Ranked 13th among Wisconsin’s largest private companies by revenue and impact by Deloitte.
What You'll Do
As a Senior Investigator, you will:
Conduct objective and impartial investigations into fraud, misconduct, and other complex and/or sensitive incidents that pose a risk to Sentry leveraging advanced investigative, forensic, and analytical techniques and technology.
Oversee the collection and review of evidence and intelligence during complex investigations involving multiple investigators.
Leverage threat intelligence frameworks to identify strategic intelligence regarding potential and ongoing threats to Sentry and leverage that information to strengthen Sentry’s security controls and when appropriate report to leadership.
Analyze output from anti-fraud tools and system logs to identify fraud and remediate any outstanding issues following Investigative Services procedures.
Serve as subject matter expert relative to digital forensic investigations, providing consultation and support to key personnel on the collection of information in support of litigation and testimony when necessary.
Collect and analyze evidence from external sources such as social media and public records to conduct investigations on internal and external parties to ensure complete digital investigation to maintain associate safety.
What it Takes
Bachelors Degree or equivalent work experience.
Minimum of 7 years related work experience in information technology systems and processes, investigations and forensics.
Experience in large scale, post-incident investigations, using techniques such as network forensics, log analysis, timeline creation, and host-based forensics have been applied.
Professional designation, such as EnCE, CCE, CCFP, GCFA, GNFA, GCFE, CFCE, GCIH, GREM beneficial.
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
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.