Strategic Risk & Insurance Analyst

Imagine combining the stability of a multibillion-dollar family enterprise with the agility of a newly created seat on a high-profile team. Our client—an industry-leading distributor with campuses across the U.S., Canada, and Mexico—invests heavily in its people: think profit-sharing that actually pays, immediate 401(k) match, and occasional trips on the company’s private aircraft to strategy summits and leadership events. If you enjoy clear structure, direct feedback, and a culture that rewards results, this is your runway.

The Impact You’ll Make

Reporting to the Head of Risk Management, you will be the department’s go-to analyst—owning insurance renewals, building sophisticated forecasts, and advising senior leaders on how to balance self-insurance with third-party coverage. Your work will safeguard billions in assets, shape captive strategy, and sharpen loss-control programs across three countries.

Key Responsibilities

• Oversee insurance renewals and market submissions, collaborating with brokers, insurers, and legal counsel
• Manage insurance budgeting and forecasting processes across multiple countries (US, Canada, Mexico)
• Assess underwriting exposures and evaluate self-insurance vs. third-party coverage options
• Coordinate with captive insurance management and investment oversight
• Support claims management and defense in collaboration with external partners
• Prepare statements of values and conduct financial analysis for risk management decisions
• Serve as secondary contact for risk management partners and vendors
• Coordinate loss control programs with insurance carriers

Education & Experience:

• Bachelor's degree (Risk Management, Finance, or Accounting preferred)
• 3+ years of insurance industry experience, preferably with brokers, carriers, or corporate risk management
• Experience with insurance placement and day-to-day operations

Technical Skills:

• Strong budgeting, forecasting, and financial analysis capabilities
• Proficiency with Microsoft Office suite
• Experience with major insurance lines (property, general liability, executive risk, auto, cyber)

Essential Soft Skills:

• Exceptional written communication skills (writing assessment required)
• Strong analytical and problem-solving abilities
• Ability to communicate effectively with senior executives
• Professional resilience and adaptability to direct feedback
• Comfort working in a structured, family-owned business environment

Preferred Qualifications

• Legal background or law school experience
• Captive insurance knowledge
• Experience with SQL and Power BI
• Investment management experience related to captive funds

• Base Salary: $80,000 - $120,000 (flexible for exceptional candidates)
• Bonus: 5-10% target bonus based on company and individual performance
• Additional Compensation: Profit sharing program

Comprehensive Benefits Package:

• Complete health insurance coverage
• 401(k) with 6% employer match (immediate vesting)
• Generous paid time off and paid holidays
• Tuition assistance program
• On-site wellness facilities and fitness center
• Multiple bonus programs

Work Environment & Requirements

• Location: Pleasant Prairie, Wisconsin (relocation assistance available with sign-on bonus of $5,000-$10,000)
• Schedule: 45+ hours per week, business attire required daily
• Travel: Periodic travel opportunities on company aircraft for meetings and annual events
• Work Style: Structured environment with extensive reporting requirements
• Drug Testing: Pre-employment hair drug test and random testing throughout employment required

Ready to accelerate your career with a company that treats risk management as a strategic advantage—while giving you first-class perks along the way? Apply today and take the next step toward a leadership track in one of North America’s most admired private businesses.

Equal Employment Opportunity and Non-Discrimination Policy

Equal Employment Opportunity Statement: Both Keller Executive Search and our clients are Equal Opportunity Employers. For all positions, whether with Keller Executive Search or our clients, qualified applicants will receive consideration for employment without regard to race, skin color, religion, sex, sexual orientation, gender identity, gender expression, national origin, age, protected veteran status, disability, genetic information, or any other legally protected status.

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Compensation Information: For client positions, compensation information is available in the job post. If not provided, it will be shared during the interview process in accordance with applicable laws. When required by law, salary ranges will be included in job postings. Actual salary may depend on skills, experience, and comparison to current employees in similar roles. Salary ranges may vary based on role and location.

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• Rhode Island: We do not request or require salary history from applicants.
• Connecticut: We provide wage range information upon request or before discussing compensation.
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Note: This job posting may be for a position with Keller Executive Search or one of our clients. The specific employer will be identified during the application and interview process. Employment laws and requirements may vary depending on the employer and location.