Hippo Holdings Inc (HIPO)

Hippo Holdings Inc. experienced nine insider trading transactions over the past ninety days, totaling approximately $994,280 in sales. Key executives, including the Chief Executive Officer and Chief Financial Officer, executed these planned divestments. This activity follows a recent earnings report where the company significantly outperformed expectations, amid a 25.6% stock price increase.
Ticker: HIPO Exchange: NYS


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Insider trades have triggered activity signals for Hippo Holdings Inc. Upgrade to see score, net flow, insiders and the full signal context.

Top insiders
Trades
Abbreviations B: Buy, S: Sell, PP: Planned purchase, PlS: Planned sale, PrS: Proposed sale, O: Option / Other
Ostergaard Torben CEO Spinnaker Officer
Transaction date
Planned sale
Price
174.96
Quantity 62,571 -34.5%
Value US$1,619,096
TORBEN OSTERGAARD Officer Officer
Transaction date
Proposed sale
Price
203.26
Quantity 13,616
Value US$1,809,046
0.5
McCathron Richard Chief Executive Officer Executive Director
Transaction date
Planned sale
Price
49.24
Quantity 13,892 -46.6%
Value US$1,377,715
0.5
Richard McCathron Officer Officer
Transaction date
Proposed sale
Price
32.00
Quantity 1,000
Value US$100,000
Zeltser Guy Chief Financial Officer Officer
Transaction date
Planned sale
Price
30.98
Quantity 1,000 -1.4%
Value US$100,000
GUY ZELTSER Officer Officer
Transaction date
Proposed sale
Price
29.15
Quantity 1,669
Value US$48,651
0.5
McCathron Richard Chief Executive Officer Executive Director
Transaction date
Planned sale
Price
28.53
Quantity 5,000 -0.8%
Value US$142,650
0.5
Richard McCathron Officer Officer
Transaction date
Proposed sale
Price
28.53
Quantity 5,000
Value US$142,650
0.5
McCathron Richard Chief Executive Officer Executive Director
Transaction date
Planned sale
Price
25.00
Quantity 5,000 -0.8%
Value US$125,000
0.5
Richard McCathron Officer Officer
Transaction date
Proposed sale
Price
25.00
Quantity 5,000
Value US$125,000
Ostergaard Torben CEO Spinnaker Officer
Transaction date
Planned sale
Price
26.10
Quantity 3,667 -5.3%
Value US$95,706
TORBEN OSTERGAARD Officer Officer
Transaction date
Proposed sale
Price
26.73
Quantity 2,714
Value US$72,545
0.5
McCathron Richard Chief Executive Officer Executive Director
Transaction date
Planned sale
Price
27.10
Quantity 5,000 -0.8%
Value US$135,500
0.5
Richard McCathron Officer Officer
Transaction date
Proposed sale
Price
27.10
Quantity 5,000
Value US$135,500
0.5
McCathron Richard Chief Executive Officer Executive Director
Transaction date
Planned sale
Price
26.05
Quantity 5,000 -0.8%
Value US$130,250
0.5
Richard McCathron Officer Officer
Transaction date
Proposed sale
Price
26.05
Quantity 5,000
Value US$130,250
0.5
McCathron Richard Chief Executive Officer Executive Director
Transaction date
Planned sale
Price
25.86
Quantity 5,000 -0.8%
Value US$129,300
0.5
Richard McCathron Officer Officer
Transaction date
Proposed sale
Price
25.86
Quantity 5,000
Value US$129,300
Ostergaard Torben CEO Spinnaker Officer
Transaction date
Planned sale
Price
30.44
Quantity 600 -1.3%
Value US$18,266
TORBEN OSTERGAARD Officer Officer
Transaction date
Proposed sale
Price
28.85
Quantity 1,553
Value US$44,804
Ostergaard Torben CEO Spinnaker Officer
Transaction date
Planned sale
Price
28.57
Quantity 6,105 -11.6%
Value US$174,391
TORBEN OSTERGAARD Officer Officer
Transaction date
Proposed sale
Price
28.26
Quantity 6,105
Value US$172,527
0.5
McCathron Richard Chief Executive Officer Executive Director
Transaction date
Planned sale
Price
29.14
Quantity 5,000 -1.1%
Value US$145,700
0.5
Richard McCathron Officer Officer
Transaction date
Proposed sale
Price
29.14
Quantity 5,000
Value US$145,700
0.5
McCathron Richard Chief Executive Officer Executive Director
Transaction date
Planned sale
Price
31.52
Quantity 5,000 -1.1%
Value US$157,600
0.5
Richard McCathron Officer Officer
Transaction date
Proposed sale
Price
31.52
Quantity 5,000
Value US$157,600
Stienstra Michael GM & Chief Insurance, HHIP Officer
Transaction date
Planned sale
Price
31.12
Quantity 3,900 -5.2%
Value US$121,366
MICHAEL STIENSTRA Officer Officer
Transaction date
Proposed sale
Price
30.89
Quantity 3,900
Value US$120,471
0.5
McCathron Richard Chief Executive Officer Executive Director
Transaction date
Planned sale
Price
29.82
Quantity 5,000 -1.1%
Value US$149,100
0.5
Richard McCathron Officer Officer
Transaction date
Proposed sale
Price
29.82
Quantity 5,000
Value US$149,100
Ostergaard Torben CEO Spinnaker Officer
Transaction date
Planned sale
Price
32.63
Quantity 152 -0.3%
Value US$4,960
Ostergaard Torben CEO Spinnaker Officer
Transaction date
Planned sale
Price
31.96
Quantity 3,493 -5.9%
Value US$111,632
TORBEN OSTERGAARD Officer Officer
Transaction date
Proposed sale
Price
31.58
Quantity 3,645
Value US$115,109
Zeltser Guy Chief Financial Officer Officer
Transaction date
Planned sale
Price
32.74
Quantity 100 -0.1%
Value US$3,274
Zeltser Guy Chief Financial Officer Officer
Transaction date
Planned sale
Price
32.12
Quantity 1,719 -2.4%
Value US$55,220
GUY ZELTSER Officer Officer
Transaction date
Proposed sale
Price
31.54
Quantity 1,819
Value US$57,371
Zeltser Guy Chief Financial Officer Officer
Transaction date
Planned purchase
Price
7.23
Quantity 665 +1.0%
Value US$4,808
Zeltser Guy Chief Financial Officer Officer
Transaction date
Planned sale
Price
38.05
Quantity 200 -0.3%
Value US$7,609
Zeltser Guy Chief Financial Officer Officer
Transaction date
Planned sale
Price
37.46
Quantity 4,977 -6.2%
Value US$186,423
GUY ZELTSER Officer Officer
Transaction date
Proposed sale
Price
37.21
Quantity 5,177
Value US$192,636
0.5
McCathron Richard Chief Executive Officer Executive Director
Transaction date
Planned sale
Price
34.12
Quantity 2,725 -0.6%
Value US$92,969
0.5
McCathron Richard Chief Executive Officer Executive Director
Transaction date
Planned sale
Price
34.00
Quantity 2,275 -0.5%
Value US$77,351
0.5
RICHARD LYN MCCATHRON Director; Officer Executive Director
Transaction date
Proposed sale
Price
32.96
Quantity 5,000
Value US$164,800
1.4
Len FW Investor, LLC Former 10% Owner
Transaction date
Sale
Price
28.17
Quantity 514,309 -17.2%
Value US$14,488,085
Ellis Stewart Officer Officer
Transaction date
Proposed sale
Price
30.27
Quantity 5,125
Value US$155,137
Ellis Stewart Officer Officer
Transaction date
Proposed sale
Price
28.31
Quantity 10,000
Value US$283,068
Ostergaard Torben CEO Spinnaker Officer
Transaction date
Planned sale
Price
29.95
Quantity 2,444 -3.7%
Value US$73,198
TORBEN OSTERGAARD Officer Officer
Transaction date
Proposed sale
Price
27.10
Quantity 2,444
Value US$66,232
1.1
Wand Assaf Officer; Director Executive Director
Transaction date
Proposed sale
Price
27.86
Quantity 500,000
Value US$13,930,000
Ostergaard Torben CEO Spinnaker Officer
Transaction date
Planned sale
Price
24.61
Quantity 4,889 -6.8%
Value US$120,317
TORBEN OSTERGAARD Officer Officer
Transaction date
Proposed sale
Price
24.35
Quantity 4,889
Value US$119,047
1.1
Wand Assaf Officer; Director Executive Director
Transaction date
Proposed sale
Price
23.50
Quantity 12,250
Value US$287,814
1.1
Wand Assaf Officer; Director Executive Director
Transaction date
Proposed sale
Price
23.04
Quantity 12,250
Value US$282,195
1.1
Wand Assaf Executive Chairman BoD Executive Director
Transaction date
Planned sale
Price
25.04
Quantity 12,250 -2.5%
Value US$306,701
1.1
Wand Assaf Officer; Director Executive Director
Transaction date
Proposed sale
Price
25.04
Quantity 12,250
Value US$306,700
Ellis Stewart Officer Officer
Transaction date
Proposed sale
Price
25.98
Quantity 10,000
Value US$259,763
1.1
Wand Assaf Executive Chairman BoD Executive Director
Transaction date
Planned sale
Price
28.90
Quantity 12,250 -2.5%
Value US$354,045
1.1
Wand Assaf Officer; Director Executive Director
Transaction date
Proposed sale
Price
28.90
Quantity 12,250
Value US$354,045
Stienstra Michael GM & Chief Insurance, HHIP Officer
Transaction date
Planned sale
Price
30.02
Quantity 2,329 -3.8%
Value US$69,913
MICHAEL STIENSTRA Officer Officer
Transaction date
Proposed sale
Price
30.11
Quantity 2,329
Value US$70,126
Ostergaard Torben CEO Spinnaker Officer
Transaction date
Planned sale
Price
30.29
Quantity 19,285 -26.0%
Value US$584,174
Ostergaard Torben CEO Spinnaker Officer
Transaction date
Planned sale
Price
30.05
Quantity 21,146 -22.2%
Value US$635,437
TORBEN OSTERGAARD Officer Officer
Transaction date
Proposed sale
Price
27.28
Quantity 37,409
Value US$1,020,518
1.1
Wand Assaf Executive Chairman BoD Executive Director
Transaction date
Planned sale
Price
27.22
Quantity 4,202 -0.8%
Value US$114,391
1.1
Wand Assaf Executive Chairman BoD Executive Director
Transaction date
Planned sale
Price
26.52
Quantity 8,048 -1.6%
Value US$213,408
1.1
Wand Assaf Officer; Director Executive Director
Transaction date
Proposed sale
Price
26.76
Quantity 12,250
Value US$327,798
Ostergaard Torben CEO Spinnaker Officer
Transaction date
Planned sale
Price
27.25
Quantity 3,022 -3.1%
Value US$82,359
Ostergaard Torben CEO Spinnaker Officer
Transaction date
Planned sale
Price
25.77
Quantity 3,022 -3.0%
Value US$77,872
TORBEN OSTERGAARD Officer Officer
Transaction date
Proposed sale
Price
26.21
Quantity 9,066
Value US$237,620
Ellis Stewart CFO/ Chief Strategy Officer Officer
Transaction date
Planned sale
Price
26.64
Quantity 4,333 -1.3%
Value US$115,441
Ellis Stewart CFO/ Chief Strategy Officer Officer
Transaction date
Planned sale
Price
26.11
Quantity 5,667 -1.7%
Value US$147,974
1.1
Wand Assaf Executive Chairman BoD Executive Director
Transaction date
Planned sale
Price
26.51
Quantity 3,754 -0.7%
Value US$99,517
1.1
Wand Assaf Executive Chairman BoD Executive Director
Transaction date
Planned sale
Price
25.81
Quantity 8,496 -1.6%
Value US$219,255
1.1
Wand Assaf Officer; Director Executive Director
Transaction date
Proposed sale
Price
26.02
Quantity 12,250
Value US$318,772
Ellis Stewart Officer Officer
Transaction date
Proposed sale
Price
26.34
Quantity 10,000
Value US$263,416
Notification date Transaction date B/S Transaction type Insider and/or position Nb. shares
Price
Value
Number of shares Price Value Details
2026-08-18 2026-08-17 PlS Planned sale

CEO Spinnaker

Officer
62,571 -34.5%
174.96
US$1,619,096
62,571 -34.5% 174.96 US$1,619,096
2026-08-17 2026-08-17 PrS Proposed sale

Officer

Officer
13,616
203.26
US$1,809,046
13,616 203.26 US$1,809,046
2026-08-12 2026-08-10 PlS Planned sale

Chief Executive Officer

Executive Director
13,892 -46.6%
49.24
US$1,377,715
13,892 -46.6% 49.24 US$1,377,715
2026-08-10 2026-08-10 PrS Proposed sale

Officer

Officer
1,000
32.00
US$100,000
1,000 32.00 US$100,000
2026-07-30 2026-07-28 PlS Planned sale

Chief Financial Officer

Officer
1,000 -1.4%
30.98
US$100,000
1,000 -1.4% 30.98 US$100,000
2026-07-28 2026-07-28 PrS Proposed sale

Officer

Officer
1,669
29.15
US$48,651
1,669 29.15 US$48,651
2026-07-13 2026-07-09 PlS Planned sale

Chief Executive Officer

Executive Director
5,000 -0.8%
28.53
US$142,650
5,000 -0.8% 28.53 US$142,650
2026-07-09 2026-07-09 PrS Proposed sale

Officer

Officer
5,000
28.53
US$142,650
5,000 28.53 US$142,650
2026-06-11 2026-06-09 PlS Planned sale

Chief Executive Officer

Executive Director
5,000 -0.8%
25.00
US$125,000
5,000 -0.8% 25.00 US$125,000
2026-06-09 2026-06-09 PrS Proposed sale

Officer

Officer
5,000
25.00
US$125,000
5,000 25.00 US$125,000
2026-05-19 2026-05-15 PlS Planned sale

CEO Spinnaker

Officer
3,667 -5.3%
26.10
US$95,706
3,667 -5.3% 26.10 US$95,706
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
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