1. What have you found most challenging as a CEO or executive of a large enterprise?

Keeping everyone across the organization aligned. It is a never-ending task that requires tremendous focus to achieve.

2. How did you become a CEO or executive of a large enterprise? Can you please briefly tell the story?

TL;DR I joined TeamSnap as an early engineer and through helping to grow the company was able to grow myself into the role of CTO, where I have happily served for the last six years.

3. How do you structure your work days from waking up to going to sleep?

Loosely. The first hours of my day are spent focused on dousing fires and coming up to speed with anything that happened outside of my primary timezone. From there I transition into a 4-5 hour meeting bonanza. I round out my day focused on various strategic projects and ensuring everything is calm before signing off later in the evening.

4. What's the most recent significant leadership lesson you've learned?

No matter how exciting and filled with opportunity a change may have going for it, not everyone is going to be onboard, and that is okay.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

Turn the Ship Around!: A True Story of Turning Followers into Leaders by L. David Marquet. It details the story of a sub captain receiving a last-minute ship reassignment and how he was able to empower his crew by ceding control and creating a much more engaged and successful team.

6. How do you build leadership capacity in a large enterprise?

challenging your team by bringing in peers who raise the bar, while still investing in them.

7. What is one meaningful story that comes to mind from your time as a CEO or executive of a large enterprise so far?

I think the key here is that every day in your company, someone is living one of those "meaningful stories" and it is our job to both acknowledge that, but also to embrace the moments that are fleeting and that it is what we do in aggregate that will have the most meaning.