Benefits Specialist

Benefits Specialist

Location:

Rosemont, IL (On-site with travel)

The Visterra Landscape Group platform is ranked among North America's top 20 landscape service providers. Collectively, Visterra partner companies bring more than 200 years of expert landscape maintenance, enhancement, construction, sweeping, portering and critical winter services with a reputation for excellence in client service.

Incumbent partner leaders guide day-to-day operations with teams that value and prioritize safety, employee wellbeing and dynamic career pathways.

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 Grounds PRO in Ohio and Kentucky; H&M Landscaping in Northeast Ohio;
Land Corps in Tennessee;
Full Care serving Missouri and the broader Midwest region; and Clover, serving Alabama.

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.

• 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

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

Compensation

Salary range: $80,000 – $85,000, based on experience

Benefits

Visterra offers a challenging and rewarding work environment where employees are encouraged to develop and grow as professionals. In this role, you will have the opportunity to expand your technical expertise while supporting a growing organization.

· Paid time off

· Health and wellness coverage

· 401(k) savings plan

· Professional development opportunities