Mike Rosenbaum
Guidewire SoftwareAbout Mike Rosenbaum
Mike Rosenbaum, 54, is Chief Executive Officer of Guidewire Software and a director since August 2019. He previously served as EVP, Product at Salesforce (2016–2019), held multiple leadership posts at Salesforce (2005–2016), worked at Siebel Systems (2002–2005), and served as a U.S. Navy submarine officer (1994–1999). He holds a B.S. in Systems Engineering from the U.S. Naval Academy and an MBA from UC Berkeley Haas . Under his tenure, Guidewire’s Annual Recurring Revenue (ARR) reached $1,041 million in FY2025 vs $864 million in FY2024, while net income turned positive to $69.8 million in FY2025; a hypothetical $100 invested on July 31, 2020 would be worth $192.27 by FY2025, reflecting improved TSR performance . The executive bonus and PSU programs emphasize ARR and Adjusted Non-GAAP Operating Income, which reached $66.2 million in FY2025 for compensation measurement purposes .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Salesforce, Inc. | EVP, Product (vision, strategy, product mgmt, customer success) | 2016–2019 | Led product strategy and adoption for a leading cloud software platform |
| Salesforce, Inc. | Multiple leadership positions | 2005–2016 | Drove key product achievements across the portfolio |
| Siebel Systems | Technology and marketing roles | 2002–2005 | Enterprise software operating experience ahead of CRM cloud shift |
| U.S. Navy | Submarine Officer | 1994–1999 | Operational leadership, systems rigor |
External Roles
| Organization | Role | Years | Notes |
|---|---|---|---|
| DocuSign, Inc. | Director | Since Sep 2025 | Public company directorship alongside CEO role at Guidewire |
Fixed Compensation
| Component | FY2023 | FY2024 | FY2025 |
|---|---|---|---|
| Base Salary ($) | 750,000 | 750,000 | 750,000 |
| Target Bonus (% of Salary) | 100% | 100% | 100% |
Notes:
- Executive ownership guideline: CEO must hold ≥4x base salary; all NEOs employed ≥3 years, including CEO, satisfied guidelines as of July 31, 2025 .
- No perquisites beyond standard broad-based benefits; 401(k) match up to $6,000; no non-qualified deferred comp; no pension .
Performance Compensation
Annual Bonus Plan (FY2025)
| Metric | Weight | Threshold | Target | Maximum | Actual | Payout Range | FY25 Outcome |
|---|---|---|---|---|---|---|---|
| ARR (constant currency) | 51% | $958M | $1,008M | $1,058M | $1,032M | 50%–150% | Above target |
| Adjusted Non-GAAP Operating Income (Loss) | 34% | ($5M) | $25M | $55M | $66M | 50%–150% | Above max |
| Strategic Scorecard (VPMOM) | 15% | 50% | 100% | 150% | 100% | 50%–150% | At target |
| Company Performance Factor | 130% | ||||||
| CEO Cash Bonus ($) | 975,000 |
Definition note: FY2025 Adjusted Non-GAAP Operating Income used for compensation was $66.2M; reconciliation from GAAP operating income is provided in the proxy .
Long-Term Equity (Structure and FY2025 Actions)
- Time-Vesting RSUs: typically vest quarterly over 4 years; CEO granted 36,533 RSUs on 9/11/2024 (grant date fair value $6,140,102) . Vesting requires continued employment .
- Performance-Vesting RSUs (FY2025 grant): three-year program with cliff vest on 9/15/2027, measured annually on ARR (60%) and Adjusted Non-GAAP Operating Income (40%), 50%–150% payout each year averaged over 3 years; CEO target 36,533 units (grant date fair value $6,140,101) . FY2025 attainment factor for the PSU program was 135% (ARR above target; operating income above max) .
- Stock-price “PSU Kicker” modifier (CEO and President only): if Final Performance Factor >100%, additional 25%–100% of target shares may vest based on 3-year CAGR of stock price. FY2025 PSU price hurdles: $232.01 (+15% CAGR, +25% shares), $263.61 (+20% CAGR, +50%), $297.95 (+25% CAGR, +100%) measured 9/11/2024–9/11/2027; subject to continued service, with sale-event truncation mechanics as disclosed .
- Legacy FY2023 PSUs (second tranche): paid out at 120% based on FY2025 ARR of $1,040M; CEO received 35,742 shares .
| CEO Equity Grants (FY2025) | Grant Date | Type | Target/Qty | Grant-Date Fair Value ($) |
|---|---|---|---|---|
| Annual PSU | 9/11/2024 | Performance RSUs | 36,533 | 6,140,101 |
| Annual RSU | 9/11/2024 | Time RSUs | 36,533 | 6,140,102 |
Equity Ownership & Alignment
- Beneficial ownership: 171,707 shares (<1% of outstanding) as of Oct 20, 2025; includes 11,074 RSUs scheduled to vest within 60 days .
- Outstanding unvested awards at FY2025 year-end include, among others:
- Time RSUs: 29,684 (grant 9/11/2024), 29,335 (9/13/2023), 39,713 (9/15/2022), 18,615 (9/15/2022), 2,203 (9/15/2021) with stated market values at $226.22 per share .
- Performance RSUs: 36,533 (FY2025 PSU target), 52,150 (FY2024 PSU target), with market value references and program terms as disclosed .
- Options: none outstanding at FY2025 year-end; no option exercises by CEO in FY2025 .
- Vesting/selling pressure indicators: CEO had 80,204 shares vest in FY2025 (value realized on vesting $14.9M); company policy permits 10b5-1 plans; trading during blackout periods is restricted .
- Hedging/pledging: prohibited for directors and officers under insider trading policy .
- Ownership guidelines (executives): CEO ≥4x salary; status: in compliance (for executives ≥3 years) .
Employment Terms
| Scenario | Cash Severance | Equity | Health Benefits | Notes |
|---|---|---|---|---|
| Termination without Cause (non-CIC) | 1x base + 1x target bonus (CEO) = $1,500,000 | — | 12 months COBRA ($26,055) | Release required; at-will employment |
| Change in Control (no termination; awards not assumed) | — | Equity acceleration value $28,432,687 (as of 7/31/2025) | — | Based on $226.22 stock price; tranche-specific treatment disclosed |
| Involuntary Termination in Connection with CIC (double trigger) | 1.5x (salary + target bonus) = $2,250,000, lump sum | Full acceleration; equity value $65,353,827 (as of 7/31/2025) | 18 months COBRA ($39,082) | Reduction if 280G to maximize after-tax proceeds; no excise tax gross-up |
- Clawbacks: SEC-compliant mandatory recovery policy for incentive-based comp upon restatement; supplemental discretionary clawback for reputational harm and broader awards; applies to cash and equity; effective Oct 2, 2023 (prior comp under earlier policy) .
- Non-compete/non-solicit: not specifically disclosed in proxy; agreements amended from time to time (CEO agreement Aug 2019; amended Nov 2020) .
Board Governance and Director Service
- Director since 2019; CEO is the sole non-independent director; 8 of 9 directors are independent as of the proxy date .
- Chair/CEO roles separated; independent Chair (Michael C. Keller) leads executive sessions and oversight; enhances governance and mitigates CEO-Chair dual-role concerns .
- Committees (Audit, Compensation, Nominating & Governance, Risk, Business Opportunities) comprised entirely of independent directors; CEO is not on committees .
- Board meetings and attendance: Board met 5 times in FY2025; each director attended ≥75% of applicable meetings .
- As an employee-director, Rosenbaum receives no director fees .
Multi-Year CEO Compensation (Summary)
| Metric | FY2023 | FY2024 | FY2025 |
|---|---|---|---|
| Salary ($) | 750,000 | 750,000 | 750,000 |
| Stock Awards ($) | 7,851,062 | 9,594,557 | 12,280,203 |
| Non-Equity Incentive Plan Compensation ($) | 943,500 | 915,000 | 975,000 |
| All Other Compensation ($) | 5,930 | 5,881 | 6,858 |
| Total ($) | 9,550,492 | 11,265,438 | 14,012,061 |
Compensation Structure Analysis
- Strong equity tilt: majority of CEO pay in performance- and time-based RSUs; multi-year PSUs tied to ARR and operating profitability with 50%–150% payout and cliff vesting, plus price-based PSU kicker for CEO/President linking upside to sustained stock price CAGR .
- Annual bonus plan increased weighting to financial metrics (ARR and Adjusted Non-GAAP Operating Income) to 85% from 80%, reducing discretion via strategic scorecard to 15% .
- No options granted to NEOs in FY2025; no repricing actions disclosed .
- Say-on-pay support: >98% approval at 2024 annual meeting; program largely maintained, with ongoing shareholder outreach .
Compensation Peer Group and Committee Practices
- FY2025 peer group included 16 U.S. software companies; in March 2025 for FY2026, removed Splunk and ANSYS (acquisitions), added Procore, PTC, Samsara; revenue/mcap bands ~1/3x–3x Guidewire .
- Semler Brossy is the independent compensation advisor; no conflicts identified .
- Committee composition: Compensation Committee chaired by Jeffrey Sloan; members David S. Bauer, Paul Lavin, Rajani Ramanathan .
Risk Indicators and Red Flags
- Hedging/pledging prohibited; robust insider trading controls and blackout periods; allowance for pre-cleared Rule 10b5-1 plans .
- Dual role considerations attenuated by independent Chair, fully independent committees, and regular executive sessions .
- Clawback policies in place (mandatory and supplemental); no excise tax gross-ups under 280G/4999 .
- Related-party transactions: none involving Rosenbaum disclosed; only noted item pertains to a director’s family member with non-material compensation .
Performance & Track Record Indicators
| Measure | FY2021 | FY2022 | FY2023 | FY2024 | FY2025 |
|---|---|---|---|---|---|
| ARR ($M) | 575 | 683 | 761 | 864 | 1,041 |
| Net Income (Loss) ($000s) | (66,507) | (180,431) | (111,855) | (6,103) | 69,804 |
| TSR (Value of $100) | 97.91 | 66.05 | 72.09 | 127.55 | 192.27 |
Investment Implications
- Pay-for-performance alignment is strong: annual and long-term incentives clearly anchored to ARR growth and operating profitability, with supplemental stock-price CAGR requirements for the CEO’s PSU kicker—favoring durable value creation rather than single-period outcomes .
- Retention and supply dynamics: substantial unvested equity (including FY2024/2025 PSUs with cliff vesting in 2026/2027) lowers near-term departure risk and may create periodic vesting-related supply; insider policy restricts trading windows and bans pledging/hedging .
- Change-in-control sensitivity: large double-trigger equity acceleration ($65.35M value as of 7/31/2025) and 1.5x cash multiple could influence negotiating posture in strategic scenarios; no tax gross-up mitigates shareholder concerns .
- Governance: separation of Chair/CEO and independent committees reduce dual-role risks; strong say-on-pay results (>98%) and active outreach indicate investor alignment with the compensation framework .