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Heartland

Benefits Specialist

Heartland, Kansas City, Missouri, United States, 64101

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Who We Are

At HeartLand, our roots run deep - in the landscapes we care for and the partnerships we build. Since our founding in 2016, we've grown by acquiring and empowering exceptional local landscape companies, each bringing unique talent, history and heart.

Together, we've built a national family of brands committed to a shared purpose: Delivering the ordinary in extraordinary ways through investing in people, preserving legacies and scaling success. Today, with operations across 26+ states and counting, HeartLand is one of the fastest-growing and most trusted names in the green industry.

What You'll Do

As HeartLand's Benefits Specialist, you'll be the go-to expert on all things benefits, balancing the strategic and the tactical, focusing on advocacy efforts with employees to drive utilization of our programs and cost containment offerings. Through this lens, you will collaborate with vendors, brokers, HR partners, and leadership to build programs that drive satisfaction, cost-efficiency, and cultural alignment. This is a career opportunity to grow your HR expertise with a growing, forward-thinking employer in the service industry. Responsibilities include:

Benefits Operations & Compliance Manage day-to-day benefits activities, including enrollments, life events, COBRA, and terminations. Ensure data accuracy in HRIS and maintain data integrations with vendors. Maintain compliance with ERISA, HIPAA, ACA, COBRA, and related regulations. Support annual renewal and open enrollment cycles from planning to execution. Employee Engagement & Education

Serve as a trusted resource for employees navigating benefits, onboarding, life events, and Medicare. Proactively market and educate employees on underutilized programs (Teladoc, EAPs, CancerCARE, etc.). Host webinars, info sessions, and create campaigns to drive awareness and utilization. Vendor & Broker Management

Own relationships with medical, dental, vision, 401k, FSA/HSA, and voluntary benefit vendors. Audit invoices, manage service levels, and track engagement across benefit platforms. Drive adoption of cost-saving programs and report on results. M&A Integration & Internal HR Support

Play a key role in benefits transitions during acquisitions. Partner with local HR to ensure smooth onboarding and communication. Equip HR partners with tools, training, and playbooks to support employee benefit questions. Provide reporting, insights, and audit readiness for compliance filings (5500s, ACA, etc.). Analytics & Reporting

Build dashboards tracking plan usage, cost drivers, and employee behavior. Translate broker reports into actionable insights for HR and executive teams. What You Bring

3+ years of experience in benefits administration or HR operations Proficient with HRIS platforms (e.g., Paycor, ADP) and benefits systems Working knowledge of ERISA, HIPAA, FMLA, COBRA, ACA Top proficiency in analytical tools such as Excel, Power BI, and AI tools (e.g. ChatGPT) Strong communicator: empathetic, patient, and clear Bonus points for:

Bachelor's in HR, Business, or related field Multi-site or field-based experience M&A or integration experience Spanish language skills

Your Mindset

People-Centered : You love helping employees make smart decisions about their benefits. Data-Driven : You uncover insights and translate them into action. Clarity Creator : You simplify the complex and build employee trust. Trusted Partner : You're the calm, confident bridge between employees, HR, and vendors.

Pay Range:

$75,000 - $90,000 per year