Judges Spotlight

Ask a Webby Judge: Jerry Colonna, CEO and Co-Founder, Reboot.io

Right rail, webby 24 final entry deadline

5 questions with Jerry Colonna, CEO and Co-Founder, Reboot.io, and a new member of the International Academy of Digital Arts & Sciences, reviewing the 24th Annual Webby Awards!

The Webby Awards is excited to welcome a slate of new experts to the International Academy of Digital Arts & Sciences (IADAS): the 2,000+ member body of Internet experts and luminaries who judge work entered into The Webbys each year.

Meet new Jerry Colonna, CEO and Co-Founder of Reboot.io, and a new member of the International Academy of Digital Arts & Sciences, judging the 24th Annual Webby Awards!

As the creator of an executive coaching and leadership development firm, Colonna has been dedicated to the notion that better humans make better leaders for nearly 20 years. Prior to his career as a coach, Colonna was a partner with JPMorgan.

We talked with Colonna about what expertise he brings to the Academy, what recent project on the Internet caught his attention, and more.

Read our Q&A below, and enter your work before the final deadline: Friday, Dec. 20th!

1. Why are you excited to join IADAS as a Webby Awards judge? What particular expertise or vantage point do you bring to the Academy?

I feel like a bit of an elder. As part of the team that developed one of the first ad-supported, web-based initiatives (Techweb, launched in 1994), I’ve watched with delight as the things we envisioned back then (“Wait, folks are going to be able to order lunch from the Internet?? No way.”) have come true.

Later, in my career as an early investor in some of the most important Internet-based efforts (think: Geocities), I’m proud to have been a part of a process that has made the world smaller and more connected. I have a feeling, and a hope, that that experience will be of service to the Academy.

2. Why do you think being a part of The Webby Awards community matters?

Because community, in general, matters. That which we have wrought has also exacerbated disconnection and polarization and community—especially community based on tolerance and openness—is the antidote to divisiveness. In a sense, I feel I have a responsibility to help heal and this feels like a wonderful way to do that.

3. What trend or emerging technology are you most excited about in your field of work?

As a leadership coach, I’m especially happy to see a broad movement and recognition of the importance of building psychological safety and inclusivity into the businesses and organizations which will lead the way in the next iteration of our uses of technology.

4. What specific project or service caught your attention on the Internet recently and why?

The wider-spread use of technologies and services that enable and enhance remote work. 

5. What’s your favorite Twitter account that other people haven’t heard of?

My favorite Twitter account that few folks have heard of is A Slice of Brooklyn… it makes me miss my hometown.


Make sure our judges see your work. Enter the 24th Annual Webby Awards before the Final Entry Deadline on Friday, Dec. 20th!

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