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Senior IT Product Analyst (Hybrid Work Model)

Sentry Insurance
paid time off, 401(k)
United States, Illinois, Freeport
Feb 14, 2026
As a Senior IT Product Analyst, you will collaborate to implement new features and innovative solutions while aligning customer expectations with the IT product visions and strategy. For candidates in Illinois, the base salary range for this position is $90,600 -$136,000 annually. 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: Our Senior IT Product Analysts at Sentry are essential to our success of continuing to be innovative and competitive. As a Senior Analyst you'll:
    • Gather, analyze, and define technical product requirements. Assess and interpret customer needs and requirements for complex new features and/or defects. Ensure requirements traceability to product strategy.
    • Ensure thorough test plans are executed for your assigned features, and coordinate across teams to complete end-to-end product validation. Understand the big picture and take ownership of overall acceptance criteria.
    • Develop training and change management plans to promote user adoption and ensure smooth transition of our users and business units to new technology.
    • Lead agile teams and manage small projects taking accountability for high quality project deliverables and achieving overall objectives on time and within budget.

What it Takes:

  • Degree in Information Systems, Business Analysis or related discipline. Bachelor's degree is preferred.
  • Minimum 4 years of related work experience
  • Demonstrated leadership skills and ability to drive effective product discussions
  • Experience in leading large-scale projects and initiatives
  • Demonstrated ability to incorporate external data and research in product discovery
  • Strong stakeholder management skills

If you have experience or knowledge 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.

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 Cindy Siver, HR Specialist.

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.

Thank you for your interest in Sentry!

Cindy Siver

cindy.siver@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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