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Senior Project Manager


Sentry is seeking a motivated and self-directed leader to join our Project Management Office (PMO), based in Stevens Point, Wisconsin.  Sentry’s PMO has an impressive track record of delivery and is made up of a talented team of leaders who share knowledge and delivery techniques.  You will support the organization by providing leadership, demonstrating value and delivering results which improve the efficiency, effectiveness and alignment between business units and technology.

This role is considered a foundational leadership role that gives you the opportunity to apply skills in critical thinking, communication and delivering solutions with minimal guidance.  This position can be filled as a Project Manager or Senior Project Manager based on the selected candidate’s related qualifications and experience.  

What You'll Do

  • Delivery (Execution)
    • Demonstrates knowledge of the insurance industry and how the business works
    • Drives key project decisions, meeting outcomes, risks and issues
    • Contributes deliverables consisting of lean business cases, progress trackers, dependency maps and outcome measurements
    • Analyzes and solves problems that are of moderate complexity and presents options along with recommendations to others
    • Reviews and provides feedback for work estimates, planned allocations, target dates and work output
    • Helps others identify and escalate key risks and issues to the appropriate audience
    • Motivates teams to deliver project work on time by providing clear milestones and clear expectations
    • Receives minimal instruction on daily work tasks and minimal instruction on new assignments
  • Planning and Schedule Management
    • Effectively plans, organizes and monitors work backlogs against team allocations for multiple teams to ensure alignment with the overall release schedule
    • Develops work plans, determines project critical path and uses milestones to partition projects into manageable releases
    • Works with other individuals to prepare and monitor product backlogs
    • Develops contingency plans at a team level in anticipation of possible problems
  • Reporting and Communication
    • Facilitates brainstorming sessions to develop strategies, solve problems and drive efficiency.  Typically, at the team and manager levels.
    • Facilitates project meetings to ensure the appropriate results are delivered 
    • Presents oral and written reports defining plans, problems, and resolutions to appropriate levels of management
    • Prepares and maintains project documentation such as status reports, presentation materials, spreadsheets and project dashboards
    • Provides transparency, accuracy and appropriate status including communicating any variances from communicated delivery dates. Demonstrates knowledge of when, how and to whom issues need to be escalated.
    • Communicates critical items to the appropriate audience prior to publishing or presenting information to a broader group.
  • Partnerships (Collaboration)
    • Collaborates with IT management and directors to plan for and execute key initiatives
    • Develops, fosters and maintains trust and credibility with project team members who are typically at management levels
  • Resource and Capacity Planning
    • Understands the interaction between team allocations and schedule and applies the ability to develop and monitor comprehensive delivery plans
    • Identifies skillset needs and works with leads to involve teams with the appropriate skillset  
    • Helps resolve project allocation conflicts and properly aligns the expectations of project team to achieve delivery
  • Financial and Cost Responsibility
    • Understands and assists with managing project financials in support of project objectives and cost-benefit analysis
  • Vendor Management
    • Facilitates vendor variance and issue resolution
    • Monitors and addresses vendor performance and adherence to the contract
    • Manages contracts along with consulting policies and procedures

What it Takes

•    Bachelor’s Degree in Business, Information Technology, Engineering or Business Analysis or equivalent work experience 
•    5+ years of related work experience in a fast paced, agile software development environment
•    Previous experience in an IT organization and/or the Insurance industry preferred
•    Project Management Professional (PMP) certification preferred
•    SAFe experience and/or certifications such as the SPC, SSM or RTE preferred
•    Demonstrates the ability to drive consistent delivery and improvements in a scaled agile environment
•    Demonstrates the ability to be a team player who establishes credibility and rapport with technical and non-technical team members.  Applies skills and knowledge of technical proficiencies to deliver value and improve efficiencies.  
•    Displays positive attitude, demonstrates commitment to established goals, demonstrates ability to manage multiple items and prioritize effectively

What You'll Receive

We take great pride in making Forbes’ list of America’s Best Midsize Employers since 2017. A lot of different factors go into that honor, many of which contribute to your job satisfaction.  At Sentry, your total rewards go beyond competitive compensation.  Below are some benefits and perks that you’ll receive.

  • Generous Paid-Time Off plan for you to enjoy time out of the office.
  • 401(K) plan with a dollar for dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future.
  • Group Medical, Dental, Vision and Life insurance to encourage a healthy lifestyle.
  • Pretax Dependent Care and Health Expense Reimbursement Accounts to ease taxes on health spending.
  • Extensive Work-Life Resources to lend a helping hand.
  • Sentry Foundation gift matching program to encourage charitable giving.
  • Continue your education and career development through Sentry University (SentryU).

How You’ll Apply

If you are interested in joining Sentry’s team, select the one position that you are most interested in being considered for and complete your online application details. If you have applied with us before, you will only need to provide your email address and password. If this is your first time applying, you’ll need to create an account. Please complete your application and upload your resume online.

About Sentry

All of us at Sentry—more than 4,000 associates—have various talents, skills, and backgrounds. We work together to deliver on our promises to our policyholders every day. We’re proud to offer a full line of property, casualty, and life insurance products to help protect businesses, cars, homes, lives, and retirement income.


Our headquarters is in Stevens Point, Wisconsin, with claims and service 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.


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.


Get ready to own your future at Sentry. Opportunities await.

Equal Employment Opportunity

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.

Talent Acquisition Specialist

Thank you for your interest in Sentry!

Zach Wierzba

Job Title:
Senior Project Manager
Job ID:
Salary Grade:
Stevens Point, WI
Full/Part Time:
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