Tapewire

NYSE · USD

HIPO

Hippo Holdings Inc.

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Tapewire entity
5057
SEC CIK
0001828105
Parsed reports
359

Last 12 months

Inside the activity.

1 purchase rows · 21 sale rows

Disclosed non-derivative P/S rows, by transaction month. Includes amendments and private transactions.
Monthly counts
MonthPurchasesSales
Nov 202514
Dec 202502
Jan 202601
Feb 202603
Mar 202601
Apr 202601
May 202602
Jun 202601
Jul 202602
Aug 202602
Sep 202601
Oct 202601

Latest available

Insider transactions

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Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

The cutoff filters transaction history only. Company summaries and owner relationships show the latest available disclosures. Parser corrections can improve historical records.

Transaction dateOwner / reported roleActivity / securityShares / unitsReported priceReported valueDetails
March 02, 2026 Filed Mar 6, 2026 01:02 UTC
Stienstra MichaelGM & Chief Insurance, HHIP
GrantCommon Stock 14,810 $0.00 $0.00
Disclosure

SEC source: 0002014694-26-000003 · primarydocument.xml · nonDerivative · entry 1

Stienstra Michael · CIK 0002014694 · GM & Chief Insurance, HHIP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 83,339

F1 · shares: 1/12th of the RSU shares shall vest on each quarterly anniversary of February 15, 2026 over 3 years.

Read SEC document
March 02, 2026 Filed Mar 6, 2026 01:01 UTC
Ostergaard TorbenCEO Spinnaker
GrantCommon Stock 9,874 $0.00 $0.00
Disclosure

SEC source: 0002013319-26-000003 · primarydocument.xml · nonDerivative · entry 2

Ostergaard Torben · CIK 0002013319 · CEO Spinnaker

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 70,778

F2 · shares: The reported RSUs represent performance-based awards granted March 2, 2026, subject to service and performance conditions. The award consists of (i) 50% based on relative total shareholder return over a three-year performance period (vesting after three years), (ii) 25% based on gross written premium measured over a one-year performance period (vesting upon achievement), and (iii) 25% based on adjusted return on equity measured over a one-year performance period, subject to an additional one-year service requirement prior to vesting.

F3 · balance_after: Includes 67,111 RSUs.

Read SEC document
March 02, 2026 Filed Mar 6, 2026 01:01 UTC
Ostergaard TorbenCEO Spinnaker
GrantCommon Stock 14,810 $0.00 $0.00
Disclosure

SEC source: 0002013319-26-000003 · primarydocument.xml · nonDerivative · entry 1

Ostergaard Torben · CIK 0002013319 · CEO Spinnaker

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 60,904

F1 · shares: 1/12th of the RSU shares shall vest on each quarterly anniversary of February 15, 2026 over 3 years.

Read SEC document
February 25, 2026 Filed Feb 27, 2026 21:58 UTC
Ostergaard TorbenCEO Spinnaker
SaleCommon Stock 600 $30.44 $18,266.10
Disclosure

SEC source: 0002013319-26-000002 · primarydocument.xml · nonDerivative · entry 1

Ostergaard Torben · CIK 0002013319 · CEO Spinnaker

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 46,094

F1 · kind: Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 22, 2025

F2 · price: This transaction was executed in multiple trades at prices ranging from $30.19 to $30.56. The price reported above reflects the weighted average sale price. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares and prices at which the transaction was effected.

F3 · balance_after: Includes 42,427 RSUs.

Read SEC document
February 17, 2026 Filed Feb 19, 2026 00:04 UTC
Ostergaard TorbenCEO Spinnaker
SaleCommon Stock 6,105 $28.57 $174,391.16
Disclosure

SEC source: 0002013319-26-000001 · primarydocument.xml · nonDerivative · entry 2

Ostergaard Torben · CIK 0002013319 · CEO Spinnaker

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 46,694

F1 · kind: Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 22, 2025

F2 · price: This transaction was executed in multiple trades at prices ranging from $28.10 to $28.99. The price reported above reflects the weighted average sale price. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares and prices at which the transaction was effected.

F3 · balance_after: Includes 42,427 RSUs.

Read SEC document
February 15, 2026 Filed Feb 19, 2026 00:02 UTC
Zeltser GuyChief Financial Officer
Tax withholdingCommon Stock 4,483 $28.59 $128,177.49
Disclosure

SEC source: 0002061058-26-000001 · primarydocument.xml · nonDerivative · entry 2

Zeltser Guy · CIK 0002061058 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 65,042

F2 · balance_after: Includes 50,176 RSUs.

Read SEC document
February 15, 2026 Filed Feb 19, 2026 00:03 UTC
Stienstra MichaelGM & Chief Insurance, HHIP
Tax withholdingCommon Stock 2,752 $28.59 $78,684.91
Disclosure

SEC source: 0002014694-26-000002 · primarydocument.xml · nonDerivative · entry 1

Stienstra Michael · CIK 0002014694 · GM & Chief Insurance, HHIP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 68,529

F1 · balance_after: Includes 31,502 RSUs.

Read SEC document
February 15, 2026 Filed Feb 19, 2026 00:04 UTC
Ostergaard TorbenCEO Spinnaker
Tax withholdingCommon Stock 2,408 $28.59 $68,849.30
Disclosure

SEC source: 0002013319-26-000001 · primarydocument.xml · nonDerivative · entry 1

Ostergaard Torben · CIK 0002013319 · CEO Spinnaker

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 52,799

Read SEC document
February 15, 2026 Filed Feb 19, 2026 00:02 UTC
McCathron RichardDirector · Chief Executive Officer
Tax withholdingCommon Stock 11,586 $28.59 $331,265.75
Disclosure

SEC source: 0001294172-26-000003 · primarydocument.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 431,118

F1 · balance_after: Includes 154,336 RSUs.

Read SEC document
February 09, 2026 Filed Feb 11, 2026 21:52 UTC
McCathron RichardDirector · Chief Executive Officer
SaleCommon Stock 5,000 $29.14 $145,700.00
Disclosure

SEC source: 0001294172-26-000002 · primarydocument.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 442,704

F1 · kind: Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 29, 2025.

F2 · balance_after: Includes 181,675 RSUs.

Read SEC document
January 09, 2026 Filed Jan 13, 2026 22:47 UTC
McCathron RichardDirector · Chief Executive Officer
SaleCommon Stock 5,000 $31.52 $157,600.00
Disclosure

SEC source: 0001294172-26-000001 · primarydocument.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 447,704

F1 · kind: Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 29, 2025.

F2 · balance_after: Includes 181,675 RSUs.

Read SEC document
December 22, 2025 Filed Dec 29, 2025 17:20 UTC
Stienstra MichaelGM & Chief Insurance, HHIP
SaleCommon Stock 3,900 $31.12 $121,365.66
Disclosure

SEC source: 0002014694-25-000005 · primarydocument.xml · nonDerivative · entry 1

Stienstra Michael · CIK 0002014694 · GM & Chief Insurance, HHIP

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 71,281

F1 · kind: Sales were effected pursuant to a Rule 10b5-1 trading plan dated September 21, 2025.

F2 · price: This transaction was executed in multiple trades at prices ranging from $31.01 to $31.25. The price reported above reflects the weighted average sale price. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares and prices at which the transaction was effected.

F3 · balance_after: Includes 37,874 RSUs.

Read SEC document
December 18, 2025 Filed Dec 19, 2025 21:30 UTC GiftCommon Stock 4,935 $0.00 $0.00
Disclosure

SEC source: 0001256130-25-000003 · primarydocument.xml · nonDerivative · entry 1

NICHOLS JOHN DRAKE · CIK 0001256130 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,563

F1 · shares: The reporting person donated the shares to multiple charitable organizations for no consideration.

F2 · balance_after: Includes 4,738 RSUs.

Read SEC document
December 09, 2025 Filed Dec 11, 2025 21:41 UTC
McCathron RichardDirector · Chief Executive Officer
SaleCommon Stock 5,000 $29.82 $149,100.00
Disclosure

SEC source: 0001294172-25-000005 · primarydocument.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 452,704

F1 · kind: Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 29, 2025.

F2 · balance_after: Includes 181,675 RSUs.

Read SEC document
November 21, 2025 Filed Nov 25, 2025 21:24 UTC
Ostergaard TorbenCEO Spinnaker
SaleCommon Stock 152 $32.63 $4,960.16
Disclosure

SEC source: 0002013319-25-000005 · primarydocument.xml · nonDerivative · entry 2

Ostergaard Torben · CIK 0002013319 · CEO Spinnaker

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 55,207

F1 · kind: Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 22, 2025

F3 · price: This transaction was executed in multiple trades at prices ranging from $32.58 to $32.66. The price reported above reflects the weighted average sale price. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares and prices at which the transaction was effected.

F4 · balance_after: Includes 47,549 RSUs.

Read SEC document
November 21, 2025 Filed Nov 25, 2025 21:24 UTC
Ostergaard TorbenCEO Spinnaker
SaleCommon Stock 3,493 $31.96 $111,631.74
Disclosure

SEC source: 0002013319-25-000005 · primarydocument.xml · nonDerivative · entry 1

Ostergaard Torben · CIK 0002013319 · CEO Spinnaker

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 55,359

F1 · kind: Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 22, 2025

F2 · price: This transaction was executed in multiple trades at prices ranging from $31.56 to $32.46. The price reported above reflects the weighted average sale price. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares and prices at which the transaction was effected.

Read SEC document
November 18, 2025 Filed Nov 19, 2025 21:56 UTC
Zeltser GuyChief Financial Officer
SaleCommon Stock 100 $32.74 $3,274.00
Disclosure

SEC source: 0002061058-25-000005 · primarydocument.xml · nonDerivative · entry 3

Zeltser Guy · CIK 0002061058 · Chief Financial Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 68,860

F1 · kind: Sales were effected pursuant to a Rule 10b5-1 trading plan dated June 18, 2025.

F3 · balance_after: Includes 57,997 RSUs.

Read SEC document
November 18, 2025 Filed Nov 19, 2025 21:56 UTC
Zeltser GuyChief Financial Officer
SaleCommon Stock 1,719 $32.12 $55,219.61
Disclosure

SEC source: 0002061058-25-000005 · primarydocument.xml · nonDerivative · entry 2

Zeltser Guy · CIK 0002061058 · Chief Financial Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 68,960

F1 · kind: Sales were effected pursuant to a Rule 10b5-1 trading plan dated June 18, 2025.

F2 · price: This transaction was executed in multiple trades at prices ranging from $31.52 to $32.43. The price reported above reflects the weighted average sale price. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares and prices at which the transaction was effected.

Read SEC document
November 15, 2025 Filed Nov 18, 2025 22:03 UTC
Stienstra MichaelGM & Chief Insurance, HHIP
Tax withholdingCommon Stock 2,463 $31.11 $76,633.04
Disclosure

SEC source: 0002014694-25-000004 · primarydocument.xml · nonDerivative · entry 1

Stienstra Michael · CIK 0002014694 · GM & Chief Insurance, HHIP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 75,181

F1 · balance_after: Includes 37,874 RSUs.

Read SEC document
November 15, 2025 Filed Nov 18, 2025 22:02 UTC
Ostergaard TorbenCEO Spinnaker
Tax withholdingCommon Stock 2,123 $31.11 $66,054.39
Disclosure

SEC source: 0002013319-25-000004 · primarydocument.xml · nonDerivative · entry 1

Ostergaard Torben · CIK 0002013319 · CEO Spinnaker

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 58,852

F1 · balance_after: Includes 47,549 RSUs.

Read SEC document
November 15, 2025 Filed Nov 18, 2025 22:02 UTC
McCathron RichardDirector · Chief Executive Officer
Tax withholdingCommon Stock 11,326 $31.11 $352,393.77
Disclosure

SEC source: 0001294172-25-000004 · primarydocument.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 457,704

F1 · balance_after: Includes 181,675 RSUs.

Read SEC document
November 15, 2025 Filed Nov 19, 2025 21:56 UTC
Zeltser GuyChief Financial Officer
Tax withholdingCommon Stock 4,182 $31.11 $130,117.49
Disclosure

SEC source: 0002061058-25-000005 · primarydocument.xml · nonDerivative · entry 1

Zeltser Guy · CIK 0002061058 · Chief Financial Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 70,679

Read SEC document
November 14, 2025 Filed Feb 19, 2026 00:02 UTC
Zeltser GuyChief Financial Officer
PurchaseCommon Stock 665 $7.23 $4,807.95
Disclosure

SEC source: 0002061058-26-000001 · primarydocument.xml · nonDerivative · entry 1

Zeltser Guy · CIK 0002061058 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 69,525

F1 · shares: Acquired pursuant to Issuer's Employee Stock Purchase Plan.

Read SEC document
October 01, 2025 Filed Oct 3, 2025 22:15 UTC
Hay Laura JDirector
GrantCommon Stock 2,502 $0.00 $0.00
Disclosure

SEC source: 0002013372-25-000013 · primarydocument.xml · nonDerivative · entry 1

Hay Laura J · CIK 0002013372 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,502

F1 · shares: Constitute restricted stock units ("RSUs") for which the Reporting Person is entitled to receive one (1) share of Common Stock for each RSU upon vesting. The RSUs will vest in full upon the earlier of (i) the first anniversary of the date of grant and (ii) immediately prior to the Annual Meeting that occurs following the date of grant, subject to the Reporting Person continuing in service to the Issuer and its subsidiaries through such vesting date.

F2 · balance_after: Includes 2,502 RSUs.

Read SEC document
October 01, 2025 Filed Oct 3, 2025 22:15 UTC GrantCommon Stock 2,502 $0.00 $0.00
Disclosure

SEC source: 0002090082-25-000003 · primarydocument.xml · nonDerivative · entry 1

Holliday Susan Claire · CIK 0002090082 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,502

F1 · shares: Constitute restricted stock units ("RSUs") for which the Reporting Person is entitled to receive one (1) share of Common Stock for each RSU upon vesting. The RSUs will vest in full upon the earlier of (i) the first anniversary of the date of grant and (ii) immediately prior to the Annual Meeting that occurs following the date of grant, subject to the Reporting Person continuing in service to the Issuer and its subsidiaries through such vesting date.

F2 · balance_after: Includes 2,502 RSUs.

Read SEC document
September 17, 2025 Filed Sep 19, 2025 20:33 UTC
Zeltser GuyChief Financial Officer
SaleCommon Stock 200 $38.05 $7,609.00
Disclosure

SEC source: 0002061058-25-000003 · primarydocument.xml · nonDerivative · entry 2

Zeltser Guy · CIK 0002061058 · Chief Financial Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 74,861

F1 · kind: Sales were effected pursuant to a Rule 10b5-1 trading plan dated June 18, 2025.

F3 · price: This transaction was executed in multiple trades at prices ranging from $37.98 to $38.11. The price reported above reflects the weighted average sale price. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares and prices at which the transaction was effected.

F4 · balance_after: Includes 65,817 RSUs.

Read SEC document
September 17, 2025 Filed Sep 19, 2025 20:33 UTC
Zeltser GuyChief Financial Officer
SaleCommon Stock 4,977 $37.46 $186,422.99
Disclosure

SEC source: 0002061058-25-000003 · primarydocument.xml · nonDerivative · entry 1

Zeltser Guy · CIK 0002061058 · Chief Financial Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 75,061

F1 · kind: Sales were effected pursuant to a Rule 10b5-1 trading plan dated June 18, 2025.

F2 · price: This transaction was executed in multiple trades at prices ranging from $36.95 to $37.92. The price reported above reflects the weighted average sale price. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares and prices at which the transaction was effected.

Read SEC document
September 10, 2025 Filed Sep 11, 2025 22:28 UTC
Zeltser GuyChief Financial Officer
Tax withholdingCommon Stock 1,029 $36.97 $38,042.13
Disclosure

SEC source: 0001562180-25-006168 · primarydocument.xml · nonDerivative · entry 1

Zeltser Guy · CIK 0002061058 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 80,038

F1 · balance_after: Includes 65,817 RSUs.

Read SEC document
September 10, 2025 Filed Sep 11, 2025 22:29 UTC
Stienstra MichaelGM & Chief Insurance, HHIP
Tax withholdingCommon Stock 752 $36.97 $27,801.44
Disclosure

SEC source: 0001562180-25-006170 · primarydocument.xml · nonDerivative · entry 1

Stienstra Michael · CIK 0002014694 · GM & Chief Insurance, HHIP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 77,644

F1 · balance_after: Includes 44,246 RSUs.

Read SEC document
September 10, 2025 Filed Sep 11, 2025 22:28 UTC
Ostergaard TorbenCEO Spinnaker
Tax withholdingCommon Stock 1,358 $36.97 $50,205.26
Disclosure

SEC source: 0001562180-25-006169 · primarydocument.xml · nonDerivative · entry 1

Ostergaard Torben · CIK 0002013319 · CEO Spinnaker

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 60,975

F1 · balance_after: Includes 52,671 RSUs.

Read SEC document
September 10, 2025 Filed Sep 11, 2025 22:28 UTC
McCathron RichardDirector · Chief Executive Officer
Tax withholdingCommon Stock 1,358 $36.97 $50,205.26
Disclosure

SEC source: 0001562180-25-006167 · primarydocument.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 469,030

F1 · balance_after: Includes 209,014 RSUs.

Read SEC document
September 08, 2025 Filed Sep 10, 2025 22:04 UTC
McCathron RichardDirector · Chief Executive Officer
SaleCommon Stock 2,725 $34.12 $92,969.37
Disclosure

SEC source: 0001562180-25-006163 · primarydocument.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 470,388

F1 · kind: Sales were effected pursuant to a Rule 10b5-1 trading plan adopted December 3, 2024.

F2 · price: This transaction was executed in multiple trades at prices ranging from $34.00 to $34.26. The price reported above reflects the weighted average sale price. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares and prices at which the transaction was effected.

F3 · balance_after: Includes 212,464 RSUs.

Read SEC document
August 22, 2025 Filed Aug 26, 2025 20:38 UTC
McCathron RichardDirector · Chief Executive Officer
SaleCommon Stock 2,275 $34.00 $77,350.91
Disclosure

SEC source: 0001562180-25-006012 · primarydocument.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 473,113

F1 · kind: Sales were effected pursuant to a Rule 10b5-1 trading plan adopted on December 3, 2024.

F2 · balance_after: Includes 212,464 RSUs.

Read SEC document
August 15, 2025 Filed Aug 18, 2025 21:03 UTC
Zeltser GuyChief Financial Officer
Tax withholdingCommon Stock 3,973 $30.91 $122,805.43
Disclosure

SEC source: 0001562180-25-005855 · primarydocument.xml · nonDerivative · entry 1

Zeltser Guy · CIK 0002061058 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 81,067

F1 · balance_after: Includes 67,842 RSUs.

Read SEC document
August 15, 2025 Filed Aug 18, 2025 21:10 UTC
Stienstra MichaelGM & Chief Insurance, HHIP
Tax withholdingCommon Stock 2,341 $30.91 $72,360.31
Disclosure

SEC source: 0001562180-25-005858 · primarydocument.xml · nonDerivative · entry 1

Stienstra Michael · CIK 0002014694 · GM & Chief Insurance, HHIP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 78,396

F1 · balance_after: Includes 46,271 RSUs.

Read SEC document
August 15, 2025 Filed Aug 18, 2025 21:05 UTC
Ostergaard TorbenCEO Spinnaker
Tax withholdingCommon Stock 2,016 $30.91 $62,314.56
Disclosure

SEC source: 0001562180-25-005857 · primarydocument.xml · nonDerivative · entry 1

Ostergaard Torben · CIK 0002013319 · CEO Spinnaker

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 62,333

F1 · balance_after: Includes 56,121 RSUs.

Read SEC document
August 15, 2025 Filed Aug 18, 2025 21:02 UTC
McCathron RichardDirector · Chief Executive Officer
Tax withholdingCommon Stock 10,759 $30.91 $332,560.69
Disclosure

SEC source: 0001562180-25-005854 · primarydocument.xml · nonDerivative · entry 1

McCathron Richard · CIK 0001294172 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 475,388

F1 · balance_after: Includes 212,464 RSUs.

Read SEC document
July 01, 2025 Filed Jul 3, 2025 10:02 UTC
Len FW Investor, LLCFormer 10% Owner
Len X, LLCFormer 10% Owner
LENNAR CORP /NEW/Former 10% Owner
SaleCommon Stock 514,309 $28.17 $14,488,084.53
Disclosure

SEC source: 0000950170-25-093542 · ownership.xml · nonDerivative · entry 2

Len FW Investor, LLC · CIK 0001875144 · Former 10% Owner

Len X, LLC · CIK 0001875154 · Former 10% Owner

LENNAR CORP /NEW/ · CIK 0000920760 · Former 10% Owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,476,418

F4 · kind: Represents shares of Common Stock sold pursuant to a Share Repurchase Agreement between Hippo Holdings Inc. and Len FW Investor, LLC ("LEN FW"), dated as of June 11, 2025.

F3 · balance_after: The securities are directly owned by LEN FW, the sole member of which is LEN X, LLC ("LENX"), which is a wholly-owned subsidiary of Lennar Corporation ("Lennar"), a publicly traded company with its stock listed on the NYSE. LENX and Lennar are indirect beneficial owners and disclaim beneficial ownership except to the extent of their pecuniary interest therein. LEN FW holds a proxy to vote an additional 16,470 shares, but it has no pecuniary interest in those shares.

Read SEC document
June 12, 2025 Filed Jun 16, 2025 20:47 UTC
Ostergaard TorbenCEO Spinnaker
SaleCommon Stock 2,444 $29.95 $73,197.80
Disclosure

SEC source: 0001562180-25-004854 · primarydocument.xml · nonDerivative · entry 1

Ostergaard Torben · CIK 0002013319 · CEO Spinnaker

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 64,349

F1 · kind: Sales were effected pursuant to a Rule 10b5-1 trading plan dated September 17, 2024

F2 · balance_after: Includes 61,243 RSUs.

Read SEC document
June 04, 2025 Filed Jun 6, 2025 20:50 UTC
Ostergaard TorbenCEO Spinnaker
SaleCommon Stock 4,889 $24.61 $120,316.82
Disclosure

SEC source: 0001562180-25-004571 · primarydocument.xml · nonDerivative · entry 1

Ostergaard Torben · CIK 0002013319 · CEO Spinnaker

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 66,793

F1 · kind: Sales were effected pursuant to a Rule 10b5-1 trading plan dated September 17, 2024

F2 · price: This transaction was executed in multiple trades at prices ranging from $24.0900 to $25.1300. The price reported above reflects the weighted average sale price. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares and prices at which the transaction was effected.

F3 · balance_after: Includes 61,243 RSUs.

Read SEC document
June 03, 2025 Filed Jun 5, 2025 20:48 UTC GrantCommon Stock 4,738 $0.00 $0.00
Disclosure

SEC source: 0001562180-25-004496 · primarydocument.xml · nonDerivative · entry 2

Fouche Lori Dickerson · CIK 0001860810 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 21,815

F2 · shares: Constitute restricted stock units ("RSUs") for which the Reporting Person is entitled to receive one (1) share of Common Stock for each RSU upon vesting. The RSUs will vest in full upon the earlier of (i) the first anniversary of the date of grant and (ii) immediately prior to the Annual Meeting that occurs following the date of grant, subject to the Reporting Person continuing in service to the Issuer and its subsidiaries through such vesting date.

F3 · balance_after: Includes 4,738 RSUs.

Read SEC document
June 03, 2025 Filed Jun 5, 2025 20:48 UTC GrantCommon Stock 5,801 $24.35 $141,254.35
Disclosure

SEC source: 0001562180-25-004496 · primarydocument.xml · nonDerivative · entry 1

Fouche Lori Dickerson · CIK 0001860810 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,077

F1 · shares: Vesting/settlement of 5,801 RSUs originally granted on June 4, 2024 into Common Stock

Read SEC document
June 03, 2025 Filed Jun 5, 2025 20:46 UTC GrantCommon Stock 4,738 $0.00 $0.00
Disclosure

SEC source: 0001562180-25-004494 · primarydocument.xml · nonDerivative · entry 2

FRATER HUGH R · CIK 0001059244 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 21,815

F2 · shares: Constitute restricted stock units ("RSUs") for which the Reporting Person is entitled to receive one (1) share of Common Stock for each RSU upon vesting. The RSUs will vest in full upon the earlier of (i) the first anniversary of the date of grant and (ii) immediately prior to the Annual Meeting that occurs following the date of grant, subject to the Reporting Person continuing in service to the Issuer and its subsidiaries through such vesting date.

F3 · balance_after: Includes 4,738 RSUs.

Read SEC document
June 03, 2025 Filed Jun 5, 2025 20:46 UTC GrantCommon Stock 5,801 $24.35 $141,254.35
Disclosure

SEC source: 0001562180-25-004494 · primarydocument.xml · nonDerivative · entry 1

FRATER HUGH R · CIK 0001059244 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,077

F1 · shares: Vesting/settlement of 5,801 RSUs originally granted on June 4, 2024 into Common Stock

Read SEC document
June 03, 2025 Filed Jun 5, 2025 20:44 UTC
Schaaf MarkDirector
GrantCommon Stock 4,738 $0.00 $0.00
Disclosure

SEC source: 0001562180-25-004492 · primarydocument.xml · nonDerivative · entry 2

Schaaf Mark · CIK 0001983799 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,103

F2 · shares: Constitute restricted stock units ("RSUs") for which the Reporting Person is entitled to receive one (1) share of Common Stock for each RSU upon vesting. The RSUs will vest in full upon the earlier of (i) the first anniversary of the date of grant and (ii) immediately prior to the Annual Meeting that occurs following the date of grant, subject to the Reporting Person continuing in service to the Issuer and its subsidiaries through such vesting date.

F3 · balance_after: Includes 4,738 RSUs.

Read SEC document
June 03, 2025 Filed Jun 5, 2025 20:44 UTC
Schaaf MarkDirector
GrantCommon Stock 5,801 $24.35 $141,254.35
Disclosure

SEC source: 0001562180-25-004492 · primarydocument.xml · nonDerivative · entry 1

Schaaf Mark · CIK 0001983799 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,365

F1 · shares: Vesting/settlement of 5,801 RSUs originally granted on June 4, 2024 into Common Stock

Read SEC document
June 03, 2025 Filed Jun 5, 2025 20:49 UTC
Landman SamDirector
GrantCommon Stock 4,738 $0.00 $0.00
Disclosure

SEC source: 0001562180-25-004497 · primarydocument.xml · nonDerivative · entry 2

Landman Sam · CIK 0001875287 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,272

F2 · shares: Constitute restricted stock units ("RSUs") for which the Reporting Person is entitled to receive one (1) share of Common Stock for each RSU upon vesting. The RSUs will vest in full upon the earlier of (i) the first anniversary of the date of grant and (ii) immediately prior to the Annual Meeting that occurs following the date of grant, subject to the Reporting Person continuing in service to the Issuer and its subsidiaries through such vesting date.

F3 · balance_after: Includes 4,738 RSUs.

Read SEC document
June 03, 2025 Filed Jun 5, 2025 20:49 UTC
Landman SamDirector
GrantCommon Stock 5,801 $24.35 $141,254.35
Disclosure

SEC source: 0001562180-25-004497 · primarydocument.xml · nonDerivative · entry 1

Landman Sam · CIK 0001875287 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 19,534

F1 · shares: Vesting/settlement of 5,801 RSUs originally granted on June 4, 2024 into Common Stock

Read SEC document
June 03, 2025 Filed Jun 5, 2025 20:50 UTC GrantCommon Stock 4,738 $0.00 $0.00
Disclosure

SEC source: 0001562180-25-004498 · primarydocument.xml · nonDerivative · entry 2

WIJNBERG SANDRA S · CIK 0001194455 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 21,815

F2 · shares: Constitute restricted stock units ("RSUs") for which the Reporting Person is entitled to receive one (1) share of Common Stock for each RSU upon vesting. The RSUs will vest in full upon the earlier of (i) the first anniversary of the date of grant and (ii) immediately prior to the Annual Meeting that occurs following the date of grant, subject to the Reporting Person continuing in service to the Issuer and its subsidiaries through such vesting date.

F3 · balance_after: Includes 4,738 RSUs.

Read SEC document
June 03, 2025 Filed Jun 5, 2025 20:50 UTC GrantCommon Stock 5,801 $24.35 $141,254.35
Disclosure

SEC source: 0001562180-25-004498 · primarydocument.xml · nonDerivative · entry 1

WIJNBERG SANDRA S · CIK 0001194455 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,077

F1 · shares: Vesting/settlement of 5,801 RSUs originally granted on June 4, 2024 into Common Stock

Read SEC document

Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.