Shayna Webb Dray

About Shayna Webb Dray

Shayna Webb Dray, age 38, is LifeMD’s Chief Operating Officer (COO) effective March 27, 2025, after serving as SVP, Operations (Sep 2023–Jul 2025) and Head of Supply Chain & Procurement (May 2021–Sep 2023). She holds a BS in Supply Chain Management and Marketing from Syracuse University and is noted for process optimization, cost reduction, and scaling programs, including LifeMD’s weight management offering . Company performance during her operational tenure: 2024 total net revenue rose 39% to $212.454M (Telehealth +61% to $158.439M), Telehealth Adjusted EBITDA improved to $7.397M from $(5.245)M in 2023, and cumulative TSR measured from a fixed $100 investment stood at $63.06 at 2024 year-end versus $105.61 at 2023 year-end .

Performance metric	FY 2023	FY 2024
Total revenue, net ($)	152,547,006	212,453,838
Telehealth revenue, net ($)	98,152,919	158,438,631
Telehealth Adjusted EBITDA ($)	(5,244,576)	7,397,189
Cumulative TSR – $100 initial value ($)	105.61	63.06

Past Roles

Organization	Role	Years	Strategic impact
LifeMD	Head of Supply Chain & Procurement	May 2021–Sep 2023	Built comprehensive supply chain strategy and drove annual savings
LifeMD	SVP, Operations	Sep 2023–Jul 2025	Launched and scaled weight management program; oversaw Care Center, Pharmacy, Clinical Ops, PMO
LifeMD	Chief Operating Officer	Effective Mar 27, 2025; announced Jul 31, 2025	Operational excellence, cost reduction, quality experiences, innovation

External Roles

Organization	Role	Years	Strategic impact
Kaplan Publishing (Graham Holdings)	Executive Director of Operations	Mar 2016–May 2021	Supply chain optimization yielding substantial annual savings; advised on operational/strategic initiatives

Fixed Compensation

Effective date	Component	Amount / Terms	Notes
May 3, 2021	Base salary	$165,000	Initial role Head, Supply Chain & Procurement; target bonus 20%
May 3, 2021	Equity – Options	40,000 options @ $13.74, monthly vest over 36 months	Subject to shareholder approval 6/24/2021
Apr 4, 2022	Equity – Restricted Shares	5,000 RS; vest Apr 4, 2025	Granted in annual merit review
May 11, 2022	Base salary	Increased to $175,000	Annual merit review
May 1, 2023	Base salary	Increased to $200,000	Annual merit review
Nov 8, 2023	Options canceled	Canceled 40,000 options (underwater)	Replaced with RS grants (see Performance Compensation)
Mar 31, 2025	Base salary	Increased from $300,000 to $375,000	Annual merit review
Mar 31, 2025	Target bonus	Increased from 40% to 45% of base	Annual merit review
Jul 27, 2025	Base salary	Increased to $400,000	Third Amendment to Employment Agreement

Performance Compensation

Grant date	Instrument	Quantity	Vesting schedule	Performance metrics	Change-of-control / termination terms
Nov 8, 2023	Restricted Stock (Replacement of options)	48,000 shares	Subsequent vestings include 20,000 on Jan 1, 2024; 4,000 on Mar 31, 2024; remaining unvested shares integrated into new schedule (see Second Amendment)	N/A (time- and performance-conditioned per amendments)	All Restricted Shares vest immediately upon Change in Control; subject to clawback policy
Nov 8, 2023	Restricted Stock (Contingent future)	12,000 shares	Contingent grant with subsequent vesting per First/Second Amendments	N/A	CIC acceleration as above
May 7, 2024	Restricted Stock (Additional)	150,000 shares	Vesting upon achievement of personal and Company milestones; incorporates 29,000 unvested RS + 12,000 future RS into total schedule	Personal and Company milestones (not fully specified)	All Restricted Shares vest immediately upon Change in Control; subject to clawback
Jul 27, 2025	RSUs	100,000 units	10,000 vest Jan 1, 2026; 20,000 vest Jan 1, 2027; 20,000 vest Jan 1, 2028	25,000 vest on healthcare business achieving $25M annualized EBITDA (TTM) by Dec 31, 2027; 25,000 vest on $35M annualized EBITDA (TTM) by Dec 31, 2027	Unvested RSUs vest immediately prior to closing of Change of Control; time-based RSUs scheduled <1 year from termination vest pro rata if terminated without Cause or for Good Reason; award subject to forfeiture for covenant breach

2025 RSU Performance Triggers – Detail

Metric	Weighting	Target	Period	Vesting
Healthcare business annualized EBITDA (TTM)	25,000 RSUs	$25,000,000	On/before Dec 31, 2027	RSUs vest upon achievement
Healthcare business annualized EBITDA (TTM)	25,000 RSUs	$35,000,000	On/before Dec 31, 2027	RSUs vest upon achievement

Equity Ownership & Alignment

Item	Status / Amount	Notes
Beneficial ownership (shares)	Not disclosed for Dray in 2025 proxy beneficial ownership table as of Apr 23, 2025	NEOs listed did not include Dray
Vested restricted shares	20,000 vested Jan 1, 2024; 4,000 vested Mar 31, 2024	From First/Second Amendments
Unvested/contingent restricted shares	29,000 unvested RS integrated; 12,000 contingent RS; plus 150,000 additional RS subject to milestones	Second Amendment schedule
RSUs outstanding	100,000 granted Jul 27, 2025 with time-based + EBITDA triggers	See detailed vesting above
Options	40,000 options @ $13.74 canceled Nov 8, 2023 (underwater)	Shift from options to RS/RSUs
Pledging/hedging	Prohibited for insiders (no margin, no pledging; hedging banned)	Insider Trading Policy
Clawback	Incentive Compensation Recovery Policy effective Oct 12, 2023	Awards subject to recoupment

Employment Terms

Agreement	Date	Key terms
Employment Agreement	Apr 14, 2021	Hired effective May 3, 2021; base $165k; target bonus 20%; 40,000 options @ $13.74 (later canceled)
First Amendment	Nov 8, 2023	Canceled 40,000 options; granted 48,000 RS; contingent 12,000 RS; reaffirmed 5,000 RS vest Apr 4, 2025
Second Amendment	May 7, 2024	Increased base and target bonus; reaffirmed vestings; integrated 29,000 unvested RS + 12,000 future RS; granted 150,000 RS tied to personal/company milestones; CIC immediate vest; clawback applies
Third Amendment	Jul 27, 2025	Base increased to $400k; awarded 100,000 RSUs with time-based and EBITDA conditions; pro rata vest for near-term time-based RSUs upon termination w/o Cause or for Good Reason; RSUs vest on CIC immediately prior to close
Insider Trading Policy	Filed with 10-K FY2024	10b5-1 trading plans allowed (preclearance required); bans short-swing, short sales, hedging, margin, pledging

Performance & Track Record

Led launch and scaling of LifeMD’s GLP-1 weight management program; the program had over 75,000 patient subscribers by Dec 31, 2024, coinciding with a 61% Y/Y increase in telehealth revenue in 2024 .
Operational focus on cost optimization and continuous improvement; responsibilities spanned Care Center, Pharmacy, Clinical Operations, and PMO during SVP tenure .
Market/stock context: Aug 5–6, 2025, LifeMD cut FY2025 guidance after Q2 results citing RexMD CAC and refunds in weight management, and the stock fell ~44.85% to $6.53 on Aug 6; multiple law firms announced securities class action filings regarding May 7–Aug 5, 2025 disclosures .

Compensation Structure Analysis

Shift from options to restricted stock/RSUs: underwater options (40,000 @ $13.74) canceled and replaced with RS grants, reducing risk and increasing certainty of value realization versus option leverage .
Increasing fixed pay: Base salary rose from $165k (2021) to $400k (2025), with target bonus lifted from 20% initially to 45% by Mar 31, 2025, reflecting expanded responsibilities as COO .
Strong pay-for-performance linkage: 2025 RSUs require healthcare business to reach $25M and $35M annualized EBITDA (TTM) by Dec 31, 2027; 2024 RS awards include personal/company milestone vesting .
CIC acceleration: All Restricted Shares vest immediately upon Change in Control and RSUs vest immediately prior to close, increasing potential payout sensitivity to strategic transactions; awards subject to clawback policy .

Equity Ownership & Alignment – Vesting Calendar (Trading Pressure Signals)

Date	Instrument	Quantity	Condition
Jan 1, 2026	RSUs	10,000	Time-based vest
Jan 1, 2027	RSUs	20,000	Time-based vest
Jan 1, 2028	RSUs	20,000	Time-based vest
On/before Dec 31, 2027	RSUs	25,000	Healthcare EBITDA (TTM) ≥ $25M
On/before Dec 31, 2027	RSUs	25,000	Healthcare EBITDA (TTM) ≥ $35M
Immediate at CIC	RS/RSUs	All outstanding	Accelerated vesting prior to closing

Employment Terms – Protections & Restrictions

Pro rata vesting: Time-based RSUs scheduled to vest within one year vest pro rata upon termination without Cause or for Good Reason .
Clawback: Awards subject to LifeMD Incentive Compensation Recovery Policy (effective Oct 12, 2023) .
Anti-hedging/pledging: Insiders prohibited from hedging or pledging LifeMD securities; no margin accounts; 10b5-1 plans permitted with preclearance .

Investment Implications

Alignment: Large performance RSU tranches tied to healthcare EBITDA by 2027 align incentives with profitability scaling in the core business; milestone-based RS grants further reinforce execution focus .
Retention and event risk: Time-based RSU vest dates through 2028 and pro rata vesting protections reduce near-term attrition risk, but single-trigger CIC acceleration concentrates upside in strategic transaction outcomes .
Trading signals: Known vesting dates (Jan 1, 2026/2027/2028) and potential EBITDA-trigger vest events by Dec 31, 2027 create supply windows; anti-pledging/hedging policy lowers forced selling risk .
Execution watchpoints: Post-Q2 2025 reset and related litigation highlight sensitivity to acquisition costs and refund dynamics; hitting $25–35M TTM EBITDA targets will be key to unlocking contingent RSU value and signaling operational discipline .