Zillow Insider Jay C. Hoag Buys $21‑Share Stock Amid Executive Sell‑off, Hinting at Undervalued Confidence

Insider Buying by Jay C. Hoag Signals Confidence Amid a Weak Market

On February 13, 2026, Jay C. Hoag, a long‑time Zillow executive and senior member of its investment‑management team, purchased 16,835 shares of Zillow’s Class C capital stock at $21.46 per share. The transaction brought his holdings to 23,125 shares—roughly 0.00028 % of the outstanding shares. Although the share price is down 42 % from the all‑time high, Hoag’s purchase occurs at a fraction of the current market value, suggesting a conviction that the stock is undervalued.

Why the Timing Matters

Zillow’s share price has been sliding since its September 2025 peak of $93.88, and its 52‑week low of $42.50 fell only a few days before the trade. The buy came at the tail end of a 30‑day window of declining volume and price, a period when many institutional owners have sold. Hoag’s move—against the broader trend of insider selling—implies a belief that the company’s fundamentals will rebound. The buy was also announced in a filing that received high social‑media buzz (93 % above normal intensity) but neutral sentiment, indicating that the market has taken the transaction as a routine event rather than a shock.

Comparing Hoag to the Board’s Activity

The same day, other top executives (e.g., CFO Jeremy Hofmann, CEO Jeremy Wacksman, and COO Choo Jun) sold shares in the range of 4,000 to 13,000 shares, each transaction priced around $44–$45. The disparity between Hoag’s buy and the board’s sell pattern is noteworthy. It suggests that while the senior leadership is divesting for liquidity or portfolio rebalancing, Hoag—who also holds substantial interests through multiple investment vehicles—remains bullish on Zillow’s long‑term prospects.

Implications for Investors

1. Valuation Confidence – Hoag’s purchase at $21.46 is a stark contrast to the market’s current $43.97 price. If Zillow’s growth trajectory stabilizes, the stock could move significantly higher, rewarding long‑term holders.

2. Liquidity and Share Price Pressure – Insider selling can exert downward pressure on the stock, but the presence of a buy‑side transaction by a major owner may temper that effect, especially if the buy is seen as a signal of confidence.

3. Corporate Governance Signals – The split in insider actions—buy versus sell—may reflect divergent views on timing. Investors should monitor whether this pattern continues, as sustained buying by senior owners often precedes positive catalysts (e.g., earnings beat, product launches, or regulatory wins).

4. Risk‑Adjusted Outlook – With a price‑to‑earnings ratio of 235, Zillow remains a high‑valuation play. Insider activity alone cannot override the valuation premium, but it does add a layer of qualitative assessment for risk‑averse investors.

Bottom Line

Jay C. Hoag’s recent purchase, set against a backdrop of widespread insider selling and a sharp decline in the stock, signals a degree of confidence that the market has not yet fully priced in. For investors looking for a long‑term view, this insider activity offers a nuanced signal: the company’s core team is still willing to invest in its future, even as the market remains skeptical. Whether that confidence will translate into a rebound depends on Zillow’s ability to execute on its growth strategy and regain investor trust in a highly competitive real‑estate tech landscape.