Hippo Holdings (NYSE: HIPO) executive completes preplanned stock sale

Q: Was the Hippo Holdings (HIPO) insider sale by Torben Ostergaard pre-planned?

Yes, the reported sale was pre-planned. The footnotes state that the sales were effected pursuant to a Rule 10b5-1 trading plan dated August 22, 2025, indicating the transactions were scheduled in advance rather than timed discretionarily.

Filing Impact

(Moderate)

Filing Sentiment

(Negative)

Form Type

Rhea-AI Filing Summary

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.

Insider Trade Summary 10b5-1

Net Seller: 3,667 shares ($95,706)

Net Sell 2 txns

Insider Ostergaard Torben

Role CEO Spinnaker

Sold 3,667 shs ($96K)

Type	Security	Shares	Price	Value
Sale	Common Stock	3,667	$26.0993	$96K
Tax Withholding	Common Stock	1,340	$26.4123	$35K

Holdings After Transaction: Common Stock — 65,673 shares (Direct, null)

Footnotes (1)

Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 22, 2025 This transaction was executed in multiple trades at prices ranging from $25.94 to $26.47. 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. Includes 37,430 RSUs.

Key Figures

Open-market sale: 3,667 shares at $26.0993/share Tax-withholding shares: 1,340 shares at $26.4123/share Tax withholding total value: $35,377 (approx.) +3 more

6 metrics

Open-market sale 3,667 shares at $26.0993/share Common Stock sale on May 15, 2026

Tax-withholding shares 1,340 shares at $26.4123/share Shares disposed to cover tax obligations

Tax withholding total value $35,377 (approx.) 1,340 shares × $26.4123/share

Reported RSUs held 37,430 RSUs Included in direct holdings per footnote

Shares after tax disposition 64,333 shares Total shares following the F-code transaction

Shares after open-market sale 65,673 shares Total shares following the S-code transaction

Key Terms

Rule 10b5-1 trading plan, RSUs, tax-withholding disposition, open-market sale, +1 more

5 terms

Rule 10b5-1 trading plan financial

"Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 22, 2025"

A Rule 10b5-1 trading plan is a pre-arranged schedule that allows company insiders to buy or sell stock at specific times, even if they have inside information. It helps prevent accusations of unfair trading by making these transactions look planned and transparent, rather than sneaky or illegal.

RSUs financial

"Includes 37,430 RSUs."

RSUs, or restricted stock units, are a form of company shares given to employees as part of their compensation. They are typically awarded with certain restrictions, such as a waiting period before they can be fully owned or sold, similar to earning a gift that becomes fully yours over time. For investors, RSUs can impact a company's stock offerings and reflect how much the company relies on stock-based incentives to attract and retain talent.

tax-withholding disposition financial

"transaction_action": "tax-withholding disposition""

A tax-withholding disposition is an event or transaction—such as selling or transferring securities, exercising options, or receiving compensation—that triggers a requirement to hold back part of the payment and remit it to tax authorities. It matters to investors because it reduces the cash they receive immediately and can change the timing and amount of taxable income, like a cashier taking a portion of your sale proceeds to pay taxes before you get the rest.

open-market sale financial

"transaction_action": "open-market sale""

An open-market sale is when a shareholder sells existing shares directly on a public exchange to any willing buyer, rather than through a private deal. Think of it like putting goods on a busy market stall where price is set by supply and demand; for investors it matters because such sales increase available supply, can put short-term downward pressure on the stock price, and signal changes in liquidity or investor confidence.

weighted average sale price financial

"The price reported above reflects the weighted average sale price."

Form 4 Insider Transactions: What Each Field Means →

05/19/2026 - 08:24 PM

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Ostergaard Torben

(Last)

(First)

(Middle)

C/O HIPPO HOLDINGS INC., 1 ALMADEN BLVD

SUITE 400

(Street)

SAN JOSE

CALIFORNIA

95113

(City)

(State)

(Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
Hippo Holdings Inc. [ HIPO ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director	10% Owner
X	Officer (give title below)	Other (specify below)
	CEO Spinnaker

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
05/15/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Common Stock	05/15/2026		S⁽¹⁾		3,667	D	$26.0993⁽²⁾	65,673	D
Common Stock	05/15/2026		F		1,340	D	$26.4123	64,333⁽³⁾	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)

Explanation of Responses:

1. Sales were effected pursuant to a Rule 10b5-1 trading plan dated August 22, 2025

2. This transaction was executed in multiple trades at prices ranging from $25.94 to $26.47. 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.

3. Includes 37,430 RSUs.

Remarks:

	/s /Guy Zeltser, Attorney-in-Fact for Torben Ostergaard	05/19/2026
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR

FAQ

What insider transactions did Hippo Holdings (HIPO) report for Torben Ostergaard?

Torben Ostergaard reported two Hippo Holdings stock transactions. He disposed of 1,340 shares via tax withholding and sold 3,667 shares in an open-market trade, both involving Common Stock and dated May 15, 2026.

How many Hippo Holdings (HIPO) shares did Torben Ostergaard sell and at what price?

Ostergaard sold 3,667 Hippo Holdings shares in an open-market transaction. The weighted average sale price was approximately $26.10 per share, executed through multiple trades within a price range disclosed in the filing footnotes.

Was the Hippo Holdings (HIPO) insider sale by Torben Ostergaard pre-planned?

Yes, the reported sale was pre-planned. The footnotes state that the sales were effected pursuant to a Rule 10b5-1 trading plan dated August 22, 2025, indicating the transactions were scheduled in advance rather than timed discretionarily.

What portion of Torben Ostergaard’s Hippo Holdings (HIPO) shares were used for tax withholding?

Ostergaard used 1,340 Hippo Holdings shares for tax withholding. These shares were disposed of at a weighted average price of about $26.41 per share to satisfy tax obligations related to his equity compensation in Common Stock.

How many RSUs does Torben Ostergaard hold in Hippo Holdings (HIPO)?

Ostergaard’s holdings include 37,430 restricted stock units (RSUs). A filing footnote clarifies that his reported direct ownership encompasses these RSUs, which represent future share delivery subject to vesting conditions and company-specific terms.

Does the Hippo Holdings (HIPO) Form 4 show remaining equity exposure for Torben Ostergaard?

Yes, the Form 4 shows he retains a meaningful equity position. After the tax-withholding disposition and open-market sale, he still directly holds Common Stock, including 37,430 RSUs, maintaining continued exposure to Hippo Holdings’ share performance.