ZIP ZIPRECRUITER, INC. Insider Trading

CEO Siegel sells 27,204 shares (27.2K) across 2 transactions totaling $502,811.33; holdings drop 16.2% to 140,318 shares amid -69.3% stock decline.

CEO Ian H. Siegel executed 2 separate sales totaling 27,204 shares for $502,811.33, reducing his holdings by 16.2% from 167,522 to 140,318 shares. The transactions occurred across a wide time span at materially different prices ($27.61 in October 2021 and $2.07 in April 2026), suggesting they may reflect different strategic contexts or regulatory plans rather than a single discretionary decision. The current stock price of $1.98 lies -69.3% below the 52-week high, and the company is unprofitable with annual revenue decline of -5.3%, creating a backdrop of significant shareholder losses. The substantial reduction in CEO holdings during a period of pronounced stock weakness and operational headwinds warrants investor scrutiny of the underlying business trajectory and whether additional insider selling may follow.

10% Owner Institutional Venture Management XIV sells 1,639,345 shares (99.1% of holdings) for $7.0M at $4.27

Institutional Venture Management XIV, a 10% owner, executed 2 separate sales totaling 1,639,345 shares for $7,000,003.15 at $4.27 per share on 2025-08-21, reducing holdings from 1,654,964 shares to 15,619 shares (a 99.1% reduction). The filer's prior 2 trades at ZIP both posted negative 90-day returns (-5.8% and -17.1%), with 100% well-timed sell rate at the 90-day mark. Given the company's deteriorating fundamentals—revenue declining -26.6% year-over-year, net income of -$9.5M in the latest quarter, and unprofitability over the full fiscal year—the near-complete liquidation by a major institutional investor warrants attention. Current price of $5.16 is 53.5% below the 52-week high of $11.10, suggesting the stock has already declined materially since this transaction.

10% owner Institutional Venture Management XV sold 1,639,345 shares (99.1% of holdings) at $4.27 for $7.0M on 2025-08-21

Institutional Venture Management XV, the company's largest shareholder at 10%, executed 2 separate sales totaling 1,639,345 shares (1.64M shares) for $7,000,003.15 on 2025-08-21, retaining only 15,619 shares post-transaction. This near-complete exit occurs as ZipRecruiter trades at $5.16 (down 53.5% from its 52-week high of $11.10) and faces material headwinds: annual revenue contracted 26.6% year-over-year, the company posted a $-9,506,000.00 net loss in the latest quarter, and full-year profitability remains negative. The insider's prior 2 sales at this ticker, both executed on 2025-05-20, were well-timed according to the SAME-TICKER HISTORY (both showed negative 90-day returns of -17.1%), suggesting a pattern of selling ahead of declines. The post-transaction position reduction from 1,654,964 shares to 15,619 shares represents a decisive liquidation of the venture capital firm's stake concurrent with deteriorating financial performance.

Institutional Venture Management XIV sold 3,000,000 shares at $5.32, exiting 99.2% of holdings in ZIP.

Institutional Venture Management XIV, a 10% owner, executed 2 separate sales totaling 3,000,000 shares for $15,960,000.00 on 2025-05-20, reducing its holdings by 99.2% from 3,024,294 shares to 24,294 shares. The transaction occurs as ZipRecruiter faces material headwinds: annual revenue growth is -26.6%, the company posted a net loss of $-12,831,000.00 in its latest quarter, and was unprofitable over its full fiscal year. The stock is currently down 49.6% from its 52-week high of $11.10, trading at $5.59, and has declined 19.7% over the past 90 days despite a modest 3.7% gain over the past 30 days. The near-complete exit by a major institutional holder during a period of deteriorating financial performance and significant share price depreciation signals a material shift in the fund's position in the company.

VC investor IVM XV sells 3,000,000 shares (99.2% of stake) at $5.32, leaving 24,294 shares in ZIP as company faces -26.6% revenue decline and net loss.

Institutional Venture Management XV, LLC, a 10% owner, executed 2 separate sales totaling 3,000,000 shares (3.00M shares) for $15,960,000.00 ($16.0M) at $5.32 on 2025-05-20, reducing its position from 3,024,294 shares (3.02M shares) to 24,294 shares (24.3K shares) — a -99.2% reduction. This near-complete exit by a major venture backer occurs while ZIP's fundamental trajectory shows Annual revenue growth (FY vs prior FY) of -26.6%, Net income of $-12.8M over the latest full fiscal year, and a current stock price of $5.59 that sits -49.6% from the 52-week high of $11.10. The scale and decisiveness of this divestiture by a founder-class investor signals material reassessment of the company's prospects, particularly given the company's ongoing unprofitability and significant top-line contraction.

ZIP President Travers sells 59.6K shares in 2 separate transactions for $598.1K; all 5 prior ZIP sales were well-timed at 90 days

David Travers, President of ZipRecruiter, sold 59,564 shares across 2 separate transactions on 2024-09-18 and 2024-09-19 (36,403 shares at $10.24 and 23,161 shares at $9.73, totaling $598,145.09). This represents a 5.1% reduction from his pre-transaction holdings of 1,165,269 shares. His prior 5 sales at ZIP show a consistent pattern: all 5 were well-timed at the 90-day mark, with post-sale declines ranging from 15.9% to 27.5%. The current stock price of $9.61 is 37.2% below the 52-week high of $15.29, and the company faces a 28.6% annual revenue contraction with a P/E of 19.61. The timing pattern across his ZIP trade history suggests this insider has demonstrated consistent execution in recognizing inflection points before declines, though the presence of derivative holdings conversion means the Form 4 Table I position should be viewed as a partial equity sale rather than a total position statement.