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Coordinating Life Insurance Strategies with a Buy-Sell Agreement

November 6, 2026 · Paul Hickey

A buy-sell agreement can give you a plan for what happens when an owner dies, becomes disabled, retires, or leaves the business. Yet the agreement only works if there is a realistic way to fund the purchase. Without available funds, the remaining owners may struggle to buy the departing owner’s interest while keeping the business running.

Life insurance strategies are often part of the answer for death-related buy-sell obligations. At Legacy Wealth Management, we help clients consider how insurance decisions may connect with investment management, retirement planning, and legacy-focused goals. Your attorney and tax professional should review the legal and tax details that apply to your circumstances.

Protect Your Business and Family From an Unexpected Exit

When an owner dies, their family may need liquidity, while the business may need stability. A properly coordinated life insurance policy may provide funds for the planned ownership transition, helping surviving owners purchase the deceased owner’s interest without quickly selling business assets or taking on substantial debt.

That can benefit everyone involved. Remaining owners may preserve business continuity, and the deceased owner’s family may have a clearer path for receiving the value of that ownership interest.

Still, life insurance is not a universal funding source for every exit event. Disability, retirement, divorce, bankruptcy, or a voluntary sale can create different funding needs. We encourage you to view the buy-sell agreement, insurance policies, ownership structure, and personal estate goals as connected pieces of one plan.

Match Insurance Coverage to Your Buy-Sell Terms

Your buy-sell agreement should spell out which events require or allow a purchase. It should also identify who will buy the ownership interest, how the price will be determined, and when the transaction must happen. Life insurance policies should support those terms, not create uncertainty at a difficult moment.

For death-related funding, the policy owner, beneficiary designation, and death benefit amount all matter. If those details do not match the agreement, the intended funds may not reach the right party in the expected way.

Business changes can make an older agreement less useful than it once was. We often recommend reviewing the arrangement when any of these changes occur:

Ownership percentages change

The business grows or takes on new debt

A family member becomes involved in the business

An owner’s retirement or succession plans shift

A business restructure changes the entity type

Legal counsel can review whether the agreement still reflects the owners’ intentions. Tax professionals can also help you understand tax considerations before changes are made to an agreement or insurance arrangement.

Choose a Structure That Fits Your Ownership Needs

Two common life insurance strategies are cross-purchase and entity-purchase arrangements. In a cross-purchase arrangement, owners may own policies on one another and use the proceeds to buy the deceased owner’s interest. In an entity-purchase arrangement, sometimes called a stock-redemption arrangement in certain corporate settings, the business owns the policy and may use the proceeds to redeem the owner’s interest.

Each approach can bring different administrative, ownership, tax, and estate planning considerations. A cross-purchase structure may become harder to manage when several owners are involved because multiple policies may be needed. An entity-purchase structure may be simpler in some situations, but its effects should be reviewed with qualified tax and legal professionals.

Coverage decisions should also look beyond the current business value. A policy may need to be considered alongside:

Expected business growth

Outstanding business debt

Key-person exposure

Policy duration and premium affordability

The ability of owners or the business to maintain premiums over time

Insurance should not be treated as a set-it-and-forget-it decision. As the company and its owners change, the funding plan may need attention as well.

Keep Valuations, Ownership, and Tax Details Aligned

An outdated valuation can weaken an otherwise thoughtful agreement. If the death benefit is much lower than the value of an owner’s interest, surviving owners could face a funding gap. If coverage is far higher than needed, the arrangement may no longer match the agreement’s purpose.

The agreement should clearly state how the business will be valued. Depending on the situation, that may involve a fixed value, a formula, an independent appraisal process, or another agreed-upon method. Since business value can shift after strong growth, a major operational change, or a change in profitability, regular reviews can help keep the agreement current.

Ownership and beneficiary information deserve the same attention. A marriage, divorce, estate plan update, ownership transition, entity restructuring, or change in succession plans may affect whether the current policy setup still works as intended. Before changing policy ownership, beneficiaries, or agreement terms, consult legal and tax professionals who understand your specific circumstances.

Use Year-End Reviews to Keep Coverage Current

Autumn can be a useful time to look ahead before a new year begins. A year-end review gives you and your professional team a chance to compare the business’s current reality with the documents and policies already in place.

Topics to review may include updated valuations, ownership percentages, policy death benefits, premium affordability, business debt, key employee changes, beneficiary designations, and planned retirement dates. It is also wise to discuss how insurance professionals and advisers are compensated when insurance is part of the plan. Some professionals may receive commissions related to insurance products, so clear disclosures and direct questions can help you understand how a recommendation fits your broader objectives.

A buy-sell agreement and its funding plan work best when they are reviewed together. Bringing the right questions to your attorney, tax professional, insurance professional, and our fiduciary wealth advisers can help you see where business ownership, retirement planning, investments, and legacy priorities may overlap.

An unexpected transition is never easy, but a current agreement, a realistic valuation, and properly aligned life insurance strategies can give your business and family a clearer path forward.

Bring Greater Clarity To Ownership Planning

When a buy-sell agreement is part of your succession plan, funding decisions deserve careful review as ownership and financial circumstances change. Legacy Wealth Management’s fiduciary wealth advisers can help you evaluate life insurance strategies in the context of your broader financial goals. Contact us to start a conversation about the factors that may matter to your planning.

Legacy Wealth Management, LLC is an investment adviser registered with the U.S. Securities and Exchange Commission. Registration does not imply a particular level of skill or training or constitute an endorsement by the SEC. This material is provided for informational and educational purposes only and is not intended as individualized investment, tax, or legal advice. Investing involves risk, including the potential loss of principal. The appropriateness of any investment strategy or financial plan depends on an individual's objectives, financial circumstances, risk tolerance, liquidity needs, time horizon, and other considerations.

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