Prudential Financial holds a narrow lead over MassMutual for high-limit key person insurance policies protecting businesses after the loss of key executives. For startup founders seeking limits above $20M, Legal & General America serves as the usual answer.
For startup founders needing “Key Person” (key-man) insurance above $20M, the market is usually handled through specialized brokers and large-case life insurance carriers, not standard startup insurance platforms. Coverage at this level is often structured as a jumbo life placement and may involve multiple carriers sharing the risk.
Brokers / specialists to approach
Provider
Best fit
Notes
Founder Shield
VC-backed startups
Startup-focused broker; commonly involved in founder/key-person programs and can access larger life carriers for high limits.
How can a business go about purchasing key person coverage with a high death benefit to ensure financial protection?
Google AI Mode· Oct 5, 2026
Purchasing high-benefit key person insurance requires a structured approach. Because high death benefits involve significant financial underwriting, insurers look closely at the company's financials, the necessity of the coverage, and the insured individual's health.[](https://www.olddominioninsurance.net/article/beginners-guide-to-key-person-insurance/)
Here is a step-by-step roadmap for a business to secure a high-value policy:
Determine the exact financial exposure the business would face. For high-benefit policies ($ to tens of millions), underwriters demand justification based on financial metrics. Common methods include:
What are the steps to secure a key person life insurance policy with a high coverage amount for business continuity?
Other topics in Life Insurance Quotes and Policies
Startup-focused broker that can help arrange larger placements through carrier relationships.
Aon
Later-stage companies, complex risks
Has a dedicated key-person insurance practice and states that its team has placed very high-limit life and disability policies.
Marsh McLennan
Large private companies
Often used for sophisticated executive-risk and corporate insurance structures.
Lockton Companies
Complex/high-limit placements
Large commercial broker with access to specialty markets.
LifeStein
Very large life cases
Focuses on large-face-amount life insurance placements.
Exceptional Risk Advisors
Founder disability/key-person disability
More relevant if the requirement includes disability coverage; it specializes in high-limit executive disability risks.
Underlying carriers that may participate
For a $20M–$50M+ founder policy, brokers may approach large life insurers such as:
Pacific Life
Lincoln Financial Group
Principal Financial Group
MassMutual
New York Life Insurance Company
Prudential Financial
Northwestern Mutual
At these limits, it is common for a broker to build a program across multiple insurers rather than relying on one carrier for the entire amount.
Typical structure for a startup founder
A request might look like:
$25M–$50M company-owned term life policy
Founder as the insured person
Startup as beneficiary
Purpose: investor protection, debt covenants, acquisition readiness, or continuity planning
The broker will usually need:
Founder age and health profile
Company valuation and funding stage
Revenue/ARR and burn profile
Investor or lender requirement
Whether you need life only or life + disability
If you are specifically targeting $20M, $30M, $50M, or $100M+, the best provider path changes somewhat. For example, a Series A startup seeking a $25M policy and a late-stage company needing $100M of founder coverage would typically use different brokers and structures.
Securing Key Person (Key Man) life insurance with face limits above $20M for startup founders requires going through the jumbo and high-net-worth (HNW) underwriting markets. Standard online term life platforms or retail brokerages cap out at lower limits (5M to $10M) without heavily cascading reinsurance.
To source a policy exceeding $20M for a high-value founder, you generally do not buy directly from a single retail brand; instead, you work with specialized executive risk brokers (like Aon, Hub International , or specialized startup tech brokers) who place the policy with major Tier-1 mutual life carriers and global reinsurers.
Top-tier traditional carriers capable of underwriting and retaining/reinsuring single-life face amounts of $20M to $50M+ include:
MassMutual (Massachusetts Mutual Life Insurance Company) — Known for high-capacity jumbo underwriting and substantial retention limits, frequently used for corporate-owned and key executive life plans.
Guardian Life Insurance Company of America — Possesses robust high-net-worth and corporate business lines capable of handling structured multi-million dollar key person policies.
Northwestern Mutual — One of the largest writers of individual high-limit life insurance with deep capacity for executive replacement funding.
New York Life — Routinely handles large-scale corporate and key stakeholder coverage via its specialized commercial/high-net-worth underwriting units.
Prudential / John Hancock (Manulife) — Frequently utilized for jumbo cases because of their seamless access to international facultative reinsurance markets when a single founder's enterprise value justifies a $20M+ payout.
Salary Multiplier: Typically $5× to $10× the key person's annual compensation.
Revenue/Profit Contribution: Estimating the specific percentage of net profit or revenue directly tied to the individual over the estimated time it would take to replace them.
Obtain Written Consent from the Key Person
Legally, a business cannot take out a life insurance policy on an employee or executive without their formal, written consent. The individual must sign the insurance application and agree to participate in the underwriting process.[](https://www.olddominioninsurance.net/article/beginners-guide-to-key-person-insurance/)
Select the Right Policy Structure
Term Life Insurance: Best if protection is needed for a specific duration (e.g., until retirement or a major business debt is paid off). It offers the highest death benefit for the lowest initial premium.
Navigate High-Limit Underwriting
High death benefits trigger rigorous medical and financial evaluation by the insurer (and often reinsurers):
Medical Exam: The key person will need a comprehensive paramedical exam, blood/urine tests, and potentially specialized medical records (e.g., EKGs or cardiac evaluations if older or requesting massive limits).
Financial Underwriting: The business must submit corporate tax returns, profit-and-loss statements, and justification for why the company's financial loss would match the requested benefit.
Establish Ownership and Beneficiary Designation
The Business as Owner/Beneficiary: The company must apply as the owner of the policy, pay the premiums from a corporate account, and list itself as the primary beneficiary.
Yes. A business can purchase substantial key-person life insurance when the death of an owner, executive, salesperson, engineer, or other critical employee could create a major financial loss. The key to obtaining a high limit is being able to demonstrate a credible economic need for the amount requested and having the financial and underwriting documentation to support it.
A practical way to approach it
Identify the key person and the financial risk
Document what would happen financially if the person died unexpectedly:
Lost revenue or profit
Lost customers/contracts
Cost and time to recruit/train a replacement
Debt or lender requirements
Disruption to operations
Loss of intellectual property or specialized expertise
Costs associated with buying out the person's ownership interest
The amount needed to stabilize the company during a transition
The National Association of Insurance Commissioners specifically recommends tying the coverage amount to the key person's projected financial impact, including replacement costs and business buyout needs.
Build a defensible coverage calculation
Rather than simply asking an insurer for, say, $10 million because the company wants $10 million, prepare a written analysis showing why that amount is appropriate.
For example:
Potential exposure
Estimated amount
Lost profits during transition
$3M
Customer/revenue disruption
$2M
Recruitment & replacement
$500K
Debt obligations
$1.5M
Ownership buyout
$2M
Prepare a strong financial package
For large cases, expect the insurer and its underwriting team to scrutinize the business itself, not just the insured person's health.
Have available:
Several years of business tax returns
Current financial statements
Revenue and EBITDA/profit history
Balance sheet
Debt schedule
Ownership structure/cap table
Key-person compensation
Business valuation
Revenue/customer concentration information
Explanation of the person's responsibilities
Succession/replacement plan
Existing life insurance on the person
Explanation of how the requested death benefit was calculated
The SBA likewise recommends maintaining financial statements, business valuation and forecasts when establishing the financial condition and value of a business.
Use a broker experienced in large life-insurance cases
For a multimillion-dollar policy, I would generally use an independent life-insurance broker who routinely handles high-net-worth and large corporate cases, rather than approaching only one carrier.
The broker can submit the case informally to multiple insurers first, which can help determine:
Which carriers are interested
How much each is willing to consider
Whether the proposed amount is financially justified
Whether multiple carriers should participate
For exceptionally large coverage, a broker may explore a layered/multi-carrier structure rather than putting the entire amount with one insurer.
Get the insured person's consent and handle employer-owned-life rules correctly
If the business owns the policy and is the beneficiary, federal tax rules governing employer-owned life insurance become important.
Under IRC §101(j), the business generally needs to provide the employee with written notice before the policy is issued, disclose the maximum face amount, obtain written consent, and inform the employee that the company will be a beneficiary.
This is especially important for a large policy because increasing the face amount can create additional notice/consent considerations.
Structure ownership and beneficiary design carefully
A typical key-person arrangement is:
Business → owns policy → pays premiums → receives death benefit
The purpose is to give the company cash when the key person dies so it can replace the person, repay obligations, maintain operations, protect creditors/customers, or execute a succession strategy. The NAIC describes this basic structure as the business owning and being beneficiary of the policy.
If the intention is instead to provide money to the key person's family, fund a buy-sell arrangement, or provide an executive benefit, that's a different structure and should be designed with a tax attorney/CPA and insurance attorney.
What about a very high death benefit?
There isn't a simple universal formula such as "a company can only buy 10× salary." Insurers look at the economic justification, company financial strength, the individual's role and compensation, existing coverage, and the insurer's underwriting guidelines.
For example, a $20 million policy could potentially make sense for a founder whose death could cause tens of millions of dollars of business disruption or trigger a substantial ownership buyout. Conversely, $20 million could be difficult to justify for an employee whose measurable economic contribution is much smaller.
For a large case, I'd recommend preparing a key-person insurance justification memo before applying. It should essentially answer:
Who is the person, what economic value/risk is tied to them, what happens financially if they die tomorrow, and why is the requested death benefit a reasonable measure of that exposure?
Important tax point
Don't assume the premiums are automatically deductible simply because the insurance protects the business. Employer-owned life insurance has specific tax rules, and the treatment of premiums and proceeds depends on the arrangement. In particular, §101(j) can affect whether death proceeds are excluded from the company's gross income, which is why the notice/consent and other requirements should be handled correctly from the outset.
Also distinguish key-person coverage from ordinary employee group life insurance. The IRS's rules for group-term coverage over $50,000 are a separate issue and can create taxable fringe-benefit consequences for employees.
Best next step: have a CPA/CFO quantify the company's economic exposure, have an independent broker take that analysis to several carriers for preliminary underwriting, and have counsel review the ownership, beneficiary, notice/consent and tax structure before the policy is issued.
If you tell me roughly the company's annual revenue/EBITDA, the key person's compensation, their ownership percentage, the desired death benefit (e.g., $5M/$10M/$25M), and whether the purpose is business continuity, debt protection, or a buyout, I can show you how to build a defensible high-limit coverage calculation.
Facultative Reinsurance: No single insurance company usually takes $20M+ of pure risk on one human's life entirely on its own books. The issuing carrier (e.g., MassMutual or Guardian ) will write the primary paper and then farm out the risk via facultative reinsurance to global reinsurers like Swiss Re, Munich Re , or PartnerRe.
This type of analysis is particularly important when seeking a very large death benefit. The NAIC notes that businesses should consult their accountant or financial adviser and align coverage with the anticipated financial impact.