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So Cass, when we were recruiting you, we may or may not have told you that we thought what you had in front of you was really difficult.
I don't think you actually did say that, 'cause again, you were trying to sell me-
... so I ... In fact, I think what you did say was, "This company is doing really well. This isn't you're coming in to fix everything, rip everything apart. This is coming in and taking what's already been built, and figuring out how to scale it." You know, it's hard not to get excited about that.
You're listening to Thoma Bravo's Behind the Deal. I'm Thoma Bravo founder and managing partner, Orlando Bravo, and that was Thoma Bravo operating partner Kristin Weston, speaking with Cassidy Smirnow, CEO of Apryse, a leading provider of document processing technology for developers and enterprises. And after Thoma Bravo acquired the company in May of 2021, we went to work to expand its product offerings, accelerating its growth to the point where a complete rebrand was necessary just a year later, as it quickly outgrew its original name, PDFTron. Apryse is just a phenomenal case study on how a company can have both fast growth and very high margins, and how that is done in partnership with a private equity firm in a private environment.
To give you a sense of this, a prize has a rule of 80. And that is just an exceptional case study on leadership and private equity partnership. So let's hear from Thoma Bravo operating partner, Kris Weston, and Apryse CEO, Cassidy Smirnow, to learn more about their working relationship and how it has impacted the continued growth and expansion of Apryse.
My name is Kristin Weston, and I am an operating partner with Thoma Bravo. I've been with the firm for 2.5 years. My career prior to Thoma Bravo over the next 20 plus years is I led four different software companies in both the public and private and private equity setting. And so when I joined Thoma Bravo, I viewed it as an opportunity to put all of the work and experience from running those companies to work, really helping the founders and the CEOs in the portfolio, mentoring them and helping them achieve their enterprise value creation objectives.
In the operating partner role, we develop very close relationships with the leaders, and the CEOS. And, and I remember from my time as a CEO that that can be a very lonely role, even though you have a broad executive team working with you. I'm fond of saying they love to be the recommenders and not necessarily the deciders, and so when it's time to make key decisions about the business, you can find it rather lonely. And so one of the things I love about the role is being that person that the CEO can call when they have difficult decisions or challenging times, and we can help them make those decisions, and we can also help translate that into the broader dynamics of the private equity environment.
Apryse is one of our portfolio companies that is really exciting, because they serve the broader development community and developers. So it's a highly technical product that really permits other organizations to access information, convert documents, and use AI to create a much more streamlined document management and document processing process. So when Apryse became part of the Thomo Bravo family, it was actually known as PDFTron, which was the name of the company since its founding by its founders. And as the name implies, it started and had its heritage in a number of tools for developers to create PDFs.
And over the course of the growth of the company and its expansion, both immediately before becoming part of Thoma Bravo, and certainly with the acceleration after becoming part of Thoma Bravo, the organization had really outgrown its name, because it was so much more than simply PDF creation. And so we undertook a process with the management team to create a brand that made more sense for the broad new category and future of the company.
PDFTron and its market was one that Thoma Bravo had been watching for many years, and the team within the discover fund was pretty familiar with the asset as well as all of their competitors. So when the prior control investor, who was Silversmith, was interested in a recap, they reached out to a few private equity investors, and Thoma Bravo was one of them. Uh, Thoma Bravo had an advantage in this case, because we were so involved with and had a strong understanding of both the market and the asset. So we had a leg up, we could impress, I think, the founders with our knowledge of their market and our plans to help them evolve the company. And in the end, even though the valuations were close, both the founders and the prior control investor chose Thoma Bravo as a partner for the future and the next stage of growth of the company.
So when I first got involved with the PDF transaction sort of in that immediate pre-close and then post-close timeframe, the organization was run by actually a pair of founders, so a CEO and a CTO who were a married couple, who had built the organization from scratch and through brute force, and hard work, and a lot of blood, sweat, and tears, and had done an amazing job as a set of entrepreneurial founders to bring the company up to the scale that it was at, that not a lotta founders achieve. And they had done so in a way that really provided amazing growth and foundation for the business, and they were looking for some assistance on how to take the business to the next level.
The founders had started this organization back in 1998 and they had over 20 years of great success as entrepreneurs building on growth and profitability year over year, and through the Silversmith gold period as well. The acquisition of PDFTron was finalized in the spring of 2021, and it was a absolutely phenomenal deal for Thoma Bravo. It had all the hallmarks of a great investment. We had a really large market, multiple billions, that had strong growth in the underlying market. And then we had the number one technology asset in that space, albeit small, with opportunity to grow. PDFTron was the number one asset.
So in the spring of '22 we were approaching the first year, uh, during the whole period of PDFTron and we had made a number of small [inaudible 00:06:44] acquisitions, and we were sort of on the even of closing a really large, uh, on a relative basis, acquisition that would really be a merger of equals, uh, with iText. In the highly fragmented, broad market in which PFDTron played, there was another really large asset called iText. It had a different international presence, it had a bit of a different segment coverage approach, and it had an open source approach as well. And so it was related, but highly complementary to bring iText and PDFTron together to create truly a powerhouse in the document processing space. And so it was a real opportunity to sit down with the founders and talk about what the business needed for the next stage of growth and evolution, and we collectively decided that that was a good moment for the founders to move into the role of board members and investors, and that we would bring in and build out a management team that could really hyper-charge a- again, both organically and inorganically the growth in the business.
So it was in the context of that iText acquisition that I got to know Cassidy Smirnow.
My name is Cassidy Smirnow, and I have been the CEO of Apryse for almost a year now. I am a geologist by trade, which you don't see every day, and I had a brief stint in geology because my dad taught me that you should do what you love. And I love being outside, and I love science, so I became a geologist. And, uh, a year into being a geologist, I decided I did not wanna be a geologist.
So at the time, things were going on the web and getting digitized, and I kinda moved over to environmental consulting, which led me into software. And so I have been in software for 20 years. And as a side note, my husband is also a geologist gone software developer, so there's a trend here we, we could research and, uh, see if we can pull apart. But I've been in software ever since, startup companies to Fortune 500 companies, always i- in a role, in a capacity to helping those software companies scale, that's what I love to do. I spent my first 10 years at a company in the, uh, document processing and capturing space for the transportation industry. And we grew that business and ultimately became part of Xerox, so I got to lead several lines of business there. And then I went back to the startup world, and I partnered with the founder to help grow that company. We grew it from about 10 million to 60 million through, really through a migration to SaaS.
So my journey to CEO is an interesting one, because I've always found myself number two to the CEO. I'm always the confidante, the one that gets the stuff done no matter what it is, and I loved being in that role.
We certainly worked with the recruiter to find a world-class executive to take over the company, but Cass and I, uh, hit it off, I think, really well in our first conversations. Because we had this shared history of working, actually, for the same, uh, software investor, uh, although we didn't work in the same company, working for the same software investor prior to Thoma Bravo.
I'm convinced Kris doesn't actually remember this, but Kris and I actually met a few years back, we were both part of a, a different private equity company at the time that hosted a women's leadership event. And I remember thinking she was really cool and I wanted to be like her when I grew up. And I met her very briefly, and so when she reached out to me about this opportunity, and I got on the Zoom with her, I immediately recognized her and said "I've met you before." And so like there was this initial foundation that we had established, because we had met before, we came from the same space. She explained the opportunity and what we were looking for, y- you know, Kris works a lot like I do. She's quick, she makes quick decisions. I knew her reputation and what she had done, and was really intrigued.
It was interesting during our initial conversations, because this was both a new investor, and a new portfolio company, and a new role for Cassidy to consider, and she appropriately wanted to cultivate her career. And so she had a lot of questions, not just this business, but what her personal goals were.
People always said to me, "Aren't you gonna become the CEO next?" And, you know, I had that idea, but I, I wasn't really acting on it. And when Kris found me, she was the first person to say, "It's time, like, you need to go do this."
I have a philosophy that the relationships that we have as tech executives are much longer and much broader than any one investment, and I wanted to make sure that this was the right role for Cassidy. And I really believed it was, uh, and ultimately has proven to be a great success.
This opportunity here at Apryse is my first CEO opportunity. And so there was a lot on my mind, obviously, when I came into this role.
Stick around for my conversation with Cassidy Smirnow, CEO of Apryse. Thoma Bravo's Behind the Deal will be right back.
Welcome back to Thoma Bravo's Behind the Deal. Here's my conversation with Cassidy Smirnow, CEO of Apryse.
Cassidy. It's good to see you.
Have you recovered from the board meeting yet? (laughs)
I have, yes. How about you? You probably had several yesterday, huh?
Exactly, and I-
... have a couple more today, so I can't call myself recovered until the weekend, but-
(laughs) Cass, I'm super curious to see what you remember about our first conversations.
Okay, so what I remember, Kris, is we actually met for the first time many years ago in our prior life together. And it was a very brief meeting, I can't remember who you were the CEO of back then, but I remember thinking-
... you were so cook because you were wearing a leather jacket. I don't know if you remember that.
And I thought, "Well, that woman is very cool." And I think we were introduced, but I just remembered you. And so fast-forward, you know, a couple of years later when this opportunity came across my path, and, and I figured out who you were, and I looked you up on LinkedIn and I said, "Oh my gosh, I- I've met her before. Like, I know who that is, she was wearing the leather jacket." So I was very excited-
... to meet you, uh, on the Zoom, and I remember the first thing I said was, "We've met before." And you said, "Oh my gosh, we have met before." And so I think from that moment on there was a, a comfort level just knowing that we had similar backgrounds and we had come across each other before, and I think you were key in helping me through the journey of getting here for sure.
It's so funny, because I have been thinking about the fact that we had this shared background of having worked for a couple of, uh, software-only private equity investors, and I think it really, both that and our experiences about what good looks like have made our conversations so much easier (laughs) at least for me. I said to someone recently that you've done seven years of CEO work in a year. H- so, so Cass, when we were recruiting you, what you may or may not have known that we really felt like hiring this CEO was a tall order, and with a high degree of difficulty in front of that person, because we needed to grow the business on its own organic trajectory, as you know. We needed to integrate both the small tuck-in acquisitions and a really big one.
Uh, at the same time we needed to build a culture and bridge that culture from the founder-led personality, and so we may or may not have told you that we thought what you had in front of you was really difficult.
I don't think you actually did say that. 'Cause again, you were trying to tell, me, so-
In fact, I think what you did say was, "This isn't really gonna be that hard, because" ...
"This company is doing really well. Like if, financially, first of all, if we take everything, strip everything out, you look at the numbers, this is a really highly-performant company that is doing really good things. "This isn't you're coming in to fix everything, rip everything apart. This is coming in and taking what's already been built that is working well, and figuring out how to scale it." Right? And so to me that was actually really super exciting, a- and definitely one of the selling points, was, gosh, even if you did nothing, look at- (laughs) look at how amazing this company is, and if you just apply some of these best practices that you've learned over the years, and apply some of this experience, imagine what we could do. And that was really exciting.
Yeah, it's true that it was a growth asset and had been growing for a long time. And so it was not a turnaround at all-
... in fact, the difficulty was, in some respects, don't break what's going on ...
As you make that transition to a new culture and a new go to market. But sometimes the don't break it jobs are even more difficult, right? (laughs)
And so I like to think I told you the absolute truth in addition to selling you, but it absolutely was and is a growth asset, and over the last year you've done exactly that, like it's continued to grow at a really remarkable place, and I think you've ticked the box on all of those high degree of difficulty things.
Yeah. I mean, I, I don't think you misrepresented it at all. I think it was actually-
... a very accurate representation of the situation. And I remember, you know, obviously I talked to you first, and then you slowly introduced me to other members of the Thoma Bravo team, and I kept getting these glimpses through every person that I talk to about this great company and this great product and this great opportunity, and it's so hard not to be intrigued by that, you know? To have a hugely successful, best-in-class product, organization that is already doing so well that has tremendous opportunity, tremendous TAM. You know, it's hard not to get excited about that. And I felt that through every person that I met along the way.
I, I remember one of the conversation threads that we had early on was about the fact that this business was super technical, right? Selling-
... to developers and maybe not i- immediately easy to grasp all of its bits. And one of the things that I loved was I think you understood, and you certainly have proven that you could take those core principles of how to run a great company and how to build a leadership team, and how to execute and bring them into a highly technical product. "Oh, and by the way, create a much more accessible set of go to market messages," which I think you have done and your team has done a, a stellar job of.
And I remember one of my concerns being, and I remember asking all of you about this is, you know, any time you're trying to navigate a founder-led product-centric business, you know, i- losing that founder's strategic influence is a little bit scary. They know the product, they built the product. They know the market. And how are we gonna replace that? I remember spending a lotta time thinking through that, and continue to keep some of the core Apryse team in key leadership roles, and blending them with new leadership who knows how to scale a company like this I think has been a really great solution to that, so ...
A- one of those things to build on that, I completely agree with you, it's been fun to watch. The team that you've assembled, which by the way, is world-class. Like, it's literally fun to attend board meetings with you guys, so that part's true. And then the founders are still on the board, so-
... to hear the questions that they ask sometimes, and the fact that the team is really receptive to thinking, "Oh, is there something we've missed?" Um, or sometimes the education has really, I've seen it go both ways, which has been fun to observe as well.
100%. And I remember some great advice that you gave me, Kris, at the beginning, was, "Let's think about how you want your first 30, 60 days to go." So when we made the announcement that I was gonna step in and become CEO, we did it via Zoom. So we were a remote-first organization, our headquarters are in Vancouver with offices around the globe, actually. But most people were working remote at that time, so my first sort of statement to the team was, "I'm gonna be in listen and learn mode." So I got on a plane and went out and visited everybody and spent a ton of time in person, and all of those fears went away.
And I was really clear about what got me excited about a prize, about the product, about the future, about the TAM, about this amazing, amazing culture that we have built, and just figuring out how to continue to grow that. And so I did a series of departmental round tables for my first 30 days, I met with everybody in the company, I heard a lotta great feedback. And I got to come back to the team and say, "Here's, here's what you said, right, and here's the things that you love about this company, and here's the things that you wanna see, and I'm committed to both of those," right? And I think that really set the stage for that transition that we talked about earlier, which can be really dicey.
Well, you handled it beautifully, and especially in a sort of emerging from COVID and remote environment, one of the things that we at Thoma Bravo worry about in a founder transition is that sort of organ rejection phenomenon, which-
... can happen, right? Because there- there's this great weight of history.
Uh, but we didn't have any of that, we didn't have any of that when you joined the organization, and it's a testament to your approach, I think which was hugely collaborative and then just your, your leadership style. And you had a big set of objectives for 2022, and I was reflecting recently as we were planning for 2023 on the fact that you really accomplished, I think, all of them or very close to all of them. You built out a great leadership team, world-class leadership team, uh, which the company really needed as a foundation for growth. You executed on moving from a entirely inbound to an outbound go to market approach. You rationalized the product strategy across all of the acquired entities, and you created a global culture, having integrated iText. And now the foundation is set for the next stage, even of, of growth, both organically and inorganically, and it's been, uh, pretty amazing.
Well, thank you, first of all. It's been a lot of fun. You know, it's been almost a year and a lot has happen. And for me, I think first and foremost it's building a great team, which sounds so cliché, and I'm certainly not someone who believes in luck, but I can't help but think that I got really lucky (laughs) with the team that we assembled. And, and when I reflect back on that, almost everybody on the team came from somewhere in my network or your network, and I think that's how this works, you know? To find great people that have similar backgrounds, growing, scaling software companies. They understand how this works, their, their mind is focused on the outcome that we're all achieving together, and I really have built a great team, and it's, that's what I am absolutely th- the most proud of, I would say, over the past year, for sure.
It makes sense, because when you think about it, that team is foundational to everything else. And I think y- you make a point that should not be lost, which is that that network effect, your network, my network, we were able to leverage the trust that I think we've hopefully (laughs) built over many, many years, um, and then the new trust that we had with each other. And bringing in people who knew what good looked like, were ready to be part of a team, and you knew them well enough, or I knew them well enough, that I think it just made everything go so much faster.
Uh, it's, and, and that cannot be understated that Thoma Bravo's reach, right? Which is really the network of the network of the people inside the firm, uh, is one of the superpowers, for sure.
Yeah. So one of the things coming into, you know, being a first time CEO, obviously I've got a background in private equity, and my expectation of a board and the relationship is so different than the reality, I can tell you that. Especially at Thoma Bravo. And, you know, going in my expectation was the board is something I have to do, right? It's like, some percentage of my time, I have to go do this part. These are things I have to do.
And (laughs) and I've been so pleasantly surprised that I have a really great team of Thoma Bravo resources that I get to work with often for different things, and it's really help. It's really someone who ... You know, I thi- I think the biggest difference for me is, is I assumed that I would have to have things buttoned-up and perfect before I could share them with my Thoma Bravo friends. And that is certainly not the case.
I am actually encouraged to let the team into the sausage-making and be transparent with what's working and what's not working, and say, "Hey, have you guys seem this before?" Or, "I- I'm struggling with this, wh- what have you guys seen work?" Or, "Do you have any ideas for me?" And that type of relationship is one that I did not expect at all.
I- I'm so thrilled to hear you say that that's been your experience, because it is always the goal. Doesn't always work perfectly, but it is the goal. Because one of the things I love about my relationship with Thoma Bravo and the CEOs is that it is entirely collaborative, and we're all, one of the things I think I said to you early was I really want you to feel like we're all on the same side of the table. This isn't a, "We're over here and you're over there, and here's this, you know, with a bow on it," set of results. But we're all on the same side of the table, we're completely aligned with what we want to achieve and what we get out of that, and we don't win if you don't win and you don't win if we don't win. And so I've always wanted you to feel like we could just tell each other exactly what was going on, good, bad, and ugly, and that we would solve it together. And I hope you always (laughs) feel that way, but y- you have demonstrated that over and over, and I, I think as a collective it feels like we've walked the walk a- in addition to talking the talk, and it's made it really fun.
And I think the team feels that way. I was having a one on one with one of our ELT members this morning, and they're still so shocked at how collaborative the conversation is. Like, th- they still say to me, "Wow, it's so cool to like, be able to actually talk about things-"
... "that matter to our business, and like make progress in these dialogues." And I think that's a, that's a testament to what you just said. I mean, it, it, people see that. Our team sees that.
I think part of it is the culture of Thoma Bravo and the sort of collaborative approach that we tend to take with management teams. But another piece of it, I think, is that, uh, Thoma Bravo is a software-only investor. And so I h- I've worked for non-software only investors, and I feel like there's, you can't skip to the meaty part of the conversation the way that we can as a collective-
... because the acronyms are shared, and the understanding is shared, and so we can have much deeper conversations about the thorny problems, 'cause there's this shared understanding that's really unique to the Thoma Bravo ecosystem. So, so I think we had a shared view (laughs) from the Thoma Bravo perspective and from the company, uh, that the organization had outgrown PDFTron, right? The organization was no longer strictly PDF document processing. Everyone understood and believed, but it was a little scary, uh, for all of us to think about how do we navigate a brand transition? And while we had total trust in you and your management team to do the right thing, uh, and we knew you were working on it, I think I might've asked you 112 times if you would, if you would share things with me. Uh, and you wouldn't, until the end.
I do remember that. I actually remember a step behind that, which was-
... early days, and I'm, I'm creating priorities and I'm doing all of this. And, and you said to me, "Yeah, and y- you just gotta get the rebrand done." And I was like, "Oh my God, I gotta get a rebrand."
And you said it so casually, and I was like, "I should add that to my list."
"I should 100% do a rebrand." So I remember it being a casual conversation, and I woke up the next day and said, "100%, we're doing this right now."
And we did. So the rebrand process is a whole conversation in and of itself. It was a very cool process and one that was super intimidating, as you mentioned, going into it, but ended up being a really, really cool thing. And I think, you know, if I was to reflect on this, y- the decision to bring in a new team and new leadership at, at this pivotal point in the company's trajectory where we had done, I think at the time we started this, about nine different acquisitions. And so about 50% of our employee base was from acquired companies. So we were not PDFTron any longer. We were all kinds of great companies coming together. And the, the great advantage we had in bringing in a new leadership team at that time is I had no bias. I didn't come from PDFTron or from Solid Docs or from ActivePDF. You know, I was new, and so my perspective was clean, and I didn't have bias around any of these technologies. And it was such a beautiful time, and given the feedback that we were getting from the team at the time, which was, "We never got integrated. We don't feel like we're part of this new company. We, we, we don't understand how this is all gonna work together."
"We don't understand the vision for, for this." And so to rally the team around, "We're gonna become one in every way. We're gonna become one prize, we're gonna have a new brand that we can all be committed to. We're also gonna have one functional organization, functional, global, organization. We're all gonna know we- where we fit, we're all gonna know how we can affect the future." And so it's, I think of the rebrand as a byproduct of the effort of becoming one. And so more of the win for me was building one team, one company. And sure, we got a great new name, and, and something that we can all feel proud of, but it was more about unifying the people culturally than it was anything else.
A- and that answer is so emblematic of who you are. I just love that. Because I see that in you every time we talk or have a board meeting, where you're thinking about market, strategy, people, culture, and you bring all that together really seamlessly, and so, uh, it makes sense, and it's, it's lovely to hear, because that's exactly what it looked like.
So what's head for Apryse? I mean, the best way to describe what's ahead for Apryse, I think, you know, we have been on a 20 year so far journey to create the greatest document processing toolkit for developers in the world, and we are well on that journey. And our strategy for the first 20 years was, "If we build something great, they will come." And they did. And now we are in the next phase of our journey, which is, "Let's go out and build a go to market motion so that the whole world knows who we are and what we do and how we enable developers to be more efficient in the applications they're building."
So we are the category killer today in document manipulation development toolkits, and we're gonna continue to grow market share, we're positioned to scale, and do exactly that.
Well, if we were an NFL team, we woulda called 2022 the building year, except you guys built and won the Super Bowl like all at the same time, so-
... the metaphor falls apart. Uh, but from an investment perspective, I know Thoma Bravo is very excited to watch, where you take this foundation that I think hopefully we've built together throughout the last couple of years, and to watch the next phase, because we can see the organic growth trajectory and opportunity, and the market is still huge relative to the size of the organization. And we can see the inorganic opportunity and we've got big appetite to participate, uh, in continuing that trajectory. And so, uh, I can't imagine the pace at which you will continue to succeed now that you have your foundation set.
Me too. You know, the way that I have gotten to work with the Thoma Bravo team over the past year, you know, as a first-time CEO, there was a lot of uncertainty on what that would look like, and how it would go, and how much of my time would I be spent managing my board and all of these things? And, you know, I, it has been, and I tell this to everybody that I talk to, it's been one of the most pleasant surprises, is really having true partners to run the business with. Things are my decision, and everybody always is very clear with that. "Cass, whatever you wanna do, but here's some of the things that I would think about." So to have a network of folks that I can bounce ideas off of to collaborate with, and I'm not sure that I would love my job as much as I do if I didn't have some of those great relationships that I've been able to build. So I, I feel lucky that I've gotten the, the Thoma Bravo team to support me that I have.
Well, it's great to see you, Cass, outside of the board setting. And we have done, uh, a terrible job of getting our wine date together that we have attempted many times. And so I'm, now you can hold me to it and I'm gonna hold you to it, uh, and let's get in the same ZIP code, shall we? (laughs)
That sounds awesome, and I, I know I say this to you all the time, Kris, on my random Sunday night texts-
... but I'm so grateful for you for giving me the extra push I needed to get here, because the past year has been amazing, I hope for all of us, but certainly for me, and I'm super excited to continue our relationship and see what's next. So thank you.
It's, there's no thanks needed, it's been an absolute pleasure, and oh the places you will go. So look forward to watching it.
Thanks for listening to my conversation with Cassidy Smirnow. If you want to learn more about the work that she and Apryse are doing to take document solutions to the next level, visit Apryse, A-P-R-Y-S-E.com. Stay tuned for more stories behind the deal on our next episode. I'm Kristin Weston, and thanks again for listening.
Thoma Bravo's Behind the Deal is produced by Thoma Bravo, in partnership with Pod People. Stay tuned for more stories behind the deals. I'm Orlando Bravo, thanks for listening.
Certain statements about Thoma Bravo made by portfolio company executives are intended to illustrate Thoma Bravo's business relationship with such persons rather than Thoma Bravo's capabilities or expertise with respect to investment advisory services. Portfolio company executives were not compensated in connection with their podcast participation, although they generally receive compensation and investment opportunities in connection with their portfolio company roles, and in certain cases are also owners of portfolio company securities and/or investors in Thoma Bravo funds. Such compensation and investments subject podcast participants to potential conflicts of interest.