Sydney Schaub
Opendoor TechnologiesAbout Sydney Schaub
Sydney Schaub, age 45, serves as Opendoor Technologies’ Chief Legal Officer (and Corporate Secretary) since September 2022, with prior leadership roles at Gemini Trust (CLO/GC), Rent the Runway (GC), and Square (Associate GC). She holds a J.D. from Harvard Law School and M.A./B.A. in English Literature from Stanford University . During 2024, Opendoor sold ~13,500 homes, acquired ~14,600 homes, and generated $5.2B in revenue while reducing fixed operating expenses by $50M; Adjusted Net Income (ANI) improved to a loss of $(258.0)M from $(778.0)M in 2023 . Over 2024, Opendoor’s total shareholder return (TSR) implied a $5 value on a $100 initial investment versus $117 for the peer group, underscoring stock underperformance despite operational progress .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Gemini Trust Company, LLC | Chief Legal Officer, General Counsel & Corporate Secretary | Oct 2018 – Aug 2022 | Led legal and corporate governance at a regulated digital asset exchange/custodian . |
| Rent the Runway, Inc. | General Counsel & Corporate Secretary | May 2017 – Oct 2018 | Oversaw legal/compliance at a consumer fashion-technology company . |
| Square, Inc. | Associate General Counsel | Jan 2016 – Apr 2017 | Supported product/fintech legal matters at a public technology firm . |
External Roles
| Organization | Role | Years | Note |
|---|---|---|---|
| Harvard Law School | J.D. | — | Legal education . |
| Stanford University | M.A. and B.A. (English Literature) | — | Graduate and undergraduate education . |
Fixed Compensation
| Component | FY2023 | FY2024 | Notes |
|---|---|---|---|
| Base Salary Rate | $350,000 | $425,000 | Base rate increased in Feb 2024 . |
| Actual Salary Paid | $350,000 | $409,375 | Reflects partial-year rate changes . |
| Target Annual Bonus % (of base) | 50% | 50% | Formulaic plan based on corporate ANI . |
Performance Compensation
| Plan/Grant | Metric | Weighting | Target | Actual | Payout/Outcome | Vesting |
|---|---|---|---|---|---|---|
| FY2024 Annual Cash Bonus | ANI | 100% | Target ANI: $(180.2)M; Threshold: $(225.3)M; Max: $(135.2)M | ANI: $(258.0)M | 0% (below threshold) | N/A |
| 2024 PRSUs (Schaub: Target 119,047 units) | Homes Acquired | 50% | Threshold: 15,547; Target: 19,434; Max: 23,321 | 14,684 | 0% for this metric (below threshold) | One-third on 3/15/2025; remaining two-thirds over 8 quarterly installments |
| 2024 PRSUs (Schaub: Target 119,047 units) | Homes Sold | 50% | Threshold: 12,918; Target: 16,147; Max: 19,376 | 13,593 | 42% aggregate PRSUs earned across both metrics | One-third on 3/15/2025; remaining two-thirds over 8 quarterly installments |
| 2024 TRSUs (Schaub: 357,142 units) | Time-Based | — | — | — | N/A | Vests in substantially equal quarterly installments over 3 years beginning 4/15/2024 |
Equity Ownership & Alignment
| Item | Detail |
|---|---|
| Beneficial Ownership | 802,835 shares, including 583,584 directly owned and 219,251 RSUs vesting within 60 days of June 2, 2025; less than 1% of outstanding . |
| Ownership Guidelines | Executives must hold the lesser of 3x base salary or 225,000 vested shares; executives (other than the new CFO) met levels by 12/31/2024 . |
| Hedging/Pledging | Hedging, short sales, options/derivatives prohibited; margin accounts prohibited; pledging requires prior CLO consent . |
| Equity Mix | 2024: $1.8M target equity value for Schaub split ~75% TRSUs / 25% PRSUs; converted at $3.78 (40-day avg) → 357,142 TRSUs and 119,047 PRSUs . |
Employment Terms
- Employment Status: At-will; no fixed term .
- Non-Compete / Non-Solicit: Standard Confidential Information and Invention Assignment Agreement; non-solicit of customers during employment and employees during employment and 12 months post-employment; no non-compete where prohibited by law .
- Severance (Executive Severance Plan):
- Non-Change-in-Control: For NEOs other than CEO, cash severance = 0.5x base salary (paid over 6 months); COBRA up to 12 months; acceleration of time-based equity that would vest within 6 months (12 months if employed <12 months) .
- Change-in-Control (Double Trigger): For NEOs other than CEO, cash severance = 1.0x base salary (paid over 12 months) plus pro rata target bonus; COBRA up to 12 months; 100% acceleration of unvested time-based equity .
- Clawback: Mandatory recovery of erroneously awarded incentive compensation (Exchange Act Rule 10D-1; Nasdaq standard) adopted November 2023 .
- Perquisites/Tax Gross-ups: Limited perquisites; no tax gross-ups; broad-based benefits only .
Performance & Track Record
| Metric/Item | 2024 Result | Context |
|---|---|---|
| Revenue | $5.2B | Footprint and scaled operations noted . |
| Homes Purchased / Sold | Purchased ~14,600; Sold ~13,500 | Operational throughput . |
| Fixed Opex Reduction | $50M YoY reduction | Cost-efficiency initiatives . |
| ANI | $(258.0)M (vs. $(778.0)M in 2023) | Material improvement, still below 2024 bonus threshold . |
| TSR | Opendoor TSR: $5; Peer Group TSR: $117 on $100 initial investment | 2024 stock underperformance relative to peer group . |
Compensation Committee & Say-on-Pay
- Say-on-Pay: Approval ~91% of votes cast in 2024, up from 75% in 2023 .
- Peer Group Methodology: Emphasis on industry peers, gross margin, market cap; illustrative peers include Anywhere Real Estate, Compass, eXp World Holdings, Offerpad Solutions, Redfin, Zillow Group (industry peers), and selected general peers (e.g., Lyft, Peloton, Wayfair) .
Vesting Schedules & Insider Selling Pressure
- TRSUs vest quarterly over three years beginning April 15, 2024, creating regular vesting events that can increase tradable float absent holding requirements .
- 2024 PRSUs earned at 42% of target, vest one-third on March 15, 2025 and the remainder over eight quarterly installments, adding additional periodic vesting supply .
- Insider Trading Policy restricts discretionary trading windows and prohibits hedging/shorting, mitigating misalignment risks .
Investment Implications
- Pay-for-performance alignment improved (91% say-on-pay approval), with meaningful shift to performance-based incentives (ANI bonuses; PRSUs tied to volume metrics; 2025 PRSUs tied to product-level profit) .
- Retention risk appears contained: robust double-trigger severance protection, clear non-solicit covenants, and ownership guideline compliance .
- Selling pressure watch: predictable quarterly vesting cadence (TRSUs, PRSUs) into a historically volatile equity could create episodic supply; however, hedging/pledging prohibitions and ownership guidelines temper misalignment .
- Execution signal: Despite 2024 ANI improvement, bonus paid 0% due to threshold miss—indicates discipline in incentive design; as 2025 metrics pivot to product-level profit, monitoring attainment and vesting outcomes will be critical for gauging future compensation realizations .