People Operations Specialist Jobs in Wisconsin
People Operations Specialist jobs in Wisconsin are open across Milwaukee, Madison, and Kenosha and other Wisconsin metros, with employers like Molina Healthcare, Michels, and Wellpoint Care Network hiring at every experience level. Find a role that fits below and apply directly.
Find JobsOverview
Showing 5 of 27+ People Operations Specialist jobs











INTRODUCTION
Sentry’s HR Specialists serve as the key HR representative in the field office in which they are located. This role will be located at our Middleton, WI office location in a hybrid work model. The HR Specialist provides support and guidance to Sentry managers and associates across a range of areas such as associate relations and talent acquisition.
ROLE AND RESPONSIBILITIES
As an HR Specialist, you will:
- Coach and guide managers in assessing need for and developing associate-related communications, including corrective action documentation.
- Engage and meet with business unit leaders and associates developing relationships, trust and engagement. Serve as an on-site conduit for multiple HR and Corporate departments.
- Coordinate the termination process and serve as a point of contact for terminated associates.
- Coordinate the employee exit process, conduct exit interviews, and provide critical information and input into termination decisions.
- Review initial complaints, conduct investigations, and with input from Associate Relations management and in some cases inside legal counsel, recommend corrective action and provides summary reports as appropriate.
- Execute the entire recruitment cycle for assigned positions from the requisition process, the presentation of candidates, and pre-hire screens to final offer letter.
- Provide additional programs, communications or resources in areas such as performance management, employee relations, recruitment, compensation, career development and leadership development to meet the specific needs of the business function.
BASIC QUALIFICATIONS
- Bachelor’s degree or equivalent work experience.
- Minimum of 3 years of related work experience.
- Possesses a thorough knowledge of the major HR disciplines and can demonstrate the ability to provide HR support to their business partners.
- Solid understanding of fair employment practices and regulations.
- PHR certification preferred.
- Exceptional skills in written and verbal communications.
- Proficient in Microsoft Word, Excel, PowerPoint and Outlook.
- Ability to multi-task and meet deadlines under pressure.
- Excellent organizational, collaboration and follow-up skills.
PREFERRED QUALIFICATIONS
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.
ABOUT SENTRY
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!
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.
See All 27 People Operations Specialist Jobs in Wisconsin
Find roles in Wisconsin that match your experience and apply in just a few clicks.
Find JobsPeople Operations Specialist Jobs by City in Wisconsin
Where Wisconsin roles are concentrated, by current openings.
People Operations Specialist Job Market in Wisconsin
A snapshot from current Wisconsin openings, updated as new roles post.
Who's Hiring
- Molina Healthcare11

- Michels2

- Wellpoint Care Network2

- Aspirus Health1

- Big Brothers Big Sisters1

Top Industries Hiring
- Healthcare & Medical Services17
- Construction & Real Estate3
- Education3
- Manufacturing2
- Insurance1
What Wisconsin Employers Look For
The qualifications that appear most often in people operations specialist jobs across Wisconsin.
- Experience with HRIS platforms such as Workday, BambooHR, or ADP
- Bachelor's degree in human resources, business administration, or a related field
- Knowledge of HR compliance, employment law, and workplace policy
- Proficiency in managing benefits administration and open enrollment cycles
- Strong written communication skills for policy documentation and employee communications
- PHR or SHRM-CP certification preferred for mid-level and senior positions
People Operations Specialist Jobs in Wisconsin: Frequently Asked Questions
How many people operations specialist jobs are there in Wisconsin?
There are 27+ people operations specialist openings in Wisconsin on Migrate Mate as of June 2026, with the most roles in Milwaukee, Madison, and Kenosha. New positions post regularly as employers across Wisconsin hire.
How much do people operations specialists make in Wisconsin?
People operations specialists in Wisconsin earn a median of about $70,540 a year, based on May 2025 Bureau of Labor Statistics wage data, ranging from around $47,860 for the lowest 10% to over $105,270 for the top 10%. Pay rises with experience, specialty, and employer.
Which Wisconsin cities have the most people operations specialist jobs?
Milwaukee, Madison, and Kenosha have the most people operations specialist openings in Wisconsin right now, with additional roles spread across smaller metros statewide.
Which companies hire people operations specialists in Wisconsin?
Employers hiring people operations specialists in Wisconsin include Molina Healthcare, Michels, and Wellpoint Care Network, based on current listings on Migrate Mate as of June 2026.
Are there remote people operations specialist jobs in Wisconsin?
Yes. About 48% of people operations specialist openings tied to Wisconsin are remote or hybrid as of June 2026. The rest are on-site roles based in Wisconsin metros.
How do I apply for people operations specialist jobs in Wisconsin?
You can apply to people operations specialist jobs in Wisconsin directly on Migrate Mate. Search the listings above, find roles that match your experience and preferred Wisconsin location, then apply to each one that fits.
See All 27 People Operations Specialist Jobs in Wisconsin
Find roles in Wisconsin that match your experience and apply in just a few clicks.
Find Jobs