Beacon Financial Corporation – Material Contracts Watch

from 8-K 9 pages Paul A. Perrault, at the Address on File With Beacon Financial Corporation. Dear Paul,

from 8-K 4 pages Beacon Financial Corporation Equity Award Treatment Upon Retirement (“Good Leaver”) Policy

from 10-K 5 pages Confidential February 26, 2025 Michael W. McCurdy 8 Sagamore Road Wellesley, Ma 02482 Re: Retention Bonus Dear Mr. McCurdy,

from 10-K 32 pages Material contract

from 10-K 28 pages Employment Agreement

from S-8 6 pages Non-Qualified Stock Option Agreement Under the Beacon Financial Corporation 2025 Stock Option and Incentive Plan

from S-8 6 pages Incentive Stock Option Agreement Under the Beacon Financial Corporation 2025 Stock Option and Incentive Plan

from S-8 4 pages Restricted Stock Unit Award Agreement Under the Beacon Financial Corporation 2025 Stock Option and Incentive Plan

from S-8 5 pages Restricted Stock Award Agreement Under the Beacon Financial Corporation 2025 Stock Option and Incentive Plan

from S-8 17 pages Section 1. General Purpose of the Plan; Definitions

from 8-K 5 pages This Retention Agreement (This “Agreement”) Is Entered Into by Wm. Gordon Prescott (The “Executive”), Berkshire Hills Bancorp, Inc. (“Berkshire”) and Berkshire Bank in Connection With the Agreement and Plan of Merger by and Among Berkshire, Commerce Acquisition Sub, Inc., and Brookline Bancorp, Inc. (“Brookline”), Dated as of December 16, 2024 (The “Merger Agreement”), Pursuant to Which: (I) Commerce Acquisition Sub, Inc. Will Merge With and Into Brookline (The “Merger”), And, Immediately Following the Merger, Brookline Will Merge With and Into Berkshire (The “Holdco Merger”) So That Berkshire Is the Surviving Corporation in the Holdco Merger, and (II) Following the Holdco Merger, Berkshire Bank Will Merge With and Into Brookline Bank, So That Brookline Bank Is the Surviving Corporation (The “Bank Merger”) (References to the “Bank” Herein Refer to Berkshire Bank for Periods Prior to the Bank Merger and to Brookline Bank for Periods Following the Bank Merger). 1. Effectiveness and Definitions

from 8-K 5 pages This Retention Agreement (This “Agreement”) Is Entered Into by Jacqueline Courtwright (The “Executive”), Berkshire Hills Bancorp, Inc. (“Berkshire”) and Berkshire Bank in Connection With the Agreement and Plan of Merger by and Among Berkshire, Commerce Acquisition Sub, Inc., and Brookline Bancorp, Inc. (“Brookline”), Dated as of December 16, 2024 (The “Merger Agreement”), Pursuant to Which: (I) Commerce Acquisition Sub, Inc. Will Merge With and Into Brookline (The “Merger”), And, Immediately Following the Merger, Brookline Will Merge With and Into Berkshire (The “Holdco Merger”) So That Berkshire Is the Surviving Corporation in the Holdco Merger, and (II) Following the Holdco Merger, Berkshire Bank Will Merge With and Into Brookline Bank, So That Brookline Bank Is the Surviving Corporation (The “Bank Merger”) (References to the “Bank” Herein Refer to Berkshire Bank for Periods Prior to the Bank Merger and to Brookline Bank for Periods Following the Bank Merger). 1. Effectiveness and Definitions

from S-4 5 pages Confidential February 26, 2025 Michael W. McCurdy 8 Sagamore Road Wellesley, Ma 02482 Re: Retention Bonus Dear Mr. McCurdy,

from S-4 5 pages February 26, 2025 Carl M. Carlson 4 Temple Road Wellesley, Ma 02482 Re: Retention Bonus Dear Mr. Carlson,

from S-4 2 pages Fifth Amendment to Employment Agreement

from 425 33 pages Employment Agreement

from 8-K 33 pages Employment Agreement

from 8-K 29 pages Form of Registration Rights Agreement

from 425 29 pages Form of Registration Rights Agreement

from 425 46 pages Form of Securities Purchase Agreement by and Among Berkshire Hills Bancorp, Inc. and the Other Signatories Thereto [•], 2024