Casey O’Connor
Stitch FixAbout Casey O’Connor
Casey O’Connor is Chief Legal Officer and Corporate Secretary of Stitch Fix (SFIX), serving since November 2022; age 45 as of October 31, 2025. He joined Stitch Fix as its first in-house lawyer in 2016, previously served as Deputy General Counsel, and earlier held roles as in-house counsel at Yelp and as an attorney at Latham & Watkins; he holds a B.S. in Political Science (Santa Clara University) and a J.D. (Stanford Law School) . Company performance metrics used for executive pay include net revenue, Adjusted EBITDA, and active clients, with FY2024 actuals of $1,337.0 million revenue, $29.3 million Adjusted EBITDA, and 2,508k active clients; FY2025 actuals were $1,267.2 million revenue, $49.1 million Adjusted EBITDA, and 2,309k active clients . Proxy disclosures note stock price references used for severance valuations of $4.91 (FY2023), $4.09 (FY2024), and $4.49 (FY2025), indicating volatile equity performance during this period .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Stitch Fix | First in-house lawyer; Deputy General Counsel; Chief Legal Officer | Joined 2016; CLO since Nov 2022 | Built and led Legal and Indirect Procurement; institutionalized governance and insider controls |
| Yelp Inc. | In-house counsel | Not disclosed | Scaled legal support for a large consumer internet platform |
| Latham & Watkins LLP | Attorney | Not disclosed | Complex corporate/legal training supporting later in-house leadership |
External Roles
No public company board roles or committee positions disclosed for O’Connor in the proxy statements reviewed .
Fixed Compensation
| Metric | FY 2023 | FY 2024 | FY 2025 |
|---|---|---|---|
| Base Salary ($) | 479,326 | 500,480 | 500,000 |
| Target Bonus (% of Salary) | — | 50% | 50% |
| Actual Bonus Paid ($) (Non-Equity Incentive Plan) | 205,423 | 158,200 | 424,520 |
| All Other Compensation ($) | 11,400 | 11,538 | 13,800 |
Notes:
- Target bonus for non-CEO NEOs is 50% of base salary; CEO is 100% .
- Salaries reflect actual cash paid; base-level remained $500,000 across FY2024-FY2025 .
Performance Compensation
Annual Bonus Metrics and Outcomes
| Metric | Weight | FY 2024 Target | FY 2024 Actual | FY 2024 Payout | FY 2025 Target | FY 2025 Actual | FY 2025 Payout |
|---|---|---|---|---|---|---|---|
| Net Revenue ($mm) | 40% | 1,376 | 1,337.0 | 0% | 1,167 | 1,267.2 | 175.4% |
| Adjusted EBITDA ($mm) | 40% | 26 | 29.3 | 120.7% | 25 | 49.1 | 171.7% |
| Active Clients (000s) | 20% | 2,583 | 2,508 | 75.0% | 2,237 | 2,309 | 155.0% |
| Total Bonus Multiplier | — | — | — | 63.3% | — | — | 169.8% |
Notes:
- Metrics and weights: Net revenue (40%), Adjusted EBITDA (40%), Active Clients (20%) .
- FY2025 payout schedule allowed 50/100/150/200% tiers; realized 169.8% of target .
Equity Awards and Vesting
| Award Type | Grant Date | Shares/Units | Strike | Fair Value ($) | Vesting Terms |
|---|---|---|---|---|---|
| RSU | 12/8/2023 | 192,000 | — | 766,080 | 8.33% on 3/13/2024; then 8.33% quarterly for 11 quarters |
| Stock Options | 12/8/2023 | 384,000 | $3.99 | 959,155 | 8.33% on 3/13/2024; then 8.33% quarterly for 11 quarters; options expiring 12/07/2033 (3.99) and 12/14/2032 (3.80) |
| RSU | 10/28/2024 | 225,000 | — | 702,000 | 8.33% on 3/12/2025; then 8.33% quarterly for 11 quarters |
| PSU (Target) | 10/28/2024 | 225,000 | — | 337,503 | Metrics: Active Clients, net revenue, Adjusted EBITDA; 41.67% vests 12/17/2025; then 8.33% quarterly for 7 quarters upon achievement |
FY2025 stock awards table shows total stock award fair value for O’Connor of $1,650,393, which includes RSUs and PSUs valued at probable outcomes; maximum PSU scenario would increase total to $2,124,589 .
Equity Ownership & Alignment
Beneficial Ownership
| As-of Date | Class A Shares | % Ownership | Class B Shares | % Ownership |
|---|---|---|---|---|
| 10/18/2023 | 416,595 | <1% | — | — |
| 10/18/2024 | 806,914 | <1% | — | — |
| 10/17/2025 | 851,627 | <1% | — | — |
- Ownership guidelines (updated Oct 2025): other executive officers must hold the lesser of 2x base salary or 220,000 shares; company states all covered individuals are compliant or within the five-year compliance period . Hedging and pledging are prohibited under the Insider Trading Policy .
Outstanding and Unvested Awards (FY2025 Year-End)
| Category | Detail | Amount |
|---|---|---|
| Options (Exercisable) | 22.56 strike, exp 6/2/2029 | 4,869 |
| Options (Exercisable) | 18.34 strike, exp 9/26/2029 | 5,256 |
| Options (Exercisable/Unexercisable) | 3.80 strike, exp 12/14/2032 | 427,085 / 41,667 |
| Options (Exercisable/Unexercisable) | 3.99 strike, exp 12/07/2033 | 191,999 / 192,001 |
| Unvested RSUs (# / $) | Various legacy grants | 8,536 / $38,327 |
| Unvested RSUs (# / $) | Dec 2022 grant | 20,834 / $93,545 |
| Unvested RSUs (# / $) | Dec 2023 RSUs | 96,001 / $431,044 |
| Unvested RSUs (# / $) | Oct 2024 RSUs | 187,501 / $841,879 |
| Unearned PSUs (# / $) | Oct 2024 PSU target | 225,000 / $1,010,250 |
Market values above use $4.49 closing price on August 1, 2025, per proxy methodology .
Vesting and Insider Selling Pressure Indicators
- FY2025 vesting: O’Connor’s RSUs from October 2024 vest 8.33% quarterly from March 12, 2025 through 11 additional quarters; PSUs earned vest 41.67% on December 17, 2025, then 8.33% quarterly over seven periods, creating regular supply over the next two years .
- Exercises/vests realized: FY2025—31,248 options exercised ($48,159 realized) and 175,380 shares vested ($781,362 realized); FY2024—216,469 shares vested ($746,209 realized) .
Employment Terms
- Employment offer letter dated November 29, 2022; at-will; initial base salary $500,000; customary confidentiality and inventions covenants .
- Severance (non-CIC): Six months base salary and COBRA premium reimbursement (company-wide policy); estimated O’Connor amounts: severance $250,000, health care $4,999 (FY2025) .
- Change-in-control (double-trigger): 12 months base salary and COBRA premium reimbursement; full acceleration of unvested equity awards; no excise tax gross-ups .
- Potential payments (illustrative as of fiscal year-end):
- FY2024 CIC totals: severance $500,000; health care $11,690; equity acceleration—options $1,990,472; RSUs $1,076,701; total $3,578,863 .
- FY2025 CIC totals: severance $500,000; health care $9,997; equity acceleration—options $124,751; RSUs $2,415,045; total $3,049,793 .
Compensation Structure vs Performance
- Pay mix emphasizes performance: annual cash bonus tied 40/40/20 to revenue/Adjusted EBITDA/active clients; FY2025 payout at 169.8% reflects outperformance vs targets (notably Adjusted EBITDA $49.1mm vs $25mm target) .
- Equity shifted from options toward PSUs in FY2025 to heighten alignment with financial and client KPIs; O’Connor received a 50/50 RSU/PSU annual grant in October 2024 ($1.44mm grant value) .
- No perquisites or special benefits; standard 401(k) match only; hedging/pledging prohibited; clawback policy compliant with SEC/Nasdaq .
Say-on-Pay & Peer Group
Say-on-Pay Outcomes
| Year | Approval |
|---|---|
| 2023 | Over 93% approval |
| 2024 | Over 98% approval |
Compensation Peer Groups (Selection criteria: US-listed, similar industry, revenue 0.25–4.0x, market cap 0.25–5.0x)
- FY2024 peer set included: Abercrombie & Fitch, Chegg, Chico’s FAS, Designer Brands, Genesco, G-III, Guess?, Lands’ End, Rent the Runway, The Children’s Place, Torrid, Urban Outfitters, ContextLogic, Peloton, Warby Parker, GoPro, The RealReal, ThredUp, Revolve, Yelp .
- FY2025 peer adjustments added: a.k.a. Brands, BARK, Bumble, Funko, Groupon, Shutterstock, Honest Company; removed several due to size changes or acquisition .
- Committee uses peer data as a reference, not a strict percentile target .
Risk Indicators & Red Flags
- Late Section 16(a) filings: administrative delays for certain Form 4s, including O’Connor’s March 17, 2025 filing .
- Double-trigger CIC vesting prevents windfalls; no tax gross-ups; hedging/pledging prohibited; compensation risk controls deemed not likely to cause material adverse effects .
Expertise & Qualifications
- Legal leader with big-law and consumer tech in-house experience; academic credentials from Stanford Law (J.D.) and Santa Clara University (B.S.) .
- Corporate Secretary responsibilities, policy oversight, insider trading controls, and governance process stewardship .
Performance & Track Record
- FY2024→FY2025: Adjusted EBITDA improved from $29.3mm to $49.1mm; revenue moved from $1,337.0mm to $1,267.2mm; active clients from 2,508k to 2,309k; bonus payout rose from 63.3% to 169.8% of target .
- Equity vesting and exercises indicate regular, programmatic realization of awards without special perquisites; FY2025 exercises and vests reflect ongoing retention mechanics .
Compensation Committee & Advisors
- Independent advisors: Compensia supported FY2025 review; Meridian Compensation Partners retained in Spring 2025 for forward work; no conflicts of interest .
- Annual program review, risk assessment, and stock ownership policy enforcement documented .
Investment Implications
- Alignment: Strong pay-for-performance architecture (169.8% FY2025 payout) with PSUs tied to revenue, Adjusted EBITDA, and active clients increases sensitivity to operating execution; quarterly vesting cadence creates predictable insider supply but mitigates lump-sum selling risk .
- Retention: O’Connor’s unvested RSUs/PSUs and double-trigger CIC protections suggest moderate retention strength; severance without CIC is limited to six months of salary and COBRA, indicating balanced retention economics .
- Governance quality: Prohibitions on hedging/pledging, compliant clawback, and high say-on-pay support (98% in 2024) reduce governance risk and signal shareholder acceptance of the compensation program .
- Trading signals: Near-term PSU vest (41.67% on 12/17/2025) and ongoing RSU quarterly vests may modestly increase insider share supply; FY2025 option exercise activity was limited in value, suggesting equity remains primarily retention-focused rather than monetized aggressively .