Captive insurance education built for practitioners.
On-demand written guides for risk managers, CFOs, insurance professionals, and legal teams. Reference it when you need it. Build genuine expertise over time.
Follow the path
that fits your role.
The curriculum covers captive insurance end to end — but you don't need to work through every module. Each role has a recommended track: a focused set of lessons that directly supports your function. Start there, and explore further as needed.
Financial Decision-Makers
Understand the economics of captive programs — premium-to-capital ratios, accounting treatment, collateral implications, and how to evaluate whether a structure is actually performing.
Risk & Insurance Professionals
Go deep on the technical mechanics — ERD analysis, fronting carrier relationships, domicile selection, and the operational realities of running a captive program day-to-day.
Legal & Compliance Teams
Understand the regulatory landscape — risk transfer standards, IRS scrutiny, audit defence frameworks, and the compliance considerations that underpin long-term programme defensibility.
Governance & Oversight
Understand the governance context of a captive director — what the board is expected to decide, how to read statutory financial statements, and how regulatory examinations are conducted.
What's inside
the Academy.
Captive Fundamentals
What captives are, why companies form them, the major structure types, a decision framework for evaluating whether a captive makes sense, and how group captive structures and member governance work.
Captive Formation
From feasibility study through domicile licensing, initial capitalisation, and building your service provider team — an educational guide to how captive formation works.
Financial Mechanics
Premium setting, capital requirements, SSAP 62 accounting, ERD risk transfer analysis, and collateral structures — the financial engine of a captive program.
Capital & Balance Sheet Management
Reinsurance structures for captive risk management, investment policy and asset allocation, and capital repatriation and dividend strategy — optimising the balance sheet over the captive lifecycle.
Regulatory & Audit Readiness
Domicile selection and the regulatory landscape, audit readiness frameworks, and how captive structures are evaluated under challenge from regulators and examiners.
Tax & International Compliance
IRS risk transfer standards and listed transaction rules, how the 831(a) vs 831(b) election works, offshore deductibility, BEPS Pillar 2, and cross-border transfer pricing for captive programmes.
Operational Excellence
Fronting carrier relationships, captive governance and board structure, operating team decision tools, building an internal capability that scales, enterprise risk management, and rating-agency capital as a method for sizing what the captive carries.
Claims Management
The full claims lifecycle, loss reserving and IBNR methodology, how litigation is managed in captive programmes, how claims data informs structural improvements, and how reinsurance contract provisions behave when a large loss is in dispute.
Lines of Business
Deep dives into workers' compensation, cyber, medical stop-loss, professional liability, employee benefits, and property catastrophe — plus non-traditional and emerging lines, each with distinct actuarial and structural considerations.
Programme Review & Restructuring
Annual review frameworks, identifying structural weaknesses, restructuring options including domicile migration and line additions, insurance market cycle strategy, and stakeholder communication.
Captive Exit Strategies
Run-off vs. commutation, regulatory winding-up procedures, transition to a new structure, captive M&A transactions, and protecting stakeholders through the exit process.
Reference Library
Deeper-dive companions to the core modules — practical templates, negotiation packs, diagnostic checklists, and technical guides for specialists who need to go further.
Role-Based Learning Paths
Curated reference guides by function — CFO, Risk Manager, Legal Counsel, Board Member, and Captive Manager — mapping the curriculum to each role's priorities, key decisions, and ongoing responsibilities.
Module 01 is free to read. Full access unlocks all 11 modules, the Reference Library, and the role-based learning paths.
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- Module 01: Captive Fundamentals — all 5 lessons
- Reference access to free lessons
- In-lesson reference material
- All 11 modules & 79 lessons
- Unlimited reference access
- Module reference cards & lesson guides
- New content as it's published
- Role-based learning tracks
- All 11 modules & 79 lessons
- Unlimited reference access
- Module reference cards & lesson guides
- New content as it's published
- Role-based learning tracks
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Educational Disclaimer. The content provided through Retained Academy is intended solely for general informational and educational purposes. It does not constitute, and should not be relied upon as, professional legal, tax, actuarial, regulatory, accounting, or financial advice. Captive insurance structures involve significant legal, financial, and regulatory complexity that varies by jurisdiction, programme type, and individual circumstance. Before forming, operating, restructuring, or winding down a captive insurance programme — or making any decision based on material covered in this curriculum — you should consult qualified independent professionals, including licensed legal counsel, a credentialed actuary, a certified public accountant, and any other advisers appropriate to your specific situation. No attorney-client, advisory, fiduciary, or other professional relationship is created or implied by your use of this content. Retained Academy™ makes no representations as to the completeness, accuracy, or current applicability of any material herein. Laws, regulations, IRS guidance, and market practices change; content reflects conditions as of the date of publication and may not reflect subsequent developments.