Hippo Holdings HIPO Insider Ownership

NYSE HIPO

$37.31 +1.81 (+5.10%)

At close: Oct 20, 2026 · 4:00 PM EDT

Insider Holdings by Owner

5.20Mn Shares

Insider Ownership Statistics

as of 30 Sep, 2026

Insider Ownership

21.37%

▼-0.110% pp QoQ

Shares Held by Insiders

5.60Mn

filed for Sep 2026

▼-0.51% QoQ

Shares Outstanding

26.20Mn

26,203,128 shares

Direct Holdings

5.01Mn

Indirect: 587.63K

Net Shares Traded (QoQ)

-28.92K

net selling in Sep 2026

Insiders Holding Shares

with Form 4 holdings on file

Shares Owned by Insiders

Shares held % of outstanding

Latest —

Average ownership —

Peak ownership —

Shares Purchased/Sold by Insiders

Bought Sold

Latest quarter —

Net over range —

Buying quarters —

Insider Ownership Summary

Updated Oct 10, 2026

In the last 12 months, insiders at Hippo Holdings made open-market sales of $2.11 million (72.57K shares) and bought no shares on the open market.

Hippo Holdings' open-market sales in the past 12 months came from 4 insiders; no insider bought.
Richard McCathron (Chief Executive Officer) sold the most Hippo Holdings stock on the open market over the past 12 months, $1.44 million (50K shares), most recently on September 9, 2026.
In transactions other than open-market trades, Hippo Holdings insiders received 310.56K shares in stock awards, gave up 72.14K shares to cover taxes or exercise prices and gave away 4.93K shares as gifts over the past 12 months.
Business Quant data shows Hippo Holdings insiders holding 5.6Mn shares in total in their latest Form 4 filings, down 0.51% from 5.63Mn shares at the end of Q2 2026 and down 0.92% from 5.65Mn shares at the end of Q3 2025.
By type of ownership, HIPO insiders hold 89.51% of their shares directly (5.01Mn shares) and 10.49% indirectly (587.63K shares).
HIPO's insider total is spread across 19 insiders who have filed a Form 4 in the past two years.
HIPO's three largest insider shareholders, per their latest Form 4 filings, are Len FW Investor, LLC (10% owner, 2.91Mn shares), Assaf Wand (Executive Chairman Board, 1.16Mn shares) and Richard McCathron (Chief Executive Officer, 567.13K shares).
The largest insider, Len FW Investor, LLC, holds 51.94% of HIPO's insider total.
Institutional investors held 44.44% of Hippo Holdings stock at the end of Q2 2026, while the latest Form 4 filings of its insiders account for about 21.37%; other investors, including the public, hold roughly 34.19%.
Over the trailing 12 months, 15 insiders reported transactions in HIPO stock across 51 Form 4 filings.
Insider figures for HIPO include Form 4 filings through September 11, 2026.

Form 4 Holdings

Insiders Holding HIPO

Insiders 26

Shares held 5.20Mn

Of outstanding 19.83%

#	Insider	Position	Direct	Indirect	Total	Share of Insiders	Last Filed
1	Fw Investor, Llc Len	TenPercentOwner	2,908,829	0	2,908,829	56.0%	19 Aug, 2022
2	Richard Mccathron	Chief Executive Officer	562,132	0	562,132	10.8%	13 Oct, 2026
3	Assaf Wand	Executive Chairman Bod	0	474,564	474,564	9.1%	03 Apr, 2025
4	Ran Harpaz	Chief Operating Officer	162,599	0	162,599	3.1%	17 Nov, 2022
5	Stewart Ellis	Cfo/ Chief Strategy Officer	126,455	0	126,455	2.4%	19 Aug, 2026
6	Guy Zeltser	Chief Financial Officer	116,618	0	116,618	2.2%	18 Aug, 2026
7	Anirudh Badia	Chief Accounting Officer	102,315	0	102,315	2.0%	08 Nov, 2024
8	Yuval Harry	Chief Revenue Officer	97,251	0	97,251	1.9%	22 Oct, 2024
9	Christopher Donahue	General Manager, Mga Cuo	95,019	0	95,019	1.8%	16 Nov, 2023
10	Michael Stienstra	Gm Chief Insurance, Hhip	89,901	0	89,901	1.7%	18 Aug, 2026
11	Laura Boettcher	Chief Operating Officer	71,381	0	71,381	1.4%	18 Aug, 2026
12	Simon Fleming-Wood	Chief Marketing Officer	66,068	0	66,068	1.3%	17 May, 2023
13	Torben Ostergaard	Ceo Spinnaker	61,824	0	61,824	1.2%	18 Aug, 2026
14	Wall Ventures Management Gp, Llc Fifth	TenPercentOwner	0	38,475	38,475	0.7%	18 Aug, 2022
15	Sam Landman	Director	29,080	0	29,080	0.6%	04 Jun, 2026
16	Lori Dickerson Fouche	Director	26,623	0	26,623	0.5%	04 Jun, 2026
17	Hugh R Frater	Director	26,623	0	26,623	0.5%	04 Jun, 2026
18	Sandra S Wijnberg	Director	26,623	0	26,623	0.5%	04 Jun, 2026
19	Eric Feder	Director	21,815	0	21,815	0.4%	04 Jun, 2026
20	John Drake Nichols	Director	21,371	0	21,371	0.4%	04 Jun, 2026
21	Mark Schaaf	Director	20,911	0	20,911	0.4%	04 Jun, 2026
22	Noah Knauf	Director	11,794	0	11,794	0.2%	09 Jun, 2023
23	Aviad Pinkovezky	Chief Product Officer	11,332	0	11,332	0.2%	17 Feb, 2022
24	Amy Errett	Director	11,276	0	11,276	0.2%	04 Aug, 2023
25	Laura J Hay	Director	7,310	0	7,310	0.1%	04 Jun, 2026
26	Susan Claire Holliday	Director	7,310	0	7,310	0.1%	04 Jun, 2026

Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.

Form 4 Filings

466 Insider Transactions

Source SEC Form 4

Latest quarter Sep 2026

Date	Insider	Position	Transaction	Shares	Price	Value	Shares Held After	Ownership
09 Oct, 2026	Richard Mccathron	Chief Executive Officer	Disposed S	5,000	$34.18	$170.90K	562,132	Direct
09 Sep, 2026	Richard Mccathron	Chief Executive Officer	Disposed S	5,000	$32.23	$161.15K	567,132	Direct
15 Aug, 2026	Stewart Ellis	Director	Acquired A	5,350	$33.04	$176.76K	126,455	Direct
15 Aug, 2026	Richard Mccathron	Chief Executive Officer	Disposed F	8,301	$32.83	$272.49K	572,132	Direct
15 Aug, 2026	Torben Ostergaard	Ceo Spinnaker	Disposed F	1,340	$32.83	$43.99K	62,993	Direct
15 Aug, 2026	Michael Stienstra	Gm Chief Insurance, Hhip	Disposed F	1,259	$32.83	$41.33K	89,901	Direct
15 Aug, 2026	Guy Zeltser	Chief Financial Officer	Disposed F	3,945	$32.83	$129.50K	116,618	Direct
15 Aug, 2026	Laura Boettcher	Chief Operating Officer	Disposed F	1,586	$32.83	$52.06K	71,381	Direct
17 Aug, 2026	Torben Ostergaard	Ceo Spinnaker	Disposed S	1,169	$33.00	$38.58K	61,824	Direct
10 Aug, 2026	Richard Mccathron	Chief Executive Officer	Disposed S	5,000	$32.00	$160.00K	580,433	Direct
28 Jul, 2026	Guy Zeltser	Chief Financial Officer	Disposed S	1,669	$30.98	$51.71K	120,563	Direct
09 Jul, 2026	Richard Mccathron	Chief Executive Officer	Disposed S	5,000	$28.53	$142.65K	585,433	Direct
10 Jun, 2026	Laura Boettcher	Chief Operating Officer	Acquired A	11,674	$0.00	$0	72,967	Direct
09 Jun, 2026	Richard Mccathron	Chief Executive Officer	Disposed S	5,000	$25.00	$125.00K	590,433	Direct
03 Jun, 2026	Stewart Ellis	Director	Acquired A	4,820	$0.00	$0	121,105	Direct
02 Jun, 2026	Sandra S Wijnberg	Director	Acquired A	4,738	$25.40	$120.35K	21,815	Direct
02 Jun, 2026	Mark Schaaf	Director	Acquired A	4,738	$25.40	$120.35K	16,103	Direct
02 Jun, 2026	John Drake Nichols	Director	Acquired A	4,738	$25.40	$120.35K	16,563	Direct
02 Jun, 2026	Lori Dickerson Fouche	Director	Acquired A	4,738	$25.40	$120.35K	21,815	Direct
02 Jun, 2026	Sam Landman	Director	Acquired A	4,738	$25.40	$120.35K	24,272	Direct

Showing 1 to 20 of 466 transactions