It’s easy to write off corporate retreats as an obligatory series of meetings and tired speeches, but Cloudflare’s retreats are uniquely engaging, personalized, fun, and inspiring. Having grown with Cloudflare over the last year (I started just before our 2017 retreat), I wanted to share some of my experiences to highlight Cloudflare’s incredible culture.

The office was buzzing with different languages and laughter as people hugged and shook hands for the first time after working online together for a year or more. Everyone’s Google calendar looked like a rainbow as we each mined for white space to squeeze in those coveted 1:1s, all-hands presentations, and bowling offsites with our global colleagues.  The buses and Google chats felt like summer camp, with people claiming pride around their table numbers and sharing group photos.

Cloudflare team in Napa

The first big theme of the retreat was reflecting on the positive company culture and achievements over the last year. Zack, who works on product strategy, and I chatted at a breakfast table about how good it feels to be surrounded by hundreds of colleagues we genuinely respect, admire, and enjoy working with. We talked about how proud we are that Cloudflare builds products that authentically make the Internet a better place. We'd seen several Internet users donate tens of thousands of dollars to Girls Who Code to be first in line for our recent Registrar product launch.

Members of Cloudflare's Global Afroflare group

Throughout retreat, the product and engineering teams were busy launching the 1.1.1.1 app and Spectrum for UDP product. The customer support and SRE teams took selfless night shifts to cover 24/7/365 support lines from one single time zone, while other teams delivered donuts to perk them up. Team members across sales and marketing sparked conversations about better ways to share best practices, experiments, and wins across regional offices.

Members of Cloudflare’s Global BDR team bowling outing

It was eye-opening to connect with different team members about why they joined Cloudflare in the first place. Greg, our sales leader in the central region, talked about the family considerations that played into his decision to join the Cloudflare team. Given that he lives in Chicago and has worked at larger companies prior to his transition, taking a remote sales leadership position at a company with less brand awareness in the Central US region certainly offered up some risk but one that he and his family felt was worth taking. Having been here now for several months, he remarked on the infectiously warm culture, impressive product innovation, and his confidence that the decision was the right one.

Members of Cloudflare's Global Proudflare group

The second big theme of the retreat was seeing that Cloudflare fosters an environment for employee development. Every employee had a chance to select and participate in break-out sessions including financial literacy, mindfulness, whiteboarding, speed reading, mentoring, lock picking, and how to be a better writer. I chose “Improv: Think Quickly on your Feet,” (a soul-hugging, hilarious session which still hasn’t left my mind), and the Harvard Business School case study called “Dealing with Hot Issues Without Getting Burned” by Professor Mike Wheeler and award-winning journalist and executive media coach, Jeff Ansell.

Emma, Alexander, Shannon, Mustafa, and two Bats Improvisational Comedy Coaches pretending to be chameleons after the Improv session

The HBS pre-reading was a case study on two companies implicated in the death of several consumers after using their products. As I walked in, Matthew Prince, our CEO, said, “This is a really special session.” He reflected on how taking this particular course during his time at HBS better prepared him for challenging media interviews about Internet privacy and due process of law. I don’t want to give away the secret sauce of this session, but I will recommend everyone take it if you ever have the chance. Having learned from an HBS professor, I felt that Cloudflare’s retreat was like a mini-MBA in a day.

Nicole from our Office Operations team selected the session called “Visual Communication through Whiteboarding.” She reflected on how it can be hard to convey new ideas through words, and that the whole point of the class was to explain complicated concepts through simple drawings. The instructor taught them how to storyboard and visually communicate business ideas like an app or invention. Nicole said she partnered with a colleague she’d never met before, and “we pretty much instantly understood what the other was trying to convey through drawings.”

Icons created during Nicole's Whiteboarding session

Mickie from our Austin engineering team took the session called “Boost Your Productivity through Speed Reading and Memorization.” Reflecting on the course, she said, “I have a keen ability to immediately forget names right after I’m introduced, and with 760 new faces and names at Retreat, I felt like I needed a masters course in information retention. So I was particularly excited to attend [this session]. We started by evaluating our reading speed and measuring it again after learning tricks to improve reading speed and comprehension (you can’t improve what you don’t measure after all!). We also learned mnemonics to remember information, and by the end of the session, I confidently remembered the names of an entire group of co-workers, making it easier to stay in touch in the future.”

Aliza, who heads up our APAC region, attended the Harvard Business School case study session called “Mentoring and Talent Development.” She shared, “The mentoring session was not at all what I expected, which was half the fun! We read a case study about an employee who was a fantastic salesperson and built up a strong division for Morgan Stanley in an industry where the bank had been failing, but who violated many cultural norms and annoyed most of his colleagues. We were each tasked with determining whether to promote or fire the employee (no half-measures allowed).

According to the professor, usually the room is split, but our group was around 60% fire, 40% promote. We spent most of the time in a healthy debate, with various individuals sharing their perspectives and the professor giving us additional data and asking provocative questions along the way. It was a really engaging session which got each of us thinking about what the bank should value most and how that might apply to our own situations. One of the key lessons was that things would never have come to such a difficult point if the protagonist's boss had coached and mentored him properly along the way (another takeaway for each of us). As with all sessions, it was great to meet other people from Cloudflare with whom I'd never interacted.”

The third big theme of retreat was having fun. We work hard every day, and Cloudflare does a great job of creating an environment for employees to unwind and have fun. Introverts and extroverts alike found ourselves bonding with people from all corners of the globe given the cross-functional seating arrangements and wide array of activities. I met folks from the Platform Engineering team in Austin, Technology team in Poland, Policy team in Cyprus, and beyond. I kayaked for the second year in a row with a friend from my onboarding class. We found our kayaks stuck in a marsh at one point, and I was impressed by his navigation skills as we chatted about his exciting work transition from London to Singapore. I had dinner with one of our engineers in Nairobi who previously attended a coding bootcamp and now works on the main Cloudflare website; we bonded over our love for ugali and nsima. I also learned about the extensive world of art collection from one of our legal team leaders, who reminded me how important it is to spend money on art made by marginalized folks who often receive less funding for their work. I love that Cloudflare’s retreat is a time for depth, not surface-level conversations.

Group of Cloudflarians hiking through Napa

It was also inspiring to see how engaged the executive team was with employees across the company. I got into a conversation with our CTO, John, at one point, and asked how he and our CEO, Matthew, originally met. John mentioned they were both speakers at a conference, and they each individually sought the other out as someone interesting to follow up with. Years later, it was clear throughout the retreat how much mutual respect the entire executive team shares. As an individual contributor, it’s important to see that our executive team genuinely collaborates, inspires, respects, and has fun together. This type of energy permeates across the organization, causing a positive ripple effect on the overall culture.

On the final day of retreat, as we bussed across the Bay Bridge into San Francisco, buzzing with happy conversations, we passed one of Cloudflare’s billboards from our first offline advertising campaign. It was heartwarming to see our cofounders, Matthew and Michelle, smile and laugh at the sight.

Michelle, Matthew, and Michael passing Cloudflare's billboard on the bus ride home

The annual retreat really gives Cloudflare a strong foundation, which employees build upon throughout the year to help make the Internet a safer, faster, more magical place. I would be silly not to mention that we’re hiring. Visit our careers page and come join us so you can attend next year’s retreat!

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.

The team (now 20) loaded in a bus to head to Murphys, CA on Thursday. I had suggested we watch "The Descent" on the ride up. Somehow Michelle was convinced it was an inspirational film about people surviving getting stuck in a cave. For those of you who haven't seen it, it's not exactly that.

We had a great dinner at Angelo's Steakhouse Italiano which was very good and the staff was a lot of fun. Sri only had to leave once during dinner to fend off a DDoS attack.

The night ended with karaoke at a local in Murphys where we learned that we are much better at making the web faster and safer than we are at singing or playing pool.

The next morning the team loaded back in the bus to head to the Moaning Caverns. If you've ever been on a cave tour where you walk along a well lit path with railings safe for school groups, this wasn't that. Instead, it started with getting suited up for a rappel down nearly 200 feet into the cave.

The guide's advice that you "never let go of the rope" was punctuated by the large pile of at least 30,000 years worth of fossilized bones piled directly below the hole we were rappelling into.

Chris here is hanging about 160 feet above the cave floor in a cavern large enough that it could hold the Statue of Liberty.

Matthieu's rock climbing experience made him a natural.

We don't have any pictures of what happened next because the guides advised us if we brought cameras in they would likely get crushed, smashed, scratched or broken. That wasn't exaggeration. Over the next several hours we made our way through chambers and tight passages like the Roach Motel, the Meat Grinder, the Guillotine, and the Birth Canal. To give you a sense, this is a photo from the cave's website showing someone emerging from the Meat Grinder.

When I first saw the photo I thought it couldn't really be like that. I was wrong, it is exactly like that. We squeezed through holes I wouldn't have thought I could ever fit through. I'm a little clausterphobic, so it was a mental challenge for me. Having colleagues I trust from Team CloudFlare on the journey helped in those times I wasn't sure I could do it. It was very intense and unlike anything I've ever done before.

At several points along the journey you could exit if you weren't feeling up for the next challenge (I made it to Godzilla's Nostril). Six of the team made it all the way to the end, 45 feet straight up the Chimney and then down the appropriately named Wedgie Hill.

Muddy? Yes. Bruised? A little. Shellshocked? Probably still the next day. But closer as a team and a little more confident we can overcome any challenge.

Sound like fun? We're growing quickly and always looking for smart, talented, and adventurous people to join our team and help make the Internet faster, safer, and better.