Project Manager (Hybrid Work Model)

001 Sentry Insurance Company; Madison (WI); Hybrid; USD 85,000 - 120,000; Full time

Benefits offered by this job

Hybrid work model

Home office setup

Meal subsidy

401(K) plan with match

Tuition Reimbursement

Paid time off

Health and wellness benefits

Job summary

Sentry in Wisconsin is seeking a Project Manager to lead department level projects and contribute to cross-department portfolio initiatives across IT and business areas. You will guide planning, scheduling, risk management, and stakeholder alignment with input from managers to directors.

The role rewards strong analytical skills and a background in fast-paced environments, with preference for Agile/PM certification and prior insurance industry experience.

Qualifications

• 5+ years of project experience in IT or business environments.
• 2+ years leading department or cross‑department projects.
• Agile and/or PMP certification preferred.
• Experience in the insurance industry is advantageous.

Responsibilities

• Lead department level projects and assist with cross‑department initiatives across IT and business areas.
• Facilitate communication and negotiation across teams from manager to director level.
• Lead planning, scheduling, risk management, and project artifacts.
• Provide financial tracking and cost management for department projects.
• Promote partnerships with vendors and impacted business areas.

Skills

5+ years of project experience

2+ years leading projects

Agile and/or PMP certification

Insurance industry experience

Analytical and problem-solving

Education

Bachelor's Degree or equivalent

Job description

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

What You’ll Do

• 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.

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.

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 associates are the most important part of our company. We became one of the most financially strong mutual insurance companies in the U.S. by striving to provide the best possible service to our business customers. We do this by having conversations, forming relationships, and getting to know the people we work with and their businesses. We make that same commitment to our associates. When you join Sentry, we don’t just want you to perform tasks each day. We want you to enjoy your time with us. You’re in the driver’s seat of your career path here—sharing feedback, creating goals, accessing professional development resources, and identifying how you can contribute to both your success and the success of the company. Yes, we work hard. But we work with the purpose of helping others, and with the understanding that there’s more to life than work. We invite you to learn more about us. You’ll find we’re much more than insurance.

Talent Acquisition Specialist

Thank you for your interest in Sentry!

Katelynne Rivera [e-mail]