Benefits Manager

Job Description

Team: People Team / Benefits
Salary Range: $95k - $130k USD
Location: Chicago

This role is aligned to our hub locations. While we're especially interested in candidates in or near these areas, we welcome applications from outside of these locations as well.

Opportunity for Impact

Applied is where insurance technology gets reinvented, and we build it fast. Our cloud software and AI-powered solutions reach thousands of agencies and brokers worldwide, setting the pace for what modern insurance can do.

We're looking for a Benefits Manager to join our People Team and lead the design and delivery of our benefits and wellness programs, along with the AI-enabled systems that keep them running smoothly.


What You'll Do

• Implement and manage benefit and wellness programs aligned to our total rewards philosophy, including open enrollment, vendor implementations, and M&A benefit integrations
• Create inclusive, AI-assisted benefits communications and resources that drive awareness, engagement, and utilization across the platforms employees use
• Govern benefits technology, including the HRIS benefit module, enrollment platform, and carrier feeds, and help shape our automation roadmap and human-AI decision boundaries
• Build analytics dashboards and share utilization data and benchmark insights that inform plan design, vendor selection, and budget decisions
• Build strong relationships with benefit vendors, consultants, and administrators, and monitor regulatory changes that affect plan administration
• Keep compliance documentation current and support ERISA activities, including 5500 preparation, plan document reviews, and discrimination testing

What We're Looking For

• Bachelor's degree in Human Resources, Communications, Information Systems, or a related field (or equivalent experience), plus 5-8 years of progressive experience in benefits administration, benefits program management, or HRIS/benefits technology
• Proven project management experience leading cross-functional benefits initiatives end to end, from open enrollment to vendor implementations and system transitions
• Hands-on experience testing and administering a benefits module within a major HRIS platform (UKG strongly preferred)
• Working knowledge of federal and state benefit regulations, including ERISA, COBRA, HIPAA, FMLA, and ACA
• Experience managing benefits communications programs and employee engagement initiatives

Bonus points if you also have:

• CEBS or CBP certification
• Experience with M&A benefit integrations or similar system and program transitions
• Familiarity with AI writing tools and an understanding of RPA and workflow automation concepts

Talent shows up in a lot of different ways, and we mean that. We welcome candidates from all backgrounds and experience levels, including military members and their spouses and those without a traditional degree or tech background. If this role speaks to you, apply.

Why You'll Like Working on Team Applied
The best work happens when smart people move fast, together. For over 40+ years, Applied has built technology that solves real problems for insurance professionals - and we're still pushing what's possible.

You'll be part of our people-first culture built on trust, inclusion, and growth - where you're supported to deliver, collaborate with teammates who care, and grow with leaders invested in your success.

How We'll Support You

We invest in the whole person, not just the role. Our benefits and resources are built to support your health, your time, and your life outside of work:

• Medical, Dental, and Vision Coverage
• Holiday and Vacation Time
• Health & Wellness Days
• A Bonus Day for Your Birthday

Compensation Transparency

Our targeted starting base salary in the United States for this position considers a variety of factors, including depth and breadth of experience, skills and role scope. Depending on the role, team members may also be eligible for additional compensation plans (bonus and commission).

Your Security Matters
Our candidates' personal information and online safety are top of mind. Applied communicates with candidates only via a secure @appliedsystems.com email address or through our official careers portal. Recruiters will never request payments or ask for financial account or sensitive personal information like Social Security numbers.

Background Checks

Employment is contingent upon successful completion of applicable pre-employment background checks and verification processes.

AI Utilization

We leverage AI tools to streamline parts of our recruitment workflow (such as resume parsing and interview scheduling). However, final decisions are always conducted by real humans.

EEO Statement


Applied Systems is proud to be an Equal Employment Opportunity Employer. Diversity and Inclusion is a business imperative and is a part of building our brand and reputation. At Applied, we don't discriminate, and we are committed to recruit, develop, retain, and promote regardless of race, religion, color, national origin, sexual orientation, gender identity, disability, age, veteran status, and other protected status as required by applicable law.


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