Jonathan Allison
About Jonathan Allison
Jonathan Allison, 58, is Chief Administrative Officer (CAO) at Root, Inc., serving since May 2023 after six years as General Counsel (2017–June 2023) . His remit spans Legal, Human Resources, Claims, and Customer Service; earlier, he was EVP at CareSource (2015–2017) and a partner at Carpenter Lipps LLP (2010–2015), with prior public-service leadership as Chief of Staff to Ohio Governor Bob Taft and oversight of Ohio’s largest business regulatory agency . During 2024, Root achieved first-time net profitability, grew gross written premiums 66% YoY, increased policies-in-force 21%, improved gross accident period loss ratio to 59.9%, and refinanced its term loan; NEO incentives were tightly linked to Adjusted EBITDA, loss ratio, and growth outcomes .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Root, Inc. | Chief Administrative Officer | May 2023–present | Leads Legal, HR, Claims & Customer Service; supports profitability and operational scale |
| Root, Inc. | General Counsel | 2017–June 2023 | Built regulatory/compliance function; supported capital structure and governance |
| CareSource | Executive Vice President | May 2015–June 2017 | Senior managed-care leadership; operational oversight |
| Carpenter Lipps LLP | Partner | Dec 2010–May 2015 | Legal practice leadership |
External Roles
No public-company board roles disclosed in the proxy; executive biography focuses on internal responsibilities and prior public-service roles .
Fixed Compensation
| Metric | 2023 | 2024 |
|---|---|---|
| Base Salary ($) | $500,000 | $520,000 |
| Salary Earned ($) | $488,846 | $514,615 |
| Target Annual Cash Incentive (% of Base) | 100% | 100% |
Performance Compensation
Annual Cash Incentive (2024 STI Plan)
| Component | Target/Framework | Actual Result | Payout |
|---|---|---|---|
| Accident Period Gross Loss Ratio | Matrix target 63%–67% | 59.9% | Contributed to 192% matrix achievement; combined with Adjusted EBITDA and qualitative measures, payout capped at 300% of target |
| Policy-in-Force Growth | Matrix target 20,000–140,000 policies | ~73,000 policies | See above; combined payout capped at 300% |
| Adjusted EBITDA Self-Funding | Up to 10% of Adjusted EBITDA (applies when matrix ≥ target) | +69% contribution | Included in capped payout |
| Cash Paid ($) | Target $520,000 | 300% of target | $1,560,000 paid; determination in Feb 2025 |
PSUs – 2024 Grants (Performance period: CY2025; vesting begins 2026)
| Item | Details |
|---|---|
| Metrics | 2025 Adjusted EBITDA and New Writings; earn up to 200% of target PSUs |
| Target PSUs | 35,790 |
| Max PSUs | 71,580 |
| Grant Date Fair Value ($) | $2,703,935 |
| Vesting | 25% upon certification (expected Feb 2026), then 25% annually on Jan 1 until fully vested |
PSUs – 2023 Grants (Stock-price tranches)
| Tranche | Price Threshold | Status | Shares Earned |
|---|---|---|---|
| Tranche 1 | $16.76 per share (45-day average) | Achieved; time condition met | 2,147 gross shares (Allison) vested on Apr 1, 2025 |
| Future Scheduled Vesting | Subject to price thresholds | Apr 1, 2026; Apr 1, 2027 | 6,442 (2026) and 8,589 (2027) PSUs scheduled to vest if price conditions met |
RSUs – 2023 Grants (Time-based)
| Vesting Date | Shares |
|---|---|
| Apr 1, 2026 | 18,117 |
| Apr 1, 2027 | 18,117 |
| Note | 17,335 RSUs vested Apr 1, 2025 per award schedule |
Equity Ownership & Alignment
| Item | Detail |
|---|---|
| Beneficial Ownership (Class A) | 18,416 shares; <1% |
| Options (Class B) – Exercisable | 12,024 shares; strikes: $5.15 (2017), $43.20 (2019) |
| Unvested RSUs (Dec 31, 2024) | 53,569 units; MV $3,888,574 (@ $72.59) |
| Unvested PSUs (Dec 31, 2024, at threshold) | 17,895 units; MV $1,298,998 (@ $72.59) |
| Pledging/Hedging | Hedging/short sales prohibited; pledging generally prohibited without CFO/GC approval; none pledged by executives as of proxy date |
| Ownership Guidelines | Not disclosed for executives; director policy disclosed separately |
Employment Terms
| Provision | Terms |
|---|---|
| Agreement | Executive employment agreement dated Nov 2021; at-will |
| Severance (No CIC) | 12 months base salary; pro-rata annual bonus for partial year; up to 12 months COBRA; 12 months’ equivalent time-based equity vesting acceleration |
| Change-in-Control (CIC) | If terminated without cause or resigns for good reason within 12 months post-CIC, 100% of unvested equity fully vests (double-trigger) |
| Death/Disability | Pro-rata bonus for year of termination (per committee discretion) |
| Illustrative Value (Dec 31, 2024) | Equity vesting value: $1,625,943 (no CIC); $7,945,266 (with CIC), using $72.59 stock price |
| Clawback Policy | SEC/Nasdaq-compliant clawback for restatements; broadened to allow recovery of incentive/equity comp for intentional misconduct causing financial/reputational harm |
| Insider Trading Policy | Prohibits hedging; pledging requires prior approval; short sales and derivatives are prohibited |
Investment Implications
- High pay-for-performance alignment: 2024 cash incentive paid at 300% of target based on materially improved loss ratio, growth, and Adjusted EBITDA, with equity heavily in PSUs tied to 2025 EBITDA and New Writings; indicates strong linkage of Allison’s variable comp to profitability and growth levers .
- Near-term vesting and potential selling pressure: Multiple RSU/PSU tranches scheduled for Apr 1, 2026 and Apr 1, 2027, plus 2024 PSUs beginning vesting in Feb 2026; monitor Form 4s around these dates for potential sales or net-share settlements .
- Retention and change-in-control economics: Double-trigger full acceleration under CIC and 12-month cash/benefit severance reduce retention risk but create event-driven optionality; total CIC equity value for Allison calculated at ~$7.9M as of year-end 2024 .
- Alignment safeguards: Anti-hedging/pledging policies, a broadened clawback, and no executive pensions or tax gross-ups (per general policy) reduce governance red flags; none of the executives had pledged shares as of the proxy .
- Shareholder support: Say-on-Pay passed with ~97% approval in 2024, suggesting broad investor endorsement of program design linking pay with performance outcomes achieved in 2024 .