Pinterest Inc. is accelerating its transformation into an AI-driven shopping powerhouse through a sweeping C-suite reorganization, as CEO Bill Ready positions the visual discovery platform to capture a burgeoning Gen Z audience amid intensifying competition in digital advertising.

The changes, announced January 20, 2026, include the appointment of Lee Brown as the company’s first chief business officer and Claudine Cheever as chief marketing officer, both reporting directly to Mr. Ready. Longtime chief revenue officer Bill Watkins is departing after more than a decade, during which he helped scale Pinterest from zero revenue to billions in annual advertiser spend, according to Business Chief.

“The new Chief Business Officer role brings together all customer-facing touch-points at a moment where we have a number of new revenue opportunities,” Mr. Ready said in a statement. Mr. Brown, previously at DoorDash and Spotify, will oversee global sales, advertising, content partnerships, and customer operations, consolidating functions to deepen ties with small and medium-sized businesses and expand internationally.

New Leaders Align with Monetization Push

Ms. Cheever joins from Amazon, where she spent over a decade in senior marketing roles, including vice president of global brand and marketing. Her mandate centers on crafting a narrative around Pinterest’s shift to AI-personalized shopping that “feels rich and useful,” she said, avoiding the “creepy or weird” pitfalls of intrusive ads. This comes as former CMO Andréa Mallard exits to Microsoft AI, per MediaPost.

Mr. Watkins’s exit marks the end of an era, but he endorsed the transition: “I have known Lee Brown since our days at Yahoo, and I’m excited for him to lead the business organization on this next leg of the journey,” according to BestMediaInfo. Under his watch, Pinterest listed publicly, expanded geographically, and rolled out AI ad tools, evolving from 200 employees and 60 million users to hundreds of millions today.

The hires signal Pinterest’s bet on performance advertising and commerce, with Mr. Brown noting his track record at prior firms: “Whether it’s Spotify, DoorDash or BuzzFeed—at all of these companies, I’ve turned consumer demand to strong advertising opportunities by deepening client relationships, customer operations and content partnerships.”

AI for Positivity Redefines User Experience

Since Mr. Ready’s arrival in June 2022, when Pinterest posted a $93 million net operating loss and struggled with an aging user base, the company has posted nine straight quarters of record users, hitting 600 million monthly actives. Gen Z now comprises over half, drawn to what Mr. Ready calls “AI for positivity,” which prioritizes saved content over rage-inducing feeds, as detailed in Vogue.

“By tuning AI for positivity and rejecting engagement via enragement, Pinterest can be a brand that can make a lot more,” Mr. Ready stated. This includes stricter teen controls—no public boards for under-16s, school-hour prompts—and tools like the Pinterest Assistant chatbot, which offers outfit suggestions like a “friend you love shopping with.” Gen Z board creation has surged 340% in five years; 85% use the platform for product discovery.

Financially, Q3 2025 revenue climbed 17% to $1.049 billion, with guidance for Q4 at $1.313-$1.338 billion, per earnings releases. AI recommendations outperform off-the-shelf models by 30 points on shopping relevancy, Mr. Ready told analysts.

Gen Z Shift Powers Revenue Engine

Pinterest’s “taste graph” blends human-curated boards with AI to suggest real-world combinations, powering 80 billion monthly searches that are “highly commercial in nature,” as Mr. Ready noted in Business Insider. Users arrive with intent—for outfits, recipes, decor—making it a visual search leader versus endless feeds elsewhere.

The strategy resonates: Gen Z is twice as likely as millennials to research via AI assistants (34% vs. 17%). Platforms like TikTok prioritize view time through triggers; Pinterest elevates uplifting content, boosting daily visits to 38% among Gen Z.

Challenges persist—some users spot AI-generated oddities like one-eyed cats, per CNN Business—but Mr. Ready views AI as inevitable: “Over time, AI will follow a similar trajectory to Photoshop. Almost every piece of content you see will have been at a minimum edited by AI.”

Global Expansion and Ad Yield Focus

The C-suite moves aim to lift average revenue per user via connected TV, programmatic ads, and SMB outreach. Mr. Ready’s background—PayPal COO, Google commerce president, Braintree CEO—equips him for this, as noted on Pinterest Investor Relations. Safety leads include private under-16 accounts and phone-free school support.

On X, industry voices like Adweek highlighted the hires: “Pinterest is evolving into a major shopping platform,” while Axios’s Sara Fischer noted the consolidation under Mr. Brown. Recent X chatter echoes the strategy’s momentum amid Chinese AI model adoption for cost savings.

Pinterest projects 30-34% adjusted EBITDA margins long-term, investing in R&D for AI while navigating ad market caution. Mr. Ready’s vision: a purposeful internet “better for users and for business,” proving positivity drives profits.