OptimizeRx Corp

Adoption of 10b5-1 Trading Plan

During the year ended December 31, 2023, certain of our officers and directors adopted Rule 10b5-1 trading arrangements as follows:

On June 15, 2023, Mr. William J. Febbo, the Chief Executive Officer of the Company, adopted a written plan for the purchase or sale of our securities that was intended to satisfy the affirmative defense conditions of Rule 10b5-1(c) (the “Febbo Rule 10b5-1 Trading Plan). The Febbo 10b5-1 Trading Plan, which has a term ofone year, provides for the sale of up to 300,000 shares of common stock pursuant to the terms therein.

On June 15, 2023, Ms. Marion Odence-Ford, the General Counsel & Chief Compliance Officer of the Company, adopted a written plan for the purchase or sale of our securities that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c) (the “Odence-Ford Rule 10b5-1 Trading Plan). The Odence-Ford 10b5-1 Trading Plan, which has a term ofone year, provides for the sale of up to 7,000 shares of common stock pursuant to the terms therein.

William Febbo’s Employment Agreement

On April 12, 2024, the Company entered into an amended and restated employment letter agreement with William J. Febbo (the “Febbo Employment Agreement”) which updates and supersedes in its entirety his prior employment agreement, as amended (the “Febbo Prior Employment Agreement”) to, among other things, eliminate the single trigger cash severance which was payable to Mr. Febbo in connection with a change in control, remove the Company’s 280G tax gross-up payment obligation afforded to Mr. Febbo under the Febbo Prior Employment Agreement, and provide for an equity grant to Mr. Febbo of 90,000 restricted stock units which vest over three years. In connection with the Febbo Employment Agreement, the Compensation Committee amended the OptimizeRx Corporation Executive Severance Plan to make Mr. Febbo a participant of such plan (as described below). As a result, all of Mr. Febbo’s prior rights to severance and change in control benefits under the Febbo Prior Employment Agreement were removed from the Febbo Employment Agreement. Mr. Febbo’s amended severance and/or change in control benefits are now set forth in full in the Amended Severance Plan (as defined below).

The foregoing summary of Mr. Febbo’s Employment Agreement is not complete and is qualified in its entirety by reference to the complete text of the Febbo Employment Agreement, a copy of which is filed as Exhibit 10.26 to this Form 10-K and is incorporated herein by reference.

Stephen Silvestro’s Employment Agreement

On April 12, 2024, the Company entered into an amended and restated employment letter agreement with Stephen Silvestro (the “Silvestro Employment Agreement”) which updates and supersedes in its entirety his prior employment agreement, as amended (the “Silvestro Prior Employment Agreement”) to, among other things, remove the Company’s 280G tax gross-up payment obligation afforded to Mr. Silvestro under the Silvestro Prior Employment Agreement.

The foregoing summary of Mr. Silvestro’s Employment Agreement is not complete and is qualified in its entirety by reference to the complete text of the Silvestro Employment Agreement, a copy of which is filed as Exhibit 10.27 to this Form 10-K and is incorporated herein by reference.

Amended Executive Severance Plan

On April 12, 2024, the Compensation Committee amended the OptimizeRx Corporation Executive Severance Plan (the “Amended Severance Plan”) to include Mr. Febbo as a participant in the Amended Severance Plan, to remove former and add new executive management team members, and to increase the Severance Benefits (as defined below) payable to Mr. Silvestro.

The Amended Severance Plan provides that if Mr. Febbo or Mr. Silvestro is terminated without cause or resigns for Good Reason, he will be paid (i) an amount equal to 1.5 times his base salary, paid in installments over 18 months, (ii) an amount equal to his target annual bonus in effect at the time of termination, paid in a lump sum, and (iii) payment by the Company of COBRA premiums for such executive and his spouse and eligible dependents for up to 12 months following termination (the payments in (i), (ii) and (iii) collectively referred to as “Severance Benefits”).

The Amended Severance Plan also provides Change in Control termination and death benefits to executive management team members. Mr. Silvestro’s benefits under such provisions were not changed in connection with the Amended Severance Plan. The Amended Severance Plan provides that if Mr. Febbo is terminated without cause or resigns for Good Reason three months prior to or 24 months following a Change in Control, in addition to the Severance Benefits, Mr. Febbo will be paid a lump sum payment equal to 5.0 times his then current base salary. The Severance Plan also provides that if Mr. Febbo is terminated due to death or disability, he (or his estate) will be paid an amount equal to his target annual bonus in effect at the time of termination, paid in a lump sum. Terms not otherwise defined herein have the meanings assigned to them in the Amended Severance Plan.

The foregoing description of the Amended Severance Plan is not complete and is qualified in its entirety by reference to the complete text of the Amended Severance Plan, a copy of which is filed as Exhibit 10.28 to this Form 10-K and is incorporated herein by reference.