Karen Bailo serves as Executive at PROGRESSIVE CORP/OH/, where they oversee executive responsibilities. Since joining the company, Karen Bailo has executed 28 insider transactions totaling $6.8M, demonstrating a bearish approach to their equity position. Their most recent transaction on Jan 8, 2026 involved receiving (via award) 965.91 shares valued at $0.
Karen Bailo currently holds 16,059.94 shares of PROGRESSIVE CORP/OH/ (PGR), valued at approximately $0. This represents their equity stake as Executive.
Based on SEC Form 4 filings, Karen Bailo has been a net seller of PGR stock. They have purchased $0 and sold $6.8M worth of shares.
Karen Bailo's most recent insider trade was on Jan 8, 2026, when they sold 965.91 shares at $0.00 per share.
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| $249.24 |
| Discretionary |
| Jul 25, 2025 | PGR | $1.8M | Payment | 7,164 | $249.44 | Discretionary |
| Jul 25, 2025 | PGR | $0 | Award | 16,086.46 | $N/A | Discretionary |
| Jul 22, 2024 | PGR | $1.7M | Sale | 7,882 | $214.01 | Planned |
| Jul 19, 2024 | PGR | $1.3M | Payment | 5,916 | $221.75 | Discretionary |
| Jul 19, 2024 | PGR | $0 | Award | 13,798.78 | $N/A | Discretionary |
| Mar 5, 2024 | PGR | $1.6M | Sale | 8,464 | $189.49 | Planned |
| Jan 16, 2024 | PGR | $75.2K | Payment | 445 | $168.93 | Discretionary |
| Jan 16, 2024 | PGR | $0 | Option Exercise | 1,511.88 | $N/A | Discretionary |
| Jan 1, 2024 | PGR | $127.8K | Payment | 796 | $160.52 | Discretionary |
| Jan 1, 2024 | PGR | $0 | Option Exercise | 2,521.3 | $N/A | Discretionary |
| Nov 27, 2023 | PGR | $0 | Award | 3,489.66 | $N/A | Discretionary |
| Nov 27, 2023 | PGR | $168.0K | Payment | 1,026 | $163.74 | Discretionary |
| Jan 1, 2023 | PGR | $0 | Option Exercise | 3,029.92 | $N/A | Discretionary |
| Jan 1, 2023 | PGR | $121.8K | Payment | 940 | $129.53 | Discretionary |
| Dec 20, 2022 | PGR | $644.5K | Sale | 5,000 | $128.90 | Discretionary |
| Aug 25, 2022 | PGR | $181.2K | Payment | 1,439 | $125.95 | Discretionary |
| Aug 25, 2022 | PGR | $0 | Award | 3,280.61 | $N/A | Discretionary |
| May 1, 2022 | PGR | $0 | Option Exercise | 2,806.23 | $N/A | Discretionary |
| May 1, 2022 | PGR | $134.3K | Payment | 1,233 | $108.90 | Discretionary |
| Jan 1, 2022 | PGR | $0 | Option Exercise | 3,450.47 | $N/A | Discretionary |
| Jan 1, 2022 | PGR | $109.1K | Payment | 1,069 | $102.08 | Discretionary |
| Aug 19, 2021 | PGR | $607.0K | Sale | 6,325.88 | $95.96 | Discretionary |
| Jul 16, 2021 | PGR | $107.4K | Payment | 1,135 | $94.64 | Discretionary |
| Jul 16, 2021 | PGR | $0 | Award | 3,801.18 | $N/A | Discretionary |
| Jan 1, 2021 | PGR | $124.9K | Payment | 1,287 | $97.08 | Discretionary |
| Jan 1, 2021 | PGR | $0 | Option Exercise | 4,065.71 | $N/A | Discretionary |