Job Title: VP, Program Operations & Compliance
Company: Captives.Insure
Location: Remote - Company Headquarters: Knoxville, TN
Job Type: Full-time, Senior Level
Job Summary:
We are seeking a seasoned operations and finance leader to build the operational infrastructure and compliance framework required to scale our growing captive insurance MGA. The VP, Program Operations & Compliance will own the operational and financial backbone of our delegated underwriting program—premium flows, policy issuance and administration, licensing, and regulatory compliance—across multiple states and lines of business. This is not a technical underwriting role; rather, the successful candidate will champion operational excellence and compliance discipline firm-wide, partnering closely with underwriting, our Controller, fronting carriers, reinsurers, captive managers, and brokers to ensure scalable, audit-ready, and profitable program execution.
Reporting & Scope:
Reports directly to the Chief Executive Officer.
Owns the program operations and compliance function, including policy issuance/administration, premium flow stewardship, licensing, and operational regulatory compliance.
Partners with our Controller, who owns the bookkeeping and accounting function; this role provides operational and funds-flow oversight, not accounting/booking responsibility.
Does not hold underwriting authority; collaborates with, but does not direct, the underwriting function.
Builds and leads the operations team, with policy administration and operations staff reporting into this role as the function scales.
This is a senior functional leadership role reporting to the CEO.
Key Responsibilities:
Own end-to-end program operations for the MGA's delegated authority book, including policy issuance, endorsement, and policy administration workflows, ensuring accuracy, timeliness, and adherence to carrier and reinsurer obligations.
Govern premium flows—premium collection, trust/fiduciary handling, carrier and reinsurer remittance, and bordereaux production and reconciliation—working alongside the Controller, who performs the bookkeeping and accounting function.
Champion the firm's licensing strategy: drive expansion of producer, MGA, and surplus lines licensing into new domiciles and states, and ensure ongoing compliance with all licensing requirements and renewals.
Serve as the firm's operational compliance authority, monitoring multi-state regulatory obligations, surplus lines filings/taxes, and program reporting requirements, escalating structural or regulatory issues with profitability and capital impacts.
Establish, document, and continuously improve operational processes, controls, and SLAs supporting delegated underwriting authority and program agreements.
Build and lead the operations team, hiring and mentoring policy administration and operations staff as the function scales.
Act as the operational liaison to fronting carriers, reinsurers, captive managers, and brokers, supporting audits, program reviews, and bordereaux/data reporting.
Partner with leadership on systems, automation, and platform initiatives to drive scalable, efficient operations.
Required Qualifications:
Minimum of 8 years of progressive insurance operations and/or finance experience, with demonstrated leadership running program business for a P&C MGA, program administrator, or insurance agency.
Deep working knowledge of premium flows, including trust/fiduciary premium handling, carrier and reinsurer remittance, and bordereaux reconciliation.
Extensive insurance compliance experience: obtaining and monitoring producer/MGA/surplus lines licensing, multi-state regulatory requirements, and policy issuance and administration obligations.
Proven ability to build, document, and scale operational processes and controls within a delegated authority environment.
Strong financial acumen and the ability to partner effectively with a Controller/accounting function (without owning the bookkeeping).
Demonstrated people leadership, with experience building and managing operations teams.
Proficiency in Microsoft Office Suite (Excel, Word) and familiarity with policy administration and insurance operations systems.
Preferred Qualifications:
Experience operating within or alongside AM Best-rated fronting carrier and reinsurance structures.
Familiarity with captive insurance structures and alternative risk transfer mechanics.
Multi-state surplus lines and MGA licensing experience across multiple domiciles.
CPCU, ACI, AINS, AU, ARe, or equivalent professional designation.
Experience with operations and process automation or insurtech platform implementation.
Expected Working Conditions:
Location: Fully remote; open to qualified candidates nationwide within the continental U.S.
Office Environment: Home office setting with standard business hours; flexibility is required to accommodate the demands of the role and multiple time zones.
Travel: Occasional travel required for carrier/reinsurer meetings, audits, team gatherings, or industry events (up to 15%).
Work Hours: While the standard workweek is 40 hours, the role can occasionally require additional hours, including evenings and weekends, to meet deadlines and manage urgent issues.
Stakeholder Interaction: High level of interaction with carriers, reinsurers, captive managers, brokers, and internal teams, requiring excellent interpersonal and leadership skills.
Compensation and Benefits:
Placement within the range provided below is based on the individual's relevant experience, skills for the role, and location. Salary ranges are only one component of our total compensation package. We value your goals and needs, at work and in life. At Captives.Insure, you'll be supported with resources, benefits, and work-life balance so you can thrive in ways that matter to you.
Salary Range $200,000–$225,000 per annum for non-production roles.
100% company paid medical, dental and vision benefits (both employee and family).
The company does not have any limits on Paid Time Off, we just ask for reasonable advance notice.
401k with 3% employer match.
Company profit sharing.
Relocation assistance if required.
Headquartered in Tennessee, Captives Insure ("C.I.") is an award-winning captive insurance consulting and underwriting firm. Recipients of multiple industry awards, C.I. works with sophisticated global captive managers and brokers to provide captive insurance solutions designed to maximize control and premium retention for high-performing businesses around the world. Highly respected within the industry, our distribution network includes independent third-party captive managers and well over half of the top 100 brokerage agencies in the US (as measured by Business Insurance Magazine).
We believe in a diverse and inclusive workforce and are proud to be an equal opportunity employer and welcome applications regardless of ethnicity or cultural background, age, gender, nationality, religion, disability or sexual orientation. We encourage you to bring your whole self to work, no matter where you are from, what you look like, who you love or what you believe in.
SUBMIT A RISK