Benefits Specialist

Location: Rosemont, IL (On-site with significant travel)

About Us

Visterra Landscape Group is a leading commercial landscaping platform and one of the top 50 landscaping companies in the United States. Through its growing family of partner companies, Visterra delivers expert landscape maintenance, enhancements, construction, and critical winter services with a strong focus on safety, operational excellence, and client service. With incumbent partner leaders continuing to guide day-to-day operations, Visterra is actively expanding its platform while prioritizing employee well-being, safety, and long-term career growth opportunities.

Visterra’s partner companies include Outdoor Pride and Riverside Services in New Hampshire and Massachusetts; Dyna-Mist and Texas Landscape Group in Texas, Oklahoma, Louisiana, and Arkansas; Oberson’s and GroundsPRO in Ohio and Kentucky; H&M Landscaping in Northeast Ohio; Land Corps in Tennessee; and Full Care serving Missouri and the broader Midwest region. For more information, visit www.vlgllc.com.

Role Overview

The Benefits Specialist is a key member of the Human Resources team and is responsible for supporting the day-to-day administration of employee benefits programs across Visterra Landscape Group and its partner companies. This role serves as a primary point of contact for benefits-related questions, enrollments, eligibility changes, life event updates, and employee support. This position plays a highly visible, employee-facing role, requiring frequent on-site travel to support open enrollments, acquisitions, and employee engagement initiatives, including wellness programs. The Benefits Specialist partners closely with HR, Payroll, external vendors, brokers, and the Total Rewards Manager to ensure accurate, compliant, and timely benefits administration while delivering a positive employee experience.

Responsibilities

• Administer employee benefits programs, including enrollments, life events, eligibility changes, and terminations
• Serve as the primary point of contact for employee benefits questions and support
• Ensure accurate benefit deductions, system updates, audits, and benefits bill reconciliation
• Lead and facilitate onsite open enrollment sessions annually and for newly acquired companies, including employee education and presentations in English and Spanish
• Partner with HR, Payroll, brokers, and vendors to ensure compliant and effective benefits administration
• Support company-wide wellness initiatives, including creating and promoting wellness challenges and engagement programs
• Travel 50–60% to company locations to support enrollments, acquisitions, and employee engagement efforts

Qualifications

Required Qualifications

• Bilingual in English and Spanish
• 2–4 years of experience in benefits administration, HR operations, payroll, or a related HR function
• Hands-on experience administering health and welfare benefits, including enrollments, eligibility changes, and employee support
• Experience with benefits bill reconciliation
• Ability and willingness to travel 50–60% to field locations and partner companies
• Strong understanding of benefits eligibility rules, deductions, and employee communications
• High attention to detail with the ability to manage sensitive and confidential information
• Excellent customer service, communication, and interpersonal skills

Preferred Qualifications

• Bachelor’s degree in Human Resources, Business, or a related field
• Experience facilitating onsite open enrollment meetings or employee group presentations
• Experience supporting benefits integration during company acquisitions
• Familiarity with HRIS and payroll systems (ADP or similar platforms preferred)
• Working knowledge of COBRA, ACA, and general benefits compliance requirements
• Experience supporting or coordinating wellness programs or employee engagement initiatives

Benefits

• Paid time off
• Health and wellness coverage
• 401(k) savings plan