Berkshire Hills Bancorp : 2024 Notice of Meeting and Proxy Statement

CEO, Nitin J. Mhatre

Chairperson, David M. Brunelle

April 5, 2024

Dear Berkshire Hills Bancorp Shareholder:

It is our pleasure to invite you to attend the 2024 Annual Meeting of Shareholders, which will be held on Thursday, May 16, 2024 at 10:00 a.m, Eastern Time at our offices at:

Berkshire Bank

99 North Street

Pittsfield, MA 01201

Please see the Notice of Annual Meeting on the next page for more information about our meeting procedures.

We urge you to vote your proxy online, or by telephone, or by completing and returning a proxy card by mail as soon as possible, even if you plan to attend the Annual Meeting.

Your vote is important to us. Thank you for your attention to the enclosed materials, and for your continued support of our company.

Nitin J. Mhatre, Chief Executive Officer

David M. Brunelle, Chairperson of the Board of Directors

Table of Contents

• BERKSHIRE HILLS BANCORP, INC. | 2024 Proxy Statement

Berkshire Hills Bancorp, Inc.

Proxy Statement

Proxy Statement Summary

This summary gives you an overview of selected information in this year's proxy statement. We encourage you to read the entire proxy statement carefully before voting. We have also provided you with the 2023 Summary Annual Report and the 2023 Annual Report on SEC Form 10-K.

Annual Meeting of Shareholders

Time and Date: 10:00 a.m. Eastern Time, Thursday, May 16, 2024

Place: Berkshire Bank, 99 North Street, Pittsfield, Massachusetts 01201

Record Date: Shareholders as of the close of business on March 21, 2024 are entitled to vote

We are providing this proxy statement to you in connection with the solicitation of proxies for the 2024 Annual Meeting of Shareholders and to transact any other business that may properly come before the meeting. In this proxy statement, we also refer to Berkshire Hills Bancorp, Inc. as "Berkshire" or the "Company". We also refer to its subsidiary, Berkshire Bank, as the "Bank". We are mailing a notice of the Annual Meeting and this proxy statement to shareholders of record as of March 21, 2024, beginning on or about April 5, 2024.

Summary of Proposals for 2024

1 - Election of Directors. The Company's Board of Directors is presenting eleven (11) nominees for election as directors at our Annual Meeting. Two of the thirteen current directors, Messrs. Adofo-Wilson and Zaitzeff, are not standing for re-election. Director Callahan was appointed by the Board in September 2023. All nominees currently serve as directors on our Board of Directors. In 2023, all director nominees received at least 98% of the votes cast regarding their nomination. Provided with this proposal is information about our directors, director nominees, corporate governance, and director compensation.

2 - Advisory Vote on Executive Compensation. This advisory vote is for the approval of the Company's Named Executive Officer compensation as set forth within this proxy statement. Berkshire strives to promote shareholder value and sound risk management by aligning executive pay and company performance. The Compensation Discussion and Analysis ("CD&A") explains the Board's processes and decisions with respect to executive compensation. In 2023, 97% of the votes cast were in favor of the proposal "FOR" the advisory approval of our Executive Compensation. Provided with this proposal is the Compensation Discussion and Analysis, the Compensation Committee Report, and Summary Compensation and Other Tables.

3 - Ratification of Independent Registered Public Accounting Firm. This advisory vote ratifies the selection of Crowe LLP ("Crowe") as the Company's independent registered public accounting firm for fiscal year 2024. Crowe has served in this capacity since fiscal year 2017. In 2023, 99% of the votes cast were in favor of the proposal for the appointment of Crowe.

• BERKSHIRE HILLS BANCORP, INC. | 2024 Proxy Statement

PROXY STATEMENT | PROXY STATEMENT SUMMARY

2023 Company Highlights

Berkshire had a solid year of performance in 2023, building on core elements of its strategy to strengthen operations, deliver growth, and improve its long-term outlook. Earnings per share ("EPS") totaled $1.60 in 2023 compared to $2.02 in 2022. Results in 2023 included a $25 million ($0.58 per share) non- operating charge for the sale of securities. The Company's non-GAAP measure of operating earnings totaled $2.14 per share in 2023 compared to $2.19 in 2022. This measure is reconciled to GAAP measures in Exhibit A.

Bank industry operations in 2023 were affected by rising market interest rates and the related impacts on profitability, liquidity and capital, especially following a banking emergency in the first quarter that resulted in the second, third, and fourth largest bank failures in U.S. history. Berkshire maintained steady operations and proactively responded to changing industry conditions while also pursuing its longer term strategic objectives:

• Talent Recruitment. The Company opportunistically recruited executives and front-line commercial relationship talent with an emphasis on deposit, private banking, and wealth management professionals.
• Balance Sheet Growth. Total loans increased 8% and total deposits increased 3% year-over-year, producing a 7% increase in net interest income.
• Balance Sheet Strength. Capital, liquidity, and asset quality metrics all remained solid and supportive of financial soundness, organic growth, and shareholder returns through dividends and buybacks.
• Expense Management. Ongoing procurement and optimization activities resulted in further branch consolidations, the sales of excess premises, and a workforce realignment.
• Technology. The Company introduced its new mobile/digital banking platform, which positions the Bank well to respond to changing customer needs and competitive market offerings.
• Corporate Responsibility. Human capital management practices contributed to record high employee engagement and improved retention. ESG ratings remained in the banking sector top quartile. Berkshire allocated an amount equal to its landmark $100 million sustainability bond to create affordable/workforce housing and green development.

Due to the challenges of the environment, one year and two year total shareholder return was negative for Berkshire, its proxy peers, and the KBW Regional Banking Index (KRX). While Northeastern banks underperformed this national index in both years, Berkshire was favorable to both its proxy peers and the national index for the two year TSR. Over three years, BHLB's 55% TSR exceeded both of these industry groups as well as the S&P 500 index (SPX).

2023 Executive Compensation Highlights

Included later in this report are compensation tables, including a Summary Compensation Table which details executive compensation provided in 2023, as well as a Compensation Discussion and Analysis which provides information about the compensation management process and compensation decisions.

The Compensation Committee maintained the same overall balanced structure for compensation management in 2023.

• Direct compensation includes salary, the cash-basedshort-term incentive, and the equity-basedlong-term incentive.
• Performance based compensation constitutes the majority of targeted direct compensation.

For those Named Executive Officers who served in their positions for the full year, total targeted direct compensation increased 7% year-over-year, reflecting higher salaries and incentives. Total direct compensation earned by these positions was 1% below target and decreased by 8% year-over-year, including the impact of performance below objectives in 2023.

The Committee's decisions resulted in a compensation structure that rewarded the achievement of Company objectives and decreased compensation from targets where objectives were not met. Compensation management was aligned with shareholder interests and provides ongoing incentives to improve shareholder value.

• BERKSHIRE HILLS BANCORP, INC. | 2024 Proxy Statement

PROXY STATEMENT | PROXY STATEMENT SUMMARY

Shareholder Engagement and Responsiveness

In addition to its active outreach and interactions with the investment community, the Company also solicits discussion and feedback annually on corporate stewardship with its thirty largest institutional shareholders.

During 2023, the most frequent topics in these discussions included processes for managing board membership and shareholder meetings; governance of corporate sustainability programs; management of growth, efficiency, and employee turnover; and connecting strategy and compensation through the Company.

There is discussion related to these matters in following sections of the proxy statement. Based on the affirmative shareholder vote of 97% or higher for all items on last year's Annual Meeting agenda and based on investor feedback and recognition of Berkshire's vision, positioning, and initiatives, we believe that our investors are strongly supportive of our programs for governance and company performance.

Corporate Responsibility and Sustainability

Berkshire's Approach

Since its founding in 1846, Berkshire remains a purpose-driven and values-guided institution working to achieve its vision of becoming a high-performing,relationship-driven,community-focused bank. Berkshire empowers the financial potential of its stakeholders by delivering industry-leading financial expertise and a full suite of tailored banking solutions through its consumer banking, commercial banking and wealth management divisions to clients in New England and New York. For more than 175 years, Berkshire has provided strength, stability and trusted advice to create a positive impact for its clients and communities while upholding equitable, ethical, responsible and sustainable business practices.

Berkshire's longstanding commitment to operating equitably, responsibly and sustainably is interwoven into the company's vision, mission, business practices, and strategic goals. Berkshire's integrated approach to managing environmental, social and governance externalities helps reduce risk and unlock new business opportunities to create an ecosystem of positive impact and value, which in turn drives Berkshire's commercial performance, creating capacity to invest more in its business, employees, customers, shareholders and communities.

2023 Highlights

• Record high employee engagement contributing to declining turnover
• Allocated an amount equal to the proceeds of Berkshire's $100MM sustainability bond to create affordable/ workforce housing and green building development
• 100% on-premises renewable electricity and reduced Greenhouse Gas emissions
• Recognized with the Communitas Award for Leadership in Corporate Social Responsibility, named one of America's Most Trustworthy Companies and America's Best Regional Banks by Newsweek and America's Best Midsize Employers by Forbes.
• Top 20% aggregated ESG rating*, achieving one of five major strategic goals

*National ranking among U.S. banks as of December 31, 2023

Oversight & Responsibility

The management of material environmental, social and governance factors is integral to Berkshire's business practices, risk management program, competitive positioning and its ability to deliver on its strategic priorities and vision. Berkshire was one of the first banks in the country to establish a dedicated committee of its Board of Directors to oversee corporate culture, diversity and sustainability. The Company is a leader among community banks in integrating these practices into its business strategy and operations.

The Company's strong foundation of governance systems include:

• Board level oversight of Culture, Sustainability, Community, Climate Change, and Diversity
• Environmental, Social and Governance (ESG) Committee
• Responsible & Sustainable Business Policy and Climate Risk Management Program
• Lending, credit, deposit and investment policies which incorporate environmental and social considerations along with due diligence requirements
• Active involvement from business unit leaders and front lines in managing externalities and risks
• Senior leadership for corporate responsibility and sustainability

• BERKSHIRE HILLS BANCORP, INC. | 2024 Proxy Statement

PROXY STATEMENT | PROXY STATEMENT SUMMARY

The Board of Directors including its Corporate Responsibility & Culture Committee (CRCC) has ultimate oversight responsibility for environmental, social and governance matters. The CRCC meets quarterly to review performance, examine related risks, and approve relevant policies. Berkshire's comprehensive approach ensures that the board receives regular reports from management on environmental and social dimensions of its business such as human capital management, diversity, stakeholder relations, climate change, community impact, and cybersecurity. It allows the board to develop a sufficient understanding of the Company's impacts, management's programs to mitigate those risks and capture opportunities. It helps inform strategic planning, create accountability and, along with management committees and senior leaders, provides visibility throughout the organization.

Berkshire regularly engages directly with its stakeholders to share information about the progress it's made in its performance, including through its website, corporate annual report, and proxy statement. Additionally, Berkshire's Sustainability Report, which is informed by Sustainability Accounting Standards Board ("SASB") and Task Force on Climate-Related Financial Disclosure (TCFD) disclosure standards, details the Company's programs and performance. The report is available at berkshirebank.com/esg

Climate Change

Climate change manifesting in the form of both physical or transition risks could adversely affect either directly or indirectly, Berkshire's operations, businesses, customers, communities, and its stakeholders. As the transition to a low-carbon economy accelerates, new policies emerge, and market dynamics shift, Berkshire expects that its efforts to manage its environmental footprint, mitigate the risks associated with climate change, and support the transition will allow it to strengthen its competitive positioning. The Company continues to evolve its practices to align with its mission, current and expected regulations as well as the size, scope, and complexity of its operations.

Climate change and its associated physical and transition risks are managed through Berkshire's formal Climate Risk Management Program which outlines roles and responsibilities for the board, management and all employees, definitions, along with procedures for identifying, measuring and assessing climate risk. The program also lays out Berkshire's system of controls which include governance mechanisms, formal policies, due diligence and insurance requirements, exclusionary criteria, business continuity planning, external relations, and employee education. Finally, the program sets expectations for responses to risk events or elevated risk levels, reporting and external disclosure. Further information on Berkshire's environmental sustainability activities and its approach to governance, risk management, strategy, metrics & targets and next steps can be found in its most recent Sustainability Report.

Equity & Inclusion

Creating a diverse, accessible, inclusive and equitable workplace is an essential enabler to advancing the Company's strategic goals, social and environmental commitments and vision. Ultimately Berkshire's goal is to attract and retain individuals from a wide range of backgrounds, cultures and experiences so that the workforce, executives and board composition reflect the diversity of the communities in which it operates. It also seeks to ensure equity, accessibility, fairness and impartiality in all aspects of the Company's workplace, banking practices and financial solutions while fostering an inclusive environment where all employees feel valued, respected and empowered.

The Company advances those goals through an integrated approach that includes:

• Strong oversight and governance practices through the Corporate Responsibility & Culture Committee of the Board of Directors and management committees
• Talent management and recruitment
• Education and training and workplace programming
• Seven employee resource groups
• Workplace programming
• Multicultural community engagement
• Equitable product and service development and supplier diversity

Additional detailed information on Berkshire's Human Capital Management and Diversity, Equity & Inclusion practices can be found in the Company's annual SEC report on Form 10-K and annual Sustainability Report, which details the company's environmental, social and governance programs.

• BERKSHIRE HILLS BANCORP, INC. | 2024 Proxy Statement

Proposal 1:

Election of Directors for a One-

Year Term

The Company's Board of Directors has nominated and recommends a vote "FOR" each of the eleven (11) nominees listed below for election as a director. All of the nominees currently serve on the Company's Board of Directors.

Background. The Company's Board of Directors is presenting eleven (11) nominees for election as directors at our Annual Meeting. Two of the thirteen current directors, Messrs. Adofo-Wilson and Zaitzeff, are not standing for re-election. All of the nominees currently serve as directors on the Company's Board of Directors. Each director elected at the meeting will serve for a one-year term until our 2025 Annual Meeting or until a successor is duly elected and qualified. Each director nominee has consented to being named in this proxy statement and to serving as a director if elected. If a nominee is unable to be a candidate when the election takes place, the shares represented by valid proxies will be voted in favor of the remaining nominees. The Board of Directors does not currently anticipate that any of the nominees will be unable to be a candidate for election.

Election. The affirmative vote of a plurality of the Company's outstanding common stock present at the Annual Meeting or by proxy at the Annual Meeting is required to elect the nominees for directors; provided, however, in the case of an uncontested election of directors, it is the Company's policy that if a director is elected by a plurality but not a majority of the votes cast for such director, such director must submit his or her resignation to the Board of Directors, which will be subject to review by the Corporate Governance/Nominating Committee of the Board of Directors. The Corporate Governance/Nominating Committee will then make a recommendation to the Board of Directors as to whether to accept or reject the director's resignation. Unless otherwise instructed, the proxy holders will vote the proxies received by them "FOR" the election of the nominees as directors.

THE BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS THAT SHAREHOLDERS VOTE "FOR" THE ELECTION OF ITS DIRECTOR NOMINEES.

• BERKSHIRE HILLS BANCORP, INC. | 2024 Proxy Statement