Apr 24, 2025 | 21 min read

Best Of: Growth and Continuous Innovation with Chris Brown

By: Patrick Emmons

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At the start of last year, we had a really inspiring conversation with Chris Brown and are excited to reshare it this year, in our “Best Of” series. Originally published 01/25/24.
An exceptional company culture builds when steadfast employee commitment meets deep trust by customers. Chris Brown encountered this when he joined Relativity as Chief Product Officer in 2018. Chris joined the team in the early stages of their transition to SaaS and embraced the moment of disruption and opportunity—a familiar territory in his career, which included ten years at Orbitz Worldwide. From the perspective of CPO, Chris offers unique insights into the transition period from on-prem to SaaS, addressing legacy technology, embracing the customer as a co-innovator by building plentiful touchpoints, and the intricate SaaS sales process. Speaking on what SaaS can inimitably provide, Chris muses on “a continuous stream of innovation at high availability” and customer success.

In this episode, Chris looks ahead to the future to discuss how AI and LLMs will impact the law industry and finding effective uses for the technology. He shares how one of the oldest industries in the world can embrace the best of AI’s capabilities while mitigating the risks by including the law's critical element: human decision-making and validation.

With experience as a CEO and CPO, Chris shares the distinctions between the roles that stem from the needs of a particular company and offers how his arrival at Relativity reflected intentional scaling that led to further success. In discussing the Chicago startup environment and continued growth at Relativity, Chris talks about acquiring the contract review company Heretik and considering an acquisitive approach as one path of innovation and building a strong product portfolio. 

  • (02:24) – Introducing Chris Brown
  • (04:56) – CPO vs. CEO
  • (06:30) – Sales in the SaaS world
  • (08:59) – Relativity
  • (10:58) – Building an effective SaaS company
  • (15:43) – Co-innovating with customers
  • (17:59) – AI and the law industry
  • (22:18) – Looking ahead
  • (23:59) – An acquisitive approach

About Our Guest

Chris Brown is the Chief Product Officer at Relativity, a cloud review software that helps users “organize data, discover truth, and act on it.” Previously, he served as Senior Vice President and Chief Product Officer at Orbitz Worldwide and CEO and Board Member of Kapow! Chris earned a bachelor's degree in computer engineering from the University of Illinois Urbana-Champagne.

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Podcast episode production by Dante32.

Full Show Transcript 

Patrick Emmons: Hello fellow innovators. This is Patrick Emmons. Today we're resharing insights from our previous guest on the show, Chris Brown, a visionary who has consistently been at the forefront of tech-driven change.

Patrick Emmons: Hello, fellow innovators. This is Patrick Emmons.

Shelli Nelson: And this is Shelli Nelson.

Patrick Emmons: Welcome to the Innovation and the Digital Enterprise Podcast, where we interview successful visionaries and leaders, giving you an insight into how they drive and support innovation within their organizations. Today we're in for a treat as we engage with Chris Brown, a visionary who has consistently been at the forefront of tech-driven change. Currently serving as a chief product officer at Relativity, Chris oversees the evolution of pioneering e-discovery software, and under his leadership, relativity has soared, securing a coveted spot on Deloitte's technology Fast 500 and earning a reputation is one of Chicago's top workplaces. Chris's illustrious career, boasts significant leadership roles. He was the chief product officer of Orbit's worldwide and later took the helm as the CEO and board member of Kapow Events, stamping his mark on the digital and events sector.

He's a proud alumnus of the University of Illinois Urbana Champagne. Chris not only pursued a BS in computer engineering, but also showcased his tenacity on the men's volleyball court. With Relativity, Chris doesn't just guide, he crafts a visionary future, meticulously defining product trajectories, he's instrumental in shaping product strategies, always in close collaboration with expert engineering teams. And off the tech grid, Chris channels his passion and energy into coaching his four children in diverse sports, so be it on the soccer field or snowy mountain tops, Chris is out there leading the charge. So join us today as we delve into the journey of a tech giant, equally adept in the boardroom strategies and basketball drills. So welcome to the show, Chris.

Chris Brown: Hey, Patrick and Shelli, great to be here. I've never been introduced that well, thank you very much. That was a blessing.

Patrick Emmons: Well, that's why people hang out with me, my intro skills. Whenever we go out, I'm just introducing people in very loud and fabulous ways.

Chris Brown: 10% of it's true. I really...

Shelli Nelson: Chris, if you don't mind, can you help our listeners understand a little bit more about your role at Relativity?

Chris Brown: Yes, I can. I'm the Chief Product Officer here at Relativity Software. So that means I run our product management department, all of our product managers, our user experience and design folks, our documentation teams. I also look after our security team as well, and I work with our fellow engineering teams in the building and together we effectively guide the research and development budget for this organization, which is over $100 million of investment each year that we put to work for our customers and partners around the world. So it's a product manager role on steroids, I guess, and I'm sure you've talked with a couple other CPOs at this point. It's been a great role to have here and any place where there's a lot to do.

Patrick Emmons: Awesome. You do have a very interesting career journey through Chicago. I'm a couple of years older than you are, but I know we've witnessed a couple of very similar, I guess, stages of the tech development, but it's really interesting background going from CPO, CEO, CPO leading, you might sharing how that happens, some of the decisions you went through?

Chris Brown: Got it. I'll say before I ended up becoming the chief product officer at Orbits or even joining Orbits, I was actually, I am a Chicago native, but I was living in Austin, Texas at the time for a number of years, and I was looking at my next move. And I was working in the retail space at the time and I was looking for what would be a great opportunity at that time to come back to Chicago, work in an area or an industry that was going through some kind of disruption because a belief around targeting those areas that have that moment of disruption if we can harness that moment can help deliver some great new capabilities to the market, build value, et cetera, have fun as an innovator.

And so I particularly got interested in online travel because I was a consumer of online travel. I was an very early consumer of Orbit's services. I was probably the first user of e-trade when they put banking online. There was all kinds of things that I was doing as a user that I was very interested in being a part of as a leader. And so when I targeted Orbits, it was with that in mind, which was let's be a part of an environment that is trying to respect how things used to be done, but offer in a new way on how they could be done in a new medium. In that case, the disruptive event was really the internet and take it from there. So that was what landed me at Orbits, and I spent about 10 years there.

Patrick Emmons: I have this perception that the CEO is in essence the chief product officer of the business, and that there's a lot of similarities in thinking strategically, creating clarity, putting roadmaps together, which I think is what great product officers can do. And I just think sometimes a good CEO, a growth minded CEO, has that capacity as well of thinking about what the future is. Not so much of a manager or an operator, but almost as a chief product officer of the business as a whole.

Chris Brown: Yeah, I think the roles are certainly different. Obviously having been a CEO briefly as well, they are different. But when you are working in a company where your software, like your business is the product, the role of CEO and CPO are very much intertwined because the direction of the company is so tied to the direction of the software. That's the case in any of these technology led disruptions. So in the case of Orbits, the product ultimately was booking travel, but it was delivered through a tremendous amount of technology. And so the vision for the product was essential to the vision of the company. Similarly, at Kapow Events, it was an online marketplace for corporate events, and so the entire solution was delivered through software. And so as the software went, so did the business. And so we had to think about them together.

And then at Relativity, as a SaaS company, now very similarly, we have to think about the business holistically through where the software can take us. I will say there's another nuance in SaaS businesses, the product is really inclusive of the product plus the go-to market activities because in a SaaS world, you're hosting the whole service for customers. So all the things that maybe traditionally were other departments and maybe some things offline, some things online, from a product perspective, you have to be thinking inclusively of how do I embrace all of that activity with our software inclusive of the starting with the product, the onboarding, if there's updates to it and things like that. And conscious of how that affects all the different departments.

Patrick Emmons: That's interesting. And I think the sales strategies around SaaS, it's a whole different model from a pricing standpoint, but also from a sales engagement standpoint. It's created a whole new industry of sales resources, these type of, I know we've had sales engineers before, but it's more of the, I know they call them success, whatever, right?

Chris Brown: Customer success.

Patrick Emmons:Customer success, but there's a sales component of demoing the product, really understanding the business needs, does this fit that, where it's a little bit more stepwise versus the big sales move, right?

Chris Brown: Yeah. If you think about it from the buyer perspective, when they were buying licensed software, large component of their consideration was, what kind of hardware do I need in my own data center or in a closet in my office? What kind of capabilities do I need to host this software? I'm now making a big one-time purchase. How should I treat it financially? When do I do maintenance to that software? Well, I only have capacity to do it once a year. And so it had a different financial model, a different model on the accounting, on the books, and it had a bit of a different value proposition. You ran it in your own house, but you did it to the level you could do it. Whereas in the SaaS space, much of that is being done for you. And what you're really buying is a continuous stream of innovation at high availability, and you are benefiting from that.

And that's one of the reasons customer success is such a thing is because there's constantly more and more innovation coming and helping people try that, get used to it, onboard to it, et cetera, is more of a thing in the SaaS space. And since it's a more full tilt service, it is at times more expensive, but you're now getting all that value and you're paying every year, whether it's an annual subscription or some kind of monthly subscription. And so all those parts of the process become very important.

Shelli Nelson: I don't think I've ever heard it said that way. Continuous stream of innovation. That's great.

Patrick Emmons: Let's pivot over to Relativity. So when you joined, they were not a SaaS product, were they?

Chris Brown: They were on their way. They probably had, so they had announced a product called RelativityOne, which was a very big move for the business to decide to become a SaaS company and to transform the business from being purely on-prem software provider to a SaaS business. So they were about a year into the journey, maybe two years into the journey, but still pretty early days where the vast majority of the business was still on-prem back in November of 2018.

Patrick Emmons: And so with your background, is that part of why you got brought in? Is that what your mandate?

Chris Brown: Yes, absolutely. So Andrew, the founder I had met while I was previously working at Kapow. In fact, we hosted a couple of events for the Relativity team and I'd met Andrew that way. And as he was looking to scale the business, when you make the decision to go after SaaS is a competitive and large market as e-discovery was worldwide and where Relativity was at, it was a big choice and a big endeavor, and it was a multi-year effort. And so he was building out and had been building out the teams, the capital, the skills to go after that in earnest.

And so part of his plan was to hire a chief product officer. Part of his plan was to hire a chief technology officer. Part of his plan was to bring in other folks, a new CEO as he was going to move to the chairman position. So he really had an incredible foresight to not only understand the business that they were and what they wanted to become, but also the teams and talent he'd need to build to help make that happen. And really incredible for a founder to have that kind of foresight and then be so deliberate about achieving it.

Patrick Emmons: That's awesome. And what do you think was some of the most important things, obviously Relatively has been tremendously successful and one of the crown jewels of Chicago from a tech standpoint, from your experience, so building an effective SaaS business, what are some of the key elements?

Chris Brown: Well, I joined in 2018, the business had been around for at least 10 years prior, more than 10 years prior. And they had been massively successful in two growth curves prior to SaaS. They had originally became a document review company very early in their existence and then moved to a full suite end-to-end discovery platform and also became very successful in that growth curve. So if you look at those as two different eras, we came into SaaS being the third one. But those first two eras, they built amazing company culture. They had massive tech talent in Chicago that they had accrued over time. They were focused in the Microsoft sphere of technologies by design because in the legal space, that made a lot of sense for the customers that we were working with.

But they had incredible product-led culture. They did a lot of heroic things with technology back then. They met with their customers, they responded to their requests a lot. And so we inherited, when I joining a company that had such a great culture to begin with, both of building products but also of impact in the community, have having won over clients and customers in a way that you don't often see when you look at other companies. There are raving fans of Relativity. They've been working in the platform for years. There's people who have built their careers as users of Relativity certified in all the various certifications and things like that. There are people who teach it in colleges around the United States.

So I say all that to say as you look and build a great SaaS company, you couldn't have been better off than having all this past success in some of these eras. We met the mark in those areas. And yet what you need to build a SaaS company is some very different things than all of those things as well. So some of the skills are transferable, some are not. So really as you go to build a SaaS company, you're now taking ownership for the overall software you need to make it widely available. You need to be able to monitor it effectively, scale it rapidly, keep it up for customers, ensure that their data is highly secure and protected. So in the world of discovery, the data is really sensitive.

And so you need an absolute great security platform both for how you're protecting the software, how you're protecting the full fortress of your employees, as well as how you're thought leading the other purveyors in the industry. And so we put a lot of investments in all those things to be a full-fledged SaaS company, including also things like really pushing on much deeper partnership with Microsoft and from a cloud perspective. So those are some of the things you mentioned, Patrick, customer success, a strong motion that didn't really exist as an on-prem business. We built more direct touch points with our clients in addition to our channel touchpoints, we developed a whole service delivery organization that can help onboarding, training, et cetera. And so there's a whole bunch of these things that grew out of that decision to go to be a SaaS company.

Shelli Nelson:I'm just curious, having been there five years, what's been the biggest surprise?

Chris Brown:I think coming in, I had heard a lot of good things about Relativity, and I'd also heard warts as well. They're not always good things that you hear all the time, but I was blown away in the first year or two of just how great the employees are, their real commitment to the community, not just the software and the customers. So I was blown away by that, the real interest in that. And the second thing I was was their actual community of customers and partners of the business, it took decades to build that level of trust and appreciation and collaboration with that community. As somebody who walks into that, that is a real moat, really having that many clients around the world and customers, top law firms, corporations, government entities, public sector that have real investment in Relativity. That was a surprise to me. I've never worked in an organization that had that kind of trust built over many years.

I will say equally, you learn some things that are like, wow, you guys are getting away with just this piece of legacy technology here. We should probably upgrade that. There's now a lot more people in the software, so you equally have some of those things. And having come from Orbits, which was more of built in the dot-com era, built originally as a multi-tenant solution in the cloud, there are some technologies that were moving differently in that type of environment because it was a different type of business.

Patrick Emmons:It is interesting how much Relativity really belongs at the center of the legal industry now, where like you mentioned, there's so many pieces that people connect with and that moat where it's become. And then to still have the commitment because I do think that community, as you mentioned, is that critical piece that I think most organizations may lose when they start to grow and scale. What are some of the things that you think that commitment, how does it manifest itself? You mentioned culture. Is there certain activities or behaviors? You mentioned the fest as well.

Chris Brown:Yeah. How does it manifest in a variety of ways, but to be more specific, we do meet with our, inclusive of the pandemic, but that created some dents in our strategy. But we're an organization who meets with our customers as often as possible and builds them, our customers and our partners, into our innovation cycles. So what I mean by that is a lot of our software that we build, we have advanced access cycles with four or five customers who are there with the design phase, the deployment phase, the first feature phase, second feature phase, MVP phase. So we're co-building with them because the market and their needs are really complex in different geographies, different use cases, different workflows, different segments. So not only do we co-innovate with them, we also help them do marketing to their end users. We often participate in helping them win business.

When we have things like our large user conferences like Relativity Fest here in Chicago, we provide tons and tons of training access to all kinds of people inside the building, but also experts around the world. And we help sponsor that here. We do it in Europe, we do it in APAC and other locations. And so we try to manifest this culture of we are not perfect, we are not right all the time, but we are going to work with you and we're pretty steadfast, and if we don't have it right today, we'll keep working at it. And so it's also recognition that the industry, you're not like a very transient partner. You're partnered for three, five, 10 years, and so we're going to get it right over time and we keep coming at you.

And so if you look at our business, we continue to steadily climb. So it looks boring in the sense that it's steadily increasing, but to achieve that, it's sort of like a real frenetic focus on always doing the most important things. And that looks boring out of the rear-view window out of the dashboard. It's a lot of being able to turn the steering wheel fast to address new market challenges. In this most recent year with the advent of generative AI, there was a lot of turn the steering wheel to ensure that we are setting up our customers and partners for success around this new type of technology. And so that's being very agile to address those new things in the rear-view mirror that shows a partner like a software company like Relativity is pretty steady over multiple decades because we're willing to turn the steering wheel.

Patrick Emmons:How do you see things like LLMs and AI, impact wise, what do you think is the huge advantage that you're trying to seize on whatever you feel comfortable sharing?

Chris Brown: Yeah, I think you were talking a little bit about the legal industry prior, and Relativity is placed in it. It's interesting. The legal industry is one of the oldest industries in the world, and so many people are an important part of it. And you'd say over the hundreds and hundreds of years people have been practicing law, software has only been really important in the last 50 years. We've had law around for a long, long time. Software has only started to make a penetration in the last 50 years. And in the last 20 years, where Relativity has really grown is the advent of digital evidence. Prior to about 20 years ago, most of the evidence was, you guessed it, paper or human testimony. And so with digital evidence has come this whole industry around how do you best handle safely, securely, and importantly digital evidence.

And so in the sphere of law, there are a number of really important data repositories or silos. There is the evidence, that's a place where relativity plays. There is case law precedent and what is that law in this jurisdiction in Massachusetts and what are the recent precedents in this case? There's that. And then there's the work product from all the expert attorneys and the expert firms that have been around for decades and decades and decades. And anytime there's a legal matter, an investigation, or any of the use cases around that space, you're usually trying to deliver the best advice and then manifest the best outcome by all three of those things. Looking and understanding case law and research, understanding the evidence you potentially have in front of you, taking your best expert attorneys and their best opinions and weaving that into a strategy.

So when it comes to generative AI, the interesting thing here is because it sits on top of the tracks already laid by cloud transformation, it can more easily dip into those three repositories and help us articulate smart responses back to the attorneys so they can deliver smart responses back to their customers. And so we view it as a disruptive moment as many industries do, as big as some of the ones we've already heard about, like cloud transformation, advent of mobile, the advent of the internet, we'll learn over time how big of a disruption generative AI is. Depending on your industry, it's going to be very big. We believe in legal, it's going to be very big. And we aim to help our customers and partners usher through it.

Patrick Emmons: It's amazing to think about the potential impacts from positive and a negative standpoint, where it's like the risks, the sensitivity of the data, where are things flowing, who owns what? Definitely it's one thing to get somebody's marketing strategy, but getting somebody's legal defense through this would be-

Chris Brown:You'll see. And I mean to that point, when we think about when responsible AI at Relativity and others do as well in their various places, there's so many different ways that we're building best practices to really use AI wisely. So whether it's generative or I guess more historical AI, and that is one, ensuring it's really fit for purpose so that you're almost narrowing the use case. So you can use the best of the AI capabilities without getting some of the risks associated with it, or at least reducing or mitigating the risks associated with it. You've got to provide transparency and control to the user. So if you're using a model, large language model AI or something else to enrich a data set or generate some text or recommend a decision, ultimately a human's got to be responsible for validating that decision.

But certainly in the sphere of law, you're often dealing with things that are disputes, and so you'll get feedback about one side and the other side, but ultimately it has to go to some arbiters, humans, to decide ultimately what the outcomes will be. And so just thinking about through how our AI can lay into that and also be very focused on privacy of data, the security of the data and all those other things that can help bring it to market. We've done a number of different things depending on the actual use case to help make it more useful to bring AI into the equation, but also put humans more in control of it.

Patrick Emmons:Awesome. Yeah, it's interesting. So let's look forward real quick. 2025, what do you see? What's your vision?

Chris Brown:I think as we move forward, where generative AI certainly will be employed in more and more use cases, it's the current and next best tool to apply in a number of areas to help people be more productive. I'll give you a super easy example. I'm using Microsoft 365 copilot right now, so I'm using it in my email, my Word and office documents. There's people who use Google Docs and have similar technology being developed there. So even in just normal knowledge work, we're starting to bring more generative AI into the equation. So that's going to produce some productivity. It may also produce a couple of false starts or weird emails sent and things like that. So we'll start to embrace it. Our engineers are starting to embrace it in some level of code development. In the case of GitHub, when it comes to these industries very similarly, some common use cases, people rely on it for more and more things so that they can then focus their time on more valuable pursuits.

So we'll see adoption, like if you looked at the end of '22 and into '23, the level of adoption of generative AI was like, hey, have you tried ChatGPT? Made it write a poem or a song that's not necessarily wide scale adoption. That's very speculative adoption and things like that. And I think you're going to see real professional adoption of it in a number of enterprises in '24, and coming into '25, it's going to be a significant part of how most businesses work. Inside of Relativity, that will mean that many of the use cases inside of Relativity are powered by those types of technology as well.

Patrick Emmons:Very interesting. We've talked about how Relativity is a huge part of the Chicago ecosystem, so do you mind sharing a little bit about the strategy behind the Heretic acquisition and is that something, are you guys looking to do more acquisitions and any kind of lessons learned?

Chris Brown:Yes, absolutely. So Heretic actually interestingly was founded as a software company, focused on the contract analytics space by a couple of former Relativityians, and it had some investment from Relativity and other venture firms in the Chicago area. And over time had built a great contract analytics tool that could integrate into Relativity. And so we had a choice as an organization to buy it and bring it back into the fold as part of our RelativityOne or our cloud offering. And so they've now been acquired, the team, actually some of them report to me. We've been very busy integrating their product suite into our SaaS solution, and we just launched it in August and it's going gangbusters.

Patrick Emmons:That's awesome.

Chris Brown:So in terms of a story where everybody's very happy about the entire process, I think speaking for everybody, knock on wood, is the team is great, the software is compelling. We've introduced a new product-led growth model into our offering so that our customers can easily acquire it. So one of the challenges that Heretic had as an separate entity is it's one thing if you're selling to a consumer or you're selling software to a SMB, but if you're selling software to the largest advisory firms in the world, or the biggest law firms or the biggest corporations, procurement is difficult. Security and InfoSec is difficult. All the contracting is difficult. And many of those firms see a high degree of risk with a small startup, and they want you to take that risk in the form of massive liability, which a small startup obviously cannot do.

And so by bringing them into relativity, reducing that contracting risk, building the products in an integrated way, it's a win-win-win for everybody involved, including the employees of former Heretic who get to realize some of their dream and bring this product to a wider audience. In terms of the story for Chicago, there's many of these opportunities in Chicago, having been part of another startup here and being part of that community as an investor. I'll say for Relativity, we often look at startup size software that we can bring into the business and help in various areas that make sense from the strategy. So in addition to the contracts solution, we also did a licensing agreement a number of years ago with another firm here in Chicago for the redact solution, and we brought that into RelativityOne.

That was also an ecosystem play that benefited the customers, benefited both firms, and allowed us both to continue to innovate. We also acquired an AI company out of the West Coast a couple of years back, and a few more. We also acquired a company focused on enterprise data migrations out of New Jersey about three years ago. So a number of these acquisitions have helped us bring excellent people into the business, grow our product portfolio and our skillset, and then bring them to market in a slightly different way. So that's been super helpful and we're going to continue to be, the fancy word is acquisitive, but we'll continue to be acquisitive if it makes sense for customers and partners and delivering on the vision.

Patrick Emmons:Awesome. Well, congratulations on all your success. Obviously Shelli, having worked there previously, and I remember when Relativity was another name and watching them grow has been a lot of fun. And so congratulations on your success. We wish you nothing but the best in the future, and thank you for being on the show today.

Shelli Nelson:Yeah, thank you Chris.

Chris Brown: Awesome. Thank you both. It was been my pleasure. Really appreciate it.

Patrick Emmons: So we also want to thank our listeners. We really appreciate everyone taking the time to join us.

Shelli Nelson: And if you'd like to receive new episodes as they're published, you can subscribe by visiting our website at dragonspears.com/podcast or find us on iTunes, Spotify, or wherever you get your podcasts.

Patrick Emmons:This episode was sponsored by DragonSpears and produced by Dante32.

About Patrick Emmons

If you can’t appreciate a good sports analogy, movie quote, or military reference, you may not want to work with him, but if you value honesty, integrity, and commitment to improvement, Patrick can certainly help take your business or your career to the next level. “Good enough,” is simply not in his vernacular. Pat’s passion is for relentlessly pushing himself and others to achieve full potential. Patrick Emmons is a graduate of St. Norbert College with a Bachelor of Science degree in Computer Science and Mathematics. Patrick co-founded Adage Technologies in 2001 and in 2015, founded DragonSpears as a spin-off dedicated to developing custom applications that improve speed, compliance and scalability of clients’ internal and customer-facing workflow processes. When he is not learning about new technology, running a better business, or becoming a stronger leader, he can be found coaching his kids’ (FIVE of them) baseball and lacrosse teams and praising his ever-so-patient wife for all her support.

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