Benefits Manager

Job Title: Benefits Manager

Department: Human Resources Reports to: VP, HR Operations

Location: Chicago

Work Arrangement: Hybrid Set - In office 2-3 Days

Employment Type: Full-Time, Exempt

Salary Range: $91,000 - 114,000 Annually

Company Background

Highstreet Insurance Partners (Highstreet) is one of the fastest-growing insurance agencies in the U.S. Founded with the mindset of putting people first, Highstreet brings technical expertise and industry experience together to serve and protect customers while providing agencies with the tools and resources to grow.

We love to help people pursue life's opportunities with tenacity and confidence to create stronger, more resilient communities. We do it for all our futures.

Position Summary

Reporting to the VP, HR Operations, the Benefits plays a critical role in shaping the employee experience by designing and managing a comprehensive, competitive, and compliant benefits program that supports the organization's ability to attract, retain, and engage top talent. This role is responsible for the strategic planning, administration, and continuous improvement of all employee benefits offerings, including health and welfare programs, voluntary benefits, and leave policies. The Benefits Manager serves as a key advisor to leadership and a trusted resource for employees, ensuring that benefits programs are aligned with organizational objectives, financial parameters, and the evolving needs of the workforce.

In addition to day-to-day oversight, the Benefits Manager is expected to analyze utilization data and market trends, recommend program enhancements, lead vendor negotiations, and ensure compliance with all applicable federal, state, and local laws. This role requires strong project management skills, exceptional attention to detail, and a proactive, employee-centric approach.

Key Areas of Responsibility

• Develop and manage the company's benefits strategy in alignment with overall HR and organizational goals.
• Oversee day-to-day administration of all benefits programs, including medical, dental, vision, life, disability, and wellness programs.
• Oversee and reconcile monthly benefits billing, ensuring accuracy of carrier invoices, timely payments, and proper allocation of costs across departments or entities
• Lead the annual open enrollment process, including communications, system setup, employee education, and vendor coordination.
• Evaluate and recommend new benefit programs or changes to existing programs to improve employee satisfaction and manage costs.
• Ensure compliance with all applicable laws and regulations (e.g., ERISA, ACA, HIPAA, COBRA, FMLA).
• Manage relationships with external vendors and brokers to ensure service levels and contract terms are met.
• Provide expert guidance to employees regarding benefit plan coverage, eligibility, and claims resolution.
• Create and maintain accurate benefits documentation and policies.
• Partner with Payroll, Finance, and Legal teams to ensure benefits are processed and recorded accurately.
• Analyze benefits utilization and costs, prepare reports and recommendations for senior leadership.
• Support M&A activities, including benefits integration and harmonization.
• Supervise and develop benefits staff (if applicable).

Required Competencies

• Bachelor's degree in Human Resources, Business Administration, or related field
• 5+ years of progressive experience in benefits administration; at least 2 years in a leadership role.
• In-depth knowledge of employee benefits and related regulations.
• Experience managing benefits in a multi-state or multi-FEIN environment preferred.
• Strong analytical, communication, and project management skills.
• CBP certification desirable.
• Proficient in HRIS systems and Microsoft Office Suite

Key Personal Attributes

• Treats people with respect and dignity
• Keeps commitments and demonstrates exceptional follow through
• Team-first orientation; high integrity, and mature character
• Positive, get it done personality
• Sense of urgency: "All hands-on deck"
• Exhibits confidence in self and others
• Comfortable expressing vulnerability
• Effectively influences outcomes and gives appropriate recognition to others

Benefits:

• Employer Paid Life & AD&D
• Employer Paid Short- & Long-term disability
• Paid Holidays
• 401k with employer match
• Voluntary Health, Vision, Dental and many other benefits!

Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions of the position as described above.