Associate VP - Underwriting

Avid Holdings / Compass Insurance Company

100% Remote | Anywhere in the United States

Help build a growing specialty insurance platform:

Compass Insurance Company is seeking an experienced insurance professional to join our fast-growing, entrepreneurial team. This is a tremendous opportunity to own a critical function and shape the systems, processes, performance metrics, and reporting supporting our expanding portfolio.

Our current programs include passenger auto, paid family leave, and pet insurance, with others on the horizon. MGAs operate these programs, and MGAs/TPAs handle claims. You will evaluate new opportunities and provide disciplined carrier oversight, holding partners accountable for underwriting quality, profitability, and performance.

Our team is fully remote, and this position will remain 100% remote for the foreseeable future. We welcome candidates anywhere in the United States—no relocation or proximity to a major city required.

The Role:

Approximately 30%–40% of your time will focus on program due diligence and launch readiness , with 60%–70% devoted to ongoing program and claims oversight , including KPI development and reporting.

You will evaluate prospective programs and monitor active operations through read-only system access, recurring data, and targeted file reviews. A central responsibility is building repeatable monitoring processes across current and future programs, tailored to each line of business. You will report findings to senior management and drive corrective actions through resolution.

Key Responsibilities:

Program Due Diligence & Launch Readiness

• Lead and coordinate evaluations of prospective programs and MGA/TPA partners, drawing on internal underwriting, claims, actuarial, finance, and compliance expertise.
• Assess historical production and loss results, pricing assumptions, projected profitability, underwriting guidelines, distribution, and exposure concentrations.
• Evaluate partner experience, financial condition, operational controls, claims capabilities, and data quality.
• Identify risks, challenge assumptions, and manage diligence requests; present recommendations, unresolved issues, and approval conditions to senior management.
• Establish system access, reporting requirements, KPIs, and oversight procedures before launch.

Program Monitoring & Underwriting Oversight

• Monitor performance against underwriting guidelines, delegated authority, business plans, and profitability thresholds.
• Track premium growth, concentrations, pricing, business mix, retention, and loss experience.
• Conduct policy reviews and targeted audits to identify exceptions, documentation gaps, and control weaknesses.
• Lead performance reviews with management and MGA partners; recommend changes and track corrective actions through resolution.

Claims Oversight

• Monitor MGA/TPA compliance with claims-handling standards, authority limits, and reporting requirements.
• Review selected files for timeliness, investigation quality, documentation, reserving, and settlement practices.
• Track frequency, severity, reserve development, closure rates, litigation, expenses, and large-loss activity.
• Identify claims leakage and emerging trends; coordinate technical reviews with Compass’s Chief Claims Officer and incorporate findings into underwriting decisions.

KPI Development, Systems & Reporting

• Build scalable dashboards, scorecards, and exception reports with program-specific metrics and thresholds.
• Define data requirements, reporting schedules, escalation triggers, and corrective-action accountability.
• Validate data completeness and reconcile reported results with underlying systems.
• Continuously improve review processes and deliver clear management reporting on performance, risks, and recommended actions.

What We’re Looking For:

• Meaningful experience in insurance program due diligence, program oversight, delegated underwriting, or claims oversight at a carrier, MGA, or TPA.
• Strong understanding of property and casualty operations, underwriting controls, claims practices, loss development, and program economics.
• Experience evaluating partners, analyzing loss data, conducting audits or file reviews, and managing corrective actions.
• Strong analytical skills and comfort with insurance systems, spreadsheets, and reporting tools; experience developing KPIs and dashboards.
• Sound judgment, clear communication, and confidence challenging partners constructively.
• An entrepreneurial mindset and the ability to work independently while building processes and managing daily responsibilities.

Experience across multiple programs or lines of business is particularly valuable. CPCU, ARM, AIC, or similar designations are a plus.

Why Join Us:

• Build and own a critical function. Shape how Compass evaluates and oversees its programs.
• Have a direct impact. Work closely with senior leadership on growth, profitability, and risk.
• Grow with the business. Expand your responsibilities across a developing insurance platform.
• Work from your community. Join a fully remote team without relocating.

We are looking for someone who enjoys both identifying a problem and getting it fixed.

Interested? Apply through LinkedIn with your resume and a brief note describing your program due diligence, MGA oversight, or claims experience.

Thank you for your interest in Avid Holdings and Compass Insurance Company.