Last week, legal technology company Clio named Curt Sigfstead, a veteran technology, finance and investments professional, as its new chief financial officer.

Sigfstead was formerly CFO at Clearco, a Toronto-based fintech company that provides growth capital to e-commerce businesses through a unique model in which the investment is repaid through revenue sharing.

Before joining Clearco, Sigfstead was with J.P. Morgan for nearly 23 years, most recently as head of West Coast technology investment banking. For 18 years, he was managing director and global head of technology systems investment banking.

The news comes two months after Clio announced the expansion of its leadership team, naming four people to C-suite positions as chief operating officer, chief people officer, chief technology officer and chief marketing officer.

Last Friday, a few days into his new role, Sigfstead joined me via Zoom for a conversation about what attracted him to Clio and where he sees the company heading. What follows is a transcript of our conversation, which I have edited for clarity, concision and continuity.

AMBROGI: Tell me what it was that attracted you to Clio. Why did you want to make this move?

SIFGSTEAD: Well, a couple things, Bob. First, Jack [Newton] is an exceptional CEO and he’s built an incredible team, and obviously he, and with early members and other co-founders of the company, have created an incredible platform. So that was number one.

Number two is the company is at a stage and scale where I think my skillset can be really helpful. Now it’s completed some M&As. It’s been adding capabilities. It’s been accessing larger capital pools in the United States. It’s been maturing its organization. So I think that was number two.

And number three, I’m attracted to the mission of really helping lawyers and counselors run their businesses more effectively so we can continue to ensure that the foundations of our democracy are protected and people can get the help that they need to make sure they’re living the lives they want.

All three of those were incredibly attractive to me.

AMBROGI: You’re making a leap into a different industry. What do you think the challenges will be in that for you?

SIFGSTEAD: I’m humble about what I need to learn and I’m sure that the curve will be pretty steep in terms of what’s important to lawyers and how we build our platform and all the intricacies of that. But I hope that what I do bring is a perspective in terms of how a tech business can optimize its opportunity and to how we can think about our own strategic and financial goals and making sure that everything’s in place to achieve those. So, yeah, I’ve got a lot to learn, no doubt, but hopefully I can bring a lot of that tech and later-stage tech experience to bear for the company.

AMBROGI: I just got off a call in which we had a panel of people talking about the top stories in legal tech for the past year. One of the top stories that we were all talking about was the fact that there were three major IPOs in legal tech, when there hadn’t really been one in the United States in 20 years before that. There’s been a lot of conjecture around a number of companies – Clio among them – of IPOs to come. What are your thoughts on that? Is that something that’s on the horizon?

SIFGSTEAD: Well, yeah, it’s definitely one of the potential outcomes or goals for the company. I don’t have a particular view yet on timing, exactly, of when that might be. But I think it’s less and less about the IPO is necessarily always that ultimate step, because we just don’t know when that’s going to come. Jack’s made some comments publicly about when he thinks it might be. Look, I think as the company’s found too, the private markets have been incredibly receptive – institutional investors – to funding businesses with Clio’s profile of high growth, reoccurring revenue and leadership in its industry.

We could be doing a lot of different things as we grow the company, but the ultimate goal here is to build a 100-year enduring company, put everything in place, all the foundations, and when the time’s right or the circumstances are to our advantages, perhaps go public or continue to grow privately for a little while. So, we’ll see.

AMBROGI: Clio this year – just a few months ago – launched Clio Ventures. Will you be involved in that? If so, what will your role be with that?

SIFGSTEAD: I’m sure I will be. I’m not necessarily the day-to-day person on it, Bob, but I’m sure I’ll be involved from a finance standpoint, given my responsibility. But I haven’t even – I’ve been drinking from a fire hose this week, right, so I’m  not focused on that right away.

AMBROGI: I think you literally just started at Clio this week.

SIFGSTEAD: I started three days ago. You’re catching me really early. I’m happy, always, to get back on with you when I’ve got more runway under my feet here.

AMBROGI: I understand. Acknowledging that you’ve just been there a few days and you’re soaking a lot up, do you have a sense of what your immediate priorities or goals are as you get started?

SIFGSTEAD: Yeah. I think there’s a couple of things. One is I want to ensure that I understand and I have a good sense of what’s already been in place. Look, the company has been incredibly successful. Rob [Froment] – our current CFO and now retiring – he’s done a phenomenal job, having scaled the finance organization over the last, I think it’s seven, eight years. So, really, my first job of the first week here is just to really understand what’s in place.

But, goal-wise, one, we want to be focused on having an organization that can scale or support the business in all aspects of growth, whether that’s M&A or organic.

Two is we want to ensure that we have an organization that, if asked or if we need to be preparing to go public, is ready to do that.

Three, we need to be sure we have all the systems and software and processes in place so that we can scale without adding a lot of costs.

So one is get my head around things and then those are the three priorities.

AMBROGI: This is a tough question for anybody to answer about themself, but what do you see, personally, as the strengths that you bring to Clio – the unique strengths that you bring based on your experience?

SIFGSTEAD: Well, I’ve been very fortunate. I’ve worked with hundreds of technology investors and executives and board members over my career. I have a good sense – I don’t have a cornered market on this – but I have a good sense of what works well in tech and what doesn’t and what we need to do to build that 100-year, enduring company, and one that will be very highly appreciated by investors.

I’ve taken probably close to 80 companies public in my career, and I’ve done a lot of capital raising – multi-billions of dollars and hundreds of billions of dollars of tech M&As. So it certainly informs and helps me help Jack and the board and the executive team think about just how we can make this a global leader in tech and do that right out of Vancouver and also out of our other locations globally, as we expand.

AMBROGI: Where are you, in Toronto?

SIFGSTEAD: No. I was born in Canada and did my high school years in the province of British Columbia, but I live in San Francisco.

AMBROGI: Anything else that you’d like to point out about your new role or joining the company?

SIFGSTEAD: I think this is a really exciting area. I think the legal profession is really starting to embrace technology to accelerate and improve their business operations so they can focus on the important aspects of their clients. And I think it’s very early, so I think we got a lot to see.

The last thing I would say is we’re at a really interesting intersection of software enablement with payments and financial products coming to bear in terms of how that can be helpful in terms of collections, payments, financing for clients – again, with all the benefit of just leveling the playing field so that these services are as accessible as possible.

AMBROGI: The payments area is really interesting in legal right now, and I know Clio launched Clio Payments. Is that something also that you’re going to be involved with in some way?

SIFGSTEAD: I don’t have any product oversight over that, but I’m excited about that. That gives us a lot to start thinking about in terms of other solutions that we can add to that to help, like buy-now, pay-later types of opportunities for clients.

AMBROGI: Maybe I should check back with you in six months.

SIFGSTEAD: Yeah, more to help you or give you a better perspective, but I do appreciate you reaching out, Bob, and obviously you can follow up with any questions anytime.  Happy to give you an update at some point, once I’ve got a few months under my belt.

AMBROGI: That’d be great. I appreciate your time.

Photo of Bob Ambrogi Bob Ambrogi

Bob is a lawyer, veteran legal journalist, and award-winning blogger and podcaster. In 2011, he was named to the inaugural Fastcase 50, honoring “the law’s smartest, most courageous innovators, techies, visionaries and leaders.” Earlier in his career, he was editor-in-chief of several legal publications, including The National Law Journal, and editorial director of ALM’s Litigation Services Division.