Jill Olmstead
LendingTreeAbout Jill Olmstead
Jill Olmstead is LendingTree’s Chief Human Resources Officer, serving since October 2018; she is 61 and holds an M.A. in Human and Organizational Behavior (Fielding Graduate University) and a B.S. in Business (Clemson University) . Company execution in 2024 included Adjusted EBITDA of $104 million (+33% year over year) with strong Q4 momentum and segment growth, alongside leverage reduction from 5.3x to 3.5x and liquidity to retire remaining 2025 converts—context for pay-for-performance and retention frameworks administered by HR leadership . Pay-versus-performance disclosures show 2024 compensation actually paid tracked with outcomes, while the Company’s 2024 “say-on-pay” received ~97% support, signaling investor endorsement of compensation governance .
Past Roles
| Organization | Role | Years | Strategic impact |
|---|---|---|---|
| Spivey & Olmstead (Charlotte) | Founding partner/owner (HR consulting) | 2010–2018 | Built HR advisory capability prior to joining LendingTree |
| Wells Fargo/Wachovia | HR leadership positions; EVP, MD & Head of HR for Corporate & Investment Banking | ~25 years (prior to 2010) | Led HR for CIB; deep financial services HR expertise |
External Roles
| Organization | Role | Years | Strategic impact |
|---|---|---|---|
| — | — | — | No current public company directorships or committee roles disclosed for Olmstead |
Fixed Compensation
| Metric | FY 2023 | FY 2024 |
|---|---|---|
| Base Salary ($) | $400,000 | $420,000 |
| Target Bonus (% of Salary) | 60% | 60% |
| Actual Cash Bonus Paid ($) | $120,000 | $252,000 |
Key observations:
- Base salary rose 5% in 2024 to $420K; target bonus stayed at 60% of salary .
- Actual FY2024 bonus paid equals 60% of salary ($252K), aligned to Company AEBITDA performance and 100% pool funding .
Performance Compensation
| Component | Metric | Weighting | Target | Actual | Payout | Vesting |
|---|---|---|---|---|---|---|
| Annual Bonus (FY 2024) | Corporate AEBITDA | 100% | $118,488,300 pre-bonus AEBITDA | $119,000,000 pre-bonus AEBITDA | Bonus pool funded at 100% (individual payout per plan) | Cash paid in 2025 per program |
| RSUs (grant date 3/1/2024) | Time-vested RSUs | — | 30,000 RSUs; grant-date fair value $1,199,400 | — | — | Vests in 3 equal annual installments starting 3/1/2025 |
| Prior RSUs | Time-vested RSUs | — | 7,500 RSUs (50/25/25 schedule) | — | — | 50% on 3/2/2024, then 25% on second and third anniversaries |
Program features:
- NEO annual bonus tied solely to corporate AEBITDA—explicit pay-for-performance design .
- 2024 equity awards for NEOs (including Olmstead) granted as RSUs to drive retention and alignment; CEO/President also had PSUs with price hurdles, but Olmstead did not receive PSUs .
Equity Ownership & Alignment
| Item | Detail |
|---|---|
| Stock ownership guidelines | NEOs must hold 1.5x–3x base salary; CEO 6x; directors 5x retainer |
| Hedging/pledging | Hedging prohibited; pledging/margin accounts prohibited absent Legal approval |
| Clawback | Dodd-Frank Rule 10D-compliant recovery policy effective Oct 25, 2023 for erroneously awarded incentive pay over prior 3 years |
Beneficial ownership (as of April 16, 2025):
- Shares beneficially owned: 65,003; percentage of class: less than 1% .
- Includes 40,733 stock options exercisable within 60 days .
- Shares outstanding: 13,535,034 .
Vested vs. unvested and award composition (as of Dec 31, 2024):
| Category | Detail |
|---|---|
| Options (exercisable/unexercisable) | 8,951 exercisable; 4,477 unexercisable at $113.27 strike (3/2/2032); plus other legacy option lots (strikes $218.33, $253.42, $275.82, expirations 2028–2031) |
| Unvested RSUs | 2,355 (3/2/2023 grant, 3 equal annual installments); 7,500 (3/2/2024 grant, 50/25/25); 30,000 (3/1/2024 grant, 3 equal annual installments from 3/1/2025) |
Insider transactions (vesting/tax withholding, 2025):
| Date | Code | Shares | Price | Post-transaction holdings |
|---|---|---|---|---|
| 03/01/2025 | M (RSU to common) | 9,999 | — | 22,893 |
| 03/01/2025 | F (tax) | 2,981 | $40.39 | 19,912 |
| 03/02/2025 | M (RSU to common) | 2,355 | — | 22,267 |
| 03/02/2025 | F (tax) | 674 | $40.39 | 21,593 |
| 03/02/2025 | M (RSU to common) | 3,750 | — | 25,343 |
| 03/02/2025 | F (tax) | 1,073 | $40.39 | 24,270 |
Notes:
- 2023 Form 4s show RSU vesting and F-code tax withholdings—non-discretionary—consistent with typical equity settlement mechanics .
- No open market discretionary sales disclosed in these filings; F-code entries reflect tax obligations on vest .
Employment Terms
Executive Severance Plan participation (Olmstead) and change-in-control protections:
- Outside change-in-control involuntary termination: cash severance $420,000; health continuation $17,948; equity acceleration/payout $624,030 (hypothetical at $38.75) .
- Within 12 months of change-in-control with involuntary termination (double-trigger): cash severance $1,596,000; health continuation $22,435; equity acceleration/payout $1,544,381 (hypothetical at $38.75) .
- Restrictive covenants (post-termination): non-compete and customer non-solicitation 24 months; employee non-solicitation 18 months; vendor/supplier/contractor non-solicitation 12 months (Bengel has shorter durations; Olmstead falls under standard durational terms) .
- Hedging prohibited; pledging restrictions enforced; clawback recovery policy adopted Oct 25, 2023 for erroneously awarded incentive compensation .
Compensation Structure Analysis
- Equity mix increased in 2024: RSU grant $1.199M vs $495K in 2023, reflecting retention/alignment priorities amid return to growth .
- Cash vs equity: 2024 cash bonus doubled vs 2023 ($252K vs $120K) with 100% pool funding on AEBITDA target achievement (pre-bonus AEBITDA $119M) .
- Committee explicitly noted Olmstead’s compensation not set below median given her experience and strategic importance—indicating targeted investment in HR leadership .
- Governance positives: no option repricing; no excise tax gross-ups; strict ownership and clawback policies .
Say-on-Pay & Compensation Committee
- Say-on-pay support: 2023 ~86% “FOR”; 2024 ~97% “FOR” .
- Compensation Committee: Steven Ozonian (Chair), G. Kennedy Thompson, Mark Ernst (independent); FW Cook engaged as independent consultant in 2024 and 2025; peer groups updated to reflect marketplace/fintech comparables .
Company Performance Context During Tenure
| Metric ($USD) | FY 2017 | FY 2018 | FY 2019 | FY 2020 | FY 2021 | FY 2022 | FY 2023 | FY 2024 |
|---|---|---|---|---|---|---|---|---|
| Revenues | $617,736,000 | $764,865,000 | $1,106,603,000 | $909,990,000 | $1,098,499,000 | $984,992,000 | $672,502,000 | $900,219,000 |
| EBITDA* | $75,037,000* | $100,228,000* | $137,744,000* | $54,255,000* | $47,575,000* | $2,949,000* | $21,859,000* | $59,621,000* |
*Values retrieved from S&P Global.
Additional qualitative performance:
- 2024: AEBITDA $104M (+33%) with Insurance segment revenue $549M (+120%) and segment profit $159M (+54%); Consumer and Home segments stabilized/improving; leverage reduced, liquidity preserved, and capital structure optimization underway .
Investment Implications
- Alignment: Strong ownership/anti-hedging/anti-pledging and clawback regime, plus RSU-heavy grants for NEOs, indicate durable alignment; Olmstead’s 2024 RSU grant and ongoing vesting suggest retention priorities without aggressive option-based risk .
- Retention risk: Robust double-trigger change-in-control protections and lengthy non-compete/non-solicit terms reduce near-term attrition risk; hypothetical CIC cash and equity payouts (~$3.16M total) are material but standard for senior officers and tied to termination post-CIC .
- Selling pressure: Recent Form 4 activity shows RSU conversions with F-code tax withholding, not discretionary open-market sales—limited indication of voluntary selling pressure .
- Pay-for-performance: Annual bonus fully tied to corporate AEBITDA; 2024 pool funded at 100% after target met—clear linkage that supports governance credibility and reduces pay inflation risk; high say-on-pay support corroborates this .
- Execution risk: Company is re-accelerating growth after industry dislocation; HR leadership continuity (since 2018) across cycles is a stabilizer for talent strategy, but macro-sensitive segments (Home/Consumer) remain exposure points; monitoring RSU vesting cadence and any 10b5-1 plans can flag future transactional activity .
Sources: LendingTree 2025 and 2024 DEF 14A proxy statements; SEC Form 4 filings for Jill Olmstead; S&P Global financials via tool.