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Hippo Holdings Inc (HIPO)

Over the last 90 days, Hippo Holdings Inc. has seen 8 insider transactions, all of which were sales totaling approximately $950,000. Notably, CEO Richard McCathron and Officer Torben Ostergaard have made multiple planned and proposed sales. The company's stock has experienced a 5.3% increase in the last 90 days.
Stock chart
Ticker: HIPO Exchange: NYS


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Purchase Sale Planned purchase Planned sale Net purchase Net sale Activity signal Earnings
Top insiders
Trades
McCathron Richard
Chief Executive Officer
1 sale — total 100,000 USD
Planned sale 9 Jun 2026
Value US$2,394,191.68 | Price 120.92 | Shares 80,773
Proposed sale 9 Jun 2026
Value US$3,314,302.78 | Price 80.37 | Shares 41,644
Planned sale 15 May 2026
Value US$95,706.13 | Price 26.10 | Shares 3,667
Proposed sale 15 May 2026
Value US$72,545.22 | Price 26.73 | Shares 2,714
Planned sale 11 May 2026
Value US$135,500.00 | Price 27.10 | Shares 5,000
Proposed sale 11 May 2026
Value US$135,500.00 | Price 27.10 | Shares 5,000
Planned sale 9 Apr 2026
Value US$130,250.00 | Price 26.05 | Shares 5,000
Proposed sale 9 Apr 2026
Value US$130,250.00 | Price 26.05 | Shares 5,000
Planned sale 9 Mar 2026
Value US$129,300.00 | Price 25.86 | Shares 5,000
Proposed sale 9 Mar 2026
Value US$129,300.00 | Price 25.86 | Shares 5,000
Planned sale 25 Feb 2026
Value US$18,266.10 | Price 30.44 | Shares 600
Proposed sale 25 Feb 2026
Value US$44,804.05 | Price 28.85 | Shares 1,553
Planned sale 17 Feb 2026
Value US$174,391.16 | Price 28.57 | Shares 6,105
Proposed sale 17 Feb 2026
Value US$172,527.30 | Price 28.26 | Shares 6,105
Planned sale 9 Feb 2026
Value US$145,700.00 | Price 29.14 | Shares 5,000
Proposed sale 9 Feb 2026
Value US$145,700.00 | Price 29.14 | Shares 5,000
Planned sale 9 Jan 2026
Value US$157,600.00 | Price 31.52 | Shares 5,000
Proposed sale 9 Jan 2026
Value US$157,600.00 | Price 31.52 | Shares 5,000
Planned sale 22 Dec 2025
Value US$121,365.66 | Price 31.12 | Shares 3,900
Proposed sale 22 Dec 2025
Value US$120,471.00 | Price 30.89 | Shares 3,900
Planned sale 9 Dec 2025
Value US$149,100.00 | Price 29.82 | Shares 5,000
Proposed sale 9 Dec 2025
Value US$149,100.00 | Price 29.82 | Shares 5,000
Planned sale 21 Nov 2025
Value US$4,960.16 | Price 32.63 | Shares 152
Planned sale 21 Nov 2025
Value US$111,631.74 | Price 31.96 | Shares 3,493
Proposed sale 21 Nov 2025
Value US$115,109.10 | Price 31.58 | Shares 3,645
Planned sale 18 Nov 2025
Value US$3,274.00 | Price 32.74 | Shares 100
Planned sale 18 Nov 2025
Value US$55,219.61 | Price 32.12 | Shares 1,719
Proposed sale 18 Nov 2025
Value US$57,371.26 | Price 31.54 | Shares 1,819
Planned buy 14 Nov 2025
Value US$4,807.95 | Price 7.23 | Shares 665
Planned sale 17 Sep 2025
Value US$7,609.00 | Price 38.05 | Shares 200
Planned sale 17 Sep 2025
Value US$186,422.99 | Price 37.46 | Shares 4,977
Proposed sale 17 Sep 2025
Value US$192,636.17 | Price 37.21 | Shares 5,177
Planned sale 8 Sep 2025
Value US$92,969.37 | Price 34.12 | Shares 2,725
Planned sale 22 Aug 2025
Value US$77,350.91 | Price 34.00 | Shares 2,275
Proposed sale 22 Aug 2025
Value US$164,800.00 | Price 32.96 | Shares 5,000
Sale 1 Jul 2025
Value US$14,488,084.53 | Price 28.17 | Shares 514,309
Proposed sale 17 Jun 2025
Value US$155,137.37 | Price 30.27 | Shares 5,125
Proposed sale 16 Jun 2025
Value US$283,067.50 | Price 28.31 | Shares 10,000
Planned sale 12 Jun 2025
Value US$73,197.80 | Price 29.95 | Shares 2,444
Proposed sale 12 Jun 2025
Value US$66,232.40 | Price 27.10 | Shares 2,444
Proposed sale 11 Jun 2025
Value US$13,930,000.00 | Price 27.86 | Shares 500,000
Planned sale 4 Jun 2025
Value US$120,316.82 | Price 24.61 | Shares 4,889
Proposed sale 4 Jun 2025
Value US$119,047.15 | Price 24.35 | Shares 4,889
Proposed sale 2 Jun 2025
Value US$287,813.75 | Price 23.50 | Shares 12,250
Proposed sale 1 May 2025
Value US$282,194.68 | Price 23.04 | Shares 12,250
Planned sale 1 Apr 2025
Value US$306,700.80 | Price 25.04 | Shares 12,250
Proposed sale 1 Apr 2025
Value US$306,700.46 | Price 25.04 | Shares 12,250
Proposed sale 19 Mar 2025
Value US$259,763.00 | Price 25.98 | Shares 10,000
Planned sale 3 Mar 2025
Value US$354,044.60 | Price 28.90 | Shares 12,250
Proposed sale 3 Mar 2025
Value US$354,045.08 | Price 28.90 | Shares 12,250
Planned sale 18 Feb 2025
Value US$69,913.32 | Price 30.02 | Shares 2,329
Proposed sale 18 Feb 2025
Value US$70,126.19 | Price 30.11 | Shares 2,329
Planned sale 5 Feb 2025
Value US$584,173.51 | Price 30.29 | Shares 19,285
Planned sale 4 Feb 2025
Value US$635,437.30 | Price 30.05 | Shares 21,146
Proposed sale 4 Feb 2025
Value US$1,020,517.52 | Price 27.28 | Shares 37,409
Planned sale 3 Feb 2025
Value US$114,390.63 | Price 27.22 | Shares 4,202
Planned sale 3 Feb 2025
Value US$213,408.01 | Price 26.52 | Shares 8,048
Proposed sale 3 Feb 2025
Value US$327,798.13 | Price 26.76 | Shares 12,250
Planned sale 29 Jan 2025
Value US$82,358.87 | Price 27.25 | Shares 3,022
Planned sale 8 Jan 2025
Value US$77,872.10 | Price 25.77 | Shares 3,022
Proposed sale 8 Jan 2025
Value US$237,619.86 | Price 26.21 | Shares 9,066
Planned sale 2 Jan 2025
Value US$115,441.09 | Price 26.64 | Shares 4,333
Planned sale 2 Jan 2025
Value US$147,974.44 | Price 26.11 | Shares 5,667
Proposed sale 2 Jan 2025
Value US$263,416.00 | Price 26.34 | Shares 10,000
Planned sale 2 Jan 2025
Value US$99,516.66 | Price 26.51 | Shares 3,754
Planned sale 2 Jan 2025
Value US$219,255.42 | Price 25.81 | Shares 8,496
Proposed sale 2 Jan 2025
Value US$318,771.93 | Price 26.02 | Shares 12,250
Planned sale 23 Dec 2024
Value US$78,297.30 | Price 25.91 | Shares 3,022
Planned sale 18 Dec 2024
Value US$310,958.40 | Price 25.91 | Shares 12,000
Proposed sale 18 Dec 2024
Value US$310,958.40 | Price 25.91 | Shares 12,000
Planned sale 17 Dec 2024
Value US$2,720.00 | Price 27.20 | Shares 100
Planned sale 17 Dec 2024
Value US$52,639.80 | Price 26.43 | Shares 1,992
Proposed sale 17 Dec 2024
Value US$144,317.08 | Price 28.22 | Shares 5,114
Planned sale 2 Dec 2024
Value US$396.48 | Price 33.04 | Shares 12
Planned sale 2 Dec 2024
Value US$93,375.92 | Price 32.21 | Shares 2,899
Abbreviations B: Buy, S: Sell, PP: Planned purchase, PlS: Planned sale, PrS: Proposed sale, O: Option / Other
Notification date Transaction date B/S Transaction type Insider and/or position Nb. shares
Price
Value
Number of shares Price Value Details
2026-06-11 2026-06-09 PlS Planned sale

Chief Executive Officer

Executive Director
80,773 +47.5%
120.92
US$2,394,192
80,773 +47.5% 120.92 US$2,394,192
2026-06-09 2026-06-09 PrS Proposed sale

Officer

Officer
41,644
80.37
US$3,314,303
41,644 80.37 US$3,314,303
2026-05-19 2026-05-15 PlS Planned sale

CEO Spinnaker

Officer
88,546 +41.6%
426.24
US$4,918,517
88,546 +41.6% 426.24 US$4,918,517
2026-05-15 2026-05-15 PrS Proposed sale

Officer

Officer
2,714
26.73
US$72,545
2,714 26.73 US$72,545
2026-05-13 2026-05-11 PlS Planned sale

Chief Executive Officer

Executive Director
5,000 -0.8%
27.10
US$135,500
5,000 -0.8% 27.10 US$135,500
2026-05-11 2026-05-11 PrS Proposed sale

Officer

Officer
5,000
27.10
US$135,500
5,000 27.10 US$135,500
2026-04-13 2026-04-09 PlS Planned sale

Chief Executive Officer

Executive Director
5,000 -0.8%
26.05
US$130,250
5,000 -0.8% 26.05 US$130,250
2026-04-09 2026-04-09 PrS Proposed sale

Officer

Officer
5,000
26.05
US$130,250
5,000 26.05 US$130,250
2026-03-11 2026-03-09 PlS Planned sale

Chief Executive Officer

Executive Director
5,000 -0.8%
25.86
US$129,300
5,000 -0.8% 25.86 US$129,300
2026-03-09 2026-03-09 PrS Proposed sale

Officer

Officer
5,000
25.86
US$129,300
5,000 25.86 US$129,300
2026-02-27 2026-02-25 PlS Planned sale

CEO Spinnaker

Officer
600 -1.3%
30.44
US$18,266
600 -1.3% 30.44 US$18,266
2026-02-25 2026-02-25 PrS Proposed sale

Officer

Officer
1,553
28.85
US$44,804
1,553 28.85 US$44,804
2026-02-18 2026-02-17 PlS Planned sale

CEO Spinnaker

Officer
6,105 -11.6%
28.57
US$174,391
6,105 -11.6% 28.57 US$174,391
2026-02-17 2026-02-17 PrS Proposed sale

Officer

Officer
6,105
28.26
US$172,527
6,105 28.26 US$172,527
2026-02-11 2026-02-09 PlS Planned sale

Chief Executive Officer

Executive Director
5,000 -1.1%
29.14
US$145,700
5,000 -1.1% 29.14 US$145,700
2026-02-09 2026-02-09 PrS Proposed sale

Officer

Officer
5,000
29.14
US$145,700
5,000 29.14 US$145,700
2026-01-13 2026-01-09 PlS Planned sale

Chief Executive Officer

Executive Director
5,000 -1.1%
31.52
US$157,600
5,000 -1.1% 31.52 US$157,600
2026-01-09 2026-01-09 PrS Proposed sale

Officer

Officer
5,000
31.52
US$157,600
5,000 31.52 US$157,600
2025-12-29 2025-12-22 PlS Planned sale

GM & Chief Insurance, HHIP

Officer
3,900 -5.2%
31.12
US$121,366
3,900 -5.2% 31.12 US$121,366
2025-12-22 2025-12-22 PrS Proposed sale

Officer

Officer
3,900
30.89
US$120,471
3,900 30.89 US$120,471
2025-12-11 2025-12-09 PlS Planned sale

Chief Executive Officer

Executive Director
5,000 -1.1%
29.82
US$149,100
5,000 -1.1% 29.82 US$149,100
2025-12-09 2025-12-09 PrS Proposed sale

Officer

Officer
5,000
29.82
US$149,100
5,000 29.82 US$149,100
2025-11-25 2025-11-21 PlS Planned sale

CEO Spinnaker

Officer
152 -0.3%
32.63
US$4,960
152 -0.3% 32.63 US$4,960
2025-11-25 2025-11-21 PlS Planned sale

CEO Spinnaker

Officer
3,493 -5.9%
31.96
US$111,632
3,493 -5.9% 31.96 US$111,632
2025-11-21 2025-11-21 PrS Proposed sale

Officer

Officer
3,645
31.58
US$115,109
3,645 31.58 US$115,109
2025-11-19 2025-11-18 PlS Planned sale

Chief Financial Officer

Officer
100 -0.1%
32.74
US$3,274
100 -0.1% 32.74 US$3,274
2025-11-19 2025-11-18 PlS Planned sale

Chief Financial Officer

Officer
1,719 -2.4%
32.12
US$55,220
1,719 -2.4% 32.12 US$55,220
2025-11-18 2025-11-18 PrS Proposed sale

Officer

Officer
1,819
31.54
US$57,371
1,819 31.54 US$57,371
2026-02-18 2025-11-14 PP Planned purchase

Chief Financial Officer

Officer
665 +1.0%
7.23
US$4,808
665 +1.0% 7.23 US$4,808
2025-09-19 2025-09-17 PlS Planned sale

Chief Financial Officer

Officer
200 -0.3%
38.05
US$7,609
200 -0.3% 38.05 US$7,609
2025-09-19 2025-09-17 PlS Planned sale

Chief Financial Officer

Officer
4,977 -6.2%
37.46
US$186,423
4,977 -6.2% 37.46 US$186,423
2025-09-17 2025-09-17 PrS Proposed sale

Officer

Officer
5,177
37.21
US$192,636
5,177 37.21 US$192,636
2025-09-10 2025-09-08 PlS Planned sale

Chief Executive Officer

Executive Director
2,725 -0.6%
34.12
US$92,969
2,725 -0.6% 34.12 US$92,969
2025-08-26 2025-08-22 PlS Planned sale

Chief Executive Officer

Executive Director
2,275 -0.5%
34.00
US$77,351
2,275 -0.5% 34.00 US$77,351
2025-08-22 2025-08-22 PrS Proposed sale

Director; Officer

Executive Director
5,000
32.96
US$164,800
5,000 32.96 US$164,800
2025-07-03 2025-07-01 S Sale

Former 10% Owner

514,309 -17.2%
28.17
US$14,488,085
514,309 -17.2% 28.17 US$14,488,085
2025-06-17 2025-06-17 PrS Proposed sale

Officer

Officer
5,125
30.27
US$155,137
5,125 30.27 US$155,137
2025-06-16 2025-06-16 PrS Proposed sale

Officer

Officer
10,000
28.31
US$283,068
10,000 28.31 US$283,068
2025-06-16 2025-06-12 PlS Planned sale

CEO Spinnaker

Officer
2,444 -3.7%
29.95
US$73,198
2,444 -3.7% 29.95 US$73,198
2025-06-12 2025-06-12 PrS Proposed sale

Officer

Officer
2,444
27.10
US$66,232
2,444 27.10 US$66,232
2025-06-11 2025-06-11 PrS Proposed sale

Officer; Director

Executive Director
500,000
27.86
US$13,930,000
500,000 27.86 US$13,930,000
2025-06-06 2025-06-04 PlS Planned sale

CEO Spinnaker

Officer
4,889 -6.8%
24.61
US$120,317
4,889 -6.8% 24.61 US$120,317
2025-06-04 2025-06-04 PrS Proposed sale

Officer

Officer
4,889
24.35
US$119,047
4,889 24.35 US$119,047
2025-06-02 2025-06-02 PrS Proposed sale

Officer; Director

Executive Director
12,250
23.50
US$287,814
12,250 23.50 US$287,814
2025-05-01 2025-05-01 PrS Proposed sale

Officer; Director

Executive Director
12,250
23.04
US$282,195
12,250 23.04 US$282,195
2025-04-03 2025-04-01 PlS Planned sale

Executive Chairman BoD

Executive Director
12,250 -2.5%
25.04
US$306,701
12,250 -2.5% 25.04 US$306,701
2025-04-01 2025-04-01 PrS Proposed sale

Officer; Director

Executive Director
12,250
25.04
US$306,700
12,250 25.04 US$306,700
2025-03-19 2025-03-19 PrS Proposed sale

Officer

Officer
10,000
25.98
US$259,763
10,000 25.98 US$259,763
2025-03-05 2025-03-03 PlS Planned sale

Executive Chairman BoD

Executive Director
12,250 -2.5%
28.90
US$354,045
12,250 -2.5% 28.90 US$354,045
2025-03-03 2025-03-03 PrS Proposed sale

Officer; Director

Executive Director
12,250
28.90
US$354,045
12,250 28.90 US$354,045
2025-02-19 2025-02-18 PlS Planned sale

GM & Chief Insurance, HHIP

Officer
2,329 -3.8%
30.02
US$69,913
2,329 -3.8% 30.02 US$69,913
2025-02-18 2025-02-18 PrS Proposed sale

Officer

Officer
2,329
30.11
US$70,126
2,329 30.11 US$70,126
2025-02-06 2025-02-05 PlS Planned sale

CEO Spinnaker

Officer
19,285 -26.0%
30.29
US$584,174
19,285 -26.0% 30.29 US$584,174
2025-02-06 2025-02-04 PlS Planned sale

CEO Spinnaker

Officer
21,146 -22.2%
30.05
US$635,437
21,146 -22.2% 30.05 US$635,437
2025-02-04 2025-02-04 PrS Proposed sale

Officer

Officer
37,409
27.28
US$1,020,518
37,409 27.28 US$1,020,518
2025-02-05 2025-02-03 PlS Planned sale

Executive Chairman BoD

Executive Director
4,202 -0.8%
27.22
US$114,391
4,202 -0.8% 27.22 US$114,391
2025-02-05 2025-02-03 PlS Planned sale

Executive Chairman BoD

Executive Director
8,048 -1.6%
26.52
US$213,408
8,048 -1.6% 26.52 US$213,408
2025-02-03 2025-02-03 PrS Proposed sale

Officer; Director

Executive Director
12,250
26.76
US$327,798
12,250 26.76 US$327,798
2025-01-31 2025-01-29 PlS Planned sale

CEO Spinnaker

Officer
3,022 -3.1%
27.25
US$82,359
3,022 -3.1% 27.25 US$82,359
2025-01-10 2025-01-08 PlS Planned sale

CEO Spinnaker

Officer
3,022 -3.0%
25.77
US$77,872
3,022 -3.0% 25.77 US$77,872
2025-01-08 2025-01-08 PrS Proposed sale

Officer

Officer
9,066
26.21
US$237,620
9,066 26.21 US$237,620
2025-01-03 2025-01-02 PlS Planned sale

CFO/ Chief Strategy Officer

Officer
4,333 -1.3%
26.64
US$115,441
4,333 -1.3% 26.64 US$115,441
2025-01-03 2025-01-02 PlS Planned sale

CFO/ Chief Strategy Officer

Officer
5,667 -1.7%
26.11
US$147,974
5,667 -1.7% 26.11 US$147,974
2025-01-03 2025-01-02 PlS Planned sale

Executive Chairman BoD

Executive Director
3,754 -0.7%
26.51
US$99,517
3,754 -0.7% 26.51 US$99,517
2025-01-03 2025-01-02 PlS Planned sale

Executive Chairman BoD

Executive Director
8,496 -1.6%
25.81
US$219,255
8,496 -1.6% 25.81 US$219,255
2025-01-02 2025-01-02 PrS Proposed sale

Officer; Director

Executive Director
12,250
26.02
US$318,772
12,250 26.02 US$318,772
2025-01-02 2025-01-02 PrS Proposed sale

Officer

Officer
10,000
26.34
US$263,416
10,000 26.34 US$263,416
2024-12-26 2024-12-23 PlS Planned sale

CEO Spinnaker

Officer
3,022 -2.9%
25.91
US$78,297
3,022 -2.9% 25.91 US$78,297
2024-12-20 2024-12-18 PlS Planned sale

CFO/ Chief Strategy Officer

Officer
12,000 -3.5%
25.91
US$310,958
12,000 -3.5% 25.91 US$310,958
2024-12-18 2024-12-18 PrS Proposed sale

Officer

Officer
12,000
25.91
US$310,958
12,000 25.91 US$310,958
2024-12-19 2024-12-17 PlS Planned sale

CEO Spinnaker

Officer
100 -0.1%
27.20
US$2,720
100 -0.1% 27.20 US$2,720
2024-12-19 2024-12-17 PlS Planned sale

CEO Spinnaker

Officer
1,992 -1.9%
26.43
US$52,640
1,992 -1.9% 26.43 US$52,640
2024-12-17 2024-12-17 PrS Proposed sale

Officer

Officer
5,114
28.22
US$144,317
5,114 28.22 US$144,317
2024-12-04 2024-12-02 PlS Planned sale

Executive Chairman BoD

Executive Director
12 -0.0%
33.04
US$396
12 -0.0% 33.04 US$396
2024-12-04 2024-12-02 PlS Planned sale

Executive Chairman BoD

Executive Director
2,899 -0.6%
32.21
US$93,376
2,899 -0.6% 32.21 US$93,376
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