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Director of Project Management (Hybrid Work Model)

Sentry Insurance
paid time off, 401(k)
United States, Wisconsin, Stevens Point
1800 North Point Drive (Show on map)
Sep 30, 2025
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.

The Director of Project Management is responsible for the operation of Sentry's centralized, Project Management Office and is responsible for managing the continuing development and implementation of the PMO strategy, Project management lifecycle methodology, and aligning the PMO vision with the overall organizational vision.

What You'll Do

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:

  • Innovate: Through our agile development process, you'll have the opportunity to apply your creativity and innovation to drive new solutions.

  • Learn: Sentry provides several resources to help you further your career and continue your personal development, including Sentry University, LinkedIn Learning, and peer-led educational sessions and communities.

  • Grow: Sentry provides many opportunities to grow in your career. Through meaningful, ongoing conversations around growth and development, we encourage all associates to take ownership in their career path.

  • Contribute: As the Director of Project Management, you will:

    • Oversee and lead project management staff to ensure the team meets or exceeds customer expectations.

    • Assign project management staff to projects based upon skill requirements and availability.

    • Administer human resource-related activities including timely performance and salary reviews and ensure all subordinates adhere to human resources policies and practices. Select, develop, motivate, and recognize staff.

    • Determine the need for outsourcing of projects, reviews the resources available and selects a vendor to meet the project needs.

    • Participate in overall strategic project budgeting, CBA creation, and cross-project resource management.

    • Manage the IT project pipeline to ensure projects are not held up by bottlenecks, project priorities are adjusted based upon business needs, and adequate attention is given to projects.

    • Responsible for developing, implementing and maintaining the standard processes and procedures to be used in the delivery of projects, including Systems Development Life Cycle (SDLC), urgent project methodology, and quality assurance principles.

    • Develop and maintain standard project management tools, including a central project repository, time tracking,

    • requirements database, etc. Mature a PMO practice that involves complex system development and business projects.

    • Prepare, in conjunction with the Project Manager and project team, a formal proposal and recommendation for each project. Review the project work plan which includes identification of all tasks and development of a timetable in which each task is to be accomplished.

    • Ensure that the appropriate project analysis steps have been completed for each project, including problem and

    • solution statements, as well as scope and size definitions.

  • What it Takes:

    • Bachelors Degree or equivalent work experience.

    • Minimum 8 years of related work experience.

    • Degree in Information Technology, industrial engineering or project management.

    • Previous experience in a Project Management role.

    • Previous experience in a supervisory role or training in supervisory skills beneficial.

    • Analytical ability to research, develop and make conclusive decisions.

    • Good human relations and communications skills.

    • Organization, leadership, and people management skills.

If you have experience in the skills listed above, please consider joining our Sentry team!

What You'll Receive

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.

About Sentry

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.

Our Stevens Point campus offers a full-service fitness center, swimming pool, basketball and racquetball courts, auto center, credit union, on-site Aspirus clinic, restaurants, boutique hotel, and the award-winning SentryWorld golf course.

How You'll Apply

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.

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.

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