The Smartest People I Know #2: Meet Tope Awotona

Welcome to another edition of The Smartest People I Know: my monthly series here on LinkedIn, sharing the wisdom of some of the incredible people I’ve met on my career journey. 

In my past roles at companies like Hootsuite and Vidyard, and today as president and COO at Berkshire Grey, I’ve had the privilege of meeting — and learning from — some of the sharpest minds in business, leadership and tech. I thought it was about time to share those takeaways with you. Follow along for a regular roundup of insights, inspiration and thought-provoking ideas from the smartest people I know. Let me know what you think in the comments — looking forward to getting the conversation going.

Meet Tope Awotona

Tope Awotona is best known as the Atlanta-based founder and CEO of Calend.ly, the popular scheduling tool has served 30 million-plus users this past year by revolutionizing a task everyone hates – coordinating calendars. But his journey to success (like many entrepreneurs!) has been full of fascinating starts, stops and U-turns along the way. The lessons Tope has gleaned through his childhood in Nigeria, early sales jobs, bumpy start-ups, and growing a game-changing business are truly a source of inspiration. Recently, I was lucky enough to speak with him about some of his biggest career takeaways. 

What was a little moment in your life that ended up changing everything?

I joined a startup in 2007 and during my onboarding, I heard the company's founding story, directly from its founder. It ended up inspiring me to pursue entrepreneurship myself, which has changed the course of my life.

What's the most under-rated skill for leaders?

Empathy. It's not quite under-rated, but leaders can never have enough of it.

The secret to fulfillment in work (and life) is ...

Maniacal prioritization. 

What do you wish you could tell your younger self?

Always be grateful and celebrate the wins. 

What's the single most impactful book you've ever read?

Outliers by Malcolm Gladwell.

Who's the smartest person that you know?

My mother. She taught me the importance of generosity, having a plan and acting with urgency. 

Sum up your career or business philosophy in seven words or less.

When there's a will, there's a way!

#OneBigIdea

“Stay curious, and take calculated risks.”

—Tope Awotona

What I’ve Been Reading (and Writing!)

Making AI’s Influence Count

This Technology Review story posits five ways that artificial intelligence can be a greater force for good, in 2021 and beyond. Bias in AI programming is nothing new, but I appreciated seeing tactical steps to combat this, from reducing corporate influence in research to refocusing on common-sense understanding.

Getting Comfortable “Handing Over the Mic”

As many of us find ourselves working in remote settings, opportunities for mentorship don’t always bubble up naturally these days. This Inc story was a great reminder that leaders need to be more direct than ever to help develop and build-up their team. One easy way? Set up explicit opportunities for promising junior employees to get face-time with top-level leaders … even if it’s over Zoom.

What’s Next in Fulfillment Tech

One thing I love about my job: it sometimes feels like a sneak peek of the future. Covid has accelerated the evolution of smart robotics, logistics and the supply chain by a decade in the matter of just a year. I wrote about what’s next for fulfillment technology for Entrepreneur this month. 

Reader Feedback

I recently asked my LinkedIn followers about the worst career advice they didn’t take — and the responses flowed in. In particular, this comment from Philip Edgell, president of Vantage Technology, stuck with me:

You should be more like <insert person here>. Developing my own style and personal value prop is the most valuable work I could have done, instead of inauthentic mimicry.

Thanks so much to Tope Awotona for sharing his words of wisdom with me — and thanks to you for reading. If you found The Smartest People I Know interesting, feel free to follow me on LinkedIn ... or, better yet, share this with the smartest person you know. More to come next month!