Project Manager (Hybrid Work Model)
Confirmed on the employer's own hiring board on Nov 5, 2026. First seen by Alion on Oct 29, 2026. Sentry Insurance scores A on the Alion truth index.
This position can be filled as a Project Manager or Program Manager based on the experience and qualifications of the selected candidate.
What You'll Do
As a Project Manager, you will:
- Deliver department-level projects or assist with cross-department projects or portions of portfolio-level initiatives, typically involving multiple teams across IT functions or business areas, with a focus on initiatives involving cloud & platform engineering, infrastructure technology, workplace technology, AI and machine learning engineering, or data analytics.
- Facilitate communication, problem-solving and negotiation across teams, while collaborating at the manager to director level to ensure stakeholder and general project alignment.
- Lead core project delivery activities such as planning, schedule management and project risk management including contributing ideas and content such as solutions, risks, issues, and other project related artifacts.
- Provide financial tracking and cost management support for department level projects.
- Promote collaborative partnerships across the core project team, vendors, and impacted business areas ensuring common direction and delivery tactics.
What it Takes
- Bachelor’s Degree or equivalent work experience.
- Minimum of 5 years related work experience with a minimum of 2 years’ experience in leading projects.
- Demonstrated experience in a fast paced, information technology environment preferred.
- Experience in cloud & platform engineering, infrastructure technology, workplace technology, AI and machine learning engineering, or data analytics areas desired.
- Agile and/or Project Management Professional certification preferred.
- Excellent analytical and problem-solving skills with a strong operational focus preferred.
- Previous experience in the insurance industry preferred.
Here is what you can look forward to as part of our team:
At Sentry, your total rewards go beyond competitive compensation. We’re committed to supporting the whole you, which is why we offer a comprehensive package designed to help you thrive both professionally and personally.
- Hybrid Flexibility: Enjoy the best of both worlds. With optional work from home on Mondays and Fridays and join your team in the office Tuesday through Thursday to collaborate and learn. We provide the technology and tools you need for both your office and home workspace from day one.
- Dining on Us: Depending on your location, we may provide a stipend that can be used at our on-site cafeteria or a meal allowance to keep you fueled.
- Continuous Learning: Unlock your potential through Sentry University and take advantage of our tuition reimbursement program.
- Comprehensive Benefits: We support your whole self with group medical, dental, and vision insurance along with parental leave, pet insurance, caregiver leave, and wellness resources. Options for HSA, FSA, and Dependent Care FSA are available.
- Work-Life Balance: Enjoy your generous Paid Time Off allowance to rest and take advantage of paid Volunteer Time Off to support your community.
- Investing in Your Future: We’re committed to your long-term financial well-being. We offer a 100% company match on the first 8% you contribute to your 401(k) each pay period, and those funds vest immediately.
- Giving Back: Through the Sentry Foundation, we’re proud to support the United Way and make a difference in our communities.
Why Join Sentry?
At Sentry, we believe our people are the heart of our success. We’re proud to be recognized for the culture we’ve built, earning spots on Forbes’ lists for America’s Best Midsize Employers and Best Employers for New Grads, as well as Newsweek’s America’s Greatest Workplaces for Women and Diversity. These honors reflect our commitment to your professional satisfaction and growth.
Building on a Legacy
Our future is bright, but it’s anchored in a long history of stability. Since our founding in 1904, we’ve dedicated ourselves to helping businesses protect their futures. That trust has made us one of the largest and most financially stable mutual insurance companies in the U.S. We’re proud to have maintained an A+ rating from A.M. Best, the industry’s leading authority, for over 30 years.
Your Career, Our Community
Whether you’re working at our headquarters in Stevens Point, Wisconsin, or one of our many offices across the country, you’ll find a challenging and rewarding environment. Explore the Our Teams tab on our Career Page to see the diverse career paths we offer, with a focus on ongoing development and professional growth.
Ready to own your future? Join us at Sentry, opportunities await!
For this position, Sentry does not offer employment to holders of F-1, J-1, and H-1 Visas.
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.