Benefits Specialist

Description

At Ryan Lawn & Tree, we believe taking care of our people is just as important as taking care of our customers. As a 100% employee-owned (ESOP) company, our benefits aren't just a checkbox — they're a core part of how we show up for every associate, every day. We're looking for a Benefits Specialist who is passionate about people, sharp on compliance, and ready to own one of the most important functions in our HR team.

Who We Are

Ryan Lawn & Tree is one of the most respected lawn and tree care companies in the Midwest, serving customers across Kansas, Missouri, Oklahoma, and Nebraska. When Ryan grows, every associate grows with it — and the Benefits Specialist plays a direct role in making that promise real.

About the Role

The Benefits Specialist is the go-to expert for all things benefits at Ryan — serving as the primary point of contact for employee and manager questions, owning day-to-day administration and compliance across all benefit programs, and ensuring our people always have access to the coverage and support they've earned. This role touches everything from health and wellness plans to 401(k), ESOP, and leave administration, while partnering closely with payroll to maintain accurate deductions and airtight data integrity. A working knowledge of payroll is required. Experience with ESOP administration and bilingual communication skills are a definite plus.

This is a highly detail-oriented role that requires someone who can balance compliance precision with genuine care for people — someone who sees every question as an opportunity to make an associate feel supported and informed.

What You'll Do

Benefits Program Management

• Administer all employee benefit programs including health, dental, vision, FSA/HSA, life insurance, disability, EAP, wellness initiatives, and voluntary benefits
• Plan and execute the annual open enrollment process from start to finish
• Manage COBRA administration including timely notifications, enrollment, and carrier coordination
• Handle day-to-day benefits operations — life event changes, plan interpretation, problem resolution, and policy guidance
• Partner closely with payroll to ensure accurate, timely benefit deductions and airtight data integrity
• Process monthly vendor invoices and distribute wellness participation reports to stakeholders
• Participate in vendor evaluation and selection, providing subject matter expertise recommendations to leadership as needed
• Support leadership and finance during special projects including benefits-related M&A activity as needed

Leave & Compliance Administration

• Manage all leave of absence programs including FMLA, ADA, short-term disability, and company leave policies and coordinate information with workers' compensation as needed
• Process leave of absence certifications in accordance with company policies and regulatory requirements.
• Own full case management for leave — communicating approvals, denials, extensions, recertifications, and return-to-work plans to employees and managers
• Manage short-term disability claims, including coordination with carriers, tracking claim status, and communicating outcomes to employees and managers.
• Ensure ongoing compliance with federal, state, and local laws governing employee benefits and leave policies

401(k) Plan Management

• Oversee all aspects of 401(k) administration and compliance — monthly enrollments, employer contributions, annual compliance testing, and employee education
• Serve as the primary point of contact for the 401(k) service provider and ensure completion of annual audits
• Conduct regular meetings with new hires and participants to answer retirement benefit questions and coordinate with fund professionals as needed
• Interpret and administer retirement benefits in accordance with plan documents.
• Draft and distribute correspondence to participants and beneficiaries regarding retirement benefits.

ESOP Administration

• Assist in managing all aspects of the Employee Stock Ownership Plan (ESOP) including compliance reporting and employee education
• Act as the primary liaison with third-party ESOP administrators
• Oversee ESOP enrollment and communications so every associate truly understands their ownership stake

HR Support

• Pitch in across other HR functions as needed — including but not limited to new hire orientation, performance management, talent acquisition, and special  HR projects and initiatives

Requirements

What You Bring

Required

• Bachelor's degree in Human Resources, Business Administration, or a related field
• Minimum of 3–5 years of benefits administration experience including 401(k) and leave management
• Working knowledge of payroll processes and benefit deductions required
• Strong knowledge of ERISA, ACA, HIPAA, FMLA, ADA, and other benefits-related regulations
• Proficiency in HRIS and benefits administration systems
• Strong analytical, problem-solving, and project management skills
• Excellent verbal and written communication skills
• Ability to multitask in a fast-paced environment with a collaborative, team-first approach

Preferred

• SHRM certification
• Experience with ESOP administration
• Bilingual (English/Spanish) — a strong plus given our workforce demographics

Working Conditions & Physical Requirements

• This role operates in a professional office environment and routinely uses standard office equipment.
• Occasional travel may be required to company branch locations or for meetings, benefits fairs, conferences, or vendor engagements.
• Extended periods of sitting and computer use are typical.
• Consistent attendance is required, with some after-hours work during peak times.

Why Ryan Lawn & Tree?

• Competitive Compensation — $70,000-$80,000 depending on experience 
• Employee Ownership — 100% ESOP — a real stake in our success
• Full Benefits — Health, Dental & Vision insurance
• 401(k) — With company match
• Time Off — 17 PTO days + 11 paid holidays
• Culture — A tight-knit HR team that values doing things the right way

Ryan Lawn & Tree is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all associates.

Ready to Make a Real Impact on Real People?

Every benefit you administer, every leave you manage, every question you answer — it matters to the associates who depend on you. If you're a benefits professional who takes that responsibility seriously and wants to work somewhere that does too, we want to hear from you.

Apply today and help us take care of the people who take care of our customers.