GRAYSON BLAKE JEFFREY 4
4 · DOCUSIGN, INC. · Filed Jun 17, 2026
Research Summary
AI-generated summary of this filing
DocuSign (DOCU) CFO Grayson Jeffrey Exercises Derivatives, Buys ESPP
What Happened
- Grayson Blake Jeffrey, CFO of DocuSign, converted/settled 37,452 derivative awards (reported as "M" transactions) on 2026-06-15 and simultaneously had 15,251 shares withheld/disposed to cover tax obligations (reported as "F"). Those derivative conversions were reported at $0 exercise cost, consistent with settlement of RSUs/PSUs rather than a priced option exercise.
- Separately, on 2026-04-03 he purchased 255 shares through DocuSign’s Employee Stock Purchase Plan (ESPP) at $41.11 per share for a total of $10,483 (ESPP purchase price was 85% of the April 3, 2026 closing price).
Key Details
- Transaction dates and prices:
- 2026-04-03: Acquired 255 ESPP shares at $41.11 each (total ~$10,483). (Code A)
- 2026-06-15: Converted/settled 37,452 derivative shares at $0 (Code M, acquisition) and multiple M-code disposals totaling 37,452 shares; 15,251 shares disposed under code F to satisfy tax withholding.
- Net effect on holdings: Filing reports conversions and withholding/surrenders but does not state total post-transaction beneficial ownership in the submitted excerpt.
- Notable footnotes:
- F1: ESPP purchase priced at 85% of the closing price for the April 3, 2026 purchase period.
- F2/F4–F11: Conversions relate to RSUs and performance-based PSUs with multi-year vesting and performance conditions (PSUs subject to FY25 subscription revenue and free-cash-flow metrics; vesting schedules and caps noted).
- Timeliness: Filing dated 2026-06-17 for transactions on 2026-06-15 — no late filing indication in the report.
Context
- The $0 exercise price and footnotes indicate these were vesting/settlement events for restricted stock units (RSUs) and performance stock units (PSUs), not the exercise of priced stock options. The multiple M-code disposals and the F-code tax withholding reflect shares surrendered/withheld to cover tax obligations at settlement (a common administrative step), not an open-market sale signal.
- The ESPP purchase is a direct purchase by the CFO (a modest-dollar purchase of 255 shares) and is a straightforward employee purchase at a discounted price.
Insider Transaction Report
Form 4
DOCUSIGN, INC.DOCU
GRAYSON BLAKE JEFFREY
Chief Financial Officer
Transactions
- Award
Common Stock
[F1]2026-04-03$41.11/sh+255$10,483→ 134,051 total - Exercise/Conversion
Common Stock
2026-06-15+37,452→ 171,503 total - Tax Payment
Common Stock
[F2][F3]2026-06-15−15,251→ 156,429 total - Exercise/Conversion
Restricted Stock Units
[F4][F5][F6]2026-06-15−23,141→ 92,565 total→ Common Stock (23,141 underlying) - Exercise/Conversion
Restricted Stock Units
[F4][F7][F6]2026-06-15−5,119→ 40,954 total→ Common Stock (5,119 underlying) - Exercise/Conversion
Restricted Stock Units
[F4][F8][F6]2026-06-15−5,186→ 31,113 total→ Common Stock (5,186 underlying) - Exercise/Conversion
Performance Stock Units
[F9][F10]2026-06-15−1,659→ 7,208 total→ Common Stock (1,659 underlying) - Exercise/Conversion
Performance Stock Units
[F9][F11]2026-06-15−2,347→ 1,710 total→ Common Stock (2,347 underlying)
Footnotes (11)
- [F1]Shares acquired pursuant to the Docusign, Inc. 2018 Employee Stock Purchase Plan ("ESPP"), for the ESPP purchase period of October 6, 2025, through April 3, 2026. In accordance with the ESPP, these shares were purchased at a price equal to 85% of the closing price of the issuer's common stock on April 3, 2026.
- [F10]The PSUs will vest depending on the Company's subscription revenue for the twelve-month period ended January 31, 2025 (the "FY25 Performance Period"). The maximum number of subscription revenue-based PSUs that may vest is capped at 200% of the target number of subscription revenue-based PSUs. To the extent achieved, 1/3 of any achieved subscription revenue-based PSUs will vest following the one-year anniversary of the vesting commencement date and the balance will vest in eight equal quarterly installments thereafter, subject to continued service with certain limited exceptions.
- [F11]The PSUs will vest depending on the Company's free cash flow for the FY25 Performance Period. The maximum number of free cash flow-based PSUs that may vest is capped at 200% of the target number of free cash flow-based PSUs. To the extent achieved, 1/3 of any achieved free cash flow-based PSUs will vest following the one-year anniversary of the vesting commencement date and the balance will vest in eight equal quarterly installments thereafter, subject to continued service with certain limited exceptions.
- [F2]Represents shares withheld by the Issuer to satisfy a tax obligation realized by the Reporting Person upon the vesting and settlement of restricted stock units ("RSUs") and performance-vested restricted stock unit ("PSUs").
- [F3]Includes 177 shares acquired by the Reporting Person on October 3, 2025, pursuant to the Docusign, Inc. ESPP.
- [F4]Each RSU represents a contingent right to receive one share of the Issuer's common stock.
- [F5]The RSUs will vest in sixteen equal quarterly installments over four years, with a vesting commencement date of June 10, 2023, in each case subject to the Reporting Person being a service provider through each such date. The RSUs are subject to accelerated vesting in the event of a termination of employment of the Reporting Person including under certain circumstances following a change in control of the Issuer.
- [F6]The RSUs do not expire; they either vest or are canceled prior to vesting date.
- [F7]The RSUs will vest in equal quarterly installments over four years, with a vesting commencement date of May 10, 2024, in each case subject to the reporting person being a service provider through such date.
- [F8]The RSUs will vest quarterly over a four year period commencing May 10, 2025, with 40% vesting during year 1, 35% vesting during year 2, 15% vesting during year 3, and 10% vesting during year 4, in each case subject to the Reporting Person being a service provider through each such date.
- [F9]Each PSU represents a contingent right to receive one share of the Issuer's common stock.
Signature
/s/ Derrick Chapman, Attorney-in-fact|2026-06-17