Charles Ursini
About Charles Ursini
Charles “Chuck” Ursini is System1’s co-founder and currently serves as President & Chief Operating Officer (age 49). He has been a director since April 2024 with a term expiring in 2027, and previously served as the company’s first CEO from 2014–2019; he also served as a director of predecessor entities until January 2022. He holds a BBA in Finance & Accounting from Washington State University and an MBA from USC, and was co-recipient of EY’s National Entrepreneur of the Year for Media, Entertainment & Communications in 2018 with co-founder Michael Blend. The latest proxy emphasizes performance-linked equity via stock appreciation rights (SARs) tied to Adjusted EBITDA for 2024 executive awards; specific TSR or revenue/EBITDA growth metrics for his evaluation were not disclosed in the filing .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| System1 / OpenMail/S1 Holdco | Co-Founder; President & COO; Director; CEO (first CEO 2014–2019) | 2014–present; Director since 2024 | Co-founded and scaled performance marketing platform; operational leadership across monetization, BI, analytics, optimization |
| Leaf Group (Demand Media) | Executive Vice President, Platforms | Not disclosed | Led BI, Analytics, Monetization & Optimization, and Demand Studios; platform operations |
| Amazon | Analyst | Not disclosed | Data/analytics role supporting operational rigor |
| Morgan Stanley; UBS | Bond Trader | Not disclosed | Markets experience; trading discipline |
Fixed Compensation
| Metric | 2023 | 2024 |
|---|---|---|
| Base Salary ($) | — | — |
| Target Bonus (%) | Not disclosed | Not disclosed |
| Actual Bonus Paid ($) | — | — |
| All Other Compensation ($) | 19,823 | 21,678 |
| Notes | No cash comp in 2023/2024 | Company-paid health and welfare premiums |
Performance Compensation
| Award Type | Grant Date | Metric | Tranche Size (Units) | Fair Value ($) | Target | Actual | Payout | Vesting Terms |
|---|---|---|---|---|---|---|---|---|
| Stock Appreciation Rights (SARs) – Tranche 1 | 7/1/2024 | Adjusted EBITDA | 625,000 | 492,474 | Not disclosed | Not disclosed | Not disclosed | Performance vesting on Adjusted EBITDA; continued service required |
| SARs – Tranche 2 | 7/1/2024 | Adjusted EBITDA | 625,000 | 595,755 | Not disclosed | Not disclosed | Not disclosed | As above |
| SARs – Tranche 3 | 7/1/2024 | Adjusted EBITDA | 625,000 | 623,162 | Not disclosed | Not disclosed | Not disclosed | As above |
| SARs – Tranche 4 | 7/1/2024 | Adjusted EBITDA | 625,000 | 644,150 | Not disclosed | Not disclosed | Not disclosed | As above |
| Total SARs Granted (2024) | 7/1/2024 | Adjusted EBITDA | 2,500,000 | 2,355,541 | — | — | — | Performance-based vesting |
Notes:
- The 2024 awards for Ursini are SARs, not RSUs/stock options; vesting is contingent on Adjusted EBITDA performance per the 2024 SARs Plan .
- The company proposed amending the 2024 SARs Plan and repricing certain outstanding SARs, which may affect economics of awards granted in 2024 .
Equity Ownership & Alignment
| Category | Detail | Amount |
|---|---|---|
| Total Beneficial Class A Ownership | Shares of Class A Common Stock | 702,560 (reported as <1%) |
| Direct Class A Shares | Held directly by C. Ursini | 300,000 |
| Indirect – FGL Labs, LLC | Class A shares; Class B units (1:1 exchange to Class A) | 107,974 Class A; 294,766 Class B units |
| Excluded/Disclaimed Interests | OpenMail2 JV; Ursini Children’s Trust; CEE Holdings Trust | 468,113 Class A (OpenMail2, jointly controlled by Blend/Ursini/Kidambi) ; 86,773 Class A and 368,458 Class B units (Children’s Trust) ; 8,768,056 Class A, 3,415,262 Class B units, and 1,409,345 warrants (CEE Holdings Trust; Ursini disclaims beneficial interest except to any pecuniary interest) |
| Vested vs Unvested Awards | Unvested equity | 2,500,000 SARs unearned/unvested as of 12/31/2024 |
| Pledging/Hedging | Disclosure | No pledging or hedging by Ursini disclosed in the proxy’s ownership section |
Reference price used by the company to value unvested equity at year-end: $0.8983 per share on 12/31/2024 .
Employment Terms
- Contract status: Ursini did not have an employment agreement in 2024; therefore, severance and change-of-control specifics are not disclosed for him .
- Clawbacks/Tax gross-ups: Company states no tax gross-ups for named executives; clawback specifics not disclosed .
Board Governance
- Board service: Director since April 2024; term expires in 2027 .
- Committee roles: Not a member of the Audit, Compensation, or Nominating & Corporate Governance committees (executive, non-independent) .
- Independence: Not independent; majority of Board is independent (Horn, Kazerani, Caswell, Civantos, Kumar, Martire, Naidu) .
- Attendance: Board met 6 times in 2024; all members attended ≥75% of Board and committee meetings .
- Dual-role implications: CEO also serves as Chairman; the Board has no Lead Independent Director—independent directors meet in executive session without a presiding director . This elevates oversight considerations for management directors like Ursini.
Multi-Year Compensation Summary (Named Executive Table Extract – Ursini)
| Metric | 2023 | 2024 |
|---|---|---|
| Salary ($) | — | — |
| Bonus ($) | — | — |
| Stock Awards ($) | — | 2,355,541 |
| Non-Equity Incentive ($) | — | — |
| All Other Compensation ($) | 19,823 | 21,678 |
| Total ($) | 19,823 | 2,377,219 |
Related Party and Risk Indicators
- Related-party share purchase: The Blend Family Foundation purchased 4,500,000 Class A shares at $0.50 per share on 5/2/2025 ($2.25M proceeds to the company); not directly attributed to Ursini but relevant to insider capital support .
- Internal controls: Multiple material weaknesses were identified (accounting resources, control design for complex transactions, IT general controls, goodwill valuation, stock-based compensation, cash flow presentation), driving restatements in 2022 and persistent remediation needs—execution risk for management teams .
- Listing compliance and reverse split: Company received NYSE notice (Section 802.01C) on 1/6/2025 for sub-$1.00 price; Board seeks authorization for a 1-for-10 to 1-for-50 reverse split, with explicit acknowledgement of risks including potential reduced liquidity and market cap impact. Compensation/equity plans and SAR strike prices would be equitably adjusted post-split .
Investment Implications
- Pay-for-performance alignment: Ursini’s 2024 compensation is equity-only via SARs contingent on Adjusted EBITDA, aligning incentives with profitability and cash generation rather than top-line growth; absence of cash salary/bonus underscores equity emphasis .
- Potential governance red flag: Board proposal to amend and reprice certain SARs could dampen performance stringency and create management-friendly outcomes; monitor final terms and any impact on vesting thresholds and strike economics .
- Ownership alignment: Direct/indirect beneficial holdings plus interests connected to trusts and OpenMail2 indicate meaningful economic exposure, though some positions are disclaimed; large trust stakes (CEE Holdings Trust) can influence voting power even if beneficial interest is disclaimed .
- Execution risk: Ongoing internal control weaknesses and remediation efforts present operational risk to delivering performance metrics tied to compensation and to timely, accurate reporting .
- Trading signals/retention pressure: Performance-vested SARs may create future selling windows upon vesting; reverse split mechanics will adjust SAR economics but may increase volatility and perception risk. No employment agreement implies limited pre-defined severance economics, increasing flexibility but potentially elevating retention risk during strategic shifts .
Overall, Ursini’s incentives are closely tied to Adjusted EBITDA through SARs. Monitor: (1) SARs plan amendments/repricing details, (2) internal control remediation progress, and (3) capital actions tied to reverse split and NYSE compliance for potential impacts on equity award realizability and insider trading patterns .