James P. Shaughnessy
Chief Legal Officer at DOCU
Executive
About James P. Shaughnessy
Chief Legal Officer at Docusign since May 2022; age 70; education includes a B.S. in Political Science from Northern Michigan University, a Master’s in Public Policy, and a J.D. from the University of Michigan . FY2025 company performance linked to his pay programs included revenue growth of 8% YoY to $2.98B and strong free cash flow achievement used in PSUs; executive incentives also used relative TSR versus the Nasdaq Composite, subscription revenue growth, non-GAAP operating income, and NNMRR . Pay governance features include stock ownership guidelines (1x base salary for executives), clawback policy adoption, and prohibitions on hedging/pledging .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Workday, Inc. | Senior Advisor, Corporate Affairs; EVP, Corporate Affairs; SVP, General Counsel & Secretary | 2011–2022 | Led corporate affairs and legal functions through growth and public-company scale transitions . |
| Orbitz Worldwide, Inc. | SVP, Chief Administrative Officer and General Counsel | 2007–2011 | Oversaw legal and administrative operations at a global online travel company . |
| Lenovo Group Ltd. | SVP and General Counsel | 2005–2007 | Managed global legal function during major PC-market integration and expansion . |
| PeopleSoft | SVP, General Counsel & Secretary | 2004 | Directed legal and corporate governance in enterprise software . |
| Hewlett-Packard; Compaq; Digital Equipment | Senior legal positions | Pre-2004 | Senior legal leadership across blue-chip technology companies . |
External Roles
No public-company directorships disclosed for Mr. Shaughnessy in Docusign’s 2025 proxy .
Fixed Compensation
| Item | FY2025 Value |
|---|---|
| Base Salary ($) | 525,000 |
| Target Bonus (% of Base) | 70% (increased from 60% in FY2024) |
| Actual Bonus Paid ($) | 421,185 (CIP payout; H1 $160,113; H2 $261,072) |
Multi-year compensation (Summary Compensation Table):
| Metric | FY2023 | FY2024 | FY2025 |
|---|---|---|---|
| Salary ($) | 321,692 | 521,539 | 525,000 |
| Stock Awards ($) | 13,203,371 | 4,126,667 | 6,064,015 |
| Non-Equity Incentive Plan ($) | 135,624 | 281,187 | 421,185 |
| All Other Compensation ($) | 7,062 | 26,075 | 25,997 |
| Total ($) | 13,667,749 | 4,955,468 | 7,036,197 |
Performance Compensation
CIP structure and outcomes (FY2025):
| Metric | Weight (%) | FY2025 1H Target | FY2025 1H Actual | FY2025 2H Target | FY2025 2H Actual | Payout/Funding |
|---|---|---|---|---|---|---|
| Revenue | 10% (H1); 15% (H2) | $1,455.8M | $1,445.7M | $2,976.1M | $2,976.7M | Company funding 117.2% (H1), 115.3% (H2) before ESG modifier |
| Non-GAAP Operating Income | 20% (H1); 30% (H2) | $407.1M | $439.2M | $854.4M | $886.0M | Company funding 117.2% (H1), 115.3% (H2) before ESG modifier |
| NNMRR | 10% (H1); 15% (H2) | Not disclosed | Not disclosed | Not disclosed | Not disclosed | Not disclosed; used in CIP |
| ESG Modifier | N/A | — | — | — | — | ESG modifier 102.7% applied to H2, resulting in 118.4% overall H2 funding for NEOs |
PSU program design (FY2025 focal grants):
| Metric | Weight (%) | Target | Actual/Payout | Vesting |
|---|---|---|---|---|
| Relative TSR vs Nasdaq Composite | 50% | Index TSR yields 100% payout; table ranges -25 pts=50%, +50 pts=200% | Ongoing through June 2027; not yet certified | Cliff vest at 3 years upon certification |
| Subscription Revenue Growth | 25% | Target 8.1%; threshold 6%; max 15% | 97.2% payout certified for FY2025 | 1/3 in June 2025; remainder vests quarterly over 2 years |
| Free Cash Flow | 25% | Target $800.0M; threshold $680.0M; max $1,120.0M | 137.5% payout certified for FY2025 | 1/3 in June 2025; remainder vests quarterly over 2 years |
PSUs achieved for Mr. Shaughnessy:
| PSU Metric | FY2024 Achieved & Eligible to Vest (Shares) | FY2025 Achieved & Eligible to Vest (Shares) |
|---|---|---|
| Subscription Revenue Growth | 6,429 | 13,102 |
| Free Cash Flow | 17,496 | 18,535 |
| Total | 23,925 | 31,637 |
CIP cash payouts (Mr. Shaughnessy, FY2025):
| Period | Base ($) | Target Bonus (%) | Weighting (%) | Funding (%) | Payout ($) |
|---|---|---|---|---|---|
| First Half | 525,000 | 70 | 40 | 117.2 | 160,113 |
| Second Half | 525,000 | 70 | 60 | 118.4 | 261,072 |
| Full Year | — | — | — | 117.9 | 421,185 |
Equity Ownership & Alignment
| Ownership Item | Value |
|---|---|
| Total beneficial ownership (shares) | 61,864 (as of March 15, 2025; “<1%” indicated) |
| Ownership as % of shares outstanding | <1% (company notation) |
| RSUs vesting within 60 days (as of March 15, 2025) | 8,489 RSUs |
| Outstanding RSUs by grant (not yet vested, 1/31/2025) | 26,348 (6/10/2022) ; 17,590 (7/25/2022) ; 21,872 (7/7/2023) ; 47,182 (7/9/2024) |
| Outstanding PSUs (unearned) | 26,961 TSR PSUs (FY2025 grant, target unearned) |
| FY2025 PSUs achieved & eligible to vest | 13,102 SRG; 18,535 FCF; total 31,637 |
| FY2024 PSUs achieved & eligible to vest | 6,429 SRG; 17,496 FCF; total 23,925 |
- Stock ownership guidelines: executives must hold at least 1.0x base salary; as of Jan 31, 2025, each NEO had either satisfied or had additional time to meet the requirement .
- Hedging/pledging: prohibited, including short sales, pledging, margin accounts, and derivatives .
- Rule 10b5-1 plans: certain directors and officers have adopted compliant plans under company policy .
Employment Terms
| Scenario | Salary Severance (months) | Bonus Severance (% of base) | COBRA (months) | Time-based Equity Acceleration | PSU Treatment |
|---|---|---|---|---|---|
| Termination without Cause / Good Reason (outside CIC period) | 12 | 100 | 12 | 12 months of vesting acceleration | Vests to extent provided in applicable PSU agreements; prorated based on service for TSR/Financial PSUs |
| Termination without Cause / Good Reason (during CIC period) | 12 | 100 | 12 | 100% acceleration of time-based awards | TSR PSUs and Financial PSUs earned as of CIC; vesting subject to award rules and double-trigger protection if assumed; otherwise fully vest upon CIC |
- No single-trigger acceleration upon change-in-control for NEOs; double-trigger required .
- Clawback policy: adopted November 2023 per SEC/Nasdaq rules; recovery upon financial restatement .
- Section 280G “best net pay” provision applies to reduce excise tax exposure only if beneficial to net after-tax outcome .
Investment Implications
- Near-term supply: 1/3 of FY2025 Financial PSUs for Shaughnessy vest in June 2025 with the remaining 2/3 vesting quarterly over eight quarters; ongoing quarterly RSU schedules across multiple grants suggest regular settlement windows that can create periodic selling pressure, typically executed via 10b5-1 plans under policy .
- Alignment and retention: Ownership guidelines, clawback policy, and prohibitions on hedging/pledging strengthen alignment; severance includes 12 months salary plus 100% of base as bonus and double-trigger equity acceleration, moderating retention risk but implying standard executive protections in CIC scenarios .
- Pay-for-performance signals: FY2025 PSU outcomes show strong free cash flow performance (137.5% payout) and near-target subscription revenue growth (97.2% payout), indicating compensation tightly linked to value-creation metrics; TSR PSUs remain a multi-year lever with market-relative hurdles .
- Governance context: Prior say-on-pay concerns were addressed with design changes; overall compensation framework now emphasizes PSUs and longer performance horizons, reducing discretionary risk and improving investor alignment .