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. reported a Form 144 notice covering 5,000 shares of Common Stock listed as securities to be sold. The filing shows two prior sales by Richard McCathron of 5,000 shares each on 02/09/2026 and 03/09/2026.
Hippo Holdings Inc. Chief Executive Officer Richard McCathron executed an open-market sale of 5,000 shares of Common Stock at $25.86 per share. The transaction was carried out on the basis of a Rule 10b5-1 trading plan dated August 29, 2025, indicating it was pre-arranged. Following this sale, he directly holds 615,650 shares, which the disclosure notes include 343,868 restricted stock units (RSUs).
Hippo Holdings Inc. reported insider sale notices on Form 144 by Richard McCathron.
The excerpt lists sales of 5,000 common shares on 01/09/2026 with the adjacent figure 157600, and 5,000 common shares on 02/09/2026 with the adjacent figure 145700. Broker listed: Merrill Lynch. The filing also references 5,000 Restricted Stock Units dated 12/24/2020.
Hippo Holdings Inc. reports that The Lennar Foundation, Inc. beneficially owns 2,071,997 shares of common stock, representing 8.0% of the class.
The percentage is calculated using 25,970,978 shares outstanding as of February 24, 2026, per the issuer's Annual Report on Form 10-K. The filing lists sole voting power and sole dispositive power of 2,071,997 shares held by The Lennar Foundation.
Hippo Holdings Inc. Chief Financial Officer Guy Zeltser reported two equity awards of common stock on March 2, 2026, acquiring a total of 61,707 shares at no cash cost. These awards are structured as restricted stock units (RSUs) with time-based vesting and performance conditions.
One RSU grant vests in equal quarterly installments over three years starting on February 15, 2026. Another performance-based RSU award, granted March 2, 2026, ties 50% of units to relative total shareholder return over three years, 25% to gross written premium over one year, and 25% to adjusted return on equity over one year plus an additional year of service. Following these awards, Zeltser directly holds 126,749 shares of common stock, including 111,883 RSUs.
Hippo Holdings Inc. reported that executive Michael Stienstra, GM & Chief Insurance, received two grants of common stock on March 2, 2026 totaling 24,684 shares at a price of $0.00 per share through awards.
After these acquisitions, his directly held common stock increased to 93,213 shares, which the disclosure notes includes 56,186 restricted stock units (RSUs). One RSU grant vests in 12 equal quarterly installments starting on February 15, 2026 over three years, while another performance-based RSU award vests based on relative total shareholder return, gross written premium, and adjusted return on equity over defined performance and service periods.
Hippo Holdings Inc. executive Torben Ostergaard reported acquiring two grants of common stock on March 2, 2026, through restricted stock unit (RSU) awards covering 14,810 and 9,874 shares at no cash cost. One RSU grant vests in 12 equal quarterly installments starting February 15, 2026 over three years.
The other RSU grant is performance-based, with 50% tied to relative total shareholder return over a three-year period, 25% tied to gross written premium over one year, and 25% tied to adjusted return on equity over one year plus an additional one-year service requirement. Following these awards, his direct holdings include 67,111 RSUs within his reported share balance.
Hippo Holdings Inc. reported that Chief Executive Officer and director Richard McCathron acquired additional common stock through equity awards on March 3, 2026. He received grants totaling 113,719 and 75,813 shares at a stated price of $0.00 per share, increasing his directly held common stock to 620,650 shares, including 343,868 restricted stock units (RSUs). A portion of the RSUs vests in equal 1/12 installments on each quarterly anniversary of February 15, 2026 over three years. The performance-based RSU awards are tied to relative total shareholder return over a three‑year period, gross written premium over a one‑year period, and adjusted return on equity over a one‑year period with an additional one‑year service requirement.
Hippo Holdings Inc. is a technology-focused insurance holding company that generated $1.1 billion of gross written premium in 2025, primarily in U.S. property and casualty markets. It operates a multi-carrier platform across homeowners, renters, casualty, commercial multi-peril, and other niche lines.
The company held $436.1 million of stockholders’ equity at year-end 2025 and had 25,970,978 common shares outstanding as of February 24, 2026. Hippo emphasizes disciplined underwriting, advanced data analytics, and reinsurance to manage catastrophe and attritional risk while pursuing diversified growth.
Management highlights significant risks, including a history of net losses, dependence on reinsurance capacity, severe weather and climate-driven catastrophes, intense competition from incumbents and insurtechs, regulatory complexity, data privacy and cybersecurity obligations, and emerging regulation of artificial intelligence and external data use in underwriting and claims.
Hippo Holdings Inc. insider Torben Ostergaard reported an open-market sale of common stock. On February 25, 2026, he sold 600 shares of Hippo Holdings common stock in an open-market transaction at a weighted average price of $30.4435 per share, executed in multiple trades between $30.19 and $30.56.
The filing states that these sales were carried out under a pre-established Rule 10b5-1 trading plan dated August 22, 2025, which is designed to allow insiders to sell shares according to a fixed schedule. Following this sale, Ostergaard directly owned 46,094 shares of common stock, which the filing notes includes 42,427 restricted stock units (RSUs).