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What I learned at my first Cloudflare Retreat


4 min read

For the last seven years, Cloudflare has taken the entire company off site for a few days at the end of the year for a company retreat. Back in 2010, this meant five people from the San Francisco office. This November, we had 453 employees from our San Francisco, Singapore, London, Champaign (Illinois), New York City, Washington (DC), and Austin (Texas) offices spend time together in Monterey, California.

Knowing that so many teammates would be coming in from all over the world, we used the days leading up to the retreat to hold global team meetings, conduct a session of our home-grown Making Great Managers workshop, and brought in Valerie Aurora from Frame Shift Consulting to lead Ally Skills workshops for the entire company.

On Thursday, buses departed from Cloudflare headquarters and took us all down to Monterey. Our CEO, Matthew Prince, delivered opening remarks over lunch. During his talk, we learned about the imminent acquisition of Neumob, his thoughts about growing pains and how to successfully scale, and were reminded that we are at our best when we are inclusive of everyone. We reflected on how far we’ve come and got an inspiring glimpse of where we are headed. I think we were all amazed to see how big the company had become when we are all gathered together in one place.

We spent the next few hours focused on our professional development with a few Harvard Business School professors. (Our founders, Matthew Prince and Michelle Zatlyn, met at HBS and actually started Cloudflare as a class project!). Four professors from Harvard Business School led the group through case studies around negotiation skills, using jazz as a metaphor for creative and innovative organizations, and successful business models.

Michelle brought the HBS professors on stage at dinner, and we heard some unique tidbits on the company’s history and early days. We learned that Matthew had a ton of business ideas in school but it wasn’t until he pitched Cloudflare to Michelle that she felt it was “a business she’d be proud to work on.” We also learned Professor Tom Eisenmann became their advisor while on a class trip to Silicon Valley in January 2009. Matthew and Michelle cornered him at the bar in the Sheraton in Palo Alto and wrote the business plan on the back of a napkin. Tom already had a full roster of students to advised but agreed to help them on one condition: they had to enter HBS’ business plan competition. Well, they did, and as Tom predicted, they won!

While we ate, Shawn Vanderhoven from The Wiseman Group led us in a discussion around leaders who amplify their teams to ultimate performance. Festivities continued late into the night with groups huddling around fire pits, enjoying a cool evening on terraces and conversing at the hotel bar.

After breakfast the next morning, the group was given four options for activities: biking, hiking, kayaking or visiting the Monterey Bay Aquarium. It was such a treat to be outside doing something active and interesting with coworkers - many from other teams and other offices.

Three weeks later, I'm still buzzing. The retreat fed the mind, but also the soul. The insights learned were super valuable, and the tools we were given will absolutely help us operate at a higher level. But I also really appreciate that we prioritized connecting with each other. That's often undervalued (if not completely overlooked), especially in companies at a similar size and stage.

It's easy to see why this is case. Many companies at our scale might view the activities as frivolous; that they're just too big to make something like this happen; that they can't keep operations running smoothly to have the entire company away at the same time or for that long. And while I hear these concerns, I'm grateful we were able to figure it out. Because you can't put a price on strengthening the ties that bind an organization.

That isn't to say that there wasn't a fair amount of pre-planning involved. Our SRE and Customer Support teams all took shifts to ensure our network operations were running smoothly and that our customers received the same high level of support they are used to. It took coordination, planning, and great work ethics but we proved this type of event is quite achievable.

When Matthew talks about what he looks for when hiring people, he looks for curiosity and empathy. The company retreat captured that—we were able to get away from our ‘regular’ jobs and learn a few new things. And by having these shared experiences with our coworkers, we now know each other better and are more empathic. This retreat was a great way to realize those values.

The goal wasn't really to "disconnect”; the train still needs to keep moving after all. But the change in scenery (and its beauty) and putting emphasis on shared values, where we came from and where we're headed made it possible to connect in meaningful ways.

We are already planning for next year, and have a few ideas on how to make it even better. Since we are an engineering-driven company, we’ll be sure to have some thought leadership activity around how to solve the biggest problems facing the Internet. We are thinking we’ll have everyone answer at least one support ticket before they leave :) We loved the beautiful setting in Monterey - and may even make it longer! I simply cannot wait!!

If this sounds like somewhere you’d want to want to work, check out our jobs page. We are hiring in all of our offices around the world.

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