Clio Con Clips 2025 – Curt Sigfstead – E03

Transcript

Robert Hanna (00:00)

Welcome to Clio Con Clips 2025, recorded live from Boston and proudly sponsored by Clio, the world’s leading legal technology company, transforming the legal experience for all. I’m your host, Rob Hannah. And over this special legally speaking podcast series, we’ll be bringing you exclusive conversation with brilliant minds behind Clio. The innovators, strategists, visionaries driving one of the most transformative companies in legal tech.

Across these interviews, we’ll explore how Clio is uniting brilliance across teams, technology and communities worldwide. From AI and data to leadership, culture and the future of client experience. You’ll hear from people shaping what’s next for law and redefining what’s possible for legal professionals everywhere. So whether you’re a lawyer, technologist or leader passionate about innovation, you’re in the right place.

This ClioCon Clips 2025 is where brilliance meets purpose and the future of law takes shape. Let’s get into it.

Welcome to the Legally Speaking podcast, recording live here from Boston for our Clio Conclipse series 2025, sponsored by Clio. And I’m joined by name, title and organization.

Curt Sigfstead (01:14)

Hi I’m Curt Sigfstead I’m the Chief Financial Officer here at Clayton.

Robert Hanna (01:19)

And it’s an absolute pleasure to welcome you back. It just seems like a minute or yesterday that we sat down in Austin and we’re talking all about the amazing series there for what a year it’s been and we’re going to dive into all of that. But for that, I’d love to know a fun fact that folks probably here at Clio Con don’t know about yourself.

Curt Sigfstead (01:34)

⁓ Sure, well ⁓ Jack and I are from the same city, we grew up in the same city in Canada, Edmonton, and that actually was a very interesting aspect of the whole process of me coming to Clio. anyway, just fun fact, we’re from the same city in Canada. Way back. We were not plotting about the future of legal tech.

Robert Hanna (01:52)

The story goes way back.

I can imagine it was not top of mind right at that point in time, but it sure is now. this year, as I sort of teased at the intro, Clio’s had a huge year. You’ve launched Clio for enterprise and deepened your investments specifically in AI. From a financial perspective, how do you decide where to focus resources next?

Curt Sigfstead (02:19)

Well, know, it’s, you know, there are a couple aspects to that question. So we’ve got a business servicing solo mid-size law firms that we know really well. understand, you know, how to invest in that business, what the ROI should be around certain aspects, either product development or go to market motions. That’s very well understood. And, you know, we just have to keep the rigor around that and sort of make sure that we…

⁓ continue to deliver on the returns that we would expect. On the enterprise side, we’ve got a number of different aspects coming together on the enterprise side. So we have ShareDo, which has been an absolutely spectacular acquisition for us. The team, and his team have been doing amazing things as they continue to refine the product and expand the capabilities. And now Vlex. And so, you know, we’ve got a complicated set of

dynamics from a financial standpoint because we have the integration of Sheridoo with the integration of Vlex, the integration of Vlex and Sheridoo with Clio, plus building ⁓ a very strong and market-leading enterprise go-to-market platform and obviously product. so, whereas on the solo and medium-sized side of the business,

that’s really like let’s continue to operate and be as clear as we have been historically. We’re going to be building and investing ⁓ in the enterprise side and where we do that and how we do that is very specific to what we’re trying to do in terms of the various aspects of the business we’re trying to build. ⁓ there’s no formula there. There’s obviously patterns that we can look at and the returns we’re trying to get but ⁓

you know, this is a real build mode for us, which is fantastic.

Robert Hanna (04:09)

Yeah, and Jack was very clear in his keynote yesterday. This isn’t us dipping the toe in. We’re all in. We’re all in. And you know, you’re coming to that challenge. And I love that. And I loved your analogy when you were on the show previously in terms of, you know, the driving in the fog, you know, and just maybe just remind our listeners about this. I love that mentality, how you kind of approach that and give some context around it. So I think it’d be a really good refresher.

Curt Sigfstead (04:31)

Yeah, absolutely. you know, in all of these aspects of our business ⁓ and in your business and anyone’s business, there’s an element of the unknown. Yeah. And if it was known, we wouldn’t have a job and it wouldn’t be about the opportunity that that unknown presents to us. Yes. And so there’s a couple of aspects or sort of frameworks we bring to the planning process around what we do at Clio to help us, you know, ensure that we continue to move forward.

But we don’t put ourselves in a position where we can’t sort of make adjustments or introduce more agility. And the analogy we talked about last time was, how do you drive or how do you navigate in the fog? The fog being an analogy for the uncertainty. And what you typically do is you slow down. You keep moving forward, but you slow down. You’re much more aware of the environment. You take pauses to understand, OK, am I going in the right direction? Am I not?

And that just helps us continue to move forward. it’s that aspect of slowing down, doing the analysis. And then two is just making sure that when we’re coming to decision points, is this a one-way decision? Like we can’t come back? if it’s a decision we can always come back to and revisit, then let’s just move through it and keep moving forward. So two aspects of that.

Robert Hanna (05:49)

I love that and I think again when we spoke I sort of said tongue-in-cheek that I wasn’t surprised but I was very excited when Clio obviously did the 900 million raise you had obviously the acquisitions and all of these exciting things because with that mission to transform the legal experience for all of course you’re going to be wanting to do the whole of the market and I guess maybe more reflecting question now many months on from that raise the Series F which was the largest in legal tech

History, what’s been the biggest lesson in managing something of that scale?

Curt Sigfstead (06:20)

managing the braids or managing the

Robert Hanna (06:22)

The process of that race? The process of the race?

Curt Sigfstead (06:25)

I don’t know if there’s a lesson, but sort of the observation is that the more success you have or the more ⁓ trust you gain from investors, because in effect, what the Series F represented was a massive investment in Clio’s future, which was based on the trust that investors had that we would be stewards of that capital, stewards of the opportunity going forward.

You know, for me, it’s not so much what I’ve learned from that, but what I’ve always taken away from that aspect given years as a CFO and in finance is that you have to earn that every day. It’s a very… trust is built over years, decades, ⁓ you know, in Cleo’s case, over the two decades that the company’s been around, but it can evaporate tomorrow. Yes. And so we have to keep earning that trust and that trust…

gives us the ability to do things like Vlex, which are industry transforming and really enable us to take the company in a different direction than frankly where we were at the end of the series app. weren’t talking about

Robert Hanna (07:38)

You know, that’s why I love having you on Kurt. It’s not tiny things we talk about when you come on. So it’s an honor to have you. And talking of trust, folks should definitely go and follow Esther Perel. Her keynote earlier this morning was fantastic. Some great advice about relationships and trust. So let’s begin then from a financial perspective on VLex and Sharedo. They are now part of Clio. How do you measure the success of an acquisition beyond just financial return?

Curt Sigfstead (08:03)

Yeah, so for us it’s ⁓ from a, you know, sort of kind of some core areas that we sort of look at. One is we look at, you know, how are the employees engaging, you know, with Clio and how happy are they? So we have tools and we have programmatic aspects to our employee engagement that really help us ensure that we’ve got team members in, you know, and new team members that are really excited about working at Clio and are aligned with the mission and the opportunities.

You know, sort of looking at that and real data for us to look at that. We look at it product velocity. You know, what’s happening from a product standpoint? Are we delivering on the features and sort of the product roadmap that we had believed that we would achieve once we went into this? And so we have real data on that. can tell I love data. Absolutely. It is the new gold. then go to market is probably the third sort of pillar to that aspect, which is…

you know, are we seeing the sales performance that we really believe we saw when we, you know, stepped forward with the acquisitions or the, know, it accelerating beyond that or is it, you know, slower for variety of reasons? And so, you know, when you, and obviously that’s reflected in, you know, the sales numbers we see and the performance of our sales team. So that’s how we sort of look at it from, you know, ⁓ through a variety of different lenses and ⁓

And then that’s all sort of reflected in terms of like how, from a finance perspective, how good are we getting at being able to forecast our business? Looking at this data, looking at it historically, projecting it so that we can deliver results with ⁓ a very high level of certainty that obviously our investors can be happy with.

Robert Hanna (09:49)

Yeah,

and look, it’s been an incredible story to date and I still get the impression and Jack was sort of saying this in his keynote, it’s still the beginning. Obviously, we’re kind of at a stage now, particularly in the AI world. So I want to ask you a specific AI related question in terms of how is AI reshaping the finance function inside Clio itself, if at all?

Curt Sigfstead (10:09)

Yeah, no, it’s having a big impact and it’s sort of, the way I describe it, my responsibility is to our audit committee. And this is a hot topic, if you might, you could guess it in terms of like, how do we ensure the integrity of our financial reporting and our financial forecasting while adopting AI tools to make us better and more efficient? Sounds like something lawyers are doing. ⁓

Robert Hanna (10:34)

Yeah, as a Clif D’Arral head.

Curt Sigfstead (10:38)

And so, know, ⁓ from an AI perspective, we have dedicated AI tools that we are using that help us accelerate basically some of the less sort of sexy parts of finance, you know, some of the more sort of repetitive tasks. And those we’ve been able to adopt very quickly. ⁓ And so an example of that is like bank reconciliations, know, we can do that now very quickly with an AI tool that we have.

On the other end of the spectrum, we’re waiting for some of our core systems, ⁓ know, our counting ERP to ⁓ embed more AI into there so that we can leverage that. So there’s systems we can adopt that are outside of our core foundational aspect that we can use right today with AI and we are adopting. And there are other systems which we cannot replace. These are like the bedrock of the stability of the whole company.

that we’re dependent upon the vendor effectively.

Robert Hanna (11:37)

I love it, I love it. There’s such deep thought in everything that you do and it’s all strategically thought out and it just blows my mind time and time again. And this year’s, last year’s theme was Amplify Your Impact and wow, Cleo has absolutely gone on and done that 10x over the space of 12 months. This year’s theme of course is Uniting Brilliance. So how does Uniting Brilliance apply to bringing different teams together and skill sets across such a fast growing organisation?

Curt Sigfstead (12:01)

Yeah, and that’s a constant challenge that we face is not only are we adding new employees all the time, but we’re adding big chunks of new employees with these recent acquisitions. I think where it starts, and I really applaud Jack and the culture that we’ve at Clio over many, years, is that there’s a phrase I use which is kind of encapsulates it, which is

We seek to understand in order to be understood. So we really listen to what’s happening, try to understand the messaging so that we can get to common ground and common understanding because so much friction that we find in growing teams and in integrating teams is just harmonizing language and harmonizing goals. And so that when we’re talking about achieving certain things.

everybody’s on the same page with respect to how that’s going to happen. And so that’s probably the number one challenge. And so, you know, there’s an old phrase of measure twice, cut once. You know, it’s like measure a thousand times, have the conversation plan, you know, think about the outcomes and then start to execute instead of running away, executing right away. Yeah.

Robert Hanna (13:20)

And just from a media perspective, obviously, we’ve been working with Clio since 2021 and you’ve had astronomical growth. It’s still not lost our cultural identity. It’s still not lost the values. It’s still not lost. And I think that is a testament to Jack, yourself and all of the leadership team that that trickles through everybody in the organization. And it’s just exciting to see what’s next. And I guess looking ahead then, what’s one trend you think will define the future of financial strategy specifically in sort of legal tech?

Curt Sigfstead (13:47)

Well, I think it’s going to be one of the aspects that we are, you know, that we see and that we’re obviously discussing is how do you talk about the ⁓ adoption of AI within your customer base? A lot of investors are now, you know, from public companies to the, you know, emerging private companies who are with AI products are dealing with the question of like what percent of your revenue is AI driven?

How many customers have adopted X? How many companies have adopted Y? Do you have a tiered pricing plan that you can charge more for AI? ⁓ And so we’re in this noisy middle part right now in this journey because some aspects of the tech landscape are early in this, some are more advanced. And what makes me so excited about what we heard yesterday at the keynote and where we’re going as a company is…

effectively everything we do is being embedded with AI. And, you know, there’s an aspect of how much AI is sort of impacting each solution. But when you saw yesterday with Grow, with Draft, with Manage, now with Work, there’s a lot of AI embedded in those products. And so, you know, in effect, I think the future of this is if you’re successful software company and you’re to be successful in legal tech is…

you’re just going to have AI embedded in your solution. It’s not going to be a separate part, a distinct part, or think different.

Robert Hanna (15:16)

think

the other thing I admire about Clio’s strategy as well is the level of due diligence, safety, compliance and rigor that goes into it and the level of, know, just again from the acquisitions and the organisations you’ve chosen to partner with and what you do. It’s not sort of just putting your finger up in the air and hoping it’s really strategically thought out and that impact has just been…

exponential as a result of things. I mean you’ve worked in the intersection of finance and innovation for decades and Kurt, very very successful. What’s one financial principle from traditional banking you still believe applies to hyper growth tech businesses? If at all.

Curt Sigfstead (15:50)

⁓

Yeah, luck favors the prepared. know, there’s very fortunate things that you can’t control. You have no sort of control of how the future is going to unfurl. ⁓ You know, we could have a very successful year. We could have a year of challenges. We don’t know. There’s a huge macro aspect to what happens in the world. But, you know, you’re able to take advantage of that or you’re able to be ⁓

to execute on your strategy more favorably the more prepared you are in terms of your planning and ensuring you’ve got the resources whichever way it goes. That’s always been there. Yeah, just keep, we keep sort of re-embedding that in whatever we do, whether we’re adopting a new platform for employee expense management to an AI, a new AI tool in the finance side is okay. So what if this goes well? What if it doesn’t? What are we going to do? How do we plan so that we have a series of outcomes and actions that we can rely on?

before we actually embark on the process.

Robert Hanna (16:49)

Yeah, absolutely. I guess just the final question before we zoom out from your sort of Clio com reflections IPO, know, it’s something, you know, that’s been sort of touched around potentially. Is that something Clio is still thinking about or what’s the sort of vision regarding that?

Curt Sigfstead (17:04)

So if I was to give you exact details, I’d have to leave my role at Cleo.

Robert Hanna (17:11)

I know, but we will push boundaries on the show.

Curt Sigfstead (17:13)

I appreciate the question and ⁓ of course it’s something we think about. ⁓ If you look at any absolute leader in their industry, they are a public company. so ⁓ it’s really a matter of where we are on our journey and what we need to do with respect to capital raising to execute on our strategy. So you know we’ve got examples of companies like Canva and Stripe.

Databricks who continue to be private and raise lots of private equity and are still ⁓ growing very rapidly. And we have companies like Service Titan in one stream and others who have recently gone public who have done really well. So it just continues to afford us optionality on that front. But at the core of it is we’re obviously building a company for 100 years.

If you’re building a hundred year company, are implementing a lot of the systems and processes and software that would obviously enable you to be able to go public whenever that.

Robert Hanna (18:18)

right

and they have the right people it’s the right skills and the knowledge to help with that. One thing I think for sure is Clio like to be first you know first sensor first now LegalTech to be servicing the whole market from Solos to to Enterprise I think it’s hugely exciting and we’re just enjoying partnering with you and all the great work so let’s just zoom out a cup before we close. What’s been a highlight moment for you of ClioCon 2075?

Curt Sigfstead (18:39)

I think it’s Jack Skeeno. And I’m not just saying that because he’s my boss. I really think and I really encourage your listeners, because I had a number of folks outside the industry, not just lawyers, not Clio, know, sort of employees come up and say, that was very helpful for me to understand kind of how to place the various aspects of both the trends, but also how lawyers are working and also how broadly software and AI is impacting the legal profession.

And to hear Jack lay that out in such a very cogent way, ⁓ think just gave a lot took a lot of anxiety out of the room for a lot of legal professionals, but also gave a lot of clarity as to what does this all mean? Because there’s so many concurrent thoughts and perspectives on what’s happening. So that is absolutely been a highlight. and and of course, being on your podcast.

Robert Hanna (19:32)

okay, that’s far too kind, far too kind. This is a seminal moment for me. But I think just the way even Jack’s keynote started, it told the story of the evolution of technology and how this is going. And Cleo’s a beautiful story in the journey along the way. And I just thought it was such a great way to explain and showcase and give confidence to people as well.

up those adoption level. One of the best keynotes I’ve ever seen. absolutely agree. Kurt, it’s been an absolute pleasure having you back on the show. Third time’s a charm. If people want to know more about Cleo or indeed yourself, where’s the best place for them to go? Feel free to share any websites, any LinkedIn handles and we’ll show them.

Curt Sigfstead (20:08)

LinkedIn that’s probably the best way obviously you can go to Cleo’s website we’ve got lots going on we’re obviously hiring so I just make that absolutely everybody out there in the world and we’re looking for great people

Robert Hanna (20:21)

Don’t need humans even in the AI world. It’s been an absolute blast having you back. Thank you so much for your time. But from all of us here on the Legally Speaking podcast sponsored by Clio, over and out. Thank you for listening to this week’s episode. If you like the content here, why not check out our world leading content and collaboration hub, the Legally Speaking Club over on Discord. Go to our website, www.legallyspeakingpodcast.com. There’s a link to join our community there. Over and out!