Scaling beyond US$2B in the AI-era: Mark (Cloudflare)

President (Revenue) @ Cloudflare

Before transitioning from a Board Member role to become President (Revenue) at Cloudflare, Mark Anderson served as CEO at Alteryx (acquired by Insight Partners for US$4B+) and President at Palo Alto Networks.

Few companies sit at the intersection of security, performance, and AI quite like Cloudflare. From protecting over 7M websites to powering ~20% of the world’s internet traffic, its influence is felt every time a page loads faster - or an attack is blocked before it begins.

In this conversation, Mark shares what it takes to evolve a GTM engine at scale, the qualities he looks for in great sales leaders, and why the future of cybersecurity - and AI - will separate the prepared from the unprepared.

Q: You were a Cloudflare board member before stepping in as President of Revenue. What drew you to make that transition?

Mark: I joined Cloudflare’s board back in 2019 - the year we went public. It was a much smaller company then, maybe doing around US$170M a year. Over my five years on the board, the business grew nearly tenfold.

I fell in love with what the company does. Cloudflare democratizes access to a faster, safer internet. Today, over 7M customers and developers use us, and we add roughly thousands of new users every month. That kind of reach matters.

When I left Alteryx, a few Cloudflare board members asked if I’d consider coming off the board to help scale operations. It felt like the right time to take what I’ve learned and help the company serve not just startups or digital natives, but enterprises and governments at global scale.

Q: Even at nearly US$2B in revenue, Cloudflare continues to grow its million-dollar customer segment. What’s the secret behind that GTM momentum?

Mark: I’ve always been drawn to companies at inflection points - where the industry is shifting, and the company has a better way to solve the problem.

At F5, we built a better mousetrap - our ROI was nine months, so adoption took off. At Palo Alto Networks, I joined when it was a US$100M business and left when it hit US$3.5B.

Across all those journeys, one thing stays constant: you need the right people, with the right stage experience, pointed in the right direction. The people who got you to US$1B aren’t necessarily the same ones who’ll get you to US$5B.

For Cloudflare, that means hiring talent who’ve sold to large enterprises - banks, governments, global Fortune 500s - people who’ve lived through hypergrowth, made mistakes, and learned how to operate at escape velocity.

You can’t teach that on the job. You have to have lived it.

Q: What do you look for in great sales leaders?

Mark: Character and stage experience.

You can teach how the technology fits together, but you can’t teach judgment, curiosity, or integrity.

When I’m hiring for a role - say, an account manager for DBS Bank in Singapore - I’m looking for someone who’s earned the permission to be a trusted advisor. Someone with intellectual curiosity, strong ethics, and who’s navigated long-term growth - 30%+ year over year for three to five years.

Hypergrowth changes everything. By the end of each year, you’re running a very different company than you were at the start. That means you need a culture of non-stop professional development - people who want to learn every day and sharpen their craft continuously.

Q: Large sales organizations often struggle to adopt AI. How is Cloudflare approaching this?

Mark: You have to - because everything is moving so fast.

Look at how quickly the AI landscape evolved. A year ago, nobody was talking about agents; now, they’re redefining workflows. In two or three years, we’ll look back and realize we’re only at Act One.

At Cloudflare, we use AI both internally and across our network. Internally, our GTM teams leverage internal models that analyze how customers use our portfolio of 80+ services - surfacing patterns that sharpen value propositions, uncover expansion signals, and customer journeys.

Externally, AI helps us detect threats faster across the significant share of global internet traffic we see each day. We see about 25% of the world’s internet traffic daily. By analyzing patterns in that traffic, we can identify indicators of compromise and predict attacks before they happen. That’s the power of scale combined with intelligence.

Q: AI is reshaping both offense and defense in cybersecurity. How do you see this playing out?

Mark: The challenge isn’t just new data - it’s legacy data.

Many large organizations still run mission-critical systems on decades-old infrastructure - mainframes that can’t support modern AI workflows. You can’t run agents off a legacy system sitting in a basement data center.

So the real race now is modernization. Companies have to rebuild their infrastructure to even begin benefiting from AI. Every CIO, CTO, and CISO I speak with feels the pressure - they know that what they’ve built over the last 30 years will matter far less in the next five.

Modernization isn’t optional anymore. It’s survival.

Q: Some say AI will make companies more efficient - but with fewer people. How do you view that shift?

Mark: I’m an optimist. I’ve lived through multiple technological revolutions - the rise of the internet, the birth of cloud computing - and every time, the world adapted.

What’s different now is the speed. The gap between winners and laggards will widen because AI is not a cheap game - companies are spending tens of billions on GPUs and infrastructure.

But AI isn’t just replacing work; it’s amplifying it. It’s making high-impact engineers even better, and it’s making the other 90% more productive.

That same dynamic will extend to knowledge workers. The companies that thrive will be the ones that reimagine roles, retrain talent, and harness AI as a multiplier, not a replacement.