DocuSign CLO exercises awards, pays taxes in shares
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Form Type
4
Rhea-AI Filing Summary
DOCUSIGN, INC. Chief Legal Officer James P. Shaughnessy reported routine equity compensation activity. On June 15, 2026, he exercised derivative awards, including restricted stock units and performance stock units, into common stock and had 9,788 shares withheld to cover tax obligations.
These transactions increased his direct common stock position through option and unit exercises while using shares, rather than cash, to satisfy taxes. Following the transactions, he directly holds 64,815 shares of DocuSign common stock.
Insider Trade Summary
20,972 shares exercised/converted
Exercise
11 txns
Insider
Shaughnessy James P
Role
Chief Legal Officer
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Restricted Stock Units | 4,392 | $0.00 | $0.00 |
| Exercise | Restricted Stock Units | 2,932 | $0.00 | $0.00 |
| Exercise | Restricted Stock Units | 2,187 | $0.00 | $0.00 |
| Exercise | Restricted Stock Units | 3,371 | $0.00 | $0.00 |
| Exercise | Restricted Stock Units | 3,457 | $0.00 | $0.00 |
| Exercise | Performance Stock Units | 536 | $0.00 | $0.00 |
| Exercise | Performance Stock Units | 1,460 | $0.00 | $0.00 |
| Exercise | Performance Stock Units | 1,092 | $0.00 | $0.00 |
| Exercise | Performance Stock Units | 1,545 | $0.00 | $0.00 |
| Exercise | Common Stock | 20,972 | $0.00 | $0.00 |
| Exercise Price or Tax Liability | Common Stock | 9,788 | $0.00 | $0.00 |
Holdings After Transaction:
Restricted Stock Units — 59,384 contracts (Direct);
Performance Stock Units — 5,870 contracts (Direct);
Common Stock — 64,815 shares (Direct)
Footnotes (13)
- F1. 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") or performance-vested restricted stock units ("PSUs").
- F2. Each RSU represents a contingent right to receive one share of the Issuer's common stock.
- F3. The RSUs will vest 35% on the one year anniversary of the grant date, 35% in equal quarterly installments after year one, 15% in equal quarterly installments after year two, and 15% in equal quarterly installments after year 3, with a vesting commencement date of June 10, 2022, in each case subject to the Reporting Person being a service provider through each such date. The restricted stock units 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.
- F4. The RSUs do not expire; they either vest or are canceled prior to vesting date.
- F5. The RSUs will vest in equal quarterly installments over four years, with a vesting commencement date of July 10, 2022, in each case subject to the Reporting Person being a service provider through each such date. The restricted stock units 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 will vest in equal quarterly installments over four years, with a vesting commencement date of May 10, 2023, in each case subject to the reporting person being a service provider through such 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.
- F10. The PSUs will vest depending on the Company's subscription revenue for the twelve-month period ended January 31, 2024 (the "FY24 Performance Period"). The maximum number of the 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 date of grant 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 FY24 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 date of grant and the balance will vest in eight equal quarterly installments thereafter subject to continued service with certain limited exceptions.
- F12. 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.
- F13. 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.
Key Figures
Tax withholding shares: 9,788 shares
Shares exercised: 20,972 shares
Post-transaction holdings: 64,815 shares
+4 more
7 metrics
Tax withholding shares
9,788 shares
Shares withheld to satisfy tax obligation on vesting
Shares exercised
20,972 shares
Total shares from derivative exercises reported in summary
Post-transaction holdings
64,815 shares
Common stock held directly after transactions
Exercise transactions
9 exercises
Number of derivative exercise transactions (M code)
Tax-withholding transactions
1 transaction
F-code disposition to cover tax liability
Tax-withholding shares detail
9,788 shares
Shares delivered instead of cash for tax obligations
PSU vesting cap
200% of target
Maximum vesting for certain performance stock units
Key Terms
Restricted Stock Units, Performance Stock Units, tax obligation, subscription revenue, +2 more
6 terms
Restricted Stock Units financial
"Each RSU represents a contingent right to receive one share of the Issuer's common stock."
Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.
Performance Stock Units financial
"Each PSU represents a contingent right to receive one share of the Issuer's common stock."
Performance stock units are a type of company award that grants employees shares of stock only if certain performance goals are met. They motivate employees to work toward specific company achievements, aligning their interests with those of shareholders. For investors, they can influence a company's future stock supply and reflect management’s confidence in reaching key targets.
tax obligation financial
"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"
subscription revenue financial
"The PSUs will vest depending on the Company's subscription revenue for the twelve-month period ended January 31, 2024"
Payments a company receives on a regular schedule from customers who pay to access a product or service over time, like a magazine or gym membership fee. Investors care because these recurring payments create more predictable sales and cash flow, make future revenue easier to forecast, and indicate customer loyalty; changes in subscription growth or churn can quickly affect a company’s valuation and financial health.
free cash flow financial
"The PSUs will vest depending on the Company's free cash flow for the FY24 Performance Period."
Free cash flow is the amount of money a company has left over after paying all its expenses and investing in its business, like buying equipment or updating facilities. It shows how much cash is available to reward shareholders, pay down debt, or save for future growth. This helps investors understand if a company is financially healthy and able to grow.
performance period financial
"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 performance period is the specific time span over which an investment’s results, an employee’s targets, or a fund’s returns are measured and judged. It matters to investors because the length and start/end of that window determine which gains or losses count toward performance fees, bonus payouts, or benchmark comparisons—much like timing a race decides who wins, the chosen period can change whether results look strong or weak.
FAQ
AI-generated questions and answers. How Rhea-AI works. Not financial advice.
What did DOCUSIGN (DOCU) Chief Legal Officer report in this Form 4?
The filing shows Chief Legal Officer James P. Shaughnessy exercised equity awards into common stock and used shares for taxes. It reflects routine compensation-related activity rather than open-market buying or selling, changing how his ownership is held but not signaling a discretionary trade.
Are the DOCUSIGN (DOCU) insider transactions open-market buys or sales?
The transactions are not open-market buys or sales. They consist of derivative exercises and a tax-withholding disposition, where equity awards like RSUs and PSUs convert into shares and some shares are withheld by the company to pay tax liabilities.
How do DOCUSIGN (DOCU) RSUs and PSUs work for this insider?
Each RSU or PSU represents a contingent right to receive one share of DOCUSIGN common stock. RSUs vest over multi‑year quarterly schedules, while PSUs vest based on subscription revenue and free cash flow performance for specified fiscal-year performance periods.
AI-generated analysis. How Rhea-AI works. Not financial advice.
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