Montgomery Jeanine, VP and CAO of MicroStrategy Inc. ($MSTR), sold shares on the open market 13 times in the last year, totaling $19.2 million. Her most recent sale occurred on March 12, 2026. These sales rank 698th among 11,678 individual insiders by value, above the average of $8.6 million across 6.4 transactions. She made no open market purchases during this period.
| Transaction Date | Company | Ticker | Insider Name | Title | Transaction Type | Security | Shares | Price | Shares Owned Following | Total Shares Outstanding | % of Owned | % of Outstanding |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| March 24, 2026 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | S | Class A Common Stock | 19 | $139.45 | 10,423.0000 | 277,660,000 | 0.18% | 0.00% |
| March 23, 2026 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | M | Restricted Stock Units | 1560 | $0.00 | 3,120.0000 | 277,660,000 | 33.33% | 0.00% |
| March 23, 2026 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | M | Class A Common Stock | 1560 | $0.00 | 10,893.0000 | 277,660,000 | 16.71% | 0.00% |
| March 24, 2026 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | S | Class A Common Stock | 250 | $137.73 | 10,643.0000 | 277,660,000 | 2.30% | 0.00% |
| March 24, 2026 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | S | Class A Common Stock | 201 | $138.98 | 10,442.0000 | 277,660,000 | 1.89% | 0.00% |
| March 17, 2026 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | A | Restricted Stock Units | 2240 | $0.00 | 2,240.0000 | 277,660,000 | 9999.99% | 0.00% |
| March 11, 2026 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | M | Restricted Stock Units | 787 | $0.00 | 2,361.0000 | 277,660,000 | 25.00% | 0.00% |
| March 12, 2026 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | S | Class A Common Stock | 260 | $137.25 | 9,333.0000 | 277,660,000 | 2.71% | 0.00% |
| March 11, 2026 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | M | Class A Common Stock | 787 | $0.00 | 9,593.0000 | 277,660,000 | 8.94% | 0.00% |
| Nov. 18, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | S | Class A Common Stock | 43 | $208.55 | 8,733.0000 | 315,393,000 | 0.49% | 0.00% |
| Nov. 17, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | M | Class A Common Stock | 100 | $0.00 | 8,776.0000 | 315,393,000 | 1.15% | 0.00% |
| Nov. 17, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | M | Restricted Stock Units | 100 | $0.00 | 0.0000 | 315,393,000 | 100.00% | 0.00% |
| July 29, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | P | Series A Perpetual Stretch Preferred Stock | 5000 | $90.00 | 5,000.0000 | 192,549,000 | 9999.99% | 0.00% |
| July 11, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | M | Class A Common Stock | 18750 | $69.12 | 27,356.0000 | 192,549,000 | 217.87% | 0.01% |
| July 11, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | M | Class A Common Stock | 25000 | $40.46 | 52,356.0000 | 192,549,000 | 91.39% | 0.01% |
| July 11, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | S | Class A Common Stock | 43750 | $430.54 | 8,606.0000 | 192,549,000 | 83.56% | 0.02% |
| July 11, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | M | Employee Stock Option (Right to buy) | 18750 | $0.00 | 0.0000 | 192,549,000 | 100.00% | 0.01% |
| July 11, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | M | Employee Stock Option (Right to buy) | 25000 | $0.00 | 15,000.0000 | 192,549,000 | 62.50% | 0.01% |
| June 5, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | M | Restricted Stock Units | 1140 | $0.00 | 2,290.0000 | 192,549,000 | 33.24% | 0.00% |
| June 6, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | S | Class A Common Stock | 28 | $372.31 | 8,892.0000 | 192,549,000 | 0.31% | 0.00% |
| June 6, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | S | Class A Common Stock | 24 | $373.74 | 8,868.0000 | 192,549,000 | 0.27% | 0.00% |
| June 6, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | S | Class A Common Stock | 128 | $374.61 | 8,740.0000 | 192,549,000 | 1.44% | 0.00% |
| June 6, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | S | Class A Common Stock | 109 | $375.43 | 8,631.0000 | 192,549,000 | 1.25% | 0.00% |
| June 6, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | S | Class A Common Stock | 24 | $376.36 | 8,607.0000 | 192,549,000 | 0.28% | 0.00% |
| June 6, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | S | Class A Common Stock | 2 | $377.14 | 8,605.0000 | 192,549,000 | 0.02% | 0.00% |
| June 5, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | S | Class A Common Stock | 1 | $370.70 | 8,944.0000 | 192,549,000 | 0.01% | 0.00% |
| June 5, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | M | Class A Common Stock | 1140 | $0.00 | 8,945.0000 | 192,549,000 | 14.61% | 0.00% |
| June 6, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | S | Class A Common Stock | 24 | $371.64 | 8,920.0000 | 192,549,000 | 0.27% | 0.00% |
| March 24, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | S | Class A Common Stock | 331 | $329.09 | 7,955.0000 | 192,549,000 | 3.99% | 0.00% |
| March 24, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | M | Restricted Stock Units | 1550 | $0.00 | 4,680.0000 | 192,549,000 | 24.88% | 0.00% |
| March 24, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | S | Class A Common Stock | 150 | $329.67 | 7,805.0000 | 192,549,000 | 1.89% | 0.00% |
| March 24, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | M | Class A Common Stock | 1550 | $0.00 | 8,286.0000 | 192,549,000 | 23.01% | 0.00% |
| March 11, 2025 | Strategy Inc | $MSTR | Montgomery Jeanine | VP & CAO | A | Restricted Stock Units | 3148 | $0.00 | 3,148.0000 | 192,549,000 | 9999.99% | 0.00% |
| Nov. 18, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | M | Restricted Stock Units | 46 | $0.00 | 100.0000 | 197,273,000 | 31.51% | 0.00% |
| Nov. 18, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | M | Class A Common Stock | 100 | $0.00 | 6,518.0000 | 197,273,000 | 1.56% | 0.00% |
| Nov. 18, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 46 | $359.56 | 6,472.0000 | 197,273,000 | 0.71% | 0.00% |
| Nov. 14, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 752 | $322.45 | 6,418.0000 | 197,273,000 | 10.49% | 0.00% |
| Nov. 14, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | M | Class A Common Stock | 1500 | $0.00 | 7,170.0000 | 197,273,000 | 26.46% | 0.00% |
| Nov. 14, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | M | Restricted Stock Units | 1500 | $0.00 | 0.0000 | 197,273,000 | 100.00% | 0.00% |
| Nov. 6, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 1900 | $260.60 | 5,670.0000 | 197,273,000 | 25.10% | 0.00% |
| Nov. 6, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 4925 | $259.33 | 7,570.0000 | 197,273,000 | 39.42% | 0.00% |
| Nov. 6, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 14025 | $258.36 | 12,495.0000 | 197,273,000 | 52.88% | 0.01% |
| Nov. 6, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 11124 | $255.54 | 50,796.0000 | 197,273,000 | 17.97% | 0.01% |
| Nov. 6, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 11445 | $256.57 | 39,351.0000 | 197,273,000 | 22.53% | 0.01% |
| Nov. 6, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 12831 | $257.53 | 26,520.0000 | 197,273,000 | 32.61% | 0.01% |
| Nov. 6, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | M | Class A Common Stock | 56250 | $69.12 | 61,920.0000 | 197,273,000 | 992.06% | 0.03% |
| Nov. 6, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | M | Employee Stock Option (Right to buy) | 56250 | $0.00 | 18,750.0000 | 197,273,000 | 75.00% | 0.03% |
| June 17, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 38 | $1441.81 | 567.0000 | 165,662,000 | 6.28% | 0.00% |
| June 17, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | M | Restricted Stock Units | 114 | $0.00 | 343.0000 | 165,662,000 | 24.95% | 0.00% |
| June 17, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | M | Class A Common Stock | 114 | $0.00 | 605.0000 | 165,662,000 | 23.22% | 0.00% |
| March 21, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | A | Restricted Stock Units | 623 | $0.00 | 623.0000 | 165,662,000 | 9999.99% | 0.00% |
| Feb. 29, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | M | Class A Common Stock | 1000 | $404.60 | 1,491.0000 | 165,662,000 | 203.67% | 0.00% |
| Feb. 29, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 1000 | $1000.00 | 491.0000 | 165,662,000 | 67.07% | 0.00% |
| Feb. 29, 2024 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | M | Employee Stock Option (Right to buy) | 1000 | $0.00 | 4,000.0000 | 165,662,000 | 20.00% | 0.00% |
| Dec. 4, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 1237 | $564.87 | 5,104.0000 | 113,209,000 | 19.51% | 0.00% |
| Dec. 4, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 800 | $565.79 | 4,304.0000 | 113,209,000 | 15.67% | 0.00% |
| Dec. 4, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 600 | $567.79 | 3,704.0000 | 113,209,000 | 13.94% | 0.00% |
| Dec. 4, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 2911 | $568.42 | 793.0000 | 113,209,000 | 78.59% | 0.00% |
| Dec. 4, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 300 | $570.02 | 493.0000 | 113,209,000 | 37.83% | 0.00% |
| Dec. 4, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 2 | $571.03 | 491.0000 | 113,209,000 | 0.41% | 0.00% |
| Dec. 4, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | M | Employee Stock Option (Right to buy) | 2500 | $0.00 | 0.0000 | 113,209,000 | 100.00% | 0.00% |
| Dec. 4, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | M | Employee Stock Option (Right to buy) | 5000 | $0.00 | 0.0000 | 113,209,000 | 100.00% | 0.00% |
| Dec. 4, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | M | Class A Common Stock | 5000 | $151.60 | 7,991.0000 | 113,209,000 | 167.17% | 0.00% |
| Dec. 4, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 100 | $558.80 | 7,891.0000 | 113,209,000 | 1.25% | 0.00% |
| Dec. 4, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 1350 | $560.52 | 6,541.0000 | 113,209,000 | 17.11% | 0.00% |
| Dec. 4, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | S | Class A Common Stock | 200 | $561.27 | 6,341.0000 | 113,209,000 | 3.06% | 0.00% |
| Dec. 4, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | M | Class A Common Stock | 2500 | $131.53 | 2,991.0000 | 113,209,000 | 509.17% | 0.00% |
| Nov. 15, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | F | Class A Common Stock | 4 | $505.95 | 491.0000 | 113,209,000 | 0.81% | 0.00% |
| Nov. 15, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | M | Restricted Stock Units | 10 | $0.00 | 20.0000 | 113,209,000 | 33.33% | 0.00% |
| Nov. 15, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | M | Class A Common Stock | 10 | $0.00 | 495.0000 | 113,209,000 | 2.06% | 0.00% |
| Nov. 13, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | M | Class A Common Stock | 150 | $0.00 | 531.0000 | 113,209,000 | 39.37% | 0.00% |
| Nov. 13, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | M | Restricted Stock Units | 150 | $0.00 | 150.0000 | 113,209,000 | 50.00% | 0.00% |
| Nov. 13, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | F | Class A Common Stock | 46 | $504.88 | 485.0000 | 113,209,000 | 8.66% | 0.00% |
| June 5, 2023 | Strategy Inc | $MSTR | Montgomery Jeanine | SVP & CAO | A | Restricted Stock Units | 457 | $0.00 | 457.0000 | 113,209,000 | 9999.99% | 0.00% |