Pinterest CRO Bill Watkins leaves amid reorganization – Digiday

After 12 years at Pinterest, Bill Watkins, the company’s chief revenue officer, is stepping down from his position at the end of the quarter.
“When I started at the company we had 200 employees, 60M global users, and exactly $0 in revenue,” he posted to LinkedIn. “Fast forward to today and we have thousands of employees, 600M global users, and tens of thousands of advertisers that have invested billions of dollars in revenue on our platform.” 
The move comes just over three weeks before the company reveals its Q4 2025 earnings update on February 12. It’s set to be an important one given the last one missed market expectations despite excelling on global monthly active users. 
Watkins joined Pinterest in 2014 where he founded the Chicago office and headed up the West Region for its large customer sales. During his tenure at the platform, Pinterest went public (2019), expanded internationally, launched ad products and programmatic efforts, and most recently joined the arms race for an AI-campaign tool with the launch of Performance+, enabling it to tap into a bigger stream of revenue from small-to-medium businesses (SMBs), all while maintaining its tagline as being the last sunny corner on the internet.
While it’s not yet clear what his next move will be, Watkins did make a point that he loves AI.
“As for me, I look forward to exploring what’s next,” he posted. “As I do that – one thing is clear to me. I love AI and the transformation it’s driving for ads & marketing. I look forward to seeing you all in my next chapter.”
This latest departure comes as Pinterest’s top seats have had a rejig, with the platform’s first-ever chief marketing officer Andréa Mallard announcing last week that she was leaving – and has since found her new role as Microsoft AI’s new CMO. But the Pinterest CMO seat has already been filled with former Amazon exec Claudine Cheever. 
Additionally, Pinterest has hired former DoorDash CRO Lee Brown as the company’s first chief business officer.
The timing of Watkins’ exit adds another dimension to it all. OpenAI has just announced its push into ads. While there’s nothing tangible to connect the two, it won’t stop anyone from trying to. 
This is a developing story. Pinterest has been contacted for comment. Digiday will update this article with their response.
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