Hippo Holdings Inc. (HIPO) Insider Trading

Last 12 months

Insiders bought $5k and sold $2.32M on the open market.

All of the selling was scheduled in advance under 10b5-1 plans.

Net open-market

−$2.32M

1 buy · 20 sales

Under a 10b5-1 plan

100%

of the value sold

Insiders who bought / sold

1 / 4

executives and directors

Last open-market buy

Nov 2025

Nov 14, 2025

Get an email when HIPO's executives or directors buy, or make a large sale outside a plan.

Trades · last 2 years

Date	Insider	Trade	Shares	Price	Value	Of their stake	Filing
Oct 15	Torben Ostergaard CEO Spinnaker	Sold10b5-1 plan	1,169	$35.03	$41k	1.9%	Form 4
Oct 9	Richard McCathron Chief Executive Officer	Sold10b5-1 plan	5,000	$34.18	$171k	0.9%	Form 4
Sep 9	Richard McCathron Chief Executive Officer	Sold10b5-1 plan	5,000	$32.23	$161k	0.9%	Form 4
Aug 17	Torben Ostergaard CEO Spinnaker	Sold10b5-1 plan	1,169	$33.00	$39k	1.9%	Form 4
Aug 10	Richard McCathron Chief Executive Officer	Sold10b5-1 plan	5,000	$32.00	$160k	0.9%	Form 4
Jul 28	Guy Zeltser Chief Financial Officer	Sold10b5-1 plan	1,669	$30.98	$52k	1.4%	Form 4
Jul 9	Richard McCathron Chief Executive Officer	Sold10b5-1 plan	5,000	$28.53	$143k	0.8%	Form 4
Jun 9	Richard McCathron Chief Executive Officer	Sold10b5-1 plan	5,000	$25.00	$125k	0.8%	Form 4
May 15	Torben Ostergaard CEO Spinnaker	Sold10b5-1 plan	3,667	$26.10	$96k	5.4%	Form 4
May 11	Richard McCathron Chief Executive Officer	Sold10b5-1 plan	5,000	$27.10	$136k	0.8%	Form 4
Apr 9	Richard McCathron Chief Executive Officer	Sold10b5-1 plan	5,000	$26.05	$130k	0.8%	Form 4
Mar 9	Richard McCathron Chief Executive Officer	Sold10b5-1 plan	5,000	$25.86	$129k	0.8%	Form 4
Feb 25	Torben Ostergaard CEO Spinnaker	Sold10b5-1 plan	600	$30.44	$18k	1.3%	Form 4
Feb 17	Torben Ostergaard CEO Spinnaker	Sold10b5-1 plan	6,105	$28.57	$174k	12%	Form 4
Feb 9	Richard McCathron Chief Executive Officer	Sold10b5-1 plan	5,000	$29.14	$146k	1.1%	Form 4
Jan 9	Richard McCathron Chief Executive Officer	Sold10b5-1 plan	5,000	$31.52	$158k	1.1%	Form 4
Dec 22, 2025	Michael Stienstra GM & Chief Insurance, HHIP	Sold10b5-1 plan	3,900	$31.12	$121k	5.2%	Form 4
Dec 9, 2025	Richard McCathron Chief Executive Officer	Sold10b5-1 plan	5,000	$29.82	$149k	1.1%	Form 4
Nov 21, 2025	Torben Ostergaard CEO Spinnaker	Sold10b5-1 plan 2 parts	3,645	$31.99 average	$117k	6.2%	Form 4
Nov 18, 2025	Guy Zeltser Chief Financial Officer	Sold10b5-1 plan 2 parts	1,819	$32.15 average	$58k	2.6%	Form 4
Nov 14, 2025	Guy Zeltser Chief Financial Officer	Bought	665	$7.23	$5k	1.0%	Form 4
Sep 17, 2025	Guy Zeltser Chief Financial Officer	Sold10b5-1 plan 2 parts	5,177	$37.48 average	$194k	6.5%	Form 4
Sep 8, 2025	Richard McCathron Chief Executive Officer	Sold10b5-1 plan	2,725	$34.12	$93k	0.6%	Form 4
Aug 22, 2025	Richard McCathron Chief Executive Officer	Sold10b5-1 plan	2,275	$34.00	$77k	0.5%	Form 4
Jul 1, 2025	Len FW Investor, LLC Large holder	SoldNo plan	514,309	$28.17	$14.5M	17%	Form 4
Jun 12, 2025	Torben Ostergaard CEO Spinnaker	Sold10b5-1 plan	2,444	$29.95	$73k	3.7%	Form 4
Jun 4, 2025	Torben Ostergaard CEO Spinnaker	Sold10b5-1 plan	4,889	$24.61	$120k	6.8%	Form 4
Apr 1, 2025	Assaf Wand Executive Chairman BoD	Sold10b5-1 plan	12,250	$25.04	$307k	1.0%	Form 4
Mar 3, 2025	Assaf Wand Executive Chairman BoD	Sold10b5-1 plan	12,250	$28.90	$354k	1.0%	Form 4
Feb 18, 2025	Michael Stienstra GM & Chief Insurance, HHIP	Sold10b5-1 plan	2,329	$30.02	$70k	3.8%	Form 4
Feb 4, 2025 – Feb 5, 2025	Torben Ostergaard CEO Spinnaker	Sold10b5-1 plan 2 parts	40,431	$30.16 average	$1.22M	42%	Form 4
Feb 3, 2025	Assaf Wand Executive Chairman BoD	Sold10b5-1 plan 2 parts	12,250	$26.76 average	$328k	2.4%	Form 4
Jan 29, 2025	Torben Ostergaard CEO Spinnaker	Sold10b5-1 plan	3,022	$27.25	$82k	3.1%	Form 4
Jan 8, 2025	Torben Ostergaard CEO Spinnaker	Sold10b5-1 plan	3,022	$25.77	$78k	3.0%	Form 4
Jan 2, 2025	Assaf Wand Executive Chairman BoD	Sold10b5-1 plan 2 parts	12,250	$26.02 average	$319k	1.0%	Form 4
Jan 2, 2025	Stewart Ellis CFO/ Chief Strategy Officer	Sold10b5-1 plan 2 parts	10,000	$26.34 average	$263k	3.0%	Form 4
Dec 23, 2024	Torben Ostergaard CEO Spinnaker	Sold10b5-1 plan	3,022	$25.91	$78k	2.9%	Form 4
Dec 18, 2024	Stewart Ellis CFO/ Chief Strategy Officer	Sold10b5-1 plan	12,000	$25.91	$311k	3.4%	Form 4
Dec 17, 2024	Torben Ostergaard CEO Spinnaker	Sold10b5-1 plan 2 parts	2,092	$26.47 average	$55k	2.0%	Form 4
Dec 2, 2024	Assaf Wand Executive Chairman BoD	Sold10b5-1 plan 3 parts	12,250	$31.67 average	$388k	1.0%	Form 4

Oct 1510b5-1 plan
Torben Ostergaard
CEO Spinnaker · sold 1,169 at $35.03
$41k
1.9% of stake
Oct 910b5-1 plan
Richard McCathron
Chief Executive Officer · sold 5,000 at $34.18
$171k
0.9% of stake
Sep 910b5-1 plan
Richard McCathron
Chief Executive Officer · sold 5,000 at $32.23
$161k
0.9% of stake
Aug 1710b5-1 plan
Torben Ostergaard
CEO Spinnaker · sold 1,169 at $33.00
$39k
1.9% of stake
Aug 1010b5-1 plan
Richard McCathron
Chief Executive Officer · sold 5,000 at $32.00
$160k
0.9% of stake
Jul 2810b5-1 plan
Guy Zeltser
Chief Financial Officer · sold 1,669 at $30.98
$52k
1.4% of stake
Jul 910b5-1 plan
Richard McCathron
Chief Executive Officer · sold 5,000 at $28.53
$143k
0.8% of stake
Jun 910b5-1 plan
Richard McCathron
Chief Executive Officer · sold 5,000 at $25.00
$125k
0.8% of stake
May 1510b5-1 plan
Torben Ostergaard
CEO Spinnaker · sold 3,667 at $26.10
$96k
5.4% of stake
May 1110b5-1 plan
Richard McCathron
Chief Executive Officer · sold 5,000 at $27.10
$136k
0.8% of stake
Apr 910b5-1 plan
Richard McCathron
Chief Executive Officer · sold 5,000 at $26.05
$130k
0.8% of stake
Mar 910b5-1 plan
Richard McCathron
Chief Executive Officer · sold 5,000 at $25.86
$129k
0.8% of stake
Feb 2510b5-1 plan
Torben Ostergaard
CEO Spinnaker · sold 600 at $30.44
$18k
1.3% of stake
Feb 1710b5-1 plan
Torben Ostergaard
CEO Spinnaker · sold 6,105 at $28.57
$174k
12% of stake
Feb 910b5-1 plan
Richard McCathron
Chief Executive Officer · sold 5,000 at $29.14
$146k
1.1% of stake
Jan 910b5-1 plan
Richard McCathron
Chief Executive Officer · sold 5,000 at $31.52
$158k
1.1% of stake
Dec 22, 202510b5-1 plan
Michael Stienstra
GM & Chief Insurance, HHIP · sold 3,900 at $31.12
$121k
5.2% of stake
Dec 9, 202510b5-1 plan
Richard McCathron
Chief Executive Officer · sold 5,000 at $29.82
$149k
1.1% of stake
Nov 21, 202510b5-1 plan
Torben Ostergaard
CEO Spinnaker · sold 3,645 at avg $31.99
$117k
6.2% of stake
Nov 18, 202510b5-1 plan
Guy Zeltser
Chief Financial Officer · sold 1,819 at avg $32.15
$58k
2.6% of stake
Nov 14, 2025
Guy Zeltser
Chief Financial Officer · bought 665 at $7.23
$5k
1.0% of stake
Sep 17, 202510b5-1 plan
Guy Zeltser
Chief Financial Officer · sold 5,177 at avg $37.48
$194k
6.5% of stake
Sep 8, 202510b5-1 plan
Richard McCathron
Chief Executive Officer · sold 2,725 at $34.12
$93k
0.6% of stake
Aug 22, 202510b5-1 plan
Richard McCathron
Chief Executive Officer · sold 2,275 at $34.00
$77k
0.5% of stake
Jul 1, 2025No plan
Len FW Investor, LLC
Large holder · sold 514,309 at $28.17
$14.5M
17% of stake
Jun 12, 202510b5-1 plan
Torben Ostergaard
CEO Spinnaker · sold 2,444 at $29.95
$73k
3.7% of stake
Jun 4, 202510b5-1 plan
Torben Ostergaard
CEO Spinnaker · sold 4,889 at $24.61
$120k
6.8% of stake
Apr 1, 202510b5-1 plan
Assaf Wand
Executive Chairman BoD · sold 12,250 at $25.04
$307k
1.0% of stake
Mar 3, 202510b5-1 plan
Assaf Wand
Executive Chairman BoD · sold 12,250 at $28.90
$354k
1.0% of stake
Feb 18, 202510b5-1 plan
Michael Stienstra
GM & Chief Insurance, HHIP · sold 2,329 at $30.02
$70k
3.8% of stake
Feb 4, 2025 – Feb 5, 202510b5-1 plan
Torben Ostergaard
CEO Spinnaker · sold 40,431 at avg $30.16
$1.22M
42% of stake
Feb 3, 202510b5-1 plan
Assaf Wand
Executive Chairman BoD · sold 12,250 at avg $26.76
$328k
2.4% of stake
Jan 29, 202510b5-1 plan
Torben Ostergaard
CEO Spinnaker · sold 3,022 at $27.25
$82k
3.1% of stake
Jan 8, 202510b5-1 plan
Torben Ostergaard
CEO Spinnaker · sold 3,022 at $25.77
$78k
3.0% of stake
Jan 2, 202510b5-1 plan
Assaf Wand
Executive Chairman BoD · sold 12,250 at avg $26.02
$319k
1.0% of stake
Jan 2, 202510b5-1 plan
Stewart Ellis
CFO/ Chief Strategy Officer · sold 10,000 at avg $26.34
$263k
3.0% of stake
Dec 23, 202410b5-1 plan
Torben Ostergaard
CEO Spinnaker · sold 3,022 at $25.91
$78k
2.9% of stake
Dec 18, 202410b5-1 plan
Stewart Ellis
CFO/ Chief Strategy Officer · sold 12,000 at $25.91
$311k
3.4% of stake
Dec 17, 202410b5-1 plan
Torben Ostergaard
CEO Spinnaker · sold 2,092 at avg $26.47
$55k
2.0% of stake
Dec 2, 202410b5-1 plan
Assaf Wand
Executive Chairman BoD · sold 12,250 at avg $31.67
$388k
1.0% of stake

How to read this. Insiders sell for many reasons: taxes, diversifying, a house. Open-market buys are rarer and say more. A 10b5-1 plan is a trading schedule set up months in advance, so those sales were not timed on news. Large holders (funds and 10% owners) are listed under Everything but not counted as insiders. If you own or watch HIPO, we send a push when an executive buys or makes a large sale outside a plan.

Source: SEC Form 4 filings, filed within two business days of each trade and checked for new ones every hour.

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Spot a number that looks wrong? Check it in HIPO's SEC filings or

Download this analysis as a PDF (Pro)

Data sourced from SEC EDGAR filings and third-party price providers. Scores, valuations, and metrics are algorithmic estimates. This is not investment advice. See our Terms and Methodology.

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