Sean Brynes of Outlier: “The most important thing you can do is listen to your customers”

The most important thing you can do is listen to your customers. Talk to them if you can, watch their behavior and look for any kind of feedback they provide. Sometimes the customers themselves don’t know what is happening, but in aggregate their behavior is the best indicator you have for what is happening and […]

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The most important thing you can do is listen to your customers. Talk to them if you can, watch their behavior and look for any kind of feedback they provide. Sometimes the customers themselves don’t know what is happening, but in aggregate their behavior is the best indicator you have for what is happening and where opportunities might hide.


As part of my series about the “Five Things You Need to Be A Highly Effective Leader During Turbulent Times,” I had the pleasure of interviewing Sean Byrnes, CEO of Outlier. In 2005, Sean started a company called Flurry that disrupted the mobile analytics market, creating entirely new advertising business models for web entities. After selling Flurry to Yahoo! in 2014, Sean created a new company: Outlier. Using AI and advanced analytics, Outlier is breaking the mold once again — helping organizations dive into their deep data pools to elevate relevant and actionable data behaviors. In his free time, Sean acts as an advisor to early stage technology companies, helping them navigate the complex world of technology innovation.


Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I’ve always enjoyed doing a variety of different things, ranging from technology to art to public service. I tried a lot of different professions ranging from radio DJ, illustrator and software developer but I always found myself wanting to do more. Starting companies had a great appeal to me as I could not only do a wide variety of things everyday, but I could also create the kind of business that I wanted to work for — one that treats its employees like people.

I’ve been lucky as well, since my skills have followed some major technological waves. I was interested in mobile software in 2005 which led to the founding of Flurry, which became the largest mobile analytics company during the smartphone revolution and we sold it in 2014. I was interested in AI starting in graduate school, and finally started Outlier to apply those techniques to business data which has since rode the wave of widespread adoption of AI. Today, I’m the CEO of Outlier as well as an angel investor and startup advisory.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful toward who helped get you to where you are? Can you share a story?

There is not just one person, there are countless people that come to mind who have helped me along the way but didn’t even realize it at the time. For example, there was a man, whom I never met, who was an early evangelist of Flurry and wrote a magazine article about us based on his love of our product. That article was one of our first successful customer acquisition channels and helped the company get off the ground. There was a woman, whom I never met, who invited Flurry to present at the JavaOne conference because she loved our product. We won an award there and got more attention than we could have hoped for as a small company. Both of these people helped Flurry get started and I don’t think they ever knew the huge impact that they had.

I do think startup companies survive due to the altruism of their early customers and supporters and many of those are anonymous but critical to success.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. When your company started, what was its vision, what was its purpose?

I agree completely. Work and life are not two separate things, and people want to have purpose in their work that goes beyond a paycheck. If you can provide that, not only do you find it easier to hire great people but you make a company that is more resilient and focused.

When starting Outlier, I was looking for problems that were huge and getting bigger. I wanted to tackle one of the definitive problems of the next decade, and finding value in the quickly growing mountains of data being assembled is exactly that. Every company and organization has more data than they can ever explore by hand, and Outlier represents the future of using AI to find the insights hiding in them automatically.

However, startup journeys are hard and that vision along was not enough. For Outlier, my co-founder and I asked ourselves “What will make Outlier worth it?”. For all the stress, hard work and struggle there had to be more. We wrote down the 5 values (see them on our website) that Outlier would be built upon, and in doing so set an example to other tech companies on how to build a better company. Technology has a lot of problems, but by setting an example of how to do things better we hope to start solving those problems. I’m happy to report that it’s early, but we have already made strong steps forward.

Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share how you lead your team during uncertain or difficult times?

It is easy to lead a team when everything is going well, but true leadership is tested when things get difficult. For me, I have seen the dotcom bubble burst, the 2008 financial crisis and now the 2020 pandemic so I have had to navigate some very uncertain waters.

The first, and most important thing to do is to trust your team. Honesty and transparency are so important for building trust, as employees won’t trust you if you don’t trust them. However, it’s also the hardest thing to do because it means you are letting go of control. You have to trust your team to handle the bad news as well as the good news, and to trust you in return. It’s hard and it requires a lot of confidence to do, especially for first-time leaders.

You also need to connect with your team as people and not just employees. During the pandemic, I encouraged employees to take extra time for themselves. We’re all so focused on getting it right for our customers but we can’t do that and ignore our own personal health and wellbeing. I asked everyone to incorporate more sleep, exercise and personal care into their workday. I also asked everyone to see each other as people, and realize that emotions can run high so we need to give each other space and not let ourselves give into anger, frustration and conflict. Keeping your team together is important, but having them support each other is even more important as it gives everyone more strength to deal with life.

Did you ever consider giving up? Where did you get the motivation to continue through your challenges? What sustains your drive?

I think everyone considers giving up when things get hard, it’s a natural response. The real question is what keeps you coming back from the edge and continuing on.

For me, I enjoy the work that I do and the problems that we solve, but I truly love the teams I’ve built and the feeling that I get from working with them everyday. I can’t imagine anything else that I would rather be doing that would give me the same fulfillment.

When the future seems so uncertain, what is the best way to boost morale? What can a leader do to inspire, motivate and engage their team?

Employee morale is a fancy way of talking about “happiness”. The first thing you have to realize is that you cannot make another person happy, the best you can do is put them in a situation that encourages them to be happy. Many founders have burned themselves out by not understanding that.

What makes your team happy varies team to team and person to person. Some people love quietly working on complex problems, others love informal chats and lunches while others want the thrill of pursuing a deal. As a result, there is no single answer for a team or company. You need to spend the time to understand the people on your team and do what you can to support all of them.

The only general advice I have is to ensure everyone has a goal. During uncertain times, it can be easy to drift and lack direction. The most important thing you can provide is a clear direction and set of goals that everyone can work towards. These goals should not be impossible, but they should be hard so that the team can focus on execution towards them.

Finally, it’s very draining to motivate other people. The best favor you can do for yourself is hire self-motivated people so that you don’t have to worry about motivating them. It means you can save the energy and direct it in more productive directions.

What is the best way to communicate difficult news to one’s team and customers?

The first step to delivering bad news happens long before you have the bad news itself. You need to focus on building trust with your team on day one, by being transparent and open with them. If you only share a rose-colored view of the world with your team, any bad news will seem like a disaster when it arrives. Instead, if you share everything honestly the team will already trust you when you share bad news.

Direct and transparent communication is the best approach for conveying bad news. Delaying or avoiding sharing it will only make it worse, so you want to do it promptly. You also need to provide the appropriate context so the team can understand and interpret the bad news. For example, what if you are fundraising and an investor fails to deliver a term sheet after you told your team to expect it? Most of your team does not understand the fundraising process enough to understand what that means and how it might affect the company. You need to share both what happened, why (if you know) and what the likely paths forward will look like.

Most founders are afraid of sharing bad news in fear that their teams will take it hard and potentially leave for other jobs. In reality, people want to know that you aren’t keeping secrets from them and will trust you if you earn it.

How can a leader make plans when the future is so unpredictable?

As leaders, we always need to plan ahead with limited information. That means building plans that have scenarios built in, and different paths forward based on what happens along the way. While the market is not usually as unpredictable as it is today, leaders always need to plan for the unexpected so the tools and approaches are the same.

A great plan provides you with goals, multiple paths to achieving those goals and a timeline. In an uncertain market your goals might be less ambitious, your paths more numerous and your timelines more flexible but the plans will look the same.

The biggest difference is that you want to keep watch for any big changes that render your plan obsolete, or change the path you choose. In an uncertain world these changes will happen more frequently so you need to be on guard and constantly scanning for any warning signs they are coming.

Is there a “number one principle” that can help guide a company through the ups and downs of turbulent times?

That’s a hard question. If I had to choose one, it’s that you need to take risks. The only way to grow is to take risks, and those risks will increase the chances that your business will suffer. It gets much harder to take risks during turbulent times, which is why many companies stop doing so, but that only makes it more important.

You shouldn’t take irresponsible risks, but calculated risks are important. You need to play to win, not just trying to avoid losing.

Generating new business, increasing your profits, or at least maintaining your financial stability can be challenging during good times, even more so during turbulent times. Can you share some of the strategies you use to keep forging ahead and not lose growth traction during a difficult economy?

The most important thing you can do is listen to your customers. Talk to them if you can, watch their behavior and look for any kind of feedback they provide. Sometimes the customers themselves don’t know what is happening, but in aggregate their behavior is the best indicator you have for what is happening and where opportunities might hide.

The second most important thing is to challenge your own assumptions. You might have 20 years of experience in your industry, but the market today is unlike anything you’d seen so those 20 years of experience are not going to help. You have to be open to learning new things and letting the data take you to potentially uncomfortable places.

For example, Outlier has many customers whose businesses have worked the same way for decades. However, during 2020 they have seen their top selling products change radically from one day to the next and customer buying habits change even faster. These companies were open to learning from the data and operating in a new way, and as a result have adapted to the current market faster than their competition which has become a competitive advantage.

Finally, you cannot just try and hold on until things “return to normal.” Things may never go back to the way you remember them and waiting for that will hold your company back. You have to look forward with what you know today and build strategies that will carry you through today’s market and whatever is waiting on the other side.

How can our readers further follow your work?

LinkedIn: https://www.linkedin.com/in/sbyrnes/

Twitter: https://twitter.com/sbyrnes

Thank you so much for sharing these important insights. We wish you continued success and good health!


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