business owners standing in front of a bar

What We Offer
For Business Owners

Business Retirement Plan Services

Comprehensive fiduciary retirement plan services for your employees.

To attract the best employees, you need a valuable benefits package, and your retirement plan is a vital part. We'll handle the fiduciary duties so your employees can plan for their future.

Our Retirement Plan Services team is committed to assisting business owners and their employees with their retirement plan needs including:
  • Support plan sponsors in managing their ERISA fiduciary responsibilities to their plan, employees, and beneficiaries
  • Provide advice as ERISA 3(38) or 3(21) Fiduciary
  • Perform investment research, review and monitor fund investments to meet plan goals and objectives
  • Customized plan solutions including 401(k), 403(b), 457, 401(a), pension or profit sharing

For more information on retirement planning, please visit our Retirement Plan Participant Resource Center.

business retirement plan graphic

2023 Q3 Market Update

Contact our Retirement Plans Services Team

Sean McGarry, AIF®
First Vice President &
Retirement Plan Services Manager
Contact Sean
Kevin Flaherty
Vice President &
Retirement Plan Services Manager
Contact Kevin
Brian Rocha, CFP®, CRPC®
Vice President &
Retirement Plan Services Financial Consultant
Contact Brian

Not Insured by FDIC or Any Other Government Agency / Not Rockland Trust Guaranteed / Not Rockland Trust Deposits or Obligations / May Lose Value

Business Insurance

Protect your family. Protect you business. Protect your legacy.

Key Person Insurance: Provides continuity and financial protection if a partner or critical employee dies or becomes disabled.
Buy/Sell Agreement: Ensure the equitable and orderly transfer of business equity, ownership, and management in the event of the death of an owner.

Long-Term Care: Addresses the expense of extended care, safeguards your assets and preserves quality of life for you and your family.
Life Insurance: Choose from various types, coverage and terms to protect your family.
Disability Insurance: Replaces a major portion of your income if you're injured or become too sick to work.

Contact us to start the discussion

Not Insured by FDIC or Any Other Government Agency / Not Rockland Trust Guaranteed / Not Rockland Trust Deposits or Obligations / May Lose Value

Business Financial Planning

Financial plans customized for your business.

Your business plan is rock solid. Let us solidify your financial plan. We assist Massachusetts and Rhode Island businesses like yours by evaluating how your potential decisions could affect taxation, wealth preservation and overall financial security. Let's work together to get your business where you want it to go.
Focused on your company's financial health.

Guided by our financial planning services, your business's short and long-term goals can stay on track while we respond to any immediate needs based on changing circumstances. Our team works with you in multiple ways.
  • Evaluate your current financial position
  • Determine your business’s specific financial goals and risk
  • Develop a plan that suits the unique needs of your business

Contact us to start the discussion

Not Insured by FDIC or Any Other Government Agency / Not Rockland Trust Guaranteed / Not Rockland Trust Deposits or Obligations / May Lose Value

Business Investment Management

Protecting assets and building wealth.

Growing your business is your primary focus. Ours is making sure you have a business investment management plan to address your current needs and future goals. Join business owners throughout Massachusetts and Rhode Island who rely on our attentive advisors for insightful advice and responsible management services.

A better investment plan for your business.

Our investment managers determine how much capital you can invest while still having cash to address new opportunities. We'll design a portfolio to reflect the appropriate balance between higher returns and cautiousness. Rely on us to pull all the details together in a comprehensive strategy.
  • Establish a business financial plan based on your business’ needs and objectives
  • Create a customized portfolio designed for your business
  • Provide on-going investment advice that’s tailored to your business
  • Set up a retirement plan for you and your employees

Contact us to start the discussion

Not Insured by FDIC or Any Other Government Agency / Not Rockland Trust Guaranteed / Not Rockland Trust Deposits or Obligations / May Lose Value

Business Owner Advisory Services

Offering continuous guidance and support to business owners.
We specialize in guiding business owners through strategic planning, including internal or external succession planning, while de-risking the outcome and exploring strategies to increase the enterprise value of your business. From valuation to negotiations, our experts are dedicated to exploring optimal returns while protecting your legacy. Our advisory services are designed to help business owners navigate this complex process by examining their business and providing a personalized approach.
Your Legacy, Our Commitment.
One of the most important decisions a business owner must face is when and how to step out of the business – in other words, business succession planning. This event is likely to represent the most important and largest financial event in the life of the business owner. Our Business Owner Advisory Strategist is available to guide you, the business owner, through the process of establishing a thorough, well-conceived plan and developing strategies as you confront key questions.  

Secure the future of your business today with our comprehensive Business Owner Advisory Services:

Initial Guidance
We start by listening to you and your goals and will provide you with an initial guidance assessment for you to review and consider. This would include guidance on both your personal and professional considerations that factor into the decisions about your business plans, the financial impacts, and needs for retirement. There is no charge for your first consultation with our team.
Business Assessment and Strategy Development
We conduct a thorough analysis of your business with one goal in mind—to assess and strengthen the business’s ability to produce sustainable revenues and earnings. The objective is to ensure the business is properly positioned to achieve your personal financial objectives and to suggest ways to improve the value before a transaction. Our business assessment and strategy development written plan will emphasize value enhancement and de-risking strategies to position your company for success. After delivering the plan, we will provide ongoing advice to guide the owner towards implementing its recommendations and achieving its strategic objectives.

The goal is to provide business owners with access to a seasoned and experienced Business Owner Advisory Strategist. We know that business owners have more strategic options when a business can validate its human capital, structural capital, customer relationships, and culture that are less dependent on the owner, which collectively establishes durable revenues and earnings post owner transition. Our Business Owner Advisory Strategist works with you, the business owner, to develop and adhere to a unique plan for your business to enhance its value in the marketplace.

Transaction Execution

Once we have assessed the readiness of your business model, identified your drivers of strategic value, and helped you optimize the attractiveness of your business, we continue to help you explore enhanced value by facilitating your selection of transaction advisors and building a complete team to run an efficient and competitive transaction process. Your team of advisors would consist of both Rockland Trust and outside experts to ensure the success of your business transaction.

About Our Business Owner Advisory Strategist:

Meet Michael Cassata

Michael's main focus is providing strategic guidance and support to business owners, ensuring they are well positioned to sell or transition business ownership when the time is right. As a former business owner turned investment banker, Mike has over 20 years of experience supporting business owner's transition their organization into the next stage and has advised over 100 businesses on growth strategies and business models, in verticals from software to business services.

Michael Cassata
FVP, Business Owner Advisory Strategist
765 Main Street
Hyannis, MA 02601
Office: 508.957.1180

Start a Conversation with Michael

Not Insured by FDIC or Any Other Government Agency / Not Rockland Trust Guaranteed / Not Rockland Trust Deposits or Obligations / May Lose Value