Benefits Specialist

Benefits SpecialistLocation: Rosemont, IL (On-site with significant travel)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.Role OverviewThe 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.Key ResponsibilitiesAdminister employee benefits programs, including enrollments, life events, eligibility changes, and terminationsServe as the primary point of contact for employee benefits questions and supportEnsure accurate benefit deductions, system updates, audits, and benefits bill reconciliationLead and facilitate onsite open enrollment sessions annually and for newly acquired companies, including employee education and presentations in English and SpanishPartner with HR, Payroll, brokers, and vendors to ensure compliant and effective benefits administrationSupport company-wide wellness initiatives, including creating and promoting wellness challenges and engagement programsTravel 50–60% to company locations to support enrollments, acquisitions, and employee engagement effortsKey QualificationsRequired QualificationsBilingual in English and Spanish2–4 years of experience in benefits administration, HR operations, payroll, or a related HR functionHands-on experience administering health and welfare benefits, including enrollments, eligibility changes, and employee supportExperience with benefits bill reconciliationAbility and willingness to travel 50–60% to field locations and partner companiesStrong understanding of benefits eligibility rules, deductions, and employee communicationsHigh attention to detail with the ability to manage sensitive and confidential informationExcellent customer service, communication, and interpersonal skillsPreferred QualificationsBachelor's degree in Human Resources, Business, or a related fieldExperience facilitating onsite open enrollment meetings or employee group presentationsExperience supporting benefits integration during company acquisitionsFamiliarity with HRIS and payroll systems (ADP or similar platforms preferred)Working knowledge of COBRA, ACA, and general benefits compliance requirementsExperience supporting or coordinating wellness programs or employee engagement initiativesBenefitsVisterra offers a challenging and rewarding working environment where employees are encouraged to develop and grow as professionals. In this role, you will have the opportunity to work on projects that will expand your experience and challenge your abilities in the global marketplace. The position also offers an excellent compensation package and a comprehensive suite of benefits.• Paid time off• Health and wellness coverage• 401(k) savings plan