Remote Strategy Transformation Jobs in Chicago, IL

The Senior Underwriting Strategy Analyst supports the Director of Underwriting Strategy in driving portfolio performance, optimizing underwriting, and advancing strategic initiatives across the underwriting lifecycle. This role blends analytics, underwriting expertise, and cross-functional leadership to improve risk selection, profitability, and operational efficiency.

Accountabilities:

Underwriting Strategy & Portfolio Management

• Support development and execution of underwriting strategies aligned to growth, profitability, and risk appetite goals
• Analyze portfolio performance trends (loss ratio, hit rate, retention, pricing adequacy) and recommend actionable improvements
• Monitor underwriting guidelines and identify opportunities for refinement based on emerging experience and market dynamics
• Assist in segmentation strategies to optimize risk selection and pricing precision

Data Analysis & Insights

• Conduct advanced data analysis to identify drivers of loss, profitability, and underwriting performance
• Develop dashboards, scorecards, and reporting frameworks for leadership visibility
• Partner with actuarial, data science, and finance teams to evaluate pricing models and assumptions
• Translate complex data into clear, actionable recommendations for underwriting leadership

Underwriting Governance & Execution

• Support governance frameworks including referral processes, authority structures, and underwriting controls
• Perform audits and quality assurance reviews to ensure adherence to underwriting guidelines
• Identify process gaps and recommend enhancements to improve consistency and decision quality

Cross-Functional Collaboration

• Partner with Product, Actuarial, Claims, Distribution, and Operations to align strategy and execution
• Contribute to product development, coverage enhancements, and market positioning initiatives
• Support field underwriting teams with insights, tools, and strategic guidance

Process Improvement & Transformation

• Identify and lead initiatives to streamline underwriting workflows and reduce friction
• Support automation, digitization, and decision-support tool development
• Drive continuous improvement in underwriting efficiency and scalability

Strategic Projects

• Lead or support high-impact initiatives such as:

• New program or segment launches
• Profitability remediation strategies
• Expansion into new markets or distribution channels

• Prepare executive-level presentations and strategic recommendations

Qualifications:

Required

• Bachelor’s degree in Finance, Economics, Risk Management, Data Analytics, or related field
• 5+ years of experience in underwriting, underwriting strategy, or analytics within insurance
• Strong understanding of underwriting principles, pricing dynamics, and risk selection
• Advanced analytical skills (Excel, SQL, or similar tools; Tableau/Power BI preferred)
• Demonstrated ability to translate data into business strategy

Preferred

• Experience in commercial lines
• Exposure to predictive modeling, pricing analytics, or portfolio optimization
• Project management experience leading cross-functional initiatives
• Professional designations (CPCU, ARM, ACAS/FCAS, etc.)

Core Competencies

• Strategic thinking and problem-solving
• Strong business and financial acumen
• Executive communication and storytelling
• Collaboration and stakeholder influence
• Detail orientation with a results-driven mindset

Pay Range:

Anticipated Hiring Range:

• $81,000 - $130,000 commensurate with experience

Get to Know GuideOne:

At GuideOne, we believe that our people are our greatest asset, and we foster a sense of collaboration among our team members so they can learn from and inspire one another to deliver excellence in risk solutions and services to our customers. For more than 75 years, we've established a reputation as a trusted partner in the communities where we live and work, and with our steadfast commitment to help make positive change possible, we're excited to see what we can accomplish during the next 75. Explore our values and culture, and learn why GuideOne might be a great fit for you!

GuideOne is proud to offer a robust benefits suite that includes:

• Competitive base salary plus incentive plans for eligible team members.
• 401(K) retirement plan that includes a company match of up to 6% of your eligible salary.
• Free Basic Life and AD&D, long-term disability and short-term disability insurance.
• Medical, dental and vision plans to meet your unique healthcare needs.
• Wellness incentives
• Generous time off program including; personal, holiday, and volunteer paid time off.
• Flexible work schedules and hybrid/remote options for eligible positions.
• Educational assistance program.

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