition. And we’ve done that obviously
through our own platform, as I just talked about. But we’ve
also built a very robust ecosystem of application integration
partners who help with their various integrations to provide very
tailored and distinct solutions for our law firm customers. So
hopefully that gives you a good overview of what we do here out of
Clio. We do that obviously from our head office here in Burnaby,
British Columbia, and we have approximately 1,400 employees, mostly
in Canada, but we’ve also got a good bunch in the U.S. and also
in Europe. And I think to give you a sense of scale and size,
we’re roughly 150,000-plus legal professionals are now on the
Clio platform. So it’s been 17 years in the making, but as we
always say here at Cleo, we’re just getting started and we
really focus on our customers. And that’s been really, I think,
the strength of Jack’s mission is really continuing for us to
focus on helping lawyers achieve their goals, and that’s really
helped us achieve our goals. So I’ll turn it back to you.
Hopefully that gives you a good sense of who we are and what
we’re trying to do and what the basic sort of pieces of the
technology platform are.

Describe the catalyst behind the Series F round?

Mark Longo: A very impressive track record
indeed, and one that led to your Series F financing. To segue into
that financing, in July of 2024, Clioo announced the closing of a
US$900-million Series F financing round. The round was led by New
Enterprise Associates. You had a valuation of US$3 billion in that
round. To give you a few of the other metrics, this deal
represented the largest venture round in Canadian history. It was
the largest round in legal cloud software history, and it was a
top-five vertical SaaS financing in 2024 globally. Osler was very
proud to support you in that transaction as your counsel. So Curt,
can you describe the catalyst behind the Series F round?

Curt Sigfstead: Yeah, absolutely. And obviously
we’re very fortunate to work with you and your team, Mark, on
that transaction and obviously benefited greatly as we had the
outcome that we did. So the initial goal for the Series F was
really liquidity for some of our early institutional investors. And
the challenge that we face now in the markets is the fact that
oftentimes fund life isn’t necessarily matched with company
life. And so we’re seeing situations where investors are
looking for an exit based on the fund life. They love the company,
they wish they didn’t really have to do it, but in this case,
we had had a number of early-stage investors who had really
supported the company in sort of the earliest periods of Clio’s
growth and we wanted to reward that. And so that was clearly a key
catalyst.

Second catalyst was really recognizing an opportunity for us to
bring on a new set of investors, investors that would help us at
our stage and scale to take us to the next level.

And the third catalyst was the opportunity for us to reward
employees at Clio who had clearly dedicated the hours and the time
and effort for us to achieve what we had achieved to date, to
enable them to realize the benefit and value of the equity that
they had earned. So those were really the three catalysts in terms
of what got the ball rolling, and what we really wanted to do as a
goal of the financing was establish a fair valuation for our
equity. We wanted the market to understand our leadership and what
we had developed at Clio from a customer and product standpoint,
and give us the fuel and the expertise to, as I mentioned, take us
to the next level, but also for us to do acquisitions like the
ShareDo deal that we recently executed, obviously with the help of
Osler as well.

So those were the main catalysts, and I can get into some of the
dynamics and the process, but at a very high level, that’s
where we entered the process and we certainly didn’t start with
a 900 number. I don’t think any CFO or board would believe me
if I said, “Oh, well absolutely, We sort of kicked it off with
900 in our minds.” It started with a much smaller number and
grew through the process, which is sort of the place you want to
be, but it surprised even us as we went through it. So hopefully
that gives you some scope and perspective and sort of an
understanding of the catalysts of why we did what we wanted to do
there.

Walk us through the process of securing term sheets

Mark Longo: Absolutely. Well, let’s unpack
the deal a little bit more. So walk us through the process of
securing term sheets, selecting NEA as the lead investor and
ultimately assembling the world-class syndicate investors that you
did.

Curt Sigfstead: Yeah, so we started 18 months
in advance. You never sort of start— cold start and capital
raise as sort of a non-starter, if you will. So there was a lot of
educating the market, attending investor conferences, really giving
Jack an opportunity to talk about the Clio story and where things
had evolved and changed, obviously since the last time we raised
capital in our Series F. And so we had a good understanding and a
good sort of set of dialogues underway with various investors
before we kicked off the formal process. But we effectively ran a
very rigorous, competitive process with top-tier investors.

And we did that through continuing to focus on transparency,
access to information, detailed conversations about our business.
And that’s where the investors really dug into the diligence,
our financial models, our technology progress, our go-to-market
areas of focus. And what we made sure of is that we gave that
access to all parties involved. We ran a very transparent process,
we kept to our dates and we updated the investors as we went
through it in terms of new insights or new perspectives on the
business. The one insight I would say is we really mapped out how
this would play out over the six to nine months and being sure that
what we started the process with, we could deliver at the end,
because investors would have effectively almost three quarters of
data that they would have in order to make their decision about
Clio. We focused on building relationships during that process,
building trust, understanding who really understood our business,
who could take us to the next level.

And then that really led to NEA. And first of all, they
completely distinguished themselves relative to the field in terms
of their understanding of SaaS, their long-term perspective,
strategic alignment, their advisory network, prior investments that
they had made and the success that they had had. And so they were a
natural fit. And then I think the personalities around the table
really jelled with Clio’s approach and vision and the
opportunities that we had ahead of us. And then we’re super
proud of the syndicate that came in with NEA, the likes of Goldman
Sachs, Sixth Street, CapitalG. We had folks from Tidemark as well
come in and there was a significant commitment of capital from
those partners, and each one of them brought another set of
experiences and strengths that, frankly, we need to take Clio to
the next level. So really no different than the NEA process in
terms of it was about building relationships and trust and then the
various different areas of expertise that those parties could bring
to the Clio story.

Can you talk about what led to that optionality and what is a
true auction process?

Mark Longo: Excellent. You ended up securing
around 20 term sheets, which is almost unheard of, particularly in
this market environment. Can you talk about some of the tactics
that led to that level of optionality and really a true auction
process?

Curt Sigfstead: Yeah. Well, I hate to sound
boring and maybe traditional on this front, but it came from
incredible amount of meticulous preparation. A lot obviously we did
with you, with Mark and your team, but with our advisors at William
Blair, and also internally as a Clio team, just to make sure that
what we were going to go to market with we could execute against,
and that we were being consistent and, frankly, very transparent.
Everything we talked about as part of the fundraising process was
consistent, or we had clear explanations as to why it differed or
was consistent with our past performance, and why we believed we
could achieve the numbers that we were talking about. I am a big
believer, and I know Jack is too, in trust; you’ve got to
use— the process is about raising capital and it’s about
bringing on new investors, but it’s also about building trust
not only with your new investors, but with the marketplace. I sort
of look at this as a huge marketing opportunity for us as much as
it is a capital raising process, because your point around 20
competing term sheets, you’re only going to pick one. So you
want all of those other 19 parties to be talking about the deal
they missed and what a great opportunity Clio represents and
talking highly of the management team and otherwise. So we sort of
took that approach and really embedded it in our process.

We obviously just like, again, it’s boring and traditional.
We had a detailed data room, our financial model, all the diligence
items that we built with your help, Mark and the team, and that
just meant that there was just no— we could move things
quickly. Folks could see that we were prepared, we had anticipated
their questions. And so that, again, built trust and the momentum
in the process. So we were able to build a competitive process that
leveraged the strong network of investors we had and created a
sense of urgency, and that drove us to be able to land with NEA and
the valuation that we achieved.

And I think one of the big questions going into it was how to
talk about the market opportunity and the long-term vision. And the
great thing about having Jack at the helm as our founder and CEO is
that he’s got that just intrinsically and authentically nailed.
And his ability to connect on that front, I think, was an
absolutely critical differentiator in our outcomes. So hopefully
that gives you a sense of how we went about this process with 20
term sheets and sort of how we were able to get the outcome that we
ultimately ended up with.

Mark Longo: It really was an incredibly
meticulous and well-planned process, even to the point of us
drafting collectively, drafting the term sheet, drafting the
definitive agreements, presenting it to all of the prospective
investors so that there really was an apples-to-apples comparison
in what came back. Not just valuation, but deal terms.

Curt Sigfstead: Yes, yes. Yeah, that was a lot
of work. I think we probably — collectively, the Clio and
Osler and our partners at Wilson — probably spent, what,
probably six weeks nailing that process from the start to actually
signing the definitive agreements, in terms of aligning those
terms, understanding how we were going to get all the investors
comfortable because of the amount of capital they were committing
behind the term sheet that NEA had presented. So yeah, just a
tremendous amount of work balancing all of that while investors
were asking for more allocation, and us as a team collectively
going back to ourselves and some of our existing investors and
thinking through, well, “Was there more shares to sell or more
capital that we wanted to raise?” And so there was just a very
fast turnaround times on a lot of this to be able to say
definitively yes or no, we could increase the allocation to these
syndicate members in the deal.

Why should management teams and board members be considering a
secondary?

Mark Longo: Exactly. And the reality is this
round was mostly secondary, where you had existing shareholders,
investors from prior rounds, stock option holders, selling shares
to these incoming investors. Just generally for our audience, why
should management teams and board members be considering a
secondary, from a liquidity perspective and from a recapitalization
perspective?

Curt Sigfstead: Well, I think secondary
financings are a way to bring clarity to the mission. And what I
mean by that is I go back to my earlier statement about the
misalignment that can occur between company goals and timelines and
investor goals and timelines. And when I say investors, I just mean
by the fact that the industry just evolves around seven- or 10-year
fund lives. It’s not anything that they’re doing that is
unnatural for them. And so, it really does align stakeholder
interests and creates liquidity for investors who frankly were
focused at Clio at a certain point in time and now we’ve sort
of grown beyond their area of focus and they can realize the
liquidity. I think too, it’s great for employees and early
investors just to be able to realize the returns based on the risk
that they took in terms of investing employee their time and
effort, but also investors early in Clio’s lifecycle.

It brings a lot more stability to the cap table just by virtue
of what I’ve talked about. And it allows us to retain the best
talent because what we can do is highlight to prospective employees
that you’re not just getting options in a company that
hasn’t seen the realization of value over time, which is often
something that I know a lot of folks in our ecosystem, when
they’re competing with employees who are contemplating public
company offers, trying to balance that option illiquidity, versus
RSU liquidity or shares, is tough. So I, and I think the dynamic
that’s changed here for all of us across the board is that
there’s just so much private capital available that secondary
financings, once viewed, I think, as a bit sort of transactions
that took place a bit in the shadows, are now, it’s just a huge
opportunity and investors have done really well by it as well. So I
think it’s here, this huge pool of capital and there’s tons
of benefits in the right situations for companies to execute a
secondary.

Mark Longo: Makes perfect sense. Yeah,
there’s so much dry powder out there in growth equity and
private equity now.

Curt Sigfstead: Yeah, and we saw that in spades
during the process.

How does this acquisition align with your broader growth
strategy?

Mark Longo: Switching gears a little bit, you
briefly mentioned ShareDo. You’ve recently acquired ShareDo,
which is a U.K.-based large law firm software provider. So tell us
a little bit more about this acquisition. How does this acquisition
align with your broader growth strategy?

Curt Sigfstead: Yeah, it’s a very
interesting transaction for us. So I think there’s a couple of
areas of where ShareDo really punctuates Clio’s opportunity.
The first is, it’s a group, it’s a significant team of
technologists, developers, go-to-market individuals focused on
legal tech, and for us, that’s invaluable. Two is it gives us
an incredible expanded presence in the U.K. and in Europe, where we
already have a significant employee base in Dublin. So having that
additional presence, additional customers, is huge. But three,
probably the most important, is it strengthens our position as the
leading end-to-end cloud technology provider globally. And what I
mean by that is ShareDo provides a case management platform that
large law firms utilize. And when I say large law firms, I mean the
world’s top hundred law firms, and they’ve got a proven
track record of building relationships with those firms, selling
platforms, supporting those platforms with the world’s most
demanding customers. And so, at the end of the day, this is about
international expansion, product expansion, customer expansion, and
gives us, as a result, a tremendous entrée to the large law
firm market opportunity, where Clio has traditionally been focused
on the mid- and small-size law firms. And for us, we think that
that, from a TAM (Total Addressable Market) perspective, could be
as large as our current market. And so we’re so excited about
the team, the technology they’ve built, and the market
opportunity that is ahead of us there.

Mark Longo: Really opens up your addressable
market.

Curt Sigfstead: Yes.

Mark Longo: Well done.

Curt Sigfstead: Yeah, thank you.

How do you see the legal industry evolving over the next couple
years?

Mark Longo: Speaking of legal tech, legal tech
is very hot right now. What trends do you see driving that
momentum? How do you see the legal industry evolving from a tech
perspective over the next couple years?

Curt Sigfstead: Yeah, so a number, I think, of
observations on this front. We’re definitely seeing an
increasing adoption of cloud-based technologies, I think at all
sizes of law firms for different reasons, but just by virtue of the
fact that cloud-based solutions deliver exceptional functionality
with incredible flexibility on the part of the law firm. And they
also, importantly, sort of trend number two, they give you the
ability to leverage AI, and AI and automation are transforming
legal workflows and improving efficiency, which is critical for law
firms of all sizes. Third, law firms of all sizes are really
demanding data-driven insights in terms of how their cases are
progressing, how their teams are being deployed, how they can
leverage electronic payments to be paid faster.

Everyone’s looking at legal much less as sort of a
partnership, and transferring it, and I think looking increasingly
as a business and sort of needing those tools to understand how the
business is performing. And I think also, importantly — I
mean this isn’t just about the lawyers or the attorneys
themselves —this is about providing better customer service
and support as well, and giving customers a better experience. As
competitive as the law industry is, I think that’s becoming
increasingly an area of focus. And so we’re seeing the
development or the expansion of platforms because, depending on the
area of the market, the larger end of the market, they’re
looking for best-of-breed solutions and the ability to deliver on
exceptional legal outcomes. And at the smaller end of the market,
more integrated platforms, one-stop shop. And our goal here at Clio
is to be able to deliver on both fronts, as you can tell by
ShareDo, and also by our core platform that we went to market with
the Series F.

What advice do you have for management teams in this current
climate?

Mark Longo: Switching gears one more time.
Considering today’s economic and geopolitical climate,
including the Trump administration’s trade policies, how do you
see these factors impacting business leaders this year? What advice
do you have for management teams in this current climate? And
we’re filming here at the end of March 2025, so, ever
evolving.

Curt Sigfstead: Yeah, this will be out of date
in approximately 10 minutes. Really, my number one message, and we
emphasize this every day here at Clio, is we can only control what
we can control. And that is the critical levers within our
business, which is how we operate and how we can continuously
communicate amongst ourselves about changes we need to make in our
business in order to ensure that the decisions we need to make are
within our control. And what I mean by that is that we don’t
have to put ourselves in a period of incredible uncertainty at the
beck and call of the markets or at the mercy of the markets, that
we can decide when we want to go to market and/or raise capital in
order to satisfy our strategic needs. So like we did last year, we
went to market when it was best for Clio.

And as we sort of go through this, my advice to financial
leaders or business leaders at this point is that, again, it sounds
old and traditional, but focus on those key, long-lasting business
principles that extend the opportunity for you to access the market
when it’s best for your company or opportunity. And that really
comes from, I think, a couple things. One is financial discipline,
ensuring that that is core and foundational to what you’re
doing, but also strategic and contingency planning. We do a lot of
that here at Clio in understanding where we might need to be
proactive in some areas to ensure that we’ve got plans. If Plan
A doesn’t work, what are we going to do for Plan B? And the
last thing is, in all of this uncertainty, you have to remember
that your customers are going through the same uncertainty.
It’s not just us as Clio in this bubble that is sort of dealing
with this. All our customers are going through this as well. And so
doing what we know we do really well is just emphasizing the
importance of our customers, supporting them where we can,
providing the tools, the information, the education that they need
to continue to prosper with their legal practices, is critical to
us. So that’s what we’re doing. I’m sure there’s
many other approaches, but we’ve just got to stay super agile
in this environment, Mark.

What’s next for Clio?

Mark Longo: Very good advice. Last question:
what’s next for Clio?

Curt Sigfstead: Well, we are focused on our
customers. We’re focused on developing and supporting solutions
that will continue to make them successful in their business and in
the industry of law. And so we’re going to continue to invest
in product, invest in our teams, invest in new geographies, to
carry on the mission of improving the legal experience for all. We
obviously, and we talk about this internally, we’re building
the foundations of being a hundred-year company. And it feels like,
each day, each quarter, each year, is like we’re just getting
started. There’s such an array of opportunities and there’s
just so much to do that we’re going to be busy for a long time
here. We’ve got large and huge and sort of ambitious revenue
goals, and we’ll execute against those as we do over time, both
through sort of a focused M&A strategy as we’ve
demonstrated with ShareDo and others historically, but also,
importantly, organically. And I think you can count on us for at
least continuing to build a strong ecosystem of partners and
application performance or application integration partners, and
helping drive the industry as a partner to where it needs to be for
it to both provide incredibly rewarding careers for lawyers and
attorneys, but also providing the best outcomes for their
customers. So lots to do, lots of, really, what we’ve been
doing over the history of Clio, but continuing to hopefully
accelerate that and reaching higher because the growth and the
opportunity demands it.

Mark Longo: A very inspirational vision. So
Curt, with that, I want to congratulate you again on the Series F.
Congratulations on the ShareDo transaction. You have built a
world-class company that is truly global, but yet proudly
headquartered in British Columbia, Canada. And I want to take the
opportunity on behalf of Osler to thank you for participating in
the Osler Deal Points Report webinar series. Thank
you.

Curt Sigfstead: Thank you, Mark. And thank you
for all you and Osler do, not only for Clio, but for Canada
broadly, across the startup ecosystem. And again, thanks for all
your help with the Series F and ShareDo and look forward to many
more years of partnering together.

Mark Longo: It is our pleasure. Thank you.

Curt Sigfstead: Thanks Mark.