Working at Cloudflare: Inside Stories from Three Team Members Across the Globe

Ever wonder what it's like to work at one of the fastest-growing internet infrastructure companies? I got to sit down with Roshni (recruiting) and Shannon (account executive) to talk about their journeys at Cloudflare, and honestly, their stories paint a pretty vivid picture of what happens when a 230-person startup scales to 1,500 employees in just a few years.

From Tiny Startup to Global Powerhouse

When Roshni joined Cloudflare four and a half years ago as employee #234, the entire recruiting team was five people working out of a cramped San Francisco office. Today, that team has grown to almost 20 recruiters spread across London, Lisbon, Singapore, New York, Austin, and San Francisco. She's worked in three different Cloudflare offices herself—starting in SF, moving to Singapore for a year and a half, then landing in New York.

What strikes me most about her story is how consistent the culture stayed despite explosive growth. Whether she was in Singapore or New York, she noticed the same thing: people genuinely passionate about their work, always pushing forward, never slacking off. The differences? Mostly surface-level stuff like local food preferences or work hours. Singapore teams tended to stay later, until 6 or 7 PM, while San Francisco wrapped up around 4 or 5 PM.

The BDR-to-AE Pipeline That Actually Works

Shannon's path shows how internal mobility really works at Cloudflare. She started as a Business Development Representative three years ago after doing personal finance marketing at NerdWallet. 👉 Learn how companies like Cloudflare scale their infrastructure to support rapid global growth

Her interest in internet infrastructure started in an unexpected place—Malawi, where she struggled to get basic internet connectivity while doing college research. That frustration led her to wonder who actually builds and secures the internet. Fast forward to today, and she's an account executive managing complex security deals.

What does an AE actually do all day? Shannon describes it as being a "glorified project manager" who lives across every communication channel imaginable—LinkedIn, Signal, Twitter, email, phone calls. She's constantly connecting with potential customers, understanding their security needs, and then coordinating with internal teams (product, engineering, solutions engineers, legal, finance) to make deals happen.

The Real Challenge: Hiring Fast Without Compromising Quality

Here's something that surprised me: Roshni says the hardest part of recruiting isn't finding interested candidates—it's not being able to hire everyone who applies. When she started, their applicant tracking system had 3,000 total applications. Last quarter alone? They received 27,000 applications.

The recruiting team looks beyond immediate role fit. When hiring BDRs, they're specifically looking for people who can grow beyond that position. Cloudflare builds its BDR bench to promote from within, which explains why someone like Shannon could move from BDR to AE within a couple of years.

The company went from relative obscurity (at least in places like Singapore) to having random people at bars congratulate Roshni on Cloudflare's IPO. That's a pretty wild shift in just a few years.

Working Through a Pandemic

Both Roshni and Shannon talked about what they miss most about office life. Roshni misses the spontaneous conversations—running into people she helped hire, grabbing coffee, seeing all the faces in the all-hands area. Shannon misses connecting with people outside her direct team, those cross-functional relationships that happen naturally when you're physically present.

But here's what's interesting: they haven't slowed down hiring. During COVID, when companies everywhere were cutting internship programs, Cloudflare doubled theirs from 40 to 80 interns. The recruiting team is still actively hiring across every function—engineering, sales, product, marketing, legal, customer support. 👉 Discover infrastructure solutions that power global teams and remote collaboration

Shannon pointed out something crucial about selling security during a pandemic: some initiatives simply can't be pushed. When companies like DoorDash became essential services overnight, they needed Cloudflare's infrastructure more than ever. Security doesn't wait for better economic conditions.

The Culture That Scales

What keeps coming through in these conversations is how Cloudflare maintains its "just do it" culture at scale. Roshni mentioned telling candidates: "There's never a boring day, and no one will really tell you no. If there's something you want to do and something you want to take on, most people are like, yeah, run with it."

That's rare at 1,500 people. Most companies at that size have already calcified into rigid hierarchies and approval processes. The fact that Cloudflare TV itself exists—giving employees a platform to share their stories and connect across offices—is evidence this culture is real, not just recruiting speak.

The transition to remote work has been challenging in predictable ways. Both mentioned the tendency to schedule back-to-back meetings without natural breaks, missing that commute buffer between home and work life. But they've also found that the level playing field of video calls makes it easier to connect with people outside your immediate team. Shannon specifically mentioned how easy it is to get virtual coffees on the calendar because everyone's hungry for that connectivity.

What This Means for Anyone Considering Cloudflare

If you're thinking about applying, here's what I took away: Cloudflare is actively building teams for problems that don't even exist yet. Roshni's advice? If it's not a fit today, it might be tomorrow. Keep reapplying, stay in touch with your recruiter, and watch the careers page.

The company is genuinely committed to promoting from within, especially in sales where the BDR program feeds the AE pipeline. And despite receiving tens of thousands of applications per quarter, they're still growing fast enough that talented people can find their place.

Whether you're in San Francisco, Singapore, New York, London, Austin, or Lisbon, the core culture seems consistent: driven people working on hard problems with the freedom to take initiative. Not a bad environment for building a career in internet infrastructure.