Ryan Caswell

About Ryan Caswell

Ryan Caswell (age 42) is an independent Class III director of System1, Inc. (SST) and has served on the Board since April 2024 . He is President of Cannae Holdings, Inc. (NYSE: CNNE) since February 2023 (formerly SVP, Corporate Finance, Sept 2020–Feb 2023) and previously was MD & Partner at Trasimene Capital Management; earlier he was a Managing Director in investment banking at BofA Securities; he holds a B.A. in economics from Stanford University . He was nominated as one of Cannae Holdings’ two permitted designees under SST’s Shareholders Agreement and is deemed independent by SST’s Board under NYSE and SEC rules .

Past Roles

External Roles

Board Governance

• Independence: The Board determined Mr. Caswell is an independent director under NYSE and SEC rules .
• Committee assignments: No current service on Audit, Compensation, or Nominating & Corporate Governance committees per 2024–2025 committee matrix .
• Board structure: No Lead Independent Director; independent directors hold executive sessions without a presiding director .
• Attendance: In 2024, each director attended at least 75% of Board and applicable committee meetings; Board met 6x; Audit 10x; Compensation 4x; Nominating & Governance 5x .

Fixed Compensation (Director)

• 2024 compensation for non-employee directors was delivered as restricted stock units (RSUs); no cash retainers or meeting fees are disclosed for 2024 (expense reimbursement provided) .
• Special Committee cash fees in Jan 2024 were paid to other directors (Kazerani, Martire, Kumar) for 2023 service; no such payment is disclosed for Caswell .

Performance Compensation (Director Equity)

• Program design: Annual RSU grant of $180,000 grant-date fair value to each eligible director, plus RSU increments for committee roles (Audit Chair $50k; Audit member $20k; Comp Chair $20k; Comp member $10k; N&G Chair $15k; N&G member $10k); vests 25% on each of three quarterly anniversaries and remaining 25% by the next annual meeting/one-year anniversary, subject to service .
• 2024 awards: Caswell received stock awards with grant-date fair value of $214,200; his unvested RSUs outstanding at 12/31/2024 totaled 60,000 units .
• 2024 cohort vesting cadence: for 2024 director RSUs, 25% commenced vesting on September 15, 2024 with quarterly vesting thereafter, subject to service .

Note: Director RSUs are service-based; no performance metrics apply to director equity awards .

Other Directorships & Interlocks

• Nomination rights: Caswell was nominated as one of two Cannae Holdings designees to SST’s Board pursuant to the Shareholders Agreement . Another director, Frank R. Martire, Jr., was also nominated as a Cannae designee .
• Significant holder linkage: Cannae Holdings, LLC beneficially owned 27,012,794 Class A shares (35.9% ownership; 28.8% voting power) as of April 15, 2025 .
• Current/prior outside boards: AmeriLife, CorroHealth, FC Lorient, TripleTree Holdings, WineDirect (public/private status not specified) .

Expertise & Qualifications

• Finance and investing: Senior roles at Cannae and Trasimene; prior MD, BofA Securities (IB) .
• Industry exposure: Leads sourcing/execution/management of Cannae’s investments; board experience across multiple portfolio companies .
• Education: B.A. in economics, Stanford University .
• Board rationale: SST cites his “extensive leadership experience at public companies” as qualification .

Equity Ownership

Additional notes:

• Pledging/hedging: No pledging or hedging disclosures specific to Caswell in the proxy; SST has an Insider Trading Policy on file .
• Section 16(a) compliance: Company notes timely-filing issues in Oct 2024 related to net settlement for certain officers, not referencing Caswell .

Governance Assessment

Strengths

• Independent director with deep capital allocation and transaction experience (Cannae/Trasimene/BofA) aligned with SST’s needs; Board cited public company leadership experience as a qualification .
• Attendance: Board reports all directors met at least 75% attendance thresholds in 2024, supporting baseline engagement .
• Equity-aligned director pay structure (time-based RSUs; no cash retainers disclosed for 2024), reinforcing shareholder alignment through stock .

Watch items and potential conflicts

• RED FLAG: Significant shareholder affiliation. Caswell serves as President of Cannae, which owned 35.9% of Class A shares and holds nomination rights; two Cannae designees sit on SST’s Board—while the Board deems him independent, investors should monitor potential conflicts in transactions and strategic decisions .
• Company-level control and audit changes: Mid‑2024 auditor change from PwC to Deloitte, and disclosure of multiple material weaknesses (including control environment, complex transactions, ITGCs) tied to prior restatements; though not specific to Caswell, these are governance risk factors during his tenure .
• Capital structure and compensation optics: 2025 proposals include a reverse stock split to address NYSE price deficiency and an amendment with repricing of certain SARs—signals to monitor for shareholder alignment and governance robustness; again, not director-specific, but relevant to overall board oversight .

Director Compensation (Detail)

Vesting and program structure:

• Annual director RSU grant $180,000; committee RSU add‑ons based on roles; quarterly vesting with final tranche by one-year or next annual meeting, subject to service .
• 2024 grants for non-employee directors began vesting 25% on September 15, 2024 with quarterly vest thereafter, subject to service .

Related-Party Transactions (Caswell-specific)

• The 2025 proxy lists related‑party transactions (e.g., sale of Protected.net to Just Develop It; 2025 private placement with The Blend Family Foundation) but does not disclose any transaction involving Caswell or Cannae in 2024–2025 beyond nomination rights .

Say‑on‑Pay and Shareholder Feedback (Company context)

• Not a voting item in 2025 proxy; stockholder engagement and governance documents referenced by the company .

Compensation Committee Analysis (Context)

• Compensation Committee membership excludes Caswell; 2024 meetings: 4; charter posted; composition independent .
• No compensation committee interlocks reported for SST’s executive officers in 2024 .

Summary Implications for Investors

• Caswell brings strong transaction and capital allocation experience with a meaningful investor perspective; independence is affirmed, but his Cannae executive role and Cannae’s large ownership and nomination rights warrant ongoing monitoring of potential conflicts (especially in capital raises, M&A, and incentive plan modifications) .
• Equity-only director pay supports alignment, though overall governance risk context includes recent control weaknesses, auditor change, and price‑deficiency remediation (reverse split), areas where board oversight quality, including by independent directors, is critical to investor confidence .