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Project Manager

Company: Sentry
Location: Madison
Posted on: October 13, 2021

Job Description:


Sentry is seeking a motivated and self-directed leader to join our Project Management Office (PMO).  Sentry’s PMO drives agile delivery of software and solutions at scale with an impressive track record of outcomes that meet the demands of our insurance operation and supporting IT platforms.  We are a talented team of leaders who share knowledge and delivery techniques to continuously innovate project management practices and inject improvements into the delivery pipeline.

  • Planning and Forecasting Assigned Initiatives
    • Facilitate collaboration between Product Management and Technical Leaders to understand the problem, define solution alternatives and build a comprehensive backlog & lean business case
    • Work with Technical Leaders to understand and document backlog dependencies, define a release strategy and identify key milestones
    • Work with Product Management and shared services to prioritize and allocate capacity resulting in a roadmap that conveys a clear plan and expectations
    • Develop and manage a risk and issue log that drives awareness and timely decision making
    • Facilitate approval to begin delivery activities
  • Delivery of Assigned Initiatives
    • Facilitate/Monitor backlog grooming sessions to maintain alignment with intended outcomes, refine dependencies and ensure adherence to committed allocations.
    • Monitor and measure delivery progress through metrics and collaboration with release train engineers
    • Maintain and manage risk and issue log escalating key information for awareness and decision making
    • Maintain roadmaps, budget forecasts and dashboard in alignment with progress, backlog refinement and allocation adjustments.
    • Facilitate continued collaboration and leadership alignment through periodic stakeholder, steering and governance ceremonies
  • Agent for Change and Improvement
    • Identify project management practice problems/opportunities
    • Participate on PMO Practice team to deliver and socialize improvements to PMO services
    • Identify inefficiencies in delivery pipeline and coach teams and contributors in key roles through improvements
  • Vendor and Budget Management
    • Facilitate vendor selection process for software or services as needed
    • Work with program leadership, financial controller and portfolio governance to understand and document budget impacts
    • Monitors and addresses vendor performance and adherence to the contract and/or established plan
  •  Bachelor’s Degree in Business, Information Technology, Engineering or equivalent work experience
  • 5+ years project management experience in a fast-paced agile software development environment
  • Demonstrated ability to:
    • drive consistent delivery and improvements in a scaled agile environment
    • be a team player who establishes credibility and rapport with technical and non-technical leaders & team members
    • create and manage accountability to established goals and commitments
  • Previous experience in an IT organization and/or the Insurance industry is preferred
  • Project Management Professional (PMP) or equivalent certification preferred
  • SAFe experience and/or certifications such as the SPC, SSM or RTE preferred

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).
  • To best support our associates and our culture, Sentry is happy to offer flexible work through scheduled work from home days on Mondays and Fridays and in office days Tuesday - Thursday after we return to the office for this position!

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.


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.


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.


Thank you for your interest in Sentry!

Zach Wierzba

Keywords: Sentry, Madison , Project Manager, Other , Madison, Wisconsin

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