Gary Steele
UPWORKAbout Gary Steele
Gary Steele (age 62) is an independent director at Upwork Inc. (UPWK) and serves as Chair of the Compensation Committee. He joined the Upwork board in 2018 and brings four decades of leadership across cybersecurity and enterprise software, including CEO roles at Splunk (2022–2024) and Proofpoint (2002–2022); he will serve as CEO of Shield AI starting May 2025. He holds a B.S. in Computer Science from Washington State University .
Past Roles
| Organization | Role | Tenure | Committees/Impact |
|---|---|---|---|
| Splunk Inc. | President & CEO | 2022–2024 | Led company to 58% revenue growth to $4.2B over two years |
| Cisco Systems | President, Go-to-Market; EVP & GM, Splunk | 2024–May 2025 | Senior go-to-market leadership for acquired Splunk |
| Proofpoint Inc. | CEO; Board Chair (2018–2021) | 2002–2022 | Founding CEO; scaled to leading security-as-a-service provider |
| Portera Systems | CEO | Pre-2002 | Enterprise software leadership |
| Sybase | VP & GM, Middleware & Data Warehousing | Prior | Enterprise software product group leadership |
| Sun Microsystems; Hewlett-Packard | Market Development Manager; Product Manager/Software Engineer | Prior | Early career roles |
External Roles
| Organization | Role | Tenure | Notes |
|---|---|---|---|
| Shield AI Inc. | CEO | Starts May 2025 | Defense technology company |
| Splunk Inc. | Director | 2022–2024 | Prior public board |
| Proofpoint Inc. | Director; Chair (2018–2021) | 2002–2022 | Prior public board |
| Aspen Digital U.S. Cybersecurity Group | Co-Chair | Current | Policy leadership in cybersecurity |
| Modernizing Medicine, Inc. | Director | Current | Private medical software company |
| Synack, Inc. | Director | Current | Cybersecurity company |
Board Governance
- Independence: Upwork’s board determined Gary Steele is independent under Nasdaq and SEC rules; all members of the Compensation, Audit, and Nominating & Governance committees are independent .
- Committee assignments: Chair, Compensation Committee (members: Steele [Chair], Gretsch, Vazquez‑Ubarri) . Board refreshed committee leadership in April 2024 when Steele succeeded Gretsch as comp chair .
- Attendance: In 2024, the Board met 7 times; Audit 6; Compensation 6; Nominating & Governance 2. Each director attended at least 75% of meetings of the Board and applicable committees .
- Stockholder engagement: Fall 2024 engagement included participation by Compensation Chair Steele; Upwork engaged holders of ~49% of outstanding shares .
Fixed Compensation
| Component | Amount/Structure | Vest/Payment Terms |
|---|---|---|
| Annual Award (director may elect cash or RSUs) | $185,000 | Vests on earlier of 1 year or immediately prior to next AGM; accelerates on Corporate Transaction |
| General Board Service Fee (elect cash or RSUs) | $55,000 per year | Cash quarterly in arrears; RSUs vest quarterly; accelerates on Corporate Transaction |
| Compensation Committee Chair Fee | $15,000 per year (cash only) | Paid quarterly in arrears; prorated for partial quarters |
| Committee Member Fee – Compensation | $7,500 per year (cash only) | Paid quarterly in arrears; prorated |
| Initial RSU Award (new directors) | $400,000 grant value | 3-year annual vesting; accelerates on Corporate Transaction |
2024 non‑employee director compensation received by Gary Steele:
| Year | Fees Earned/Paid in Cash ($) | Stock Awards ($) | Total ($) |
|---|---|---|---|
| 2024 | $12,754 | $226,664 | $239,418 |
Notes:
- As of Dec 31, 2024, Steele held 18,722 unvested RSUs (Annual Award + Board Service Fee RSU) and a fully vested stock option to purchase 150,527 shares (expires Aug 19, 2028) .
Performance Compensation
As Compensation Committee Chair, Steele oversees executive pay designs that emphasize profitable growth. 2024 program changes added profitability metrics and multi‑year PSUs.
| Plan Element | Metric(s) | Weight/Definition | Performance Period |
|---|---|---|---|
| Annual Bonus (NEOs) | Revenue; Adjusted EBITDA | 50% Revenue; 50% Adjusted EBITDA; GSV modifier up to ±20%; individual performance adj. up to ±20% (not for CEO) | 1-year (FY2024) |
| PSUs (NEOs) | Combined Financial Target Percentage | Sum of YoY revenue growth % + adjusted EBITDA margin; up to 50% vesting each of 2025 and 2026 based on performance | Multi‑year (2025–2026) |
| RSUs (NEOs) | Service-based | Quarterly vesting over 4 years | 4 years |
Other Directorships & Interlocks
| Company | Type | Role | Overlap/Interlock Risk Notes |
|---|---|---|---|
| Splunk Inc. | Public | Director (2022–2024) | Acquired by Cisco; Steele held Cisco GTM role in 2024–2025 |
| Proofpoint Inc. | Public | Director; Chair (2018–2021) | Acquired by Thoma Bravo in 2021 |
| Modernizing Medicine; Synack | Private | Director | No related-party transactions disclosed at Upwork |
- Compensation Committee Interlocks: Upwork disclosed no Item 404 relationships for compensation committee members in 2024; no reciprocal interlocks with other issuers’ committees .
Expertise & Qualifications
- Cybersecurity and technology leadership; founding Proofpoint CEO; senior GTM roles; recognized for scaling enterprise operations .
- Strategic transformation: Led Splunk to 58% revenue growth to $4.2B over two years .
- Education: B.S. Computer Science, Washington State University .
Equity Ownership
| Date (as of) | Shares Beneficially Owned | Percentage of Shares Outstanding |
|---|---|---|
| Mar 31, 2020 | 161,382 | <1% |
| Mar 31, 2021 | 173,357 | <1% |
| Mar 31, 2022 | 180,552 | <1% |
| Mar 31, 2023 | 187,222 | <1% |
| Mar 31, 2024 | 188,171 | <1% |
| Mar 31, 2025 | 215,895 | <1% |
Breakdown (selected disclosures):
- Options: 150,527 shares, fully vested and exercisable as of Dec 31, 2024; expiration Aug 19, 2028 .
- Unvested RSUs: 18,722 as of Dec 31, 2024 .
- Ownership guidelines: Non‑employee directors required to hold 3x annual cash retainer; compliance evaluated annually. As of Dec 31, 2024, all NEOs and non‑employee directors were either compliant or within 5‑year ramp period .
- Insider Trading Policy: Prohibits hedging and short sales; pledging only with approval based on financial capacity .
Governance Assessment
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Strengths:
- Independent director and Chair of Compensation Committee; committee members all independent .
- Active stockholder engagement participation (fall 2024), signaling responsiveness to investor feedback on compensation and governance .
- Clear director pay structure with mix of cash and equity; annual award election promotes ownership alignment; stock ownership guidelines enforce retention until compliance .
- No related‑party transactions disclosed beyond standard indemnification agreements since Jan 1, 2024 .
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Considerations:
- Time commitments: Concurrent high‑intensity executive role (Shield AI CEO starting May 2025) may elevate time‑management risk; however, 2024 attendance met the ≥75% threshold, and committee leadership refresh occurred in April 2024 .
- Options outstanding: Legacy director option grant remains outstanding; while not inherently problematic, ongoing equity exposure should be monitored against ownership guideline compliance and trading policy constraints .
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Signals affecting investor confidence:
- Compensation committee design changes in 2024 strengthened pay‑for‑performance via profitability metrics and multi‑year PSU structure—aligned with durable, profitable growth messaging and investor feedback channels that included direct director participation (Steele) .
RED FLAGS: None disclosed regarding related‑party transactions, hedging/pledging violations, committee interlocks, or attendance shortfalls in 2024 .