HIPO SEC Filing News — Hippo Holdings Inc.

Latest SEC filings for Hippo Holdings Inc. (HIPO) explained in plain English. Covers insider buying and selling (Form 4), proposed insider sales (Form 144), material company events (8-K), and quarterly & annual reports (10-Q / 10-K). StrongBuyAnalytics provides navigation and brief excerpts or summaries; original filings remain at the SEC/source links and were authored by their filers, not StrongBuyAnalytics. Filing dates shown are source dates. Coverage and detection can be delayed or incomplete because of SEC availability, amendments, parsing, caching, or outages. Latest source filing date shown: 2026-10-16.

Hippo Holdings Inc., together with its subsidiaries, provides property and casualty insurance products to individuals and business customers primarily in the United States. The company provides a multi-carrier platform through owned and partner managing general agents (MGAs), serving as a licensed insurance carrier for MGAs and providing admitted and non-admitted (excess and surplus) paper, regulatory licenses, and reinsurance across multiple lines of business. The company also offers insurance …
Sector: Financial Services Industry: Insurance - Property & Casualty Market Cap: $935.5M
20
Total Filings
0
Bullish Classifications
7
Bearish Classifications
12
Insider Transactions
1
Material Events (8-K)
1
Periodic Reports
Rule-based classifications for HIPO currently lean bearish. Of the 20 filing records displayed, 7 carry bearish classifications (such as insider sales or negative 8-K disclosures) versus 0 bullish. This does not necessarily signal fundamental deterioration — insiders sell for many reasons — but it is worth monitoring alongside the company's core financial metrics.
HIPO Filing Activity Snapshot 2026-07-13 — 2026-10-16
Insider Transactions (Form 4)
0 buys vs 7 sells
Net insider selling in this period — insiders sell for many reasons beyond conviction.
Largest Form 144 Filing
$170.9K
McCathron Richard (Director, Chief Executive Officer) · 2026-10-13
5,000 shares · Form 4
Form 144 Notices
6
Proposed insider sales filed — Form 144 is a notice of intent, not a confirmed transaction. Actual sales are confirmed via Form 4.
Insider Transactions 12 · Forms 3, 4 and 5

A Form 4 is filed within two business days of a company insider — an officer, a director, or a holder of more than ten percent of the stock — changing their position in the shares. All 12 filings in this group are Form 4s for Hippo Holdings Inc.

The difficulty with reading these filings as a group is that a single form type covers transactions that mean entirely different things. An executive spending their own money to buy stock and an executive having shares withheld to pay tax on a vesting grant both appear as a Form 4. Every filing below is therefore tagged with the nature of the underlying transaction, taken from the transaction code reported on the form itself.

Across the 12 insider filings shown, the breakdown is 7 open-market sale, 4 tax withholding and 1 compensation award. 7 of them involved a discretionary open-market trade; the rest are compensation and administrative mechanics.

What each transaction type means

Open-market sale ×7
The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.
Tax withholding ×4
Shares were withheld by the company to settle tax due when equity vested. This is an automatic administrative step and not a decision to sell.
Compensation award ×1
Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.
Form 4 Open-market sale Insider Selling 2026-10-16

HIPO insider Ostergaard Torben (CEO Spinnaker) sold 1,169 shares (~$41.0K)

Ostergaard Torben, listed as CEO Spinnaker at Hippo Holdings Inc., reported an open-market sale of 1,169 HIPO shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
S Open-market sale 1,169 $35.03 $41.0K
Filing: Form 4 (Insider Transaction) Insider: Ostergaard Torben (CEO Spinnaker) Shares: 1,169 Est. Value: $41.0K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-10-13

HIPO insider McCathron Richard (Director, Chief Executive Officer) sold 5,000 shares (~$170.9K)

McCathron Richard, listed as Director, Chief Executive Officer at Hippo Holdings Inc., reported an open-market sale of 5,000 HIPO shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
S Open-market sale 5,000 $34.18 $170.9K
Filing: Form 4 (Insider Transaction) Insider: McCathron Richard (Director, Chief Executive Officer) Shares: 5,000 Est. Value: $170.9K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-09-11

HIPO insider McCathron Richard (Director, Chief Executive Officer) sold 5,000 shares (~$161.1K)

McCathron Richard, listed as Director, Chief Executive Officer at Hippo Holdings Inc., reported an open-market sale of 5,000 HIPO shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
S Open-market sale 5,000 $32.23 $161.1K
Filing: Form 4 (Insider Transaction) Insider: McCathron Richard (Director, Chief Executive Officer) Shares: 5,000 Est. Value: $161.1K
View on SEC EDGAR → Open Filing Document →
Form 4 Compensation award Tax / Compensation Filing 2026-08-19

HIPO insider Form 4 filed for equity award, exercise, or tax withholding

Ellis Stewart (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.

Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.

Transactions reported on this filing
Code Nature Shares Price Value
A Compensation award 5,350 $33.04 $176.8K
Filing: Form 4 (Insider Transaction) Insider: Ellis Stewart (Director) Shares: 5,350
View on SEC EDGAR → Open Filing Document →
Form 4 Tax withholding Tax / Compensation Filing 2026-08-18

HIPO insider Form 4 filed for equity award, exercise, or tax withholding

Boettcher Laura (Chief Operating Officer) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.

Shares were withheld by the company to settle tax due when equity vested. This is an automatic administrative step and not a decision to sell.

Transactions reported on this filing
Code Nature Shares Price Value
F Tax withholding on vested shares 1,586 $32.83 $52.1K
Filing: Form 4 (Insider Transaction) Insider: Boettcher Laura (Chief Operating Officer) Shares: 1,586
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-08-18

HIPO insider Ostergaard Torben (CEO Spinnaker) sold 1,169 shares (~$38.6K)

Ostergaard Torben, listed as CEO Spinnaker at Hippo Holdings Inc., reported an open-market sale of 1,169 HIPO shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
F Tax withholding on vested shares 1,340 $32.83 $44.0K
S Open-market sale 1,169 $33.00 $38.6K
Filing: Form 4 (Insider Transaction) Insider: Ostergaard Torben (CEO Spinnaker) Shares: 1,169 Est. Value: $38.6K
View on SEC EDGAR → Open Filing Document →
Form 4 Tax withholding Tax / Compensation Filing 2026-08-18

HIPO insider Form 4 filed for equity award, exercise, or tax withholding

Stienstra Michael (GM & Chief Insurance, HHIP) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.

Shares were withheld by the company to settle tax due when equity vested. This is an automatic administrative step and not a decision to sell.

Transactions reported on this filing
Code Nature Shares Price Value
F Tax withholding on vested shares 1,259 $32.83 $41.3K
Filing: Form 4 (Insider Transaction) Insider: Stienstra Michael (GM & Chief Insurance, HHIP) Shares: 1,259
View on SEC EDGAR → Open Filing Document →
Form 4 Tax withholding Tax / Compensation Filing 2026-08-18

HIPO insider Form 4 filed for equity award, exercise, or tax withholding

Zeltser Guy (Chief Financial Officer) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.

Shares were withheld by the company to settle tax due when equity vested. This is an automatic administrative step and not a decision to sell.

Transactions reported on this filing
Code Nature Shares Price Value
F Tax withholding on vested shares 3,945 $32.83 $129.5K
Filing: Form 4 (Insider Transaction) Insider: Zeltser Guy (Chief Financial Officer) Shares: 3,945
View on SEC EDGAR → Open Filing Document →
Form 4 Tax withholding Tax / Compensation Filing 2026-08-18

HIPO insider Form 4 filed for equity award, exercise, or tax withholding

McCathron Richard (Director, Chief Executive Officer) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.

Shares were withheld by the company to settle tax due when equity vested. This is an automatic administrative step and not a decision to sell.

Transactions reported on this filing
Code Nature Shares Price Value
F Tax withholding on vested shares 8,301 $32.83 $272.5K
Filing: Form 4 (Insider Transaction) Insider: McCathron Richard (Director, Chief Executive Officer) Shares: 8,301
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-08-12

HIPO insider McCathron Richard (Director, Chief Executive Officer) sold 5,000 shares (~$160.0K)

McCathron Richard, listed as Director, Chief Executive Officer at Hippo Holdings Inc., reported an open-market sale of 5,000 HIPO shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
S Open-market sale 5,000 $32.00 $160.0K
Filing: Form 4 (Insider Transaction) Insider: McCathron Richard (Director, Chief Executive Officer) Shares: 5,000 Est. Value: $160.0K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-07-30

HIPO insider Zeltser Guy (Chief Financial Officer) sold 1,669 shares (~$51.7K)

Zeltser Guy, listed as Chief Financial Officer at Hippo Holdings Inc., reported an open-market sale of 1,669 HIPO shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
S Open-market sale 1,669 $30.98 $51.7K
Filing: Form 4 (Insider Transaction) Insider: Zeltser Guy (Chief Financial Officer) Shares: 1,669 Est. Value: $51.7K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-07-13

HIPO insider McCathron Richard (Director, Chief Executive Officer) sold 5,000 shares (~$142.7K)

McCathron Richard, listed as Director, Chief Executive Officer at Hippo Holdings Inc., reported an open-market sale of 5,000 HIPO shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
S Open-market sale 5,000 $28.53 $142.7K
Filing: Form 4 (Insider Transaction) Insider: McCathron Richard (Director, Chief Executive Officer) Shares: 5,000 Est. Value: $142.7K
View on SEC EDGAR → Open Filing Document →
Proposed Insider Sales 6 · Form 144

A Form 144 is a notice of intent to sell restricted or control securities. It is not a record that anything was sold. Hippo Holdings Inc. has 6 such notices in this period.

The distinction matters because a Form 144 is frequently reported as though it were a completed insider sale. The filer may sell all of the shares covered, some of them, or none at all, and there is no obligation to update the notice either way. A sale that is actually executed by an officer or director shows up separately on a Form 4, which is the filing to check before treating a proposed sale as a real one.

Form 144 Proposed Insider Sale 2026-10-15

HIPO Form 144 filed for proposed insider sale by TORBEN OSTERGAARD (1,169 shares) ~$40.2K

TORBEN OSTERGAARD filed a Form 144 with the SEC indicating intent to sell HIPO (Hippo Holdings Inc.) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: TORBEN OSTERGAARD Shares: 1,169 Est. Value: $40.2K
View on SEC EDGAR → Open Filing Document →
Form 144 Proposed Insider Sale 2026-10-09

HIPO Form 144 filed for proposed insider sale by Richard McCathron (5,000 shares) ~$170.9K

Richard McCathron filed a Form 144 with the SEC indicating intent to sell HIPO (Hippo Holdings Inc.) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: Richard McCathron Shares: 5,000 Est. Value: $170.9K
View on SEC EDGAR → Open Filing Document →
Form 144 Proposed Insider Sale 2026-09-09

HIPO Form 144 filed for proposed insider sale by Richard McCathron (5,000 shares) ~$161.2K

Richard McCathron filed a Form 144 with the SEC indicating intent to sell HIPO (Hippo Holdings Inc.) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: Richard McCathron Shares: 5,000 Est. Value: $161.2K
View on SEC EDGAR → Open Filing Document →
Form 144 Proposed Insider Sale 2026-08-17

HIPO Form 144 filed for proposed insider sale by TORBEN OSTERGAARD (1,169 shares) ~$38.6K

TORBEN OSTERGAARD filed a Form 144 with the SEC indicating intent to sell HIPO (Hippo Holdings Inc.) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: TORBEN OSTERGAARD Shares: 1,169 Est. Value: $38.6K
View on SEC EDGAR → Open Filing Document →
Form 144 Proposed Insider Sale 2026-08-10

HIPO Form 144 filed for proposed insider sale by Richard McCathron (5,000 shares) ~$160.0K

Richard McCathron filed a Form 144 with the SEC indicating intent to sell HIPO (Hippo Holdings Inc.) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: Richard McCathron Shares: 5,000 Est. Value: $160.0K
View on SEC EDGAR → Open Filing Document →
Form 144 Proposed Insider Sale 2026-07-28

HIPO Form 144 filed for proposed insider sale by GUY ZELTSER (1,669 shares) ~$48.7K

GUY ZELTSER filed a Form 144 with the SEC indicating intent to sell HIPO (Hippo Holdings Inc.) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: GUY ZELTSER Shares: 1,669 Est. Value: $48.7K
View on SEC EDGAR → Open Filing Document →
Material Events 1 · Form 8-K

An 8-K reports a material event in the window between scheduled reports. There is 1 in this period for Hippo Holdings Inc. Each 8-K names the item number it is filed under, and that number is the fastest way to tell a routine disclosure from a consequential one.

Item 2.02 is an earnings release, Item 5.02 is a change of directors or officers, and Item 1.01 or 2.01 covers a material agreement or a completed acquisition. Item 7.01 and Item 8.01 are the general-purpose disclosure items and carry no fixed meaning on their own.

Form 8-K Material Company Update 2026-07-30

HIPO filed 8-K — material company event

Hippo Holdings Inc. filed an 8-K with the SEC reporting a material event. Summary unavailable — view the original SEC filing for the full text.

Filing: 8-K (Material Event)
View on SEC EDGAR → Open Filing Document →
Periodic Reports 1 · Forms 10-K and 10-Q

The periodic reports are where the audited and reviewed financial statements live. This period contains 1 quarterly report (10-Q) for Hippo Holdings Inc.

The two are not equivalent in weight. A 10-K is audited by an external firm and includes the full risk factor disclosure, business description and management discussion; a 10-Q is unaudited, reviewed rather than examined, and much shorter. When a figure in a quarterly report is later revised, the annual report is usually where the correction appears.

An amended report — 10-K/A or 10-Q/A — restates or corrects something in the original filing, and is worth reading against the version it replaces.

Form 10-Q Quarterly Report 2026-07-30

HIPO filed Quarterly Report (10-Q)

Hippo Holdings Inc. filed its quarterly report with the SEC. This report includes unaudited financial statements and management discussion for the quarter.

Filing: 10-Q (Quarterly Report)
View on SEC EDGAR → Open Filing Document →

How we classify Hippo Holdings Inc.'s filings

Straight from EDGAR

Each displayed record links to an original source document. StrongBuyAnalytics provides navigation and brief excerpts or summaries, not the filing itself. Parsing may omit context or contain errors, so read the original document in full.

Transaction codes, not guesswork

The nature shown on each insider filing comes from the transaction code the filer entered on the form itself — P for an open-market purchase, A for a compensation award, F for shares withheld to pay tax, M for an option exercise. Where one filing contains several codes, the transaction table lists them line by line.

Why the distinction matters

Insider activity is routinely summarised as buying or selling, which flattens together decisions that mean very different things. Shares withheld for tax on a vesting grant are an automatic administrative step; shares bought on the open market are someone committing their own money at the current price.

What this page does not tell you

A filing records what happened, not why. Form 4 does not always disclose whether a sale was executed under a pre-arranged Rule 10b5-1 plan, and no single filing is a basis for a decision on HIPO. Read these alongside the fundamentals rather than in isolation.

Frequently Asked Questions — HIPO SEC Filings

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Publisher, sources & limitations — September 15, 2026. StrongBuyAnalytics provides navigation and brief excerpts or summaries for educational use. Original filings remain at SEC EDGAR or other displayed source links; StrongBuyAnalytics does not author them. Filing dates are source dates, not publication dates for this page. Coverage can be delayed, incomplete, amended, or unavailable because of SEC/source availability, parsing, caching, or outages. Verify every material statement in the original filing.
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