Montgomery Jeanine 4
4 · Strategy Inc · Filed Mar 25, 2026
Research Summary
AI-generated summary of this filing
Strategy (MSTR) VP Jeanine Montgomery Sells Shares
What Happened
- Jeanine Montgomery, VP & CAO of Strategy Inc (MSTR), had 1,560 restricted stock units (RSUs) vest/settle on March 23, 2026 (converted to shares) and, pursuant to a pre-existing 10b5-1 instruction, sold a portion of the shares to cover taxes.
- She sold 470 shares in open-market transactions on March 24, 2026 for total proceeds of approximately $65,017 (250 shares at a weighted avg $137.73 = $34,433; 201 shares at a weighted avg $138.98 = $27,934; 19 shares at a weighted avg $139.45 = $2,650). An additional 1,560 shares were reported disposed at $0.00 (share withholding/surrender to Strategy to satisfy tax withholding on the vested RSUs).
Key Details
- Transaction dates: RSU settlement/exercise on 2026-03-23; open-market sales on 2026-03-24.
- Sale prices: weighted averages shown — $137.73 (250 shares), $138.98 (201 shares), $139.45 (19 shares). Footnotes report transaction price ranges for each block and offer to provide per-price detail on request.
- Total cash proceeds from open-market sales: ~$65,017.
- The 1,560 shares shown as disposed at $0.00 reflect shares withheld/surrendered to Strategy to cover tax withholding on the vested RSUs.
- Plan/footnotes: Sales were effected pursuant to a Rule 10b5-1 instruction (entered May 3, 2024) specifically to satisfy the reporting person’s tax withholding obligation (F2). Each RSU represents a right to one share (F1).
- Remaining RSUs: 3,120 RSUs remain unvested and will vest in equal installments on March 21, 2027 and March 21, 2028 (F6).
- Shares owned after transaction: not specified in the provided filing excerpt.
- Filing timeliness: Reported period 2026-03-23; Form filed 2026-03-25 — appears timely.
Context
- This was not a bullish stock purchase: it was a routine tax-withholding sale following RSU vesting. Conversions of RSUs to shares (derivative exercise/conversion) were followed by share withholding and open-market sales to satisfy tax obligations.
- Sales under 10b5-1 plans are commonly automatic and do not, by themselves, indicate insider sentiment about company prospects.
Insider Transaction Report
Form 4
Strategy IncMSTR
Montgomery Jeanine
VP & CAO
Transactions
- Exercise/Conversion
Class A Common Stock
[F1]2026-03-23+1,560→ 10,893 total - Sale
Class A Common Stock
[F2][F3]2026-03-24$137.73/sh−250$34,433→ 10,643 total - Sale
Class A Common Stock
[F2][F4]2026-03-24$138.98/sh−201$27,934→ 10,442 total - Sale
Class A Common Stock
[F2][F5]2026-03-24$139.45/sh−19$2,650→ 10,423 total - Exercise/Conversion
Restricted Stock Units
[F1][F6]2026-03-23−1,560→ 3,120 total→ Class A Common Stock (1,560 underlying)
Holdings
- 5,000
Series A Perpetual Stretch Preferred Stock
Footnotes (6)
- [F1]Each restricted stock unit represents a contingent right to receive one share of class A common stock of Strategy Inc ("Strategy").
- [F2]The sales were effected pursuant to a Rule 10b5-1 instruction letter entered into on May 3, 2024 to satisfy the reporting person's tax withholding obligation upon the vesting of previously granted equity awards. Such sales were made solely to pay Strategy the tax withholding obligation due upon the vesting of restricted stock units on March 21, 2026 and their settlement on March 23, 2026.
- [F3]The reported price is a weighted average price. These shares were sold in multiple transactions at prices ranging from $137.370 to $138.350, inclusive. The reporting person undertakes to provide to Strategy, any security holder of Strategy, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each price within the range set forth in this footnote.
- [F4]The reported price is a weighted average price. These shares were sold in multiple transactions at prices ranging from $138.390 to $139.380, inclusive. The reporting person undertakes to provide to Strategy, any security holder of Strategy, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each price within the range set forth in this footnote.
- [F5]The reported price is a weighted average price. These shares were sold in multiple transactions at prices ranging from $139.385 to $139.550, inclusive. The reporting person undertakes to provide to Strategy, any security holder of Strategy, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each price within the range set forth in this footnote.
- [F6]The remaining 3,120 RSUs will vest in equal annual installments over a two-year period, with 1,560 RSUs vesting on March 21, 2027 and 1,560 RSUs vesting on March 21, 2028.
Signature
/s/ Allein Sabel, Attorney-in-Fact|2026-03-25