Driving Disruption: Rory Capern Of Redbrick On The Innovative Approaches They Are Taking To Disrupt Their Industry

An Interview With Cynthia Corsetti

At Delivra, smart email and SMS marketing software, we go back to this maniacal focus on what the user wants. Delivra has a very unique mix of clients, and our disruptive approach lies in getting incredibly close to our customers and understanding their needs in a deep way. This allows us to gain traction in that market, and build into markets that are highly strategic and also antithetical. We don’t necessarily have an interest in the markets where we see our major competitors, and we’re finding ways to satisfy and delight underserved markets that are driving a great deal of success.

In an age where industries evolve at lightning speed, there exists a special breed of C-suite executives who are not just navigating the changes, but driving them. These are the pioneers who think outside the box, championing novel strategies that shatter the status quo and set new industry standards. Their approach fosters innovation, spurs growth, and leads to disruptive change that redefines their sectors. In this interview series, we are talking to disruptive C-suite executives to share their experiences, insights, and the secrets behind the innovative approaches they are taking to disrupt their industries. As part of this series, we had the pleasure of interviewing Rory Capern.

Rory Capern is the Chief Operating Officer at Redbrick, a portfolio of disruptive, digital companies. As a former executive at Google Canada and Twitter Canada, Rory is a seasoned business leader with deep roots in technology who has worked for some of Canada’s largest and fastest-growing businesses. With a penchant for revenue and profit growth, and a passion for strategy and leadership, Rory has built a proven track record of building strong businesses and partnerships.

Thank you so much for joining us in this interview series. Before we dive into our discussion about disruption, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

I’ve been a technology person for a very long time. I spent about a decade working for large global tech companies, and I’ve always had a passion for Canadian tech. I had this incredible opportunity to learn from the very best in the world through Microsoft, Google, and Twitter, scaling technology businesses at a global level.

While my focus was primarily on Canada, I sat on Twitter’s global leadership team and also did a lot of international work at Google. That gave me the opportunity to practice in very high-performing teams for incredibly product-focused organizations.

I really wanted to bring what I learned in those roles home to the Canadian tech ecosystem, and my objective was to work for Canadian-headquartered technology companies to help keep them here. Applying my learnings from Big Tech, I was able to tailor them to the unique operational landscape of small and growing Canadian tech companies. What works for Google doesn’t work for anybody else, but I was able to take some of those principles and adapt them to the realities of the operating environment for growing Canadian companies.

My current role as COO at Redbrick is the perfect amalgamation of two things I love to do: M&A and working with operating CEOs of high-performing teams. At Redbrick, I have this incredible opportunity to work with our companies and help them deliver results. I also lead the corporate development function, which is about acquiring the next business for Redbrick.

What do you think makes your company stand out? Can you share a story?

Redbrick’s distinguishing feature lies in the composition of the partnership team. We’re all seasoned operators and business-first people with a genuine passion for growing companies. We’ve worked incredibly hard to build an environment that makes it easier to operate businesses once we’re on the other side of an acquisition.

Having spent the last 25 years doing this, I believe that the perspective you take as a business operator is different than that of a pure investor. You pick up a lot of highly applicable experience in the operating world along the way, particularly as it relates to building digital products and acquiring customers through marketing, but there’s also a common bond that we have with the CEO founders of the companies that we’re acquiring as business operators — and not as anything else.

Another thing that makes Redbrick unique is our shared services model. We provide our acquired companies with resources that are generally difficult to find and afford at their stage of growth. For instance, we have finance, people and culture, marketing, and creative teams that service all of our portfolio companies. At Redbrick, we’ve enabled the capabilities to help businesses grow faster and operate better while freeing up the time of incoming teams to focus on building and selling a better product.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

The first, and most important, is having a people orientation. Business is about people before it’s about anything else. I really take that to heart as a leader, and I make sure that I’m connecting individually with all of my teammates and focusing on people in the context of driving results. This has been a major contributor to my success.

The next is a genuine curiosity and passion for business. From the very beginning of my career, I was interested in everything. I went into strategy consulting because I couldn’t pick a major. Consulting provided me with the ability to work cross-functionally in multiple industries and satiate my appetite for learning about all of the different aspects of business. That experience helped me learn quickly and has been an important hallmark of my success.

Last but not least is a dedication to win-win business relationships. My hope is that by the time I’m ready to retire, I’ll never have done a deal where somebody felt like they got the short end of the stick in the process. I’ve learned over time that the opportunity to continue to do business is extraordinarily valuable and that always giving everybody a good deal is very important. Whether that’s with my peers at work, with my boss, or with the businesses that we’re acquiring, it’s crucial to ensure all parties believe that they’re winning by virtue of our work together.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.

Some of the hardest decisions are related to resourcing and allocation. We’re in a unique position at Redbrick where we have several high-performing business units. We try to take an infinite budget approach to any of our businesses, but the reality is that there’s always a trade-off, and it’s not money — it’s time and people.

The essence of leadership lies in the ability to objectively evaluate opportunities, even when they appear uniformly positive. It’s crucial to articulate a coherent rationale for investing in individuals, businesses, products, or projects to ensure decisions are viewed as deliberate rather than arbitrary.

We’re fortunate to have extraordinarily talented individuals dedicating significant effort to building great businesses. When faced with choices between portfolios or products, the leadership lesson that I’ve picked up along the way is the importance of being very transparent about the calculus behind those decisions.

Ironically, it’s a lot harder to do that in an environment where businesses are all thriving, as opposed to an environment where there are clear winners and laggards. That sort of financial edict in the latter scenario makes it much easier to make a good and successful decision.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Let’s begin with a basic definition so that all of us are on the same page. In the context of a business, what exactly is “Disruption”?

Disruption, in the context of a business, is an unexpected force acting on a market. It occurs when something happens to a business that would not otherwise have been foreseen.

For example, take the advent of the web. Magazine and newspaper publishers and TV producers did not see this disruption coming, and it has had an enormous impact on those industries. The disruptive nature lies in the fact that it would have been very difficult to predict in advance the inventions that enabled the internet as we know it today.

Smartphones were the next major disruption in our time, upending the entire internet economy. Now, the disruption we’re all contending with is artificial intelligence. This disruption has come from advancements in computing capabilities that often go unnoticed by the business community, until they land. In other words, predicting these developments would have been quite challenging, which is what makes it so disruptive.

How do you perceive the role of ‘disruption’ within your industry, and how have you personally embraced it? Is it a necessity, a strategy, or something else entirely in your view?

Few industries experience disruption as often or as intensely as technology, which seems to experience it every six to 18 months.

If we look at the AI race playing out right now between Google, Microsoft, OpenAI, and Facebook, disruption is a strategy. These organizations have been doing the science and research into unlocking these capabilities for many years.

For most businesses, disruption is hard to predict. If you’re not an extraordinarily well-capitalized business with tremendous intellectual property advantage and the ability to see and spend around the corner, disruption is a muscle. It’s a capability that we need to be able to respond to, with the assumption that disruptions will occur every decade. The goal is not only to develop groundbreaking technology but also to establish a culture, an organization, and an operational framework that can adapt and evolve amidst disruptions, ensuring its survival. In other words, the strategy is flexibility.

Technology inherently evolves over time, with occasional monumental shifts that redefine the landscape. This is the second category of disruption, and it has become a part of the tech industry. What makes tech different from many other sectors is the need to set up the house so as to be able to rapidly adapt to those changes. Every industry has to do it, but not as often as the technology industry.

What lessons have you learned from challenging conventional wisdom, and how have those lessons shaped your leadership style?

One of the most important lessons I’ve learned from working in incredibly fast-moving companies pertains to the underlying culture.

One essential element of cultivating a culture that challenges conventional wisdom is fostering candor within a team. Many really great ideas are left on the drafting room floor because people either don’t have the courage to share them or are not provided with the environment to air their opinions. As a leader, it’s important to me to create an environment that nurtures psychological safety, enabling people to express dissenting views or share ideas comfortably.

It’s also important to remember that ideas can come from anywhere. Balancing a senior role requires the art of receptiveness, or being open to fresh ideas from individuals regardless of their experience or seniority. That’s how innovation happens — when conventional wisdom is challenged.

Next, I’ve learned the importance of intellectual honesty — acknowledging that what we’re doing today might not be the best and being open to the possibility that a new idea could offer improvements. Often, we don’t want to hear a new idea because it’s too much work, too much of a threat, or we’re too attached to the way things are happening now. That’s where ideas die. The ability to take a new idea and consider it thoroughly and fairly, coupled with a consistent set of criteria to evaluate its quality, has shaped my leadership style.

Disruptive ideas often meet resistance. Could you describe a time when you faced significant pushback for a disruptive idea? How did you navigate the opposition, and what advice would you give to others in a similar situation?

I spearheaded Google’s rollout of programmatic advertising in Canada, which was a very forward market in its adoption of this type of advertising technology.

When launching something disruptive, it’s important to thoroughly understand the needs of all the people around the table. I had to gain a deep understanding of the operating environment, business model, and objectives of the customers or the partners. I needed to effectively convey the narrative about why programmatic advertising was more efficient from an operational perspective, and how it was destined to evolve into the dominant method of media buying that it is today.

Not only that, I had to sell that idea to a large publishing community in Canada that was reticent of Google at that time but also recognized the necessity of adapting to make the web work for their business. To navigate this, I had to take the emotion off the table and highlight the value that could be driven by programmatic advertising.

My advice to others is to stop talking about the big, innovative idea and strip it down to the immediate benefits that can be delivered. Then, articulate the value that comes behind it. The ability to keep things simple and value-driven is where the best innovations come to life, and why some great innovations don’t make it. They’re simply too complex for people to understand and implement.

What are your “Five Innovative Approaches We Are Using To Disrupt Our Industry”?

I’ll answer this in the context of Redbrick and its portfolio companies.

At Shift, an app-integrated browser, we have a maniacal focus on the user and their needs. The prevailing logic in the browser space is that the best browser is no browser at all. The goal with most browsers is to strip down the functionality from the software. but what we’ve found is that there are large groups of users who need help and who are getting value from that functionality. By focusing on user needs and building products that satisfy those needs, we’ve been able to grow a significant product. Our approach to understanding user needs leverages best-in-class tools, and we’re constantly figuring out what features provide the most user value. The approach is disruptive because we focus on how to serve a market in a contrarian position to other browsers.

At Leadpages, a lead generation platform, our innovative approach is a relentless focus on one fundamental question: “What’s our job?” Prior to its acquisition, the Leadpages product focused on providing landing page conversion. Now, we’re building an entire suite of services that satisfy lead collection and conversion for our clients, expanding that ecosystem dramatically and allowing us to drive growth. The job to be done is the innovative approach, and building services, capabilities, and features within the Leadpages ecosystem allows us to serve a higher-order need than what the product was originally designed to do.

At Delivra, smart email and SMS marketing software, we go back to this maniacal focus on what the user wants. Delivra has a very unique mix of clients, and our disruptive approach lies in getting incredibly close to our customers and understanding their needs in a deep way. This allows us to gain traction in that market, and build into markets that are highly strategic and also antithetical. We don’t necessarily have an interest in the markets where we see our major competitors, and we’re finding ways to satisfy and delight underserved markets that are driving a great deal of success.

At Animoto, a cloud-based video creation platform, our innovative approach is to focus on the output. We’ve asked ourselves, what are people doing with video and how can we take a contrarian position to our competitors? Within the realm of video production, the aim is to empower the everyday user with access to top-tier video production capabilities. What does the end result need to look like? Even if our customers aren’t aware of what the possibilities are, we’re building our product and our value proposition around “the art of the possible.” Simply put, we’re defining what is possible.

At Redbrick, a portfolio of disruptive, digital companies, our innovative approach is our focus on people. We do two things incredibly well: build a high-quality culture where people want to do their best work and build our business around that value proposition. Many companies talk the talk, but don’t walk the walk. At Redbrick, we’re taking strides to build a business that takes care of its people, creates a great environment to work in, and gets excellent results in the process. The innovation is in the execution behind a culture-first strategy that wins with amazing talent.

Looking back at your career, in what ways has being disruptive defined or redefined your path? What surprises have you encountered along the way?

Given the vantage points I’ve had along the way in my career, one of the things I’ve been surprised and delighted about is Canada’s significant role in the global tech ecosystem. Our capacity to innovate and test disruption positions us as a key player.

As a firm launching disruptive technologies, there’s always a risk of failure. If it’s a high-profile flop, it can have very dramatic consequences on the overall business. As someone who has led large Canadian tech teams, the narrative around disruption is that we can use Canada as a testing ground for disruptive technological innovation that allows us to work within a highly innovative community.

Given the size of the Canadian market, a US-based company with a global footprint could double the size of its Canadian operations without denting its global revenue.

The commercial success of the business unit is not the story. The story is about how to test products, innovations, processes, and approaches within the Canadian market, with this highly innovative community of other business leaders who all intend to do the same thing.

Canada has been a very safe place to test disruption in a lab-like environment and ship it all around the world. There are significant opportunities and markets that don’t enjoy these perfect conditions for petri dish experimentation, and we can use our own market as a testing ground. As a technology person in the Canadian market, I’ve often been over-fed for resources. I’ve been given a lot more rope and risk in the context of being able to execute because it’s known that what we do in Canada can have significant returns in other parts of the world.

As I work for smaller businesses, the same is true to some degree. It’s a huge benefit to be able to test disruptive approaches off the radar of the US market. We like that we’re not always in the spotlight, but we’re still moving yardsticks down the field dramatically.

The third leg of the stool is people. Canada has exceptionally good talent, and we can fight and win for that talent, because of this incredible country that folks want to live in.

Beyond professional accomplishments, how has embracing disruption affected you on a personal level?

Disruption has kept me curious about what’s next. You can’t get lazy in a disruptive market. That means I’m constantly facing new opportunities and challenges, which keeps things fresh. I’m extremely motivated to continue to push because it’s never boring and there’s a lot to learn and anticipate. The ability to think about products in a disruptive sense is both rewarding and challenging, so it keeps me sharp. I love what I do as a result of a constantly changing canvas to paint on.

In your role as a C-suite leader, driving innovation and embracing disruption, what thoughts or concerns keep you awake at night? How do these reflections guide your decisions and leadership?

I think a lot about resilience around disruption. It’s difficult. It requires people to think deeply and differently. Establishing a resilient culture capable of withstanding disruption or daring to anticipate market trends and become the disruptor requires a foundation of remarkable strength within the culture itself. This ties back into what we’re trying to build at Redbrick.

Without a team of people who are extremely passionate, motivated, and united in carrying out this type of work, it’s easy to give up. The companies that don’t succeed are the companies that quit early. A core aspect of what I do as a C-suite leader is building resilience within the business, team, and market. As I mentioned earlier, it’s about people before it’s about anything else. We must foster an environment where individuals can think innovatively without being held back. We must also doggedly pursue the opportunities that team members have pinpointed as potentially disruptive or responsive to a disruptive market dynamic.

In business, it’s necessary to have excellent people who are bought into what they’re doing and who are happy to do it — and that’s hard to do.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

If I could lead a movement, it would focus on enhancing objectivity within our community and empowering individuals to think critically and autonomously. This movement would encourage individuals to engage in discussions and listen to multiple sides of an argument without resorting to insults or succumbing to fear, fostering independent thinking and resilience against opposing opinions.

In my view, this has the potential to bring the most amount of good to the most people, especially during times when critical thinking skills appear to be lacking.

How can our readers further follow your work online?

Visit Rdbrck.com to learn more about the great work we’re doing at Redbrick.

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.