President of Insurance

Confidential; New York (NY); On-site; USD 250,000 - 400,000; Full time

Job summary

Confidential is seeking a President (Head) of Insurance Operations to build and lead a new, integrated insurance platform from inception through scale. This founder-level role requires entrepreneurial leadership to shape strategy, underwriting, and regulatory governance for captive and brokerage operations.

You will establish carrier relationships, fronting arrangements, and OCIPs/CCIPs expertise while recruiting and guiding a high-performing insurance organization dedicated to

Qualifications

• 8+ years of senior leadership experience in property and casualty insurance.
• Deep expertise in commercial P&C insurance with established carrier and industry relationships.
• Significant experience underwriting or placing construction-related insurance programs.
• Working knowledge of captive insurance structures, fronting arrangements, and reinsurance
• Strong understanding of statutory accounting principles (SAP) and insurance company financial analysis
• Experience within brokerage, program business, or specialty insurance platforms
• Active Property & Casualty producer license or ability to obtain one quickly
• Demonstrated success building and scaling insurance organizations, business units, or new ventures
• Experience with Owner-Controlled Insurance Programs (OCIPs), Contractor-Controlled Insurance Programs (CCIPs), and long-tail construction exposures
• Familiarity with captive insurance structures, including 831(b) programs

Responsibilities

• Lead strategy, underwriting, carrier and fronting relationships, regulatory compliance, operational execution, and financial performance across the captive insurer and brokerage operations.
• Oversee day-to-day execution with external partners (captive manager, actuarial consultants, service providers) and build a high-performing insurance organization as the platform scales.
• Set underwriting strategy and program development across construction-related lines (Builders Risk, General Liability, Excess Liability, Workers' Compensation).
• Manage pricing and reserving discipline in partnership with actuarial advisors.
• Monitor statutory accounting data to assess financial strength, carrier performance, and growth opportunities.
• Ensure licensing, regulatory compliance, and governance across both entities including producer licensing and surplus lines where applicable.
• Foster relationships with captive managers, brokers, reinsurers, fronting carriers, and strategic partners.

Job description

A rapidly growing vertically integrated real estate development and investment platform with operations spanning development, capital management, construction, and insurance is looking for a Head of Insurance to add to the executive team.

The platform develops and manages a diversified portfolio of residential, mixed-use, student housing, hospitality, and other commercial real estate projects throughout the Western United States. In addition to development and construction operations, the organization manages multiple investment vehicles and capital programs supporting its real estate platform.

Insurance is a key strategic growth initiative within the organization. The company is establishing an integrated insurance platform consisting of a captive insurance company and a construction-focused brokerage. Together, these entities will support the organization's risk management strategy by underwriting construction-related risks, retaining insurance economics within the enterprise, and providing specialized solutions for both internal projects and external clients.

We are seeking a President (Head) of Insurance Operations to build and lead this insurance platform from the ground up. This is a founder-level leadership opportunity for an executive who thrives in entrepreneurial environments and wants to shape a business from inception through scale.

The successful candidate will lead strategy, underwriting, carrier and fronting relationships, regulatory compliance, operational execution, and financial performance across both the captive insurer and brokerage operations.

Initially, you will work closely with external partners, including the captive manager, actuarial consultants, and other service providers, while owning day-to-day execution. As the platform grows, you will build and lead a high-performing insurance organization.

The ideal candidate brings deep expertise in property and casualty insurance, strong carrier relationships, and significant experience serving the construction industry.

What You Will Own

• Overall strategy, growth, and financial performance for the captive insurance company and affiliated brokerage
• Carrier and fronting relationships, including negotiation of fronting agreements, collateral structures, and reinsurance arrangements
• Underwriting strategy and program development across construction-related lines, including:
• Builders Risk
• General Liability
• Excess Liability
• Workers' Compensation and Employers Liability
• Contractors Pollution Liability
• Contractors Professional Liability
• Architects & Engineers Errors & Omissions
• Subcontractor Default Insurance
• Specialty project-related guarantee products
• Pricing and reserving discipline in partnership with actuarial advisors
• Analysis of statutory accounting (SAP) data to monitor financial strength, evaluate carrier performance, and assess strategic growth opportunities
• Licensing, regulatory compliance, and governance across both insurance entities, including producer licensing and surplus lines authority where applicable
• Management of relationships with captive managers, brokers, reinsurers, fronting carriers, and other strategic partners
• Recruiting, developing, and leading the insurance team as the business scales

Required

• 8+ years of senior leadership experience in property and casualty insurance
• Deep expertise in commercial P&C insurance with established carrier and industry relationships
• Significant experience underwriting or placing construction-related insurance programs
• Working knowledge of captive insurance structures, fronting arrangements, and reinsurance
• Strong understanding of statutory accounting principles (SAP) and insurance company financial analysis
• Experience within brokerage, program business, or specialty insurance platforms
• Active Property & Casualty producer license or ability to obtain one quickly
• Demonstrated success building and scaling insurance organizations, business units, or new ventures
• Experience with Owner-Controlled Insurance Programs (OCIPs), Contractor-Controlled Insurance Programs (CCIPs), and long-tail construction exposures
• Familiarity with captive insurance structures, including 831(b) programs