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Lead Actuary - Small Commercial

Sentry Insurance
life insurance, parental leave, tuition reimbursement, 401(k), remote work
United States, Wisconsin, Madison
Nov 13, 2025
Sentry is seeking a strategic and visionary Lead Actuary to spearhead new initiatives within Small Commercial. This role will serve as the cornerstone for actuarial leadership, driving excellence across pricing, reserving, and capital management functions. This is a high-impact opportunity to shape the future of Small Commercial at Sentry through data-driven decision-making and innovative actuarial leadership.

What You'll Do

As a Lead Actuary, you will:

  • Architect and implement dynamic pricing models, owning proprietary pricing frameworks for core Small Commercial products.

  • Oversee all state and regulatory filings to ensure competitive and profitable pricing strategies.

  • Collaborate cross-functionally with product, engineering, and data analytics teams to embed pricing directly into the underwriting and quote-to-bind experience.

  • Provide critical actuarial insights to guide capital allocation, reinsurance strategy, and long-term financial forecasting.

  • Analyze rate making assumptions (trends in frequency and severity, credibility, expenses, losses,) to provide pricing rate levels that are necessary to produce a profit.

  • Coordinate and communicates rate revisions and support documentation with executive management to facilitate an orderly transition in rate level changes.

  • Apply tactical, strategic and innovative analysis to evaluate costs, benefits and risks of various business options to achieve profitability and premium growth.

  • Analyze specific product line financials to ensure financial strength including actuarial aspects of product development and/or product maintenance for a product line, determination of pricing structure and premiums, filing and approvals, commission structure, systems specifications and other actuarial supports for product management.

  • Administer human resource-related activities including timely performance and salary reviews and ensures all subordinates adhere to human resources policies and practices.

  • Interpret and understand state and federal legislation and its impact on products and programs.

  • Analyze cash flow analysis, income projections, profit studies, competitive developments in the marketplace, and review of actuarial techniques.

  • Participate in the development of long- and short-term project priorities.

What it Takes

  • Bachelor's Degree with an emphasis in Math, Actuarial, Statistics or Economics, or equivalent work experience.

  • Strong financial and analytical skills.

  • Advanced product knowledge in the assigned product line.

  • Proficient skill level in actuarial statistics/assumptions used for rate making, loss reserving and forecasting.

  • Membership as a Fellow of the Casualty Actuarial Society or Society of Actuaries.

What You'll Receive

At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that you'll receive.

  • Sentry is happy to offer flexibility through a scheduled Hybrid work model. Monday and Friday work from home if you choose to, Tuesday through Thursday you'll work in office.

  • As a Sentry associate, you will have an in-office workspace and materials for your home office. In addition to the laptop, you will receive prior to your start, Sentry will provide equipment for your home office.

  • Meal Subsidy available for associates who report to an office.

  • 401(K) plan with a dollar-for-dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future.

  • Continue your education and career development through Sentry University (SentryU) and utilize our Tuition Reimbursement program.

  • Generous Paid-Time Off plan for you to enjoy time out of the office as well as Volunteer-Time off.

  • Group Medical, Dental, Vision, Life insurance, Parental leave, and our Health and Wellness benefits to encourage a healthy lifestyle.

  • Well-being and Employee Assistance programs.

  • Sentry Foundation gift matching program to encourage charitable giving.

About Sentry

We take great pride in making Forbes' list of America's Best Midsize Employers. A lot of different factors go into that honor, many of which contribute to your job satisfaction.

Our bright future is built on a long track record of success. We got our start in 1904 and have been helping businesses succeed and protect their futures ever since. Because of the trust placed in us, we're one of the largest and financially strongest mutual insurance companies in the United States. We're rated A+ by A.M. Best, the industry's leading rating authority.

Our headquarters is in Stevens Point, Wisconsin, with offices located throughout the United States. From sales to claims, and information technology to marketing, we enjoy a rewarding and challenging work environment with opportunities for ongoing professional development and growth.

Get ready to own your future at Sentry. Opportunities await!

Talent Acquisition Specialist

Thank you for your interest in Sentry!

Katelynne Rivera

Katelynne.Rivera@Sentry.com

Equal Employment Opportunity

Sentry is an Equal Opportunity Employer. It is our policy that there be no discrimination in employment based on race, color, national origin, religion, sex, disability, age, marital status, or sexual orientation.

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