Erica Gessert
UPWORKAbout Erica Gessert
Erica Gessert is Upwork’s Chief Financial Officer since April 2023, age 50, with prior senior finance roles at PayPal, Sprint, and Virgin Mobile; she studied Economics and Philosophy at Reed College . Under Upwork’s leadership team in 2024, the company delivered record profitability: revenue grew 12% to $769.3M, adjusted EBITDA reached $167.6M with a 22% margin, and GAAP net income was $215.6M (28% profit margin), with free cash flow of $139.1M; Gessert was credited as instrumental in the company’s record performance and capital allocation, including a $100M share repurchase . In Q3 2025, Upwork reported record quarterly revenue of $201.7M and a 30% adjusted EBITDA margin; management raised FY25 guidance, reinforcing confidence in a 35% long-term adjusted EBITDA margin target .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Upwork Inc. | Chief Financial Officer | Apr 2023–present | Instrumental in record performance; led $100M buyback; supported Objective AI acquisition; strengthened investor engagement |
| PayPal Holdings, Inc. | Chief Transformation Officer; SVP Finance & Analytics; VP Finance & Analytics | 2015–Mar 2023 | Drove transformation across global fintech operations; senior leadership in finance and analytics |
| Sprint Corporation | VP Finance Ops (Postpaid Marketing) & CFO Sprint Prepaid; Director IR | 2009–2014 | Finance leadership and investor relations for major wireless operator |
| Virgin Mobile USA, Inc. | Director Investor Relations | 2007–2009 | Led IR at wireless provider |
Fixed Compensation
| Year | Base Salary ($) | Target Bonus (% of Base) | Actual Bonus ($) |
|---|---|---|---|
| 2023 | 375,833 (pro-rated) | 80% (Offer Letter) | 183,467 (pro-rated; +13% individual adj.) |
| 2024 | 572,917 | 80% | 607,787 (106% of base; +3.6% individual adj.) |
- 2024 base salary changes were effective March 1, 2024 .
- All Other Compensation: $5,606 (2024) .
Performance Compensation
Short-Term Incentive (2024 Annual Bonus)
| Metric | Weight | Threshold | Target | Maximum | Actual | Achievement (%) |
|---|---|---|---|---|---|---|
| Revenue | 50% | $741.2M | $791.2M | $841.2M | $769.325M | 56% |
| Adjusted EBITDA | 50% | $106.5M | $136.5M | $166.5M | $167.593M | 200% |
| Weighted Average | — | — | — | — | — | 128% |
| GSV Modifier | up to +20% | $4.308B (105%) | $4.349B (110%) | $4.391B (120%) | $4.008B | No impact |
| Individual Performance Adjustment (Gessert) | +/-20% | — | — | — | +3.6% | +3.6% |
- Actual 2024 bonus paid to Gessert: $607,787 (106% of base) .
Long-Term Incentives (2024 Grants)
| Award | Grant Date | Approval Date | Target Value ($) | Shares (Target) | Shares (Max) | Vesting / Performance |
|---|---|---|---|---|---|---|
| RSU | 03/18/2024 | 02/06/2024 | 1,627,208 | 134,926 | — | Service-based; 1/16 quarterly on each quarterly anniversary after 3/18/2024 |
| PSU | 03/18/2024 | 02/20/2024 | 1,627,208 | 134,926 (Target) | 269,853 (Max) | Multi-year; up to 50% vest based on 2025 Combined Financial Target % and up to 50% on 2026 (Revenue growth % + Adjusted EBITDA margin; capped at 200% each year) |
- PSU certification after each year’s end; Earned PSUs vest on Certification Date (first certification in early 2026) .
- 2024 program introduced profitability metrics and multi-year PSU goals, aligning pay with durable, profitable growth .
Prior Sign-On Equity (2023)
| Award | Grant Value Basis | Shares | Initial Vest | Ongoing Vesting |
|---|---|---|---|---|
| RSU (Sign-on) | $9,000,000 ÷ max($15.00, 30-day avg price) | 600,000 | 25% on May 18, 2024 | 6.25% quarterly thereafter, subject to service |
Equity Ownership & Alignment
| Date (As of) | Beneficially Owned Shares | % Outstanding | Breakdown Notes |
|---|---|---|---|
| Mar 31, 2024 | 153,105 | <1% | 3,105 common (ESPP) + 150,000 RSUs vesting within 60 days |
| Mar 31, 2025 | 198,445 | <1% | 160,945 common + 37,500 RSUs vesting within 60 days |
- Stock Ownership Guidelines: Other executive officers must hold stock equal to 1x annual base salary; compliance expected within 5 years; retention requirement of 50% of net shares until compliant. As of Dec 31, 2024, all NEOs were either compliant or within the 5-year accumulation period .
- Hedging/Pledging: Hedging prohibited; pledging prohibited except with pre-approval and demonstrated ability to repay loan without resort to pledged securities .
- No specific pledges disclosed for Gessert in beneficial ownership tables .
Employment Terms
| Item | Terms |
|---|---|
| Start Date | April 25, 2023 |
| Offer Letter | March 22, 2023 |
| Base Salary (initial) | $550,000 |
| Target Bonus | 80% of base salary |
| Severance Agreement Term | 3 years; auto-renews for successive 3-year periods unless notice given ≥3 months before expiration |
| Involuntary Termination (No CIC) | Cash severance: 1x base salary; medical premiums up to 12 months; no equity acceleration (for non-CEO NEOs) |
| Change in Control (Double Trigger) | If terminated without cause or for good reason within 3 months pre-CIC (after definitive agreement) or within 12 months post-CIC: cash severance 1x base salary; pro‑rated target bonus; medical premiums up to 12 months; 100% acceleration of unvested time-based equity (excludes performance-based awards; PSU treatment per award terms) |
| 2024 PSU CIC Treatment | Earned PSUs for the CIC year equal to greater of forecast-based or target; remaining PSUs convert to time-based RSUs at target with pro‑rata quarterly vesting per original schedule and subject to Severance acceleration |
| Clawback | Compensation recovery policy mandates recoupment upon restatement; permits discretionary recoupment in certain circumstances |
| Non-Compete/Non-Solicit/Confidentiality | Confidentiality in perpetuity; non-compete during employment; non-solicit of employees/consultants for 12 months post-termination (as permitted by law) |
Performance & Track Record
| Metric | FY 2023 | FY 2024 |
|---|---|---|
| Revenue ($) | $687.3M (implied from targets; actual shown in proxy tables) | $769.3M (+12% YoY) |
| Adjusted EBITDA ($) | Prior year baseline | $167.6M; margin doubled to 22% |
| Net Income ($) | — | $215.6M; 28% profit margin |
| Free Cash Flow ($) | $39.4M | $139.1M |
- Strategic actions under management: introduced Uma (Mindful AI), acquired Objective AI, launched Business Plus, executed restructuring for efficiency, and repurchased $100M of shares .
- Q3 2025: Revenue $201.7M; adjusted EBITDA $59.6M (30% margin); GAAP net income $29.3M; new $100M repurchase authorization; raised FY25 revenue and adjusted EBITDA guidance .
Compensation Structure Analysis
- Mix evolution: For Gessert, 2023 stock awards $4.95M vs 2024 $3.25M; cash bonus increased with new profitability-based STI design tying 50% to adjusted EBITDA . The 2024 LTI added PSUs with multi-year revenue growth and adjusted EBITDA margin metrics (50/50 RSU/PSU for non-CEO NEOs) to improve pay-for-performance alignment and reduce dilution concerns via vesting cash awards to non-NEOs .
- Governance signals: No single-trigger benefits; hedging prohibited; pledging tightly restricted; robust clawback .
Equity Ownership & Insider Selling Pressure Indicators
- Quarterly RSU vesting cadence from both the 2023 sign-on grant (6.25% quarterly after initial 25% on 5/18/2024) and 2024 RSUs (quarterly 1/16 post-3/18/2024) can produce periodic share delivery that may coincide with open trading windows; retention requirements apply if below guideline thresholds .
- Company prohibits hedging; pledging only with pre-approval—reducing misalignment risks from derivative hedging or collateralization .
- Beneficial ownership remains <1% with additional RSUs vesting within 60 days noted in filings .
Say-on-Pay & Shareholder Feedback
- 2024 Say-on-Pay approval: 94% of votes cast supported NEO compensation .
- Program changes incorporated investor feedback: added profitability metrics to STI/LTI, multi-year PSU goals, differentiated metrics between short- and long-term plans, and dilution mitigation .
Investment Implications
- Compensation tied to durable, profitable growth: 2024 STI focused 50% on adjusted EBITDA; 2024 PSUs require multi-year revenue growth plus EBITDA margin, capping outsized performance at 200%—tight alignment with margin expansion narrative .
- Retention risk appears mitigated by substantial ongoing RSU vesting and double-trigger CIC protections; no single-trigger accelerations limit windfalls while ensuring competitive severance .
- Insider selling pressure is structurally moderated by anti-hedging, restricted pledging, and ownership guidelines with 50% net share retention until compliant; ongoing quarterly vesting still creates potential supply near trading windows .
- Execution risk: PSU targets are undisclosed and depend on achieving both revenue growth and margin outcomes in 2025/2026; failure to meet thresholds results in zero earn-out for that year .
- Positive strategic track record: CFO’s role in buybacks, efficiency, and AI initiatives supports margin and growth trajectory; Q3 2025 results and raised guidance reinforce confidence in operating leverage and FCF yield .