About CaptiveStack
CaptiveStack was created out of the need to reduce the cost and complexity of captive insurance for small to medium sized organizations, associations, and commercial trade groups.
Kevin Day
Founder of CaptiveStack, CanadianCaptive.com, and Ocean Falls Insurance
Background & Industry Vision
Kevin Day founded CaptiveStack to bridge the gap between complex institutional alternative risk transfer structures and mid-market organizations. For decades, Fortune 500 corporations have used captive insurance subsidiaries to escape commercial market cycles, stabilize premiums, and retain underwriting profits. CaptiveStack brings the same financial sovereignty to trade associations and member groups.
Extensive background in Property & Casualty (P&C) risk underwriting, captive structuring, digital insurance architecture, and cross-border risk management between Canada and US/offshore domiciles.
P&C and Captive Experience
As the principal behind CanadianCaptive.com (Canada's premier research portal for onshore and offshore captive domiciles) and Ocean Falls Insurance, Kevin has advised commercial organizations on alternative risk mechanisms, captive feasibility, and collateral optimization.
Active participant in international captive conferences and domicile working groups across Vermont, Utah, Delaware, Cayman, Bermuda, British Columbia, and Alberta.
In-Depth Domicile Research
Explore detailed statutory comparisons, capital guidelines, and regulatory histories at CanadianCaptive.com.
How Captive Formation Works
Forming and operating a compliant member-owned captive insurance company requires collaboration among five specialized institutional roles. CaptiveStack integrates this process from feasibility to ongoing management.
The Actuary
Performs historical loss analysis, calculates expected loss frequencies and severities, certifies rate adequacy, and prepares the independent actuarial feasibility study required by the domicile insurance commissioner.
- 5-year loss run analysis
- Binomial & frequency modeling
- Capital reserve certification
- Pro forma loss ratios
The Captive Manager
Coordinates the formal application with the domicile regulator, maintains the captive’s statutory accounting records, prepares annual NAIC or domicile regulatory filings, and oversees daily administrative operations.
- Business plan drafting
- Regulatory application submission
- Statutory accounting & audit liaison
- Board minute books & compliance
The Fronting Carrier
Provides an A-rated admitted or licensed insurance policy paper required by certificates of insurance, contractual counterparties, and lenders, while ceding retained member risk to the captive via a reinsurance agreement.
- A-rated policy issuance
- State/provincial certificate compliance
- Collateral & trust agreement administration
- Fronting fee schedules
The Reinsurer
Provides specific excess-of-loss and aggregate stop-loss treaty reinsurance, ensuring that catastrophic claims exceeding the captive’s retention detachment point are fully absorbed without further member capital calls.
- Specific excess treaty
- Aggregate stop-loss coverage
- Quota-share participation
- Tail risk protection
The Domicile Regulator
State, provincial, or offshore insurance commissioner division that reviews the feasibility study, conducts background and fitness checks on principals, issues the formal Certificate of Authority (license), and conducts periodic examinations.
- Initial charter review
- Certificate of Authority
- Annual financial audit review
- Risk-based capital monitoring
Independent Advisors, Actuaries & Fronting Partners
CaptiveStack works alongside accredited third-party service providers across North America and international domiciles.
Actuarial Partners
Network Partners AvailableIndependent credentialed FCAS / MAAA actuarial firms with specialized practices in association group captives and alternative risk financing.
- Milliman / Pinnacle / Independent practice networks
- Custom binomial prize indemnity modeling
- Formal domicile feasibility certifications
Captive Management Partners
Licensed Across All DomicilesFull-service captive management firms licensed in Vermont, Utah, Delaware, Cayman, Bermuda, Barbados, BC, and Alberta.
- Turnkey regulatory application submission
- Statutory financial statement preparation
- Corporate secretarial & board meeting support
Fronting & Reinsurance Brokers
A-Rated Paper RelationshipsIntermediaries and fronting insurers providing admitted paper and reinsurance treaties tailored to mid-market associations.
- Admitted A-rated AM Best carriers
- Structured letters of credit & standby collateral trusts
- Quota-share and excess stop-loss reinsurance
Legal & Tax Counsel
Cross-Border Practice NetworkSpecialized captive legal counsel advising on group shareholder agreements, participant subscription documents, and federal tax elections.
- IRC Section 831(b) and 953(d) elections
- Association quota-share member agreements
- Domicile statutory corporate filings
Ready to assess your association’s captive feasibility?
Run preliminary actuarial projections or submit your member profile for an initial feasibility review with our team.