Chris Riley

About Chris Riley

Chris Riley serves as General Counsel and Secretary of PLBY, a role he has held since February 2021 after serving as Playboy’s General Counsel and Secretary since January 2019. He previously held senior in-house legal roles at Ticketmaster (leading the spin-off from IAC and merger with Live Nation), was General Counsel & Secretary at Machinima (through its sale to Warner Bros), and practiced at Bingham McCutchen, Gibson Dunn & Crutcher, and Sidley Austin. Riley holds a J.D. from UC Berkeley School of Law and a B.A. in philosophy from the University of Michigan . PLBY’s insider trading policy prohibits hedging and pledging of company stock without pre-approval, and as of the record date no pledges were approved for officers or directors . In 2024, PLBY did not award performance-based cash bonuses to executives; Riley’s compensation was primarily salary, transaction/retention bonuses, and RSUs, with PSUs tied to stock-price milestones from an initial 2021 grant later amended in October 2023 .

Past Roles

External Roles

Fixed Compensation

Notes:

• 2024 includes $50,000 in non‑equity incentive plan compensation and a cash retention bonus paid in Jan 2025; 2023 includes a $150,000 retention bonus (paid Sep 2023) and a further $150,000 paid Apr 2024 per its terms .

Performance Compensation

Incentive Structure and Outcomes

Retention Agreements (Structure for Future RSUs)

Equity Ownership & Alignment

Beneficial Ownership (Record Date: April 21, 2025)

Outstanding Awards (Chris Riley at 12/31/2024)

In-the-Money Option Value (as of 12/31/2024 close $1.46)

Alignment Policies

• Hedging, pledging, margin, and derivative transactions are prohibited; pledges require written pre‑approval and as of the Record Date no pledges by officers or directors were approved .
• Director stock ownership policy requires retaining 25% of awarded shares net of taxes; no explicit executive ownership multiple disclosed .

Employment Terms

Core Terms

• Base salary $400,000; target annual bonus 80% of base .
• Annual equity award target grant-date fair value $700,000 beginning 2022 (may include performance-based grants); special Initial PSUs (~0.45% of fully diluted shares) and Initial Options (~0.18% of fully diluted shares), with potential RSU conversion if grant-date FMV > Feb 10, 2021 FMV .
• PSUs originally tied to stock VWAP milestones ($20/$30/$40/$50); amendment on Oct 9, 2023 eliminated final milestone and set remaining vesting at 6/30/2024 and 6/30/2025 .
• Company-paid life insurance ($10M) and disability insurance (≥$2.5M annualized benefit) .

Severance and Change-of-Control

• If terminated without cause or resigns for good reason: cash severance equal to base salary + target bonus over 12 months; pro‑rated bonus; up to 18 months of COBRA; accelerated vesting of 100% of non‑performance annual equity awards; continued vesting for certain performance awards based on actual performance .
• If such termination occurs within 24 months following a change in control: 1.25× base + target bonus over 15 months; 100% of then‑outstanding Initial PSUs vest; Initial Options immediately vest and become exercisable .
• Restrictive covenants: non‑solicitation of employees for 12 months post‑termination; confidentiality and invention assignment provisions .

Estimated Potential Payments (Assuming Trigger on 12/31/2024; stock price $1.46)

Compensation Structure Analysis

• Mix shift toward time-based RSUs in 2024; no stock options granted in 2024, and the Compensation Committee determined not to provide performance-based cash bonuses for 2023 or 2024 .
• Initial PSUs retained stock-price performance linkage but were amended in Oct 2023 to remove the final VWAP milestone, accelerating vesting over 2024/2025—this modification reduces performance contingency for remaining tranches .
• Clawback policy adopted Nov 20, 2023 complies with SEC/Nasdaq rules; mandatory recovery of incentive-based compensation upon any restatement; no recoveries required for 2024 .

Equity Ownership & Alignment (Skin-in-the-Game)

• Beneficial ownership of 400,575 shares (<1%); includes 199,385 options exercisable within 60 days and 15,895 RSUs settle within 60 days .
• 2024 vesting: 192,820 RSUs vested; no options exercised—indicates realized equity income without option selling pressure in 2024 .
• Anti-hedging/pledging policy and absence of approved pledges at Record Date mitigate alignment concerns related to collateralization and hedging .

Investment Implications

• Retention risk appears mitigated near term by layered one‑year RSU cliffs (2024 grant vests 6/30/2025; 2025 grant vests 4/30/2026; intended 2026 grant vests 4/30/2027), with limited cash conversion features—supporting continuity of leadership through key strategic periods .
• Pay-for-performance linkage is mixed: PSUs historically tied to stock-price milestones (75% achieved), but the 2023 amendment accelerated remaining vesting independent of hurdle attainment; 2024 compensation relied on transaction/retention bonuses and time-based RSUs rather than annual performance targets .
• Change-of-control economics (1.25× cash multiple; full acceleration of Initial PSUs and options) plus RSU acceleration could create meaningful executive monetization in strategic transactions, influencing negotiations and potential insider selling windows post‑deal .
• Ownership level is <1% with some ITM options ($0.66 strike) and significant unvested RSUs; anti‑hedging/pledging provisions strengthen alignment, but modest direct ownership relative to total shares suggests incentive alignment is primarily via unvested equity and options rather than substantial outright holdings .