You’ll play a pivotal role in driving the evolution of our IT products by leveraging your comprehensive understanding of business strategy, technology, and market trends.
At Sentry, we’re more than just insurance—and we can offer you more than just a job. We want you to enjoy a career with us, where you’re in the driver’s seat of your career path with access to resources to help you succeed personally and professionally.
We’re looking for a strategic leader to guide a team of IT business analysts, who serve as the critical connection point between business partners and technical delivery teams. In this role, you’ll manage a diverse portfolio of work, align project priorities with broader IT strategies, and ensure the delivery of exceptional products. If you excel at seeing the big picture, fostering cross-functional teamwork, and coaching analysts to reach their full potential, this may be the opportunity for you.
You’ll be a valuable contributor to our team. As a Sentry associate, we believe in your skills and knowledge. Your input and participation matters. You’ll have the opportunity to:
If you have experience in the skills listed above, please consider joining our Sentry team!
You can enjoy a complete benefits package, including generous paid time off, 8% 401(k) match, matching charitable gift program, bonus plan based on company performance, meal stipends, associate discounts, volunteer time off and more!
You want a positive work/life balance. Our hybrid work model allows you to enjoy the benefits of working from home on Monday and Friday, but also provides the opportunity for team building and collaboration when working in the office on Tuesday, Wednesday, and Thursday. To help you work effectively and comfortably in both locations, we provide you with equipment to work at home and in the office.
Our Background: We’re part of one of the largest and most financially secure mutual insurance groups in the nation. We’ve earned an A+ rating from AM Best every year since 1992. Our associates bring together diverse backgrounds, experiences, and skillsets to make Sentry who we are. We’re honored to earn a spot on Forbes list of America's Best Midsize Employers, joining a select group of 400 companies. We’re in the business of helping others, and that includes the communities where we live and work. Our annual United Way campaign has raised more than $1 million for the past several years.
We’d love for you to join us. Please complete your online application and upload your resume on our Careers site. If you have applied with us before, you only need to provide your email address and password. If this is your first time applying with Sentry, please create an account.
If you have specific questions regarding the position, application process, or are interested in learning more about Sentry, please reach out to Katelynne Rivera, Talent Acquisition Specialist Sr.
For this position, Sentry does not offer employment to holders of F-1, J-1, and H-1 Visas.
Get ready to own your future at Sentry. Your opportunity awaits.
Thank you for your interest in Sentry!
Katelynne Rivera
Katelynne.Rivera@Sentry.com
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.

In 1904, members of the Wisconsin Retail Hardware Association founded their own insurance company—one built on mutual support, shared strength, and a commitment to service. That legacy remains part of who we are today.
Our continued focus on personal service and Midwestern values helped us earn the trust of businesses across the country. Many of our customers have worked with us for generations.
And we can be there for you.
Our business insurance products are designed to help protect what matters most—your operations and your people. This includes property, casualty, life, and specialty insurance, as well as annuities and retirement.
Whether you’re a small business or a growing operation, we offer industry-specific expertise to help you manage risk with confidence.
Our Stevens Point, Wisconsin, headquarters is the flagship of our business, which is supported by claims offices strategically located throughout the United States. With assets of $27.5 billion and a policyholder surplus of $8 billion, Sentry is rated A+ (superior) by AM Best, the industry’s leading rating authority.*
To learn more about us, the industries we serve, and the products we offer, visit link.sentry.com/Sentry-HomePage.
The content provided here is for informational purposes only: link.sentry.com/Sentry-Disclaimer.
View our underwriting companies at link.sentry.com/Sentry-Disclaimer
*Assets and policyholder surplus are as of December 31, 2024, and represent the aggregate total for all members of the Sentry Insurance Group and are not reflective of any individual underwriting company. Sentry has an AM Best Financial Strength Rating (FSR) of A+ (superior), current as of June 2024. For details about AM Best’s rating scale, see ambest.com/ratings/guide.pdf.