Steve Silvestro
About Steve Silvestro
Steve Silvestro, age 47, is Chief Executive Officer of OptimizeRx (OPRX) and was appointed to the Board of Directors on June 20, 2025. He joined OPRX in April 2019 (Chief Commercial Officer), served as President (Oct 2023–Jan 2025), interim CEO (Jan–Mar 2025), and was appointed CEO effective March 10, 2025 . He holds a Master of Liberal Arts in Business Management from Harvard University and a BA in Italian and Business Management from Brigham Young University . Company performance context: OPRX reported 2024 revenue of $92,127,044 and Adjusted EBITDA (for bonus) of $11,760,615; 2024 total shareholder return (TSR) translated to a $7.82 value on a $100 base (vs $45.92 in 2023 and $53.92 in 2022) .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| OptimizeRx | Chief Commercial Officer | Apr 2019–Oct 2023 | Led commercial strategy; positioned company from single solution to omnichannel capabilities . |
| OptimizeRx | President | Oct 2023–Jan 2025 | Advanced operational excellence and customer-centric initiatives . |
| OptimizeRx | Interim CEO | Jan 2025–Mar 2025 | Conducted strategic review; set focus on recurring revenue and Rule of 40 goal . |
| OptimizeRx | CEO | Mar 10, 2025–Present | Driving profitable revenue growth and shareholder value creation . |
| CCH Tagetik (Wolters Kluwer) | VP & GM | Jan 2018–Apr 2019 | Corporate performance management; leadership in planning/reporting solutions . |
| Prognos Health | Chief Commercial Officer | Apr 2017–Jan 2018 | Commercial leadership in healthcare data analytics . |
| Decision Resources Group | EVP, Head of Global Sales (various roles) | 2007–2017 | Built global data/analytics sales organization in life sciences . |
External Roles
No additional public company directorships or committee roles disclosed for Silvestro beyond OPRX .
Fixed Compensation
| Metric | 2023 | 2024 | 2025 (CEO terms) |
|---|---|---|---|
| Base Salary ($) | $384,583 | $400,000 | $500,000 |
| Target Bonus (% of Salary) | Not disclosed | 60% | 80% |
| Actual Annual Performance Bonus ($) | $174,375 | $141,360 | Not yet determined |
Performance Compensation
| Metric | Weighting | Target | Actual | Payout | Vesting/Payment Timing |
|---|---|---|---|---|---|
| Revenue | 50% | Target aligned to guidance (revised mid-year) | $92,127,044 | Contributed to total 58.9% payout | Paid Q1 2025 |
| Adjusted EBITDA (ex-SBC) | 50% | Target aligned to guidance (revised mid-year) | $11,760,615 (bonus calc) | Contributed to total 58.9% payout | Paid Q1 2025 |
| CEO one-time equity grant (2025) | — | $1,000,000 grant value | — | — | RSUs/options vest 1/3 annually from 1st anniversary of grant date |
Notes: 2024 payout for Silvestro under Cash Bonus Plan certified at 58.9%, yielding $141,360 . Equity grants are time-based; no PSU metrics disclosed in 2024 awards .
Equity Ownership & Alignment
| Item | Detail |
|---|---|
| Beneficial Ownership (as of Apr 29, 2025) | 151,066 shares; under 1% of outstanding . |
| Options exercisable within 60 days | 78,910 shares . |
| RSUs vesting within 60 days | Not listed for Silvestro in footnote; group total disclosed . |
| Outstanding Equity Awards (12/31/2024) | Options: exercisable 38,511 @ $37.50 exp 1/7/2026; 7,817/3,909 @ $43.24 exp 3/1/2027; 26,036/13,019 @ $15.04 exp 10/2/2027; 6,546/13,093 @ $12.73 exp 12/18/2028; 0/77,742 @ $4.83 exp 12/22/2029 . RSUs: 1,928; 6,649; 13,093; 7,750; 41,408 unvested, vest in three equal annual installments from grant date anniversaries . |
| Stock Ownership Guidelines | CEO: 3x base salary; Other execs: 2x; directors: 3x; 50% of net shares retained until compliant; five-year window to comply . |
| Hedging/Pledging/Margin | Prohibited: hedging, short sales, public options, margin accounts, and pledging OPRX stock . |
| Clawback Policy | Recoup erroneously awarded incentive comp for prior 3 fiscal years following a required restatement; methods include reimbursement, cancellation, offsets . |
Employment Terms
| Provision | Terms |
|---|---|
| Employment Agreement | Amended and Restated Employment Letter dated Mar 7, 2025; effective Mar 10, 2025 . |
| Severance (Non-CIC) | If terminated without Cause or resigns for Good Reason: 1.5x base salary paid over 18 months; target annual bonus lump sum; COBRA premiums up to 12 months . |
| Change-in-Control (CIC) | If terminated without Cause or resigns for Good Reason within 3 months prior to or 24 months post-CIC: additional lump sum = 2.0x then-current base salary (on top of standard severance) . |
| 280G Treatment | Best-net approach or cutback to avoid excise tax, whichever yields greater after-tax value . |
| Non-Compete / Business Protection | Business Protection Agreement dated Mar 25, 2019 remains in effect; scope referenced in employment letter exhibits; terms enforced via severance plan conditions . |
| Equity Vesting | CEO 2025 grant: RSUs and options totaling $1,000,000 value; vest 1/3 annually from first anniversary; option exercise price at grant-date FMV . |
Board Governance
- Board Service: Appointed to the Board effective June 20, 2025; Board size increased to six .
- Committee Roles: None disclosed for Silvestro; Board committees composed entirely of independent directors .
- Leadership Structure: Independent Chair; CEO and Chair roles separated (current/prior year) .
- Independence: As CEO, Silvestro is an inside director; OPRX reaffirms committee independence and executive sessions for independent directors .
- Meeting Attendance: In 2024, the Board met 16 times; each incumbent director attended at least 75% of Board and committee meetings .
- Director Pay: Employee directors receive no additional compensation for Board service; non-employee director program includes $40,000 base cash retainer and ~$150,000 annual equity, plus committee retainers .
Director Compensation
| Component | Amount/Policy |
|---|---|
| Annual Cash Retainer (non-employee directors) | $40,000 . |
| Annual Equity Grant (non-employee directors) | ~$150,000 grant-date value . |
| Additional Chair Retainer | $40,000 . |
| Committee Retainers | Audit Chair $20,000; Audit member $10,000; Comp Chair $10,000; Comp member $5,000; N&G Chair $8,000; N&G member $4,000 . |
| Employee Directors | No additional pay for Board service . |
| Aggregate Limits | $750,000 per director per year; $1,000,000 in first year for new director . |
Performance & Track Record
| Metric | 2022 | 2023 | 2024 |
|---|---|---|---|
| TSR – Value of $100 investment | $53.92 | $45.92 | $7.82 |
| Net Income (Loss) ($) | $(11,438,440) | $(17,565,866) | $(20,110,000) |
| Revenue ($) | — | — | $92,127,044 (basis for bonus) |
| Adjusted EBITDA ($) | — | — | $11,760,615 (bonus calc) |
Highlights: The Board cited Silvestro’s impact on brand relevance, omnichannel transformation, and plans to advance recurring revenue and Rule of 40 performance . Shareholder activism subsided after Whetstone withdrew director nominations following engagement and a commitment to add an independent director .
Compensation Structure Analysis
- Mix and alignment: 2024 awards combined options and time-based RSUs; CEO 2025 package split RSUs/options 50/50, vesting over three years—balancing retention with equity leverage .
- At-risk pay: Annual bonus tied 50/50 to revenue and Adjusted EBITDA, with payouts scaled from threshold to maximum; 2024 payout was 58.9% of target, evidencing pay-for-performance calibration .
- Governance tightening: Removal of 280G tax gross-ups in updated agreements; adoption of clawback and prohibition on hedging/pledging reduce shareholder-unfriendly features .
- Say-on-pay: 64.8% support in 2024 indicates investor scrutiny; the Compensation Committee is engaging to improve alignment .
Equity Ownership & Insider Selling Pressure
- Vested vs. unvested: Significant unexercisable option tranches and unvested RSUs vest ratably over 2025–2027, creating multi-year retention hooks and potential future sale events upon vesting .
- Trading constraints: Pre-clearance, blackout windows, and strict prohibitions on hedging/pledging/margin accounts mitigate misalignment and leverage risk .
- Ownership guidelines: CEO must maintain 3x salary in stock; until compliant, must retain 50% of net shares from vesting/exercise—reducing immediate selling pressure .
Compensation & Incentives (Detail)
| Item | Grant Date | Quantity/Terms | Vesting |
|---|---|---|---|
| RSUs (2024) | Feb 15, 2024 | 7,750 RSUs | 1/3 annually from 2/15/2025 . |
| RSUs (2024) | Dec 23, 2024 | 41,408 RSUs | 1/3 annually from 12/23/2025 . |
| Options (2024) | Dec 23, 2024 | 77,742 @ $4.83; fair value $199,999 | 1/3 annually from 12/23/2025; expires 12/22/2029 . |
| CEO Grant (2025) | First day post-blackout | $500k RSUs + $500k Options at FMV | 1/3 annually from grant anniversary . |
Employment Contracts, Severance, and Change-of-Control Economics
- Severance multiples: 1.5x salary in installments + target bonus lump sum + up to 12 months COBRA for termination without Cause/Good Reason .
- CIC protection: Additional 2.0x salary lump sum if termination occurs 3 months prior to or within 24 months post-CIC, on top of standard severance .
- Clawbacks and 280G: Erroneous incentive comp recoupment; best-net or cutback for 280G excise tax .
- At-will employment: Confirmed in CEO Employment Letter .
Board Service History, Committees, and Dual-Role Implications
- Service history: Appointed as director June 20, 2025; expands Board to six .
- Committees: Not assigned; all Board committees remain independent-only .
- Dual-role implications: Independent Chair structure and independent-only committees mitigate concerns of CEO influence over oversight; independent directors meet in executive session at least quarterly .
- Attendance: Directors met attendance thresholds in 2024 (≥75% of meetings) .
- Director pay: Employee directors receive no additional board compensation .
Say-on-Pay & Shareholder Feedback
- 2024 say-on-pay approval: 64.8% .
- Management response: Ongoing engagement and program evaluation to strengthen pay-for-performance linkage .
Investment Implications
- Alignment: 2024/2025 incentive design ties cash bonuses to revenue and Adjusted EBITDA, and uses multi-year vesting in equity—supportive of long-term value creation and retention .
- Retention risk: Robust severance and CIC protections plus ownership guidelines reduce near-term attrition risk; multi-year vesting schedules create consistent retention incentives .
- Governance quality: Independent Chair, independent-only committees, clawback policy, and anti-hedging/pledging policies mitigate governance and trading misalignment risks .
- Shareholder scrutiny: Weak 2024 TSR and low say-on-pay support highlight execution risk; CEO’s plan to drive recurring revenue and Rule of 40 performance is a key catalyst to watch in 2025–2026 .