People

The People

Governance grade: B–. The board is structurally independent and the CEO has real skin in the game, but a super-voting dual-class structure leaves two co-founders with ~66% of voting power, an Elliott partner now sits on the board pursuant to a $1B convertible note, and CEO pay more than doubled in 2025 while three-year shareholder return ($100 → $39) lagged peers ($100 → $120) by a wide margin.

The People Running This Company

The operating team is heavy on commerce DNA. Ready, Donnelly, Madrigal and Walcott collectively bring PayPal, Google Shopping, Wayfair, Discover, and eBay e-commerce experience — all hired since mid-2022 to convert Pinterest from a casual-discovery surface into a transactional shopping platform. Co-founder Silbermann remains Non-Executive Chair, providing product/cultural continuity but no longer setting strategy.

Bill Ready — Hired with an unusually demanding equity package: a $19.96-strike option for 8.55M shares (essentially Pinterest's stock price the day he joined) plus a $5M open-market stock purchase he was required to make to receive his RSA. That investment requirement is one of the strongest pre-commitments any new public-company CEO has accepted in recent years. His track record (Braintree → PayPal exit; PayPal COO; Google commerce P&L) makes him the right operator to monetize Pinterest's intent-rich audience, but his 2025 paycheck of $39.3M against three-year TSR of $39 (vs. peer $120) is hard to reconcile with pay-for-performance rhetoric.

Benjamin Silbermann — His 35% voting block is the single biggest governance variable. Class B converts to Class A on his death/incapacity (after a 90–540 day delay) or a date 30 years post-IPO, so the voting overhang has a long tail. He is no longer in the operating chain.

Julia Donnelly / Matthew Madrigal — The CFO and CTO are both under-2-year tenured. They are credible on paper (HBS, Stanford; Google Shopping P&L) but unproven at PINS. Madrigal's 2024 sign-on package ($13.4M) plus 2025 grant ($21.1M) signals high replacement cost; the bridge/overlay grants in late 2025 were also designed to keep him whole through the PSU transition.

What They Get Paid

Total NEO compensation in 2025 was $102.8M for five people, with 95% of CEO pay delivered as equity (PSUs and RSUs). Salaries are uniform across NEOs at $620,833, removing any real differentiation in fixed pay; the variable component, particularly time-vesting RSUs, drives essentially all of the total.

The CEO pay mix is mostly performance equity in name (~73% of total = PSUs based on three-year relative TSR vs. the Nasdaq CTA Internet Index), with a meaningful RSU overlay (~24%). But CEO total compensation jumped from $18.1M (2024) to $39.3M (2025) — a 117% increase — even as stock performance materially trailed peers. That increase came from re-introducing PSUs to Ready's grant after a year (2024) when the bonus was effectively paid as 1-year cliff PSUs that delivered nothing.

The relative-TSR gap (PINS $39 vs peer $120 by year-end 2025) is severe: a $100 stake in the Nasdaq Internet peer index has tripled the value of the same stake in PINS over the disclosure window. The CAP framework correctly reflected that pain in 2024 (–$24.3M to Ready) but the 2025 CAP swung back to +$22M largely on the rebound from depressed 2024 marks, not on operating outperformance. CEO pay ratio is reported at 126:1 (median employee $311,466 — high because Pinterest skews to SF tech engineering staff); the absolute CEO number is what raises eyebrows, not the ratio itself.

Are They Aligned?

This section determines the case. Pinterest has both unusually strong economic alignment from its founder/CEO and an unusually weak voting alignment for outside Class A holders.

Ownership and control

Insider activity

Insider activity is mechanical, not discretionary. Form 4 filings over the last 12 months are dominated by tax-withholding dispositions (Code F) on RSU vests, scheduled 10b5-1 plan sales by directors, and one CLO gift transaction. There is no open-market buying by any NEO or director on record for the period — neither during the early-2025 tariff drawdown nor after the Elliott investment was disclosed.

Dilution and one-time grants

The 2022 $122.7M founder-style grant for Ready was front-loaded; it now mostly trades below water (option strike $19.96 vs. year-end 2025 close of $25.89, but volatility and the convertible note hedge complicate the picture). 2025 saw new "bridge" PSU/RSU awards introduced for non-CEO NEOs explicitly to "address gap in vesting for 2027" — a back-fill grant that effectively softens the multi-year vesting transition rather than tying pay to outperformance. Three-year vesting on PSUs is a recent improvement (2025) over the prior two-year cliff.

Related-party behavior

The single material related-party arrangement is the Elliott Investment Agreement (March 2026, $1B at 1.75% convertible senior notes due 2031), under which Elliott also retains its board seat through Marc Steinberg. The proceeds funded a $3.5B share-repurchase authorization. Three issues for outside Class A holders to weigh:

(1) Pricing of the convertible — A 1.75% coupon at a time when investment-grade tech debt prints in the mid-4s suggests the conversion option is being valued aggressively in Elliott's favor.

(2) Permanent governance footprint — Steinberg's board seat is now contractually tied to the agreement, not to ordinary stockholder election; the seat sits on the audit committee, which reviews related-party transactions involving Elliott itself.

(3) Buyback timing — Funding a buyback with new convertible debt during a period of advertising softness (cited in the company's own February 2026 disclosures) is financial engineering, not value creation.

Skin-in-the-game scorecard

Composite skin-in-the-game score: 6 / 10. Strong on founder/CEO economic exposure and stock ownership rules, materially weak on voting alignment and pay-for-performance discipline. The score would move to 7 if Pinterest sunset Class B (or shrunk Sciarra's voting overhang) and to 5 if a second large CEO grant lands without TSR recovering.

Board Quality

The board is twelve directors: ten independent, two non-independent (Ready and Silbermann). Lead Independent Director is Andrea Wishom. Audit, Compensation, and Governance committees are 100% independent. Average age 53; tenure ranges from under 1 year (Steelman, Reuter) to 18 years (Silbermann). Six of twelve are women.

The board is well-covered on consumer/retail, finance, and e-commerce — exactly the skills needed for the shopping-platform pivot. The two visible gaps are advertising-technology and AI/ML systems, which is awkward given that 100% of revenue is digital ad-supported and Pinterest's 2025 narrative is a visual-AI story. Madrigal-led ML is governed essentially by Ready (CEO) and the audit committee, with no specialist independent voice.

The Audit Committee chair is Scott Schenkel (CFO, Expedia) — credentialed, but he sits alongside Marc Steinberg (Elliott), creating an awkward dynamic for any future review of related-party items involving Elliott. The Compensation Committee, chaired by Leslie Kilgore (former Netflix CMO and current chair of Netflix's comp committee), is responsible for the design that just delivered a 117% YoY raise to a CEO whose stock has lagged peers materially over three years.

The Verdict

Grade: B–

Strongest positives. The CEO put $5M of his own cash on the table at hire — almost no comparable public-company CEO has accepted that condition in the last decade. Founder Silbermann remains heavily exposed economically (~$950M+ of stock at year-end 2025 prices). The committees are structurally independent; clawback, anti-hedging, and ownership-guideline architecture all meet or exceed market norms; 97% of Class A votes supported say-on-pay in 2025.

Real concerns. The dual-class structure leaves a non-employee co-founder (Sciarra) with 31% voting power. The Elliott convertible/board seat collapses the line between an active investor and a related party that the board itself is supposed to oversee. CEO pay more than doubled in 2025 against a three-year TSR running at one-third of the peer index. And a class-action complaint covering February 2025–February 2026 is moving toward a lead-plaintiff deadline of May 29, 2026, alleging the company misled investors on tariff-driven advertising weakness — exactly the same advertising softness Elliott then used to negotiate a 1.75% coupon convertible.

One thing that would most likely upgrade the grade to a B+. Sunsetting Class B super-voting rights — or contractually capping Sciarra's voting power once he ceases to be an active director or officer. That single change converts Pinterest from a controlled company into one where Class A holders actually vote the strategy.

One thing that would most likely downgrade the grade to a C. A second large make-whole CEO grant in 2026 if the stock fails to recover, layered on a settlement of the securities class action that confirms management knew about advertising weakness during the disclosure window.