Winston King
Guidewire SoftwareAbout Winston King
Winston King is Chief Administrative Officer, General Counsel, and Secretary at Guidewire Software. He has served as General Counsel and Secretary since January 2013 and has been CAO since June 2018; he is age 54, with an A.B. in Economics from Duke University and a J.D. from Vanderbilt University School of Law . For performance context, company pay-versus-performance disclosures show cumulative total stockholder return value of $192.27 for an initial $100 investment by FY2025, Annual Recurring Revenue (ARR) of $1,041 million, and FY2025 net income of $69.8 million . Executive compensation metrics emphasize ARR (51%), adjusted non-GAAP operating income (34%), and a strategic scorecard (15%), with an overall FY2025 Company Performance Factor of 130% .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Infogroup, Inc. | EVP, General Counsel & Secretary | 2007–2012 | Senior legal leadership at a data/marketing services firm |
| WilmerHale (Washington, D.C.) | Attorney | Not disclosed | Corporate legal practice experience |
External Roles
| Organization | Role | Years | Notes |
|---|---|---|---|
| — | — | — | No external public company directorships disclosed in the proxy |
Fixed Compensation
| Metric | FY2023 | FY2024 | FY2025 |
|---|---|---|---|
| Base Salary ($) | 390,000 | 397,500 | 415,000 |
| Target Bonus (% of Base) | — | 75% | 75% |
| Actual Cash Bonus ($) | 367,965 | 363,700 | 404,585 |
| All Other Compensation ($) | 5,729 | 5,699 | 6,710 |
| Total Compensation ($) | 2,578,185 | 3,432,033 | 3,840,462 |
| Base Salary Changes | FY2024 Base ($) | FY2025 Base ($) | Increase (%) |
|---|---|---|---|
| Winston King | 397,500 | 415,000 | 4% |
Performance Compensation
Annual Bonus Plan – FY2025 Structure and Outcomes
| Metric | Weighting | Payout Range (Threshold/Max) | Threshold | Target | Maximum | Actual Performance |
|---|---|---|---|---|---|---|
| Annual Recurring Revenue (ARR) | 51% | 50%–150% | $958M | $1,008M | $1,058M | $1,032M |
| Adjusted Non-GAAP Operating Income (Loss) | 34% | 50%–150% | ($5M) | $25M | $55M | $66M |
| Strategic Scorecard (VPMOM) | 15% | 50%–150% | 50% | 100% | 150% | 100% |
| Company Performance Factor (Applied to Bonus) | — | — | — | — | — | 130% |
Equity Grants – FY2025 (Grant date 9/11/2024)
| Award Type | Grant Date | Shares/Units (#) | Grant Date Fair Value ($) | Notes |
|---|---|---|---|---|
| Time-Vesting RSUs | 9/11/2024 | 8,967 | 1,507,083 | Generally vest quarterly over four years, subject to continued employment |
| Performance-Vesting RSUs (ARR & Operating Income) | 9/11/2024 | Target 8,967; Threshold 4,484; Max 13,451 | 1,507,084 (at target) | Cliff vest after three years upon FY2025–FY2027 goal attainment |
Vesting Schedules (Select Awards)
| Grant Date | Type | Schedule Details |
|---|---|---|
| 9/15/2022 | Performance RSUs | 33% of 50% after 1 year, then equal annual installments over 2 years; remaining 50% vests in year 3 upon FY2025 performance. FY2023 achieved 101.8%; FY2025 achieved 120% |
| 9/13/2023 | Performance RSUs | Cliff vest after three years based on FY2024–FY2026 predefined financial results |
| 9/11/2024 | Performance RSUs | Cliff vest after three years based on FY2025–FY2027 predefined financial results |
| Various Time-Vesting RSUs | Time RSUs | Typically vest quarterly over four years (standard under 2020 Plan) |
FY2025 Vesting and Option Activity
| Activity | Shares (#) | Value ($) |
|---|---|---|
| Shares acquired on vesting (stock awards) | 20,553 | 3,811,893 |
| Options exercised | 105 | 10,809 (value realized) |
| Outstanding options at FY2025 year-end | — | No NEO outstanding options at FY2025 year-end |
Equity Ownership & Alignment
| Beneficial Ownership (Record Date: 10/20/2025) | Shares | % of Class |
|---|---|---|
| Winston King | 17,400 | <1% |
| Outstanding Equity Awards (as disclosed) | Grant Date | Time-Based Unvested (#) | Market Value ($) | Performance-Based Unearned (#) | Market/Payout Value ($) |
|---|---|---|---|---|---|
| Winston King | 9/14/2021 | 588 | 133,017 | — | — |
| 9/15/2022 | 4,303 | 973,425 | 9,179 | 2,076,473 | |
| 9/13/2023 | 8,149 | 1,843,467 | 14,486 | 3,277,023 | |
| 9/11/2024 | 7,286 | 1,648,239 | 8,967 | 2,028,515 |
- Stock ownership guidelines: Non-CEO Section 16 officers must own at least 1.5x base salary in shares by the first July 31 following three years; all NEOs employed ≥3 years satisfied the requirement as of 7/31/2025 .
- Hedging/pledging: Company policy prohibits short sales, hedging, and pledging of equity securities; trades generally restricted to open windows or under approved Rule 10b5-1 plans .
Employment Terms
| Provision | Standard (Executive Agreement) | Winston King Specifics |
|---|---|---|
| Employment term | At-will; amended/restated agreements (King: Jan 2020) | Amended & restated in Jan 2020 |
| Severance (no CIC, involuntary termination) | Typically 1x base salary; health benefits continuation for 12 months | Cash: $420,000; Health: $25,783; Total: $445,783 (as of 7/31/2025) |
| Change-in-control (no termination; awards not assumed) | Equity acceleration if awards not assumed/continued/substituted | Equity acceleration: $6,995,401 |
| Double-trigger CIC (involuntary termination within 2 months before to 12 months after CIC) | Cash severance equals 1x (salary + target bonus) for King; health coverage 12 months; immediate equity vesting | Cash: $735,000; Equity acceleration: $12,300,939; Health: $25,783; Total: $13,061,722 |
| 280G/4999 excise tax | Cutback to optimize net benefit; no tax gross-up | Cutback applies; no gross-up |
| Clawback policy | Revised Sept 2023; applies upon material restatement due to misconduct; covers Section 16 officers and certain senior leaders | Applicable |
Compensation Structure Analysis
- Cash/equity mix: FY2025 total $3.84M comprised of salary $415k, cash bonus $404.6k, and stock awards $3.01M, with minimal perquisites ($6.7k), reflecting equity-heavy pay and strong alignment with stock performance and ARR/operating income outcomes .
- Incentive metric emphasis increased toward financials in FY2025 (ARR + Adjusted non-GAAP operating income aggregate weighting moved from 80% to 85%) vs strategic scorecard at 15%, tightening pay-for-performance linkage .
- Equity shift: Program utilizes RSUs (time- and performance-vesting) rather than options; no NEO had outstanding options at FY2025 year-end, reducing reprice risk and aligning with long-term stock value creation .
Performance & Track Record (Company-Level Context)
| Pay vs Performance Measures | FY2021 | FY2022 | FY2023 | FY2024 | FY2025 |
|---|---|---|---|---|---|
| Company TSR (value of $100 initial investment) | 97.91 | 66.05 | 72.09 | 127.55 | 192.27 |
| Annual Recurring Revenue ($MM) | 575 | 683 | 761 | 864 | 1,041 |
| Net Income (Loss) ($000s) | (66,507) | (180,431) | (111,855) | (6,103) | 69,804 |
- FY2025 bonus determination reflected strong over-target performance on ARR and adjusted operating income, with Company Performance Factor at 130% .
Equity Ownership & Insider Selling Pressure Indicators
- Quarterly RSU vesting creates regular taxable events; company policy permits 10b5-1 plans but prohibits hedging and pledging, which mitigates misalignment risk while allowing orderly sales during windows .
- FY2025 vesting realized 20,553 shares ($3.81M) and a small option exercise (105 shares; $10.8k value), with no outstanding options at year-end—suggesting equity exposure primarily via RSUs, not leverage from options .
- Beneficial ownership of 17,400 shares (<1%) and compliance with ownership guidelines (≥1.5x salary for non-CEO officers) indicate baseline alignment, though ownership level is modest relative to total shares outstanding .
Governance and Committee Context
- Compensation Committee composition: Jeffrey Sloan (Chair), David Bauer, Paul Lavin, Rajani Ramanathan .
- Bonus plan governance permits objective formulas, with discretion retained for adjustments and individual goals; FY2025 kept target bonus opportunities unchanged for NEOs (King: 75%) .
Investment Implications
- Alignment: Equity-heavy compensation (time- and performance-vesting RSUs) tied to ARR and adjusted operating income, plus strategic scorecard, aligns incentives with cloud ARR growth and profitability improvements; FY2025 over-target results drove a 130% bonus payout .
- Retention risk: Multi-year cliff-vesting performance RSUs (FY2024–2026 and FY2025–2027 cycles) and quarterly time-based vesting support retention; double-trigger CIC acceleration and 1x cash multiple reduce termination risk but can create event-driven exposure if M&A emerges .
- Selling pressure: Regular quarterly RSU vesting and permitted 10b5-1 trading plans imply potential periodic insider sales; hedging/pledging prohibitions reduce negative signaling risk .
- Change-in-control economics: In a CIC-related involuntary termination, immediate equity acceleration plus cash ($13.06M total as modeled at 7/31/2025) could be materially dilutive but provides continuity incentives; 280G cutback avoids gross-up optics .
- Pay-for-performance: Increased weighting on financial metrics and strong FY2025 performance (ARR $1,032M vs $1,008M target; adjusted operating income $66M vs $25M target) reinforce execution confidence signals for the legal/administrative lead within the broader management team .