Jason Silver of integrate.ai on driving business growth through people and the importance of never settling

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Jason Silver is the Chief Operating Officer of integrate.ai, a leading Canadian AI-powered enterprise data and software platform that dramatically improves the quality of interactions between people and businesses, delivering more profitable growth and happier customers. Prior to joining integrate.ai, Jason was one of the first Canadian employees at Airbnb, where he led sales and operations as Territory Manager for Canada, the Midwest, and Eastern United States. Jason has also founded two of his own start-ups, both focused on helping small to medium sized businesses leverage technology to grow. He holds a Master’s degree in Biomedical Engineering from Carleton University and a Bachelor’s degree in Electrical and Computer Engineering from the University of Ottawa.

Looking back five/ ten years, where did you think you’d be by this point in your career? How did you get here?

I’ve never been a long term planner when it comes to my career. While I’m a pretty structured thinker, I have never mapped out the points that I wanted to hit over a certain period of time. For me, it’s about following a north star around the things that I’m passionate about and pairing that with a priority list that is as much about my life as it is about my career. That north star encompasses two things: building things that haven’t existed before and helping others achieve things that they had no idea they would be able to accomplish. I knew that if I focused on that and stayed true to my priorities, while not paying so much attention to what other people thought I should be doing, I would get to a good place. When I think about the legacy I want to leave however; it is solely around the things that I can do to help others achieve their goals. Ensuring that integrate.ai is financially successful is very important, but for me, that is not enough.

As integrate.ai’s operations leader, how are you thinking about growing the business?

When people think about growth, it is easy to jump right into hard business metrics, but I try to focus more on the people who are behind those metrics than the metrics themselves. The people who we hire and the space that we give them to help build the company in ways we haven’t even thought of yet is what I think about first. You can’t hire great people and put them in a shoebox. You often get the best outcomes by giving people an outline of what needs to be accomplished and letting them go figure out the way to get there. Following conventional tactics and strategies immediately turns you into an average company. For some things that is fine but for others it is not.

Airbnb taught me that growth and business metrics are just a confirmation and realization that you are on the right track based on the goals, motivations, efforts and abilities of your people. I’m an engineer by training so shifting my own mindset around that was hard. As we grow revenue, we need to be thinking about how the team needs to change to support that growth and how we as a company in turn, need to support those people so that they can be successful and continue growing themselves and their impact.

What is the biggest misconception about AI and what it is going to do to the business world?

I’ll say two. The first is that AI is evil and the second is that AI is magic. On the first, we need to remember that technology is not inherently good or bad. What we need to do is set ethical boundaries around the use of AI, just like how there is an ethical way to use the internet. AI is not evil in itself. Society needs to care about how to properly deploy this technology, but the technology itself is not the problem.

AI is also not magic, it’s math. AI looks at how things were done in the past and makes statistical inferences about how likely something is to happen in the future. While that is an oversimplification, we are not yet in a place where we have general artificial intelligence that replicates the human brain. I don’t envision a world where AI takes over all of our jobs. The reality is that people need to still be involved in work. Yes, there are repeatable tasks that can be automated by AI but I see that as a way to liberate people from mundane work. Many of us don’t realize how much we already use AI. It is already used in things like our favourite streaming services or social media sites.

You’ve had quite an industrious career to date. Have there been any points where you’ve felt stuck and didn’t know what your next move was?

Having followed an unconventional path, I think I’ve had a few successes, but I’ve also had many failures. The most stuck that I’ve ever felt in my career was when one of the start-ups I was trying to build failed. We had raised some money, a number of people were involved and we failed. That was one of the lowest parts of my career. I felt more useless than I did stuck, but that was an important experience. I got over that by focusing on what I learned from the experience and by having great people around me. In my opinion, failures should be thought of more as learning opportunities because if you don’t find yourself failing enough, you likely aren’t pushing hard enough. I’ve also realized that successful people seldom get to be successful on their own and having a strong group of people around who lifted me up when I failed was vital. Asking for help when you need it is important.

What are some of the important business lessons that you had to learn the hard way, how have they made you more successful?

Any great lesson is locked in through failure. When you do something right, you only learn one way of doing it and that success might be a result of external forces. When you fail, you’ve likely banged your head against the wall a few times and run into a bunch of roadblocks that teach you what not to do in the future. It’s ultimately about finding the transferable elements of your successes and failures that apply to different situations. You don’t get that by being right all of the time, or at least I haven’t. I had to go through a big failure to teach me about how to deal with adversity and that gave me a lot of power to start prioritizing the right things. The other is about how focused you need to be on the long term success of your people. It is often easy to get people to do things in the short term, but that usually results in things like burnout and ultimately compromises long term success.

What is the one piece of advice you would give to someone in the workforce today to get ahead and find work that is fulfilling?

Don’t settle. People often compare themselves to the trajectory of others and if you do that, you are mapping yourself to the average. If you look at a group of ten people and say you want to be like them, you are immediately working from the average of that group. If you have a goal that you want to accomplish, go work towards achieving it. Being financially successful and loving your job is possible, but not if you simply choose to settle for what is in front of you. You can choose where you work and where you spend your time and it is your priority list that determines those things. If you prioritize money over a job that serves a broader personal or societal impact, you should be happy because you chose that set of priorities. On the flip side, if you haven’t actively made those choices, you’ve likely settled without knowing it. Average outcomes are achieved by taking the average path and the road of least resistance. If you have a hard or unique goal in mind, it is likely to be uncommon by definition and so you are selling yourself short the second you start comparing against averages. Be willing to make the sacrifices and trade-offs against your priorities necessary to achieve something remarkable.

Aubrey Chapnick