- John on organizational culture
From WHAT IT'S LIKE BUILDING THE TECH, AND THE TEAM, FOR A BILLION-DOLLAR BUSINESS - John & Tom · · Pause Fest & Awards
“If you give four people the title CTO early on, you're making a hell of a bet on that person. You're going to paint yourself into a corner because you've decided to complete these titles and if you don't give someone a title then they can progress in different directions.”
On , - John, Chief Technology Officer at Cloudflare, spoke about organizational culture during WHAT IT'S LIKE BUILDING THE TECH, AND THE TEAM, FOR A BILLION-DOLLAR BUSINESS - John & Tom on Pause Fest & Awards.
About - John
John Graham-Cumming stepped down as Cloudflare's CTO in March 2025 and joined the company's board of directors. In subsequent interviews, he reflected on the company's growth from 24 employees to over 1,300, describing his role as having shifted to roughly 60% outbound communication, including speaking engagements and podcasts. He stated that the hardest part of his job was firing people, saying it "really upsets me every time" and that his heart rate would spike during such conversations. He also discussed Cloudflare's culture, saying it "could have messed it up enormously" and that the company avoided early title proliferation by not creating a "senior software engineer" title. Graham-Cumming has been vocal about the impact of AI on the internet's business model, arguing that AI scrapers that provide answers without sending users to the original site "changes fundamentally the business model of the web." He noted that Cloudflare announced using the HTTP 402 "payment required" error code to allow content creators to set a price for AI crawlers. He described the current era as a "golden age for programmers" where AI assists with syntax and pitfalls, expanding the pool of people who can develop software. He also criticized CAPTCHAs as "awful" and "culturally insensitive," and highlighted Cloudflare's Turnstile product as a privacy-preserving replacement that the company gives away for free.