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. (HIPO) reported that Chief Executive Officer and director Richard McCathron sold 5,000 shares of common stock on September 9, 2026 at $32.23 per share in an open-market transaction. The sale was effected pursuant to a Rule 10b5-1 trading plan dated August 29, 2025 and left him with 567,132 shares held directly, including 276,190 RSUs.
Hippo Holdings Inc. (HIPO) is the issuer of common stock that an officer, Richard McCathron, has notified for potential sale under Rule 144. The notice covers 5,000 shares of common stock, to be sold through Merrill Lynch on the NYSE.
The filing also lists prior sales by Richard McCathron over the past three months, each for 5,000 shares of common stock on May 11, 2026, June 9, 2026, July 9, 2026, and August 10, 2026, with aggregate dollar amounts reported for each sale.
Hippo Holdings Inc. (HIPO) reported that director Ellis Stewart acquired 5,350 shares of common stock on August 15, 2026 through the vesting of restricted stock units originally granted in connection with prior employment. Following this grant/award acquisition, Stewart directly holds 126,455 shares of Hippo common stock, which includes 15,518 restricted stock units (RSUs).
Hippo Holdings Inc. (HIPO) reported an insider equity transaction by its Chief Operating Officer, Laura Boettcher. On 2026-08-15, Boettcher had 1,586 shares of Common Stock withheld or delivered at $32.8265 per share to cover the exercise price or tax liability, a disposition coded as an F transaction. After this event, she directly held 71,381 Common shares, which includes 39,561 RSUs, and indirectly held an additional 60 shares through her spouse.
Hippo Holdings Inc. (HIPO) reported that Torben Ostergaard, an officer (CEO Spinnaker), disclosed two transactions in the company’s common stock. On August 17, 2026, he sold 1,169 shares at $33.00 per share pursuant to a Rule 10b5-1 trading plan dated August 22, 2025. On August 15, 2026, 1,340 shares were disposed of at $32.8265 per share as shares delivered or withheld for payment of exercise price or tax liability. The reporting person’s disclosed holdings include 34,199 RSUs.
Hippo Holdings Inc. (HIPO) reported that officer Michael Stienstra had 1,259 shares of Common Stock disposed of on 2026-08-15 under a transaction classified as payment of exercise price or tax liability by delivering or withholding securities at a reference price of $32.83 per share. Following this withholding, he directly holds 89,901 shares, which the filing states includes 34,199 RSUs (restricted stock units).
Hippo Holdings Inc. (HIPO) reported an insider equity withholding by Chief Financial Officer Guy Zeltser. On 2026-08-15, he had 3,945 shares of common stock withheld or delivered at $32.8265 per share to cover an exercise price or tax liability. Following this transaction, he directly holds 116,618 common shares, which include 81,213 RSUs that remain subject to vesting or settlement conditions.
Hippo Holdings Inc. (HIPO) reported an insider equity withholding transaction by Chief Executive Officer Richard McCathron. On 2026-08-15, he disposed of 8,301 shares of common stock at $32.8265 per share in a transaction coded "F," which represents the payment of exercise price or tax liability by delivering or withholding securities, rather than an open-market sale. Following this transaction, McCathron directly holds 572,132 shares of Hippo common stock, which the disclosure states includes 276,190 RSUs.
Hippo Holdings Inc. director and Chief Executive Officer Richard McCathron reported a sale of 5,000 shares of common stock on August 10, 2026 at $32.00 per share, characterized as a sale in the open market or a private transaction. The company notes the sales were effected under a Rule 10b5-1 trading plan dated August 29, 2025. Following this transaction, McCathron directly holds 580,433 shares of common stock, which the company discloses include 296,227 RSUs.