Ranked 13th among Wisconsin’s largest private companies by revenue and impact by Deloitte.
Sentry Insurance is seeking a Compliance and Development Analyst to research, analyze, develop, implement and audit insurance products, programs, procedures and techniques for business or consumer products. In this role, you will establish and maintain integrated compliance policies and programs which ensure adherence to state and federal legislation/regulation, monitor regulatory activities, complete necessary filings, respond to state audits and act as Sentry’s representative on various board and bureaus.
This position will be located in Nashville, TN, Madison, WI, Stevens Point, WI, or Freeport, IL and is not a remote opportunity.
For this position, Sentry does not offer employment to holders of F-1, J-1, and H-1 Visas.
Based on qualifications and experience, this position can be filled as a Compliance and Development Analyst, Compliance and Development Senior or Compliance and Development Analyst Specialist.
What You'll Do
As a Compliance and Development Analyst, you will:
Proactively monitor, research, and interpret new and amended insurance laws, regulations, bulletins, and circulars across all relevant jurisdictions, with a focus on personal lines auto and motorcycle.
Analyze the impact of regulatory changes on existing and new insurance products, policy forms, rates, underwriting rules, and operational processes.
Translate complex legal and regulatory language into clear, actionable requirements for business and technical teams.
Collaborate closely with IT, Product Development, and Underwriting teams to integrate compliance requirements into system design, development, and testing phases.
Participate in user acceptance testing (UAT) for system enhancements and new product launches, specifically focusing on compliance validation.
Assist in the development and review of new and revised policy forms, endorsements, applications, and disclosures to ensure regulatory compliance and clarity.
Initiate procedure/sales bulletins necessary to announce and implement various forms and procedures.
Maintain current knowledge of coverages and various state and federal regulations to ensure legal compliance and adherence of filed rates and forms of Sentry products.
Work with members of the Business or Consumer marketing departments to coordinate the filing requirements for new and existing insurance products.
Support the preparation and submission of product form filings to the state Departments of Insurance, ensuring all necessary documentation and data are accurate and complete.
Identify and recommend technological solutions to enhance compliance monitoring, reporting, and efficiency.
Additionally, you will:
Establish effective communications with internal functions, industry contacts, state insurance departments, and industry bureaus.
Develop and maintain compliance documentation, including policies, procedures, and training materials.
Serve as a subject matter expert on compliance matters , providing guidance and support to internal stakeholders.
Perform other job-related duties as assigned from time to time.
What it Takes
Bachelors Degree or equivalent work experience in insurance compliance, product development, or a related regulatory role within the property & casualty insurance industry.
0-2+ years of related work experience
Previous experience with automobile insurance carriers, non-standard auto insurance carriers preferred
Ability to analyze and interpret relevant laws to determine the compliance impact to the business
Position requires the ability to provide oral and written communication regarding compliance or legal issues to various departments and levels of management as well as state departments of insurance
Demonstrated technical understanding of Business or Consumer insurance products
Previous experience as a compliance or forms analyst, an underwriter or claims/policy benefits file handler
Communication, writing and human relation skills
Insurance course work.
JD is a plus
For candidates located near our Freeport, IL office location the base salary range is:
Compliance and Development Analyst: $52,100-$78,100
Compliance and Development Analyst Senior: $61,900-$92,900
Compliance and Development Analyst Specialist: $68,100-$102,100
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
Talent Acquisition Specialist
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.

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.