Premiums are not deductible, and the rule is short. Internal Revenue Code section 264(a)(1) provides that no deduction shall be allowed for "premiums on any life insurance policy, or endowment or annuity contract, if the taxpayer is directly or indirectly a beneficiary under the policy or contract." Since being the beneficiary is the whole design of key person insurance, the premiums are a nondeductible cost of doing business. The mirror image confirms it: IRS Publication 334 lists as deductible "life insurance covering your employees if you are not directly or indirectly the beneficiary under the contract." Group life for staff is deductible; key person coverage is not.
The death benefit is not automatically tax-free, and this is the trap. Most people know life insurance proceeds are generally excluded from income under section 101(a). Section 101(j) narrows that for employer-owned contracts. Its general rule provides that for an employer-owned life insurance contract, "the amount excluded from gross income of an applicable policyholder by reason of paragraph (1) of subsection (a) shall not exceed an amount equal to the sum of the premiums and other amounts paid by the policyholder for the contract." In other words, the default is that everything above the premiums paid is taxable income to the business.
The exceptions in section 101(j)(2) restore the full exclusion, but they open with a condition that is easy to read past. They apply only "in the case of an employer-owned life insurance contract with respect to which the notice and consent requirements of paragraph (4) are met." Only then does the exclusion survive for an insured who "was an employee at any time during the 12-month period before the insured's death" or who, at the time the contract was issued, was "a director," "a highly compensated employee within the meaning of section 414(q)," or "a highly compensated individual within the meaning of section 105(h)(5)," with a modified percentage. A separate exception covers amounts paid to the insured's family, designated beneficiary, a trust for them, or the insured's estate, or used to buy an equity interest in the business from those persons.
The notice and consent are a pre-issuance formality with permanent consequences. Section 101(j)(4) sets three requirements, all of which must be satisfied "before the issuance of the contract." The employee must be "notified in writing that the applicable policyholder intends to insure the employee's life and the maximum face amount for which the employee could be insured at the time the contract was issued"; must provide "written consent to being insured under the contract and that such coverage may continue after the insured terminates employment"; and must be "informed in writing that an applicable policyholder will be a beneficiary of any proceeds payable upon the death of the employee." A business that skips the paperwork cannot cure it later, because the statute fixes the timing at issuance.
There is an annual reporting obligation. The IRS directs a business to use Form 8925, "Report of Employer-Owned Life Insurance Contracts," to report the "number of employees covered by employer-owned life insurance contracts issued after August 17, 2006" and the "total amount of employer-owned life insurance in force on those employees at the end of the tax year." The date is the enactment of the provision, so contracts issued before it are outside the regime.
Sizing the coverage is a business calculation, not a personal one. For personal life insurance the question is what a household needs. Here the question is what the business loses: the revenue attributable to that person, the cost of recruiting and training a replacement and the time it takes, any loan or lease with a guarantee or covenant tied to that individual, and the operating runway needed while the business steadies. Lenders sometimes require key person coverage as a condition of a business loan, and the required amount in that case is set by the loan rather than by the analysis.
How it differs from a buy-sell arrangement. Key person insurance funds the business through a loss of earning capacity. A buy-sell agreement funds the purchase of a departing owner's interest and pays whoever is buying that interest. A business with two owners may need both, and they are separate policies with separate purposes even where the same person is insured under each.