Zaitzeff Michael

SEC source: 0000921895-24-000533 · form412910003_02222024.xml · nonDerivative · entry 2

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · VM GP VII

Disclosed balance after: 0

F2 · ownership.nature: Securities of the Issuer beneficially owned directly by VM GP VII LLC ("VM GP VII"). The Reporting Person, as a managing member of VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by VM GP VII.

F4 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-24-000533 · form412910003_02222024.xml · nonDerivative · entry 1

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · VM GP VII

Disclosed balance after: 11,855

F1 · price: The price reported in column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $22.3050 to $22.5000. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F2 · ownership.nature: Securities of the Issuer beneficially owned directly by VM GP VII LLC ("VM GP VII"). The Reporting Person, as a managing member of VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by VM GP VII.

F4 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-24-000515 · form412910003_02162024.xml · nonDerivative · entry 3

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · VM GP VII

Disclosed balance after: 38,855

F4 · price: The price reported in column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $22.3700 to $22.4516. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F2 · ownership.nature: Securities of the Issuer beneficially owned directly by VM GP VII LLC ("VM GP VII"). The Reporting Person, as a managing member of VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by VM GP VII.

F6 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-24-000515 · form412910003_02162024.xml · nonDerivative · entry 2

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · VM GP VII

Disclosed balance after: 63,765

F3 · price: The price reported in column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $22.7123 to $22.7300. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F2 · ownership.nature: Securities of the Issuer beneficially owned directly by VM GP VII LLC ("VM GP VII"). The Reporting Person, as a managing member of VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by VM GP VII.

F6 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-24-000515 · form412910003_02162024.xml · nonDerivative · entry 1

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · VM GP VII

Disclosed balance after: 87,947

F1 · price: The price reported in column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $21.9667 to $22.0400. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F2 · ownership.nature: Securities of the Issuer beneficially owned directly by VM GP VII LLC ("VM GP VII"). The Reporting Person, as a managing member of VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by VM GP VII.

F6 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-24-000407 · form412910003_02132024.xml · nonDerivative · entry 3

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · VM GP VII

Disclosed balance after: 108,447

F4 · price: The price reported in column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $21.8800 to $22.1565. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F2 · ownership.nature: Securities of the Issuer beneficially owned directly by VM GP VII LLC ("VM GP VII"). The Reporting Person, as a managing member of VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by VM GP VII.

F6 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-24-000407 · form412910003_02132024.xml · nonDerivative · entry 2

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · VM GP VII

Disclosed balance after: 127,147

F3 · price: The price reported in column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $23.0600 to $23.1561. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F2 · ownership.nature: Securities of the Issuer beneficially owned directly by VM GP VII LLC ("VM GP VII"). The Reporting Person, as a managing member of VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by VM GP VII.

F6 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-24-000407 · form412910003_02132024.xml · nonDerivative · entry 1

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · VM GP VII

Disclosed balance after: 156,209

F1 · price: The price reported in column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $22.7217 to $22.7400. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F2 · ownership.nature: Securities of the Issuer beneficially owned directly by VM GP VII LLC ("VM GP VII"). The Reporting Person, as a managing member of VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by VM GP VII.

F6 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-24-000279 · form412910003_02082024.xml · nonDerivative · entry 8

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

SEC source: 0000921895-24-000279 · form412910003_02082024.xml · nonDerivative · entry 7

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 400

SEC source: 0000921895-24-000279 · form412910003_02082024.xml · nonDerivative · entry 6

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 800

SEC source: 0000921895-24-000279 · form412910003_02082024.xml · nonDerivative · entry 5

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,300

SEC source: 0000921895-24-000279 · form412910003_02082024.xml · nonDerivative · entry 4

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,900

SEC source: 0000921895-24-000279 · form412910003_02082024.xml · nonDerivative · entry 3

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · VM GP VII

Disclosed balance after: 176,927

F4 · price: The price reported in column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $22.4953 to $22.6400. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F2 · ownership.nature: Securities of the Issuer beneficially owned directly by VM GP VII LLC ("VM GP VII"). The Reporting Person, as a managing member of VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by VM GP VII.

F6 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-24-000279 · form412910003_02082024.xml · nonDerivative · entry 2

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · VM GP VII

Disclosed balance after: 200,054

F3 · price: The price reported in column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $22.1943 to $22.2000. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F2 · ownership.nature: Securities of the Issuer beneficially owned directly by VM GP VII LLC ("VM GP VII"). The Reporting Person, as a managing member of VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by VM GP VII.

F6 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-24-000279 · form412910003_02082024.xml · nonDerivative · entry 1

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · VM GP VII

Disclosed balance after: 219,714

F1 · price: The price reported in column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $22.3024 to $22.5680. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F2 · ownership.nature: Securities of the Issuer beneficially owned directly by VM GP VII LLC ("VM GP VII"). The Reporting Person, as a managing member of VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by VM GP VII.

F6 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-24-000206 · form412910003_02052024.xml · nonDerivative · entry 3

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · VM GP VII

Disclosed balance after: 238,108

F3 · price: The price reported in column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $22.6000 to $22.6671. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F2 · ownership.nature: Securities of the Issuer beneficially owned directly by VM GP VII LLC ("VM GP VII"). The Reporting Person, as a managing member of VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by VM GP VII.

F5 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-24-000206 · form412910003_02052024.xml · nonDerivative · entry 2

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · VM GP VII

Disclosed balance after: 258,547

F2 · ownership.nature: Securities of the Issuer beneficially owned directly by VM GP VII LLC ("VM GP VII"). The Reporting Person, as a managing member of VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by VM GP VII.

F5 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-24-000206 · form412910003_02052024.xml · nonDerivative · entry 1

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · VM GP VII

Disclosed balance after: 268,064

F1 · price: The price reported in column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $23.2300 to $23.2951. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F2 · ownership.nature: Securities of the Issuer beneficially owned directly by VM GP VII LLC ("VM GP VII"). The Reporting Person, as a managing member of VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by VM GP VII.

F5 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-24-000172 · form412910003_01312024.xml · nonDerivative · entry 5

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · VM GP VII

Disclosed balance after: 288,483

F6 · price: The price reported in column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $24.2600 to $24.7377. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F3 · ownership.nature: Securities of the Issuer beneficially owned directly by VM GP VII. The Reporting Person, as a managing member of VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by VM GP VII.

F8 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-24-000172 · form412910003_01312024.xml · nonDerivative · entry 4

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Stock Award IV

Disclosed balance after: 2,595

F5 · ownership.nature: Stock Awards granted pursuant to the Berkshire Hills Bancorp, Inc. 2018 Equity Compensation Plan vest 100% on January 30, 2025.

F8 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-24-000172 · form412910003_01312024.xml · nonDerivative · entry 3

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · VM GP VII

Disclosed balance after: 308,511

F4 · price: The price reported in column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $25.0500 to $25.2461. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F3 · ownership.nature: Securities of the Issuer beneficially owned directly by VM GP VII. The Reporting Person, as a managing member of VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by VM GP VII.

F8 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-24-000172 · form412910003_01312024.xml · nonDerivative · entry 2

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · VM GP VII

Disclosed balance after: 349,785

F2 · price: The price reported in column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $25.0950 to $25.2527. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F3 · ownership.nature: Securities of the Issuer beneficially owned directly by VM GP VII. The Reporting Person, as a managing member of VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by VM GP VII.

F8 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-24-000172 · form412910003_01312024.xml · nonDerivative · entry 1

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · HOF III Fund

Disclosed balance after: 0

F1 · ownership.nature: Securities of the Issuer beneficially owned directly by HOF III Liquidating Partnership L.P. ("HOF III Fund"). VM GP VII LLC ("VM GP VII"), as the general partner of HOF III Fund, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HOF III Fund. HoldCo Asset Management, LP ("HoldCo Asset Management"), as the investment manager of HOF III Fund, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HOF III Fund. VM GP II LLC ("VM GP II"), as the general partner of HoldCo Asset Management, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HOF III Fund. The Reporting Person, as a managing member of each of VM GP II and VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HOF III Fund.

F8 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-23-000230 · form412910003_02012023.xml · nonDerivative · entry 1

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · By Stock Award III

Disclosed balance after: 2,141

F1 · ownership.nature: Stock Awards granted pursuant to the Berkshire Hills Bancorp, Inc. 2018 Equity Compensation Plan vest 100% on January 30, 2024. HOF III Liquidating Partnership L.P. ("HOF III Fund") and VM GP VII LLC ("VM GP VII") will each receive its proportionate share of the economic benefits, if any, of this Stock Award.

F7 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-22-001718 · form412910003_05182022.xml · nonDerivative · entry 4

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · HOF III Fund

Disclosed balance after: 0

F2 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-22-000892 · form412910003_03162022.xml · nonDerivative · entry 5

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · HOF III Fund

Disclosed balance after: 1,274,279

F8 · kind: HOF III Fund received 1,274,279 shares of common stock of the Issuer in the Holdco Fund Distribution.

F8 · shares: HOF III Fund received 1,274,279 shares of common stock of the Issuer in the Holdco Fund Distribution.

F8 · price: HOF III Fund received 1,274,279 shares of common stock of the Issuer in the Holdco Fund Distribution.

F2 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

F9 · ownership.nature: Securities of the Issuer beneficially owned directly by HOF III Fund. VM GP VII, as the general partner of HOF III Fund, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HOF III Fund. HoldCo Asset Management, as the investment manager of HOF III Fund, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HOF III Fund. VM GP II, as the general partner of HoldCo Asset Management, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HOF III Fund. The Reporting Person, as a managing member of each of VM GP II and VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HOF III Fund.

SEC source: 0000921895-22-000892 · form412910003_03162022.xml · nonDerivative · entry 4

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · VM GP VII

Disclosed balance after: 398,923

F6 · kind: VM GP VII received 398,923 shares of common stock of the Issuer in the Holdco Fund Distribution.

F6 · shares: VM GP VII received 398,923 shares of common stock of the Issuer in the Holdco Fund Distribution.

F6 · price: VM GP VII received 398,923 shares of common stock of the Issuer in the Holdco Fund Distribution.

F2 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

F7 · ownership.nature: Securities of the Issuer beneficially owned directly by VM GP VII. The Reporting Person, as a managing member of VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by VM GP VII.

SEC source: 0000921895-22-000892 · form412910003_03162022.xml · nonDerivative · entry 3

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · By HoldCo Opportunities Fund III

Disclosed balance after: 0

F5 · kind: On March 16, 2022, Holdco Fund engaged in a distribution of all the shares of common stock of the Issuer beneficially owned by it to HOF III Liquidating Partnership L.P. ("HOF III Fund") and VM GP VII for no consideration (the "Holdco Fund Distribution"). Represents the distribution of 1,673,202 shares of common stock of the Issuer held by Holdco Fund pursuant to the Holdco Fund Distribution.

F5 · shares: On March 16, 2022, Holdco Fund engaged in a distribution of all the shares of common stock of the Issuer beneficially owned by it to HOF III Liquidating Partnership L.P. ("HOF III Fund") and VM GP VII for no consideration (the "Holdco Fund Distribution"). Represents the distribution of 1,673,202 shares of common stock of the Issuer held by Holdco Fund pursuant to the Holdco Fund Distribution.

F5 · price: On March 16, 2022, Holdco Fund engaged in a distribution of all the shares of common stock of the Issuer beneficially owned by it to HOF III Liquidating Partnership L.P. ("HOF III Fund") and VM GP VII for no consideration (the "Holdco Fund Distribution"). Represents the distribution of 1,673,202 shares of common stock of the Issuer held by Holdco Fund pursuant to the Holdco Fund Distribution.

F1 · ownership.nature: Securities of the Issuer beneficially owned directly by HoldCo Opportunities Fund III, L.P. ("HoldCo Fund"). VM GP VII LLC ("VM GP VII"), as the general partner of HoldCo Fund, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HoldCo Fund. HoldCo Asset Management, LP ("HoldCo Asset Management"), as the investment manager of HoldCo Fund, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HoldCo Fund. VM GP II LLC ("VM GP II"), as the general partner of HoldCo Asset Management, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HoldCo Fund. The Reporting Person, as a managing member of each of VM GP II and VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HoldCo Fund.

F2 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

SEC source: 0000921895-22-000289 · form412910003_02012022.xml · nonDerivative · entry 1

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · By Stock Award II

Disclosed balance after: 2,248

F1 · ownership.nature: Securities of the Issuer beneficially owned directly by HoldCo Opportunities Fund III, L.P. ("HoldCo Fund"). VM GP VII LLC ("VM GP VII"), as the general partner of HoldCo Fund, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HoldCo Fund. HoldCo Asset Management, LP ("HoldCo Asset Management"), as the investment manager of HoldCo Fund, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HoldCo Fund. VM GP II LLC ("VM GP II"), as the general partner of HoldCo Asset Management, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HoldCo Fund. The Reporting Person, as a managing member of each of VM GP II and VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HoldCo Fund.

F2 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

F4 · ownership.nature: Stock Awards granted pursuant to the Berkshire Hills Bancorp, Inc. 2018 Equity Compensation Plan vest 100% on January 30, 2023. HoldCo Fund (as defined above) receives the economic benefit, if any, of this Stock Award.

SEC source: 0000921895-21-001766 · form412910003_07062021.xml · nonDerivative · entry 1

Zaitzeff Michael · CIK 0001861474 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · By Stock Award I

Disclosed balance after: 1,571

F1 · ownership.nature: Stock Awards granted pursuant to the Berkshire Hills Bancorp, Inc. 2018 Equity Compensation Plan vest in three equal annual installments beginning on January 30, 2022. HoldCo Fund (as defined below) receives the economic benefit, if any, of this Stock Award.

F2 · ownership.nature: Securities of the Issuer beneficially owned by HoldCo Opportunities Fund III, L.P. ("HoldCo Fund"). VM GP VII LLC ("VM GP VII"), as the general partner of HoldCo Fund, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HoldCo Fund. HoldCo Asset Management, LP ("HoldCo Asset Management"), as the investment manager of HoldCo Fund, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HoldCo Fund. VM GP II LLC ("VM GP II"), as the general partner of HoldCo Asset Management, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HoldCo Fund. The Reporting Person, as a managing member of each of VM GP II and VM GP VII, may be deemed the beneficial owner of the securities of the Issuer beneficially owned by HoldCo Fund.

F3 · ownership.nature: The Reporting Person disclaims beneficial ownership of the securities of the Issuer reported herein except to the extent of his pecuniary interest therein, and this report shall not be deemed to be an admission that the Reporting Person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose.