Hippo Holdings Inc. filings document formal disclosures for a NYSE-listed insurance technology company with common stock trading under HIPO. Recent Form 8-K reports furnish quarterly and annual operating results, investor presentations, supplemental financial information, and reconciliations of non-GAAP measures to GAAP measures.
The company’s proxy filings cover annual meeting materials, stockholder voting matters, board governance, and public-company disclosure requirements. Together, the filing record emphasizes Hippo’s insurance-platform performance, premium and underwriting metrics, capital and equity disclosures, and governance framework.
Hippo Holdings Inc. director Hugh R. Frater reported equity awards in the form of common stock and restricted stock units. He acquired 4,808 shares of Common Stock at a price of $0.0000 per share as a grant or award, increasing his direct position.
On the same date, 4,738 restricted stock units vested and settled into shares of Common Stock at a reference price of $25.4000 per share, as described in the footnotes. Following these transactions, Frater directly holds 26,623 shares of Common Stock, which include 4,808 RSUs, and indirectly holds 43,054 shares.
Hippo Holdings Inc. director Mark Schaaf reported routine equity compensation transactions in the company’s common stock. On June 2, he acquired 4,808 restricted stock units (RSUs), each representing one future share of common stock upon vesting. The RSUs will vest in full on the earlier of the first anniversary of the grant date or immediately before the next Annual Meeting, subject to his continued service.
On the same date, 4,738 previously granted RSUs vested and were settled into common stock. Following these awards, he directly holds 20,911 shares of common stock, which include 4,808 RSUs.
Hippo Holdings Inc. director Sam Landman reported stock-based compensation rather than open‑market trades. On June 2, 2026, he acquired 4,808 shares of Common Stock at $0.00 per share and 4,738 shares at $25.40 per share, both classified as awards.
Footnotes explain that 4,738 shares resulted from the vesting and settlement of RSUs originally granted on June 3, 2025. Another block of 4,808 RSUs remains, each convertible into one share upon vesting and later settlement. After these transactions, Landman directly holds 29,080 shares of Common Stock, including the 4,808 RSUs.
Hippo Holdings Inc. executive Michael Stienstra reported a routine tax-related share disposition. On May 15, 2026, 1,259 shares of common stock were delivered at $26.4123 per share to satisfy a tax obligation, classified as a tax-withholding disposition rather than an open-market sale.
After this transaction, Stienstra directly holds 91,160 shares of Hippo common stock. A footnote explains that this holding includes 37,430 RSUs, showing he retains a substantial equity position in the company despite the tax-driven share reduction.
Hippo Holdings Inc. officer Torben Ostergaard reported two Common Stock transactions on May 15, 2026. He disposed of 1,340 shares through a tax-withholding mechanism at a weighted average price of $26.41 per share to cover obligations tied to equity compensation.
He also completed an open-market sale of 3,667 shares at a weighted average price of about $26.10 per share, executed under a pre-arranged Rule 10b5-1 trading plan dated August 22, 2025. Following these transactions, he continues to hold a direct equity position in the company, which includes 37,430 RSUs as part of his overall stake in Hippo Holdings.
Hippo Holdings Inc. Chief Financial Officer Guy Zeltser reported routine equity compensation activity. On May 14, he acquired 743 shares of common stock at $22.72 per share through the company’s Employee Stock Purchase Plan. On May 15, 4,169 shares of common stock were disposed of to cover tax obligations, at a reported price of $26.4123 per share, a tax-withholding mechanism rather than an open-market sale. After these transactions, Zeltser directly held 122,232 shares of common stock, including 88,578 RSUs, reflecting ongoing alignment of his compensation with Hippo’s equity.
Hippo Holdings Inc. Chief Executive Officer Richard McCathron reported a tax-related share disposition. On May 15, 2026, 8,779 shares of common stock were delivered at an implied price of $26.4123 per share to satisfy a tax liability by delivering securities.
After this tax-withholding disposition, he directly held 595,433 common shares, which include 296,227 RSUs. The transaction was not reported as an open-market purchase or sale, but as a payment of obligations using previously owned shares.
HIPO notice reports proposed insider sales of Common Stock submitted on a Form 144. The filing lists 10b5-1 sales by Torben Ostergaard of 600 shares on 02/25/2026 and 6,105 shares on 02/17/2026, with corresponding proceeds of $18,266.10 and $174,391.16.
Hippo Holdings Inc. reported that Chief Executive Officer Richard McCathron sold 5,000 shares of common stock in an open-market transaction on May 11, 2026 at $27.10 per share. The sale was effected under a Rule 10b5-1 trading plan dated August 29, 2025. Following this trade, he directly holds 604,212 shares of Hippo common stock, which include 340,418 restricted stock units (RSUs).
Hippo Holdings Inc. Form 144 notice reports an affiliate's planned sale of 5,000 shares of Common Stock tied to Restricted Stock Units dated 12/24/2020. The filing lists two recent dispositions by Richard McCathron: 5,000 shares on 03/09/2026 and 5,000 shares on 04/09/2026, with adjacent table figures 129,300 and 130,250.
The filing names Merrill Lynch (555 California St.) and shows NYSE listing information. The Form 144 is a notification of proposed resale by an affiliate; the filing lists dates and share counts but does not specify sale mechanics or proceeds recipients in the excerpt.