Every Form 4 that Hippo Holdings Inc. (HIPO) has filed with the SEC in the last 12 months is listed below, newest first, and each one links through to the document itself with the summary and the scores our analysis gives it.
A Form 4 covers the transactions officers, directors and large holders report, so if you follow HIPO and want that one kind of document rather than the whole filing history, this is the page to keep. The company's other filings, of every form, are on the full HIPO filings page.
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) 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.
Hippo Holdings Inc. Chief Financial Officer Guy Zeltser sold 1,669 shares of Common Stock on July 28, 2026 at $30.98 per share in an open-market or private transaction executed under a Rule 10b5-1 trading plan dated June 18, 2025. Following the sale, he holds 120,563 shares, including 88,578 RSUs.
Hippo Holdings Inc. Chief Executive Officer Richard McCathron reported an open-market sale of 5,000 shares of common stock on July 9, 2026 at $28.53 per share. According to the filing, the sale was effected under a Rule 10b5-1 trading plan dated August 29, 2025. Following the transaction, he directly holds 585,433 shares, which include 296,227 RSUs.
Boettcher Laura reported acquisition or exercise transactions in this Form 4 filing.
Hippo Holdings Inc. reported that Chief Operating Officer Laura Boettcher received a grant of 11,674 shares of Common Stock on June 10, 2026 at a price of $0.00 per share, reflecting stock-based compensation rather than an open-market purchase.
After this award, Boettcher directly holds 72,967 shares of Hippo common stock, which the filing notes include 43,749 restricted stock units (RSUs). She also indirectly owns 60 shares held by her spouse. The filing does not show any open-market buying or selling; it records a compensation-related equity grant and updated ownership totals.
Hippo Holdings Inc. Chief Executive Officer Richard McCathron sold 5,000 shares of common stock at $25.00 per share in an open-market transaction. The sale was made pursuant to a pre-arranged Rule 10b5-1 trading plan dated August 29, 2025. Following this sale, he directly holds 590,433 shares, which include 296,227 restricted stock units (RSUs).
Ellis Stewart reported acquisition or exercise transactions in this Form 4 filing.
Hippo Holdings Inc. director Ellis Stewart received an equity grant in the form of restricted stock units (RSUs). He was awarded 4,820 RSUs, each convertible into one share of common stock upon vesting. The RSUs vest in full on the earlier of the first anniversary of the grant date or immediately before the next Annual Meeting, provided he continues serving the company and its subsidiaries through that date.
Following this award, Stewart holds 121,105 shares of common stock directly and 10,335 shares indirectly through Preservation Trust Company, Inc., as trustee of the Desertfish Nevada Trust. The grant was recorded at a price of $0.00 per share, reflecting its nature as compensation rather than a market purchase.
Hippo Holdings Inc. director Lori Dickerson Fouche reported compensation-related equity transactions in the company’s common stock. She acquired 4,738 shares through the vesting and settlement of previously granted restricted stock units (RSUs) at a price of $25.40 per share.
She also received a new award of 4,808 RSUs, each representing the right to receive one share of common stock upon vesting. The new RSUs vest in full on the earlier of the first anniversary of the grant date or immediately before the next Annual Meeting, as long as she continues in service with Hippo and its subsidiaries.
WIJNBERG SANDRA S reported acquisition or exercise transactions in this Form 4 filing.
Hippo Holdings Inc. director Sandra S. Wijnberg reported equity compensation activity in the form of restricted stock units and related common stock on June 2, 2026. These are grants and vesting events, not open-market purchases or sales.
She received 4,808 restricted stock units (RSUs), which entitle her to one share of common stock per unit upon vesting. On the same date, 4,738 RSUs originally granted on June 3, 2025 vested and were settled into common stock at a reported price of $25.40 per share. Following these transactions, she directly holds 26,623 shares of common stock, which includes the 4,808 RSUs, and an additional 4,680 shares are held indirectly through The Sandra S. Wijnberg 2014 Revocable Living Trust.
Hay Laura J reported acquisition or exercise transactions in this Form 4 filing.
Hippo Holdings Inc. director Laura J. Hay reported equity awards tied to restricted stock units. On June 2, 2026, 2,502 RSUs granted on October 1, 2025 vested and settled into Common Stock at $25.40 per share.
On the same date, she received a new grant of 4,808 RSUs, each convertible into one share of Common Stock upon future vesting. Following these awards, Hay directly holds 7,310 shares and RSUs in total, reflecting routine compensation rather than open‑market trading.
Holliday Susan Claire reported acquisition or exercise transactions in this Form 4 filing.
Hippo Holdings Inc. director Susan Claire Holliday reported two equity compensation transactions in the form of common stock and restricted stock units (RSUs). She received an award of 4,808 RSUs, each convertible into one share of common stock upon vesting, and now directly holds 7,310 shares including these RSUs. A separate block of 2,502 RSUs granted on October 1, 2025 vested and settled into 2,502 shares of common stock at a stated value of $25.40 per share, which she now holds directly. These are compensation-related grants and vesting events, not open-market purchases or sales.
Hippo Holdings Inc. director John Drake Nichols reported equity awards in the form of common stock and restricted stock units. On June 2, 2026, he acquired 4,808 RSUs at $0.00 per share and 4,738 shares upon vesting of previously granted RSUs valued at $25.40 per share.
Footnotes state the 4,738 RSUs were originally granted on June 3, 2025 and vest into one share of common stock per RSU, subject to continued service until the earlier of the first anniversary of grant or the next Annual Meeting. One table entry shows 21,371 directly held common shares including 4,808 RSUs, and another shows 16,563 directly held shares. The filing also reports 50,000 shares held indirectly by Janajasa Associates L.P.
Hippo Holdings Inc. director Eric Feder reported a compensation-related stock transaction. On June 2, 2026, 4,738 restricted stock units (RSUs) vested and settled into shares of common stock at a stated value of $25.40 per share. After this grant/award acquisition, Feder directly owns 21,815 shares of Hippo common stock. The filing also lists 5,000 shares of common stock held indirectly through Beep Investments, LLC, reflecting an additional ownership position associated with him.
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.
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. executive Torben Ostergaard, CEO of Spinnaker, reported a tax-withholding disposition of 1,438 shares of common stock at $28.2089 per share, used to cover tax obligations. After this non‑market transaction, he directly holds 69,340 shares, including 63,661 RSUs.
Hippo Holdings Inc. executive Michael Stienstra, GM & Chief Insurance, HHIP, reported a routine tax-related share disposition. On April 27, 2026, 794 shares of common stock were delivered at $28.2089 per share to satisfy tax obligations tied to equity compensation. After this transaction, he holds 92,419 common shares directly, including 54,161 RSUs, indicating he retains a substantial equity position in the company.
Hippo Holdings Inc. Chief Financial Officer Guy Zeltser reported a routine tax-related share transfer. On April 27, 2026, 1,091 shares of common stock were disposed of at an implied value of $28.2089 per share to satisfy tax obligations by delivering shares rather than cash. Following this transaction, he directly owned 125,658 shares of common stock, including 109,858 restricted stock units (RSUs), indicating the move was a small, compensation-driven adjustment rather than an open-market trade.
Hippo Holdings Inc. Chief Executive Officer Richard McCathron had 1,438 shares of common stock withheld at $28.2089 per share to satisfy tax obligations. This was a tax-withholding disposition, not an open-market sale. Following the transaction, he holds 609,212 shares, including 340,418 RSUs.
Hippo Holdings Inc. Chief Executive Officer Richard McCathron executed an open-market sale of 5,000 shares of Common Stock at $26.05 per share. The transaction was carried out on April 9, 2026 pursuant to a pre-arranged Rule 10b5-1 trading plan dated August 29, 2025, indicating it was scheduled in advance rather than timed discretionarily.
Following this sale, McCathron directly holds 610,650 shares of Hippo common stock, which the disclosure notes include 343,868 restricted stock units (RSUs). The sale represents a small portion of his overall equity position and does not involve any derivative exercises or tax-withholding transactions in this filing.
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. 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. 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).
Hippo Holdings Inc. executive Torben Ostergaard, CEO of Spinnaker, reported two transactions in the company’s common stock. On February 17, 2026, he completed an open-market sale of 6,105 shares at a weighted average price of $28.5653 per share, executed under a Rule 10b5-1 trading plan dated August 22, 2025. Following this sale, he directly held 46,694 shares.
On February 15, 2026, he disposed of 2,408 shares at $28.5919 per share to cover tax withholding obligations, a common administrative transaction. A footnote states that his holdings include 42,427 restricted stock units (RSUs), which represent additional equity awards that may settle in shares over time.
Hippo Holdings Inc. executive Michael Stienstra, GM & Chief Insurance, reported a tax-related share disposition. On February 15, 2026, 2,752 shares of common stock were transferred at $28.5919 per share to satisfy tax withholding obligations. After this transaction, he directly owned 68,529 common shares, which the filing states include 31,502 restricted stock units (RSUs).
Hippo Holdings Inc. Chief Financial Officer Guy Zeltser reported two stock transactions involving the company’s common shares. On November 14, 2025, he bought 665 shares in an open-market purchase at $7.23 per share. On February 15, 2026, he disposed of 4,483 shares in a tax-withholding transaction at an implied value of $28.5919 per share to cover exercise price or tax obligations. Following these transactions, he directly held 65,042 common shares, and a footnote states this amount includes 50,176 restricted stock units (RSUs). Another footnote explains that certain shares were acquired through the company’s Employee Stock Purchase Plan.
Hippo Holdings Inc. director and Chief Executive Officer Richard McCathron reported a tax-withholding disposition of common stock under an equity award. On this transaction, 11,586 shares of common stock were disposed of at an average price of $28.5919 per share to cover tax obligations. Following this administrative transaction, McCathron’s direct holdings total 431,118 shares of Hippo common stock, which the filing notes include 154,336 restricted stock units (RSUs) that are subject to vesting conditions.
Hippo Holdings Inc. Chief Executive Officer and director Richard McCathron sold 5,000 shares of common stock on February 9, 2026 in an open-market transaction at $29.14 per share, executed under a Rule 10b5-1 trading plan dated August 29, 2025.
After this sale, McCathron beneficially owned 442,704 shares of Hippo Holdings Inc. common stock, including 181,675 restricted stock units (RSUs), all reported as held directly.
Hippo Holdings Inc. Chief Executive Officer and director Richard McCathron reported selling 5,000 shares of common stock on January 9, 2026 at $31.52 per share in an open-market transaction coded as a sale.
After this transaction, he beneficially owned 447,704 shares of Hippo common stock, including 181,675 restricted stock units (RSUs). The filing notes that the sale was carried out under a pre-established Rule 10b5-1 trading plan dated August 29, 2025, indicating the trades were scheduled in advance.
Hippo Holdings Inc. officer GM & Chief Insurance, HHIP, Michael Stienstra reported a sale of company stock. On December 22, 2025, he sold 3,900 shares of common stock at a weighted average price of $31.1194 per share, executed in multiple trades between $31.01 and $31.25. The sales were made under a pre-arranged Rule 10b5-1 trading plan dated September 21, 2025, which is designed to provide an affirmative defense for insider trading when properly used. After this transaction, Stienstra beneficially owned 71,281 shares, including 37,874 restricted stock units (RSUs), all reported as directly held.
Hippo Holdings Inc. director reports charitable stock gift
A director of Hippo Holdings Inc. reported donating 4,935 shares of common stock on 12/18/2025 in a transaction coded as a gift at a price of $0.00 per share. After this donation, the director beneficially owns 16,563 shares of common stock directly, including 4,738 restricted stock units, and 50,000 shares indirectly through Janajasa Associates L.P. The filing reflects a personal charitable transfer rather than an open-market sale.
Hippo Holdings Inc. insider activity: Chief Executive Officer and director Richard McCathron reported selling 5,000 shares of Hippo common stock on 12/09/2025 at a price of $29.82 per share. The sale was carried out under a pre-arranged Rule 10b5-1 trading plan dated August 29, 2025, which is designed to allow insiders to sell shares according to a preset schedule. Following this transaction, McCathron beneficially owns 452,704 shares of Hippo common stock, which includes 181,675 restricted stock units (RSUs).
Hippo Holdings Inc. (HIPO) reported an insider stock sale by its officer serving as CEO of Spinnaker on a Form 4. On 11/21/2025, the reporting person sold 3,493 shares of common stock at a weighted average price of $31.9587, followed by a sale of 152 shares at a weighted average price of $32.6326. Both transactions were coded as open-market sales and were made under a Rule 10b5-1 trading plan dated August 22, 2025, which is designed to pre-schedule trades. After these transactions, the reporting person beneficially owned 55,207 shares of common stock, which includes 47,549 restricted stock units (RSUs), all reported as directly owned.
Hippo Holdings Inc. (HIPO) Chief Financial Officer Guy Zeltser reported equity transactions in company stock. On 11/15/2025, 4,182 shares of common stock were disposed of in a transaction coded "F," typically used for tax withholding related to equity awards, at a reported price of $31.1137 per share. On 11/18/2025, he sold 1,719 shares at a weighted average price of $32.1231 and an additional 100 shares at $32.74, in sales noted as made under a Rule 10b5-1 trading plan dated June 18, 2025. Following these transactions, Zeltser beneficially owns 68,860 shares of Hippo common stock, which includes 57,997 restricted stock units (RSUs).
Hippo Holdings Inc. (HIPO) reported an insider equity transaction by its GM & Chief Insurance, HHIP, Michael Stienstra. On 11/15/2025, a disposition coded "F" of 2,463 shares of common stock at $31.1137 per share was reported. After this transaction, Stienstra beneficially owned 75,181 shares, which includes 37,874 restricted stock units (RSUs). The filing reflects routine reporting of changes in an executive’s equity holdings.