Jennifer Stiefel
About Jennifer D.H. Stiefel
Co-founder of Heritage Distilling Holding Company, Inc. (ticker: CASK), Jennifer D.H. Stiefel is President (since 2011), Secretary (since 2022), and a director; age 49. Her background includes staff service with the U.S. Senate Appropriations Committee, teaching elementary school in Virginia, and work in her family’s manufacturing business in Alaska; she holds a BA in Elementary Education (University of Idaho) and a Master’s in Instructional Education (Central Michigan University) . She signed the company’s 2025 proxy materials in her capacity as President and Secretary and served the same role for the August 2025 special meeting . Executive-specific TSR, revenue or EBITDA performance metrics were not disclosed in the proxies.
Past Roles
| Organization | Role | Years | Strategic impact |
|---|---|---|---|
| U.S. Senate (Appropriations Committee) | Staff member | Not disclosed | Federal policy, budgeting exposure relevant to regulatory navigation |
| Virginia elementary school | Teacher, science team lead | Not disclosed | Process and team leadership; education community engagement |
| Family manufacturing business (Alaska) | Various roles across operations | Not disclosed | Exposure to manufacturing operations and small-business execution |
External Roles
| Organization | Role | Years | Strategic impact |
|---|---|---|---|
| Several non-profit organizations | Director | Not disclosed | Community and stakeholder engagement; governance experience |
Fixed Compensation
| Metric (USD) | 2023 | 2024 |
|---|---|---|
| Base Salary | $97,962 | $139,367 |
| Bonus | — | — |
| Stock Awards (grant-date fair value) | — | $168,000 |
| All Other Compensation | $10,000 | $9,167 |
| Total Compensation | $107,962 | $316,534 |
| Note (deferred comp paid in 2025) | $63,076 paid in 2025 | $63,076 paid in 2025 |
All Other Compensation reflects deferred director fees paid after the November 2024 IPO; since the IPO, employee directors are no longer eligible for additional board compensation .
Performance Compensation
| Award | Grant date | Shares/Units | Fair value | Vesting and performance conditions |
|---|---|---|---|---|
| RSUs (double-trigger) | 06/05/2024 | 42,000 | $168,000 (at $4.00 grant value) | Requires service-based vesting plus a liquidity event: change of control; IPO lock-up expiration; sale of a Heritage brand/subsidiary (≥10% stake); or a third-party valuation/outside investment valuing the company or a subsidiary at ≥$200 million |
Plan-level provisions material to payout/vesting:
- Change-in-control/sale event treatment: if awards are not assumed/replaced, RSUs vest in full and settle; options with exercise price above deal price are canceled; performance awards settle for cash at target or at performance trend through the sale event . Section 280G/4999 excise tax cutbacks apply to awards granted after the offering, reducing payments to avoid excise taxes .
- Termination provisions: if terminated for cause, all awards are forfeited; for death/disability, vested options remain exercisable up to 12 months; for other terminations, vested options remain exercisable up to 3 months .
Equity Ownership & Alignment
| Date (Record) | Shares beneficially owned | % of class | Notes |
|---|---|---|---|
| May 30, 2025 | 330,283 | 2.74% | Includes 330,023 common + 260 shares in IRA; disclaims beneficial ownership of spouse’s shares |
| July 23, 2025 | 330,283 | 2.14% | Same breakdown; disclaims beneficial ownership of spouse’s shares |
Additional alignment indicators:
- Unvested equity: 42,000 unvested RSUs as of 12/31/2024 (double-trigger) .
- Options: None disclosed for Jennifer (no option listings in outstanding awards) .
- Hedging/pledging: Company policy prohibits directors/officers/employees from hedging, short sales, or pledging company stock; margin purchases are also prohibited .
- Trading windows: Restricted to open windows following quarterly/annual results; trading plans must be under approved Rule 10b5-1 .
Employment Terms
- Role tenure: President and director since 2011; Secretary since 2022 .
- Contracts/severance: No individual employment agreement or severance multiples disclosed in proxies for Jennifer. Equity plan includes sale-event acceleration, termination handling, clawback/recoupment provisions, anti-repricing, and 10-year plan term (through November 9, 2034) .
- Clawback: Awards subject to company recoupment/clawback policy and disgorgement for violations (e.g., non-compete, confidentiality) .
Board Governance
- Board service: Director since 2011; classified board structure (Class I/II/III) with staggered terms .
- Independence: Jennifer is not independent; Board states five independent directors, two management (CEO Justin B. Stiefel and President Jennifer D.H. Stiefel), and one consultant (Andrew Varga) .
- Committees: Audit (Alstead, Smith, Trevan), Compensation (Trevan, Wensel, Swann), Nominating & Corporate Governance (Smith, Alstead, Swann), Technology & Cryptocurrency (Swann, Trevan, Varga, Justin Stiefel). Jennifer is not listed as a member of any committee (independent directors only on Audit/Comp/Nominating) .
- Board leadership: CEO also serves as Chairman; the Board cites executive sessions and flexibility to maintain independent functioning (independent directors may meet without management; executive sessions at end of meetings) .
- Governance changes pending: Under August 2025 Subscription Agreements, Story Foundation may designate 3–5 directors; the Technology & Cryptocurrency Committee to be reconstituted as the Digital Assets Committee comprised solely of Story-designated directors; Story to designate committee members across Audit, Nominating, Compensation and appoint a Chief Investment Officer .
Director Compensation
- Program (non-employee directors): $40,000 annual cash retainer; committee fees per quarter—Chair $5,000, Member $2,500—for Audit, Compensation, Nominating & Corporate Governance, and Technology & Cryptocurrency Committees; initial RSU awards and optional stock options; reimbursements for preapproved board meeting expenses .
- Employee directors: Not eligible for board compensation post-IPO; Jennifer’s 2024 “All Other Compensation” reflected deferred director fees paid following IPO .
Compensation Structure Analysis
- Cash vs equity mix: 2024 compensation increased YoY, driven by higher base salary and a $168,000 RSU grant (42,000 units) versus no stock awards in 2023 . Equity is at risk via double-trigger and specific liquidity thresholds .
- Option use: No options granted to Jennifer in 2024; plan prohibits repricing and sets fair-market-value floors for new options/SARs .
- Performance metrics: No executive-specific financial performance metrics tied to Jennifer’s 2024 pay disclosed; RSU liquidity triggers are event-based rather than financial/TSR percentile targets .
- Clawback and governance: Robust anti-hedging/pledging policy ; plan-level clawback/recoupment rights .
Risk Indicators & Red Flags
- Dual leadership: CEO is also Chairman; Jennifer is a non-independent director and spouse of the CEO, which increases governance concentration risk; Board cites independent sessions as a mitigation .
- Share issuance/dilution: August 2025 pre-funded warrants for 370,378,890 shares at $0.0001 exercise price and related proposals create substantial dilution; automatic cashless exercise upon approval with beneficial ownership limits . Incentive Plan share increase to 35,000,000 proposed (from 5,000,000) to facilitate equity compensation .
- Listing compliance: Reverse stock split proposal (1:5 to 1:20) to regain/maintain Nasdaq $1 minimum bid; company received a delisting notice in April 2025 due to extended sub-$1 price .
- Trading and pledging: Hedging/pledging prohibited via policy .
- Related-party transactions: None disclosed involving Jennifer; one director (Andrew Varga) had a consulting agreement (contextual governance, not linked to Jennifer) .
Equity Ownership & Vesting Detail
| Category | Quantity/Status |
|---|---|
| Beneficial ownership (common + IRA) | 330,283 shares as of both 5/30/2025 and 7/23/2025; 2.74% and 2.14% respectively as share count changed |
| Unvested RSUs (12/31/2024) | 42,000 units (double-trigger liquidity + service) |
| Options | None disclosed for Jennifer |
| Pledging/Hedging | Prohibited by policy |
Employment & Contracts Snapshot
- Individual employment agreement terms (severance multiples, non-compete/non-solicit): Not disclosed.
- Equity plan sale-event acceleration and 280G cutback: Disclosed at plan level .
- Termination handling for awards: Disclosed at plan level .
Investment Implications
- Alignment and retention: Jennifer’s ownership stake (~2–3%) and double-trigger RSUs promote retention tied to strategic liquidity events; prohibition on hedging/pledging enhances alignment. However, lack of explicit financial performance metrics in incentive design reduces pay-for-performance visibility .
- Governance concentration: Non-independent spousal duo (CEO as Chairman; President as director) raises independence concerns; future board reconstitution giving Story Foundation multiple seats and control of a digital assets committee concentrates influence and changes committee compositions, impacting oversight of compensation, audit, and strategy .
- Dilution and trading dynamics: Massive warrant issuance and planned Incentive Plan expansion materially increase dilution risk; reverse split to maintain Nasdaq listing may add volatility and odd-lot frictions. These factors can elevate insider selling pressure post-liquidity events and complicate reading insider signals, while beneficial ownership limits may partially constrain concentration .
- Monitoring list: Track approvals at the special meeting (Financing, Advisory Compensation, Incentive Plan), reverse split implementation timing, RSU liquidity triggers (e.g., lock-up expiration/sale events/valuations), and changes to committee compositions that may affect compensation oversight and governance quality .