Sentry earned an A+ rating for the 34th consecutive year.
This role ensures alignment with all state and federal regulatory requirements.
In addition, you will lead and coordinate key business initiatives, collaborating across functional areas to ensure effective structuring and successful execution that meets business objectives and compliance expectations and organizational priorities.
What You'll Do
As a Compliance Manager Life & Annuity, you will:
Monitor, interpret, and implement regulatory requirements related to individual life and annuity insurance products and services to ensure compliance with all relevant state and federal laws.
Implement and maintain compliance programs, governance practices, and risk management processes aligned with state and federal regulatory requirements
Serve as the primary compliance partner to Individual Life and Annuity leadership, helping balance business objectives with regulatory and compliance expectations
Work in partnership with the Director, Life & Annuities Claims and Compliance to implement compliance policies, procedures, and governance practices supporting regulatory adherence and effective risk management
Administer human resource related activities. Select, develop, motivate, and recognize staff.
Additionally, you will:
Support compliance monitoring, assessments, and internal control activities to ensure adherence to regulatory requirements and internal policies
Partner with Legal, Enterprise Compliance, Product, Claims, Operations, and Actuarial teams to ensure consistent application of regulatory requirements
Provide leadership visibility to initiative progress, risks, and key decisions to support effective governance and decision making
Independently manage department-specific projects and supports broader cross-functional initiatives impacting the Individual Life and Annuity business unit.
Facilitate communication, problem-solving, and alignment across business, operational, and technical stakeholders to ensure initiatives progress effectively.
What it Takes
Bachelors Degree in Finance, Insurance, Risk Management, or related field preferred or equivalent work experience
5+ years of related work experience. Experience in insurance, compliance, risk management, operations and with regulatory matters strongly preferred
Experience in Individual Life and Annuity compliance, claims, operations, or product environment
Strong knowledge of Individual Life and Annuity products, operations, and regulatory environment
Demonstrated ability to lead business initiatives or organizational projects
Experience with compliance management systems and regulatory tracking tools such as SERFF
Industry designations such as AIRC, FLMI, or other compliance certifications
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!
Casey Van Der Geest
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.
Our commitment to creating a positive, people-first culture hasn’t gone unnoticed. We’re proud to be recognized for our outstanding workplace culture.
Sentry earned an A+ rating for the 34th consecutive year.

Recognized as one of America’s Greatest Workplaces for Diversity by Newsweek.

Ranked 13th among Wisconsin’s largest private companies by revenue and impact by Deloitte.
Sentry is one of America’s Best Midsize Employers, according to Forbes.

For the second year in a row, Newsweek named Sentry one of America’s Greatest Workplaces for Women.
Forbes names Sentry as one of the Best Employers for new Grads.