My Second Cloudflare Company Retreat


Last week, 760 humans from Singapore, London, Beijing, Sydney, Nairobi, Austin, New York, Miami, Washington DC, Warsaw, Munich, Brussels, and Champaign reunited with their San Francisco counterparts for our 9th annual Cloudflare company retreat in the San Francisco Bay Area. The purpose of the company retreat is to bring all global employees together under one roof to bond, build bridges, have fun, and learn – all in support of Cloudflare’s mission to help build a better Internet.

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

Company culture and achievements

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

Employee Development

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.”

Having fun

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.

Until next year

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!



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