Pinterest ramps up programmatic efforts with latest Amazon hire
By Krystal Scanlon • June 12, 2025 •
Ivy Liu
Pinterest is going all-in on programmatic, and its newest hire is the tell.
Chip Jessopp, Amazon’s former director of global accounts and North America ad tech sales, joined the visual search platform on May 27 as its first head of programmatic. Reporting to chief revenue officer Bill Watkins, he’s been tasked with building new demand channels and scaling Pinterest’s still nascent programmatic business.
With a seven year stint at the e-commerce giant under his belt, Jessopp isn’t new to this. He’s built sales teams, brokered commercial deals and helped grow an ad tech business from the ground up.
“As we pursued the hiring of our programmatic head, Chip’s track record of passion for innovation, technology, and specifically ad tech really stood out throughout the process,” said Watkins. “He’s helped advertisers grow through programmatic as well as advanced audience data strategies up and down the funnel.”
To support the build, Jessopp will bring on three more senior hires across product and sales, so far. Whether the effort pays off will come down to one thing: can programmatic broaden the pool of advertisers buying from Pinterest? Because that’s the promise of programmatic: opening the doors to more ad buyers via ad tech intermediaries. Done right, it can unlock new revenue. Done wrong, it just adds more pipes, not much dollar flow.
“It will still be the same brand safe platform and user experience, while we’re delivering outcomes for our advertisers,” said Jessopp, emphasizing that the team intends to be thoughtful about how they build to enhance, not detract from Pinterest’s core values. “Over the next 12 months, we want our ad tech and programmatic offering to be integrated with our direct offering, and enable advertisers to transact and engage with Pinterest how they want to.”
Moving forward, that’s likely to mean more partnerships like the one struck with ad tech sales house Magnite that was announced during its latest earnings call, which is overseen by Jessopp. In fact, he confirmed that he and his team will continue to look for opportunities to partner where it makes sense.
It’s a familiar inflection point for most platforms: the moment when programmatic shifts from a nice-to-have to a must-have in the race for ad dollars. Hiring someone like Jessopp is a clear signal that Pinterest knows it’s time.
“It signals a turning point in the company’s ad strategy; a pivot from ‘build’ to ‘partner and scale,’” said Chris Matheson, media, director at Markacy. “Their deal with Magnite underscores that shift: Pinterest wants to integrate more deeply into the existing programmatic ecosystem rather than reinvent it. And frankly, that’s the right call.”
After all, scaling an ads business takes real investment — something most platforms talk about but few actually pull off. Pinterest seems to think it’s the exception, and for good reason: it’s in the middle of a growth spurt, pulling in $865 million in the first quarter of the year. That bump, according to CEO Bill Ready, came from becoming more attractive to a wider range of advertisers, especially performance marketers.
According to Watkins, Pinterest’s programmatic capabilities will be “mutually beneficial” in four ways: cost effectiveness for ad spend and campaign performance, better targeting and expanded audience reach, plus greater transparency and control for SMBs (or any advertiser) — all with a goal of saving time and resources.
“The benefit for SMBs will be clear,” Watkins said.
https://digiday.com/?p=580698
