Project Manager (Hybrid Work Model)

sentryinsurance· 001 Sentry Insurance Company
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📍 Madison, WIFull time
Full time001 Sentry Insurance Company

About this role

Sentry’s Project Managers manage department specific projects and portfolio initiatives.

What You'll Do

As a Project Manager, you will:

  • Deliver department level projects or assists with cross-department projects or portions of portfolio level initiatives, typically involving multiple teams across IT functions or business areas.

  • 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

  • Bachelors 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.

  • 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.

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!

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

Katelynne.Rivera@Sentry.com

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.

Frequently Asked Questions

Is the salary disclosed for the Project Manager (Hybrid Work Model) position at sentryinsurance?
The salary for this Project Manager (Hybrid Work Model) role at sentryinsurance is not publicly listed. Click "Apply Now" to learn more about the compensation package on their official careers page.
Where is the Project Manager (Hybrid Work Model) position at sentryinsurance located?
This Project Manager (Hybrid Work Model) role at sentryinsurance is based in Madison, WI. The position is listed as on-site or hybrid. Check the full job description or apply directly to confirm the work arrangement.
Is the Project Manager (Hybrid Work Model) role at sentryinsurance full-time or part-time?
This is listed as a Full time position. It is posted as a Project Manager (Hybrid Work Model) role in the 001 Sentry Insurance Company department at sentryinsurance.
Which team or department does the Project Manager (Hybrid Work Model) at sentryinsurance belong to?
This Project Manager (Hybrid Work Model) position is part of the 001 Sentry Insurance Company department at sentryinsurance. See the full job description for more information about the team structure and responsibilities.
How do I apply for the Project Manager (Hybrid Work Model) position at sentryinsurance?
Click the "Apply Now" button on this page. You will be redirected to sentryinsurance's official application portal hosted on workday where you can submit your application directly.
When was the Project Manager (Hybrid Work Model) job at sentryinsurance posted?
This Project Manager (Hybrid Work Model) position at sentryinsurance was posted on Aug 14, 2026. Apply as soon as possible — early applications are often reviewed first.
Project Manager (Hybrid Work Model)
sentryinsurance
Apply for this role ↗

You'll be redirected to sentryinsurance's official application page on Workday.