Benefits Manager (Remote)

Perennial Services Group

Human Resources Department

Salary: $90,000-$100,000

Job Description

Position Overview

The Benefits Manager is a critical member of PSG's HR team, serving as the primary expert on all health and welfare benefit programs across a growing multi-brand platform of 35+ partner companies and approximately 1,700 employees. This is a remote role supporting a distributed workforce across multiple states. The position requires strong virtual communication skills and the ability to collaborate effectively with internal teams, partner companies, and external vendors. Occasional travel (up to 10%) may be required for acquisitions, onsite meetings, or key HR initiatives.

About PSG

Perennial Services Group is a PE-backed home services platform with 35+ partner companies, approximately 1,700 employees, and revenues of $216M. We are in an aggressive growth phase targeting $600M by 2030. Our benefits function plays a critical role in our ability to attract, retain, and serve a diverse, distributed workforce.

Key ResponsibilitiesBenefits Strategy & Broker Partnership

• Partner with Alliant (PSG's benefits broker) to evaluate, select, and administer the full suite of health and welfare benefit plans
• Manage year-over-year plan renewals with a goal of cost neutrality; analyze plan performance and recommend adjustments
• Evaluate and recommend optimal funding mechanisms — fully insured, level-funded, or self-funded — in partnership with the broker
• Present annual open enrollment options for medical, dental, vision, STD, LTD, life, HSA, FSA, COBRA, and voluntary benefits

Compliance & ACA Administration

• Own all benefits compliance obligations, with a primary focus on ACA — including look-back period calculations, measurement tracking, and remediation
• Conduct ACA testing and coordinate with outside counsel and broker on reporting requirements (Forms 1094/1095)
• Maintain current knowledge of federal and state benefits regulations; proactively identify and mitigate compliance risk

Carrier & Vendor Management

• Manage all carrier relationships and EDI/data connections to ensure accurate enrollment, premium transactions, and benefit continuity
• Serve as primary point of escalation for carrier issues; drive resolution with a zero-disruption standard for employees
• Audit enrollment data regularly to identify and correct discrepancies

Employee-Facing Administration

• Serve as a knowledgeable, approachable resource for employees and partner company HR contacts on all benefit questions
• Conduct new employee benefits orientation and ensure employees have clear, accessible information on available plans
• Design and maintain SOPs, guides, and communications materials to support employee understanding and enrollment

Seasonal Workforce Premium Management

• Develop and administer a streamlined process for collecting benefit premiums from seasonal employees (approx. 300–400) while they are off-cycle, including approximately 150 who qualify for benefits under the ACA lookback period
• Options include advance collection, check installment arrangements, and pre-season prepayment
• Process must balance employee experience with administrative simplicity and compliance requirements

Leave Administration Support

• Collaborate with HR team members and partner company administrators on STD, FMLA, and state leave processes
• Provide guidance on leave paperwork, regulatory requirements, and benefit continuation during leave periods
• Ensure consistency across partner companies on leave-related benefit handling

M&A Integration — Benefits Workstream

• Lead the benefits component of all new company integrations, including:
• Legacy plan vs. PSG plan comparison and cost impact analysis
• Gross-up modeling for employees experiencing cost increases upon PSG plan migration
• Coordination with M&A resources, broker, and target company HR/leadership
• Open enrollment setup in ADP and communication of action steps to incoming employees
• Serving as a subject matter expert and collaborative partner to newly acquired companies

Systems, Technology & Special Projects

• Manage benefits administration in ADP; maintain data integrity and optimize system configuration
• Contribute to HR technology and communications projects (e.g., intranet platforms, SOP development) as needed
• Build and maintain process documentation to support scalability as PSG continues to grow

QualificationsRequired

• 5+ years of benefits administration experience, ideally in a multi-entity or multi-location organization
• Deep expertise in ACA compliance — look-back period methodology, measurement tracking, and reporting
• Hands-on experience managing broker relationships and benefit plan design/renewal cycles
• Strong working knowledge of health and welfare plans, funding mechanisms, and carrier management
• Experience supporting M&A activity — specifically benefits due diligence and open enrollment for acquired companies
• Proficiency with HRIS/benefits administration systems (ADP experience a plus)
• Exceptional organizational and process-management skills; ability to manage multiple priorities simultaneously

Preferred

• Experience in PE-backed or high-growth platform environments
• Exposure to seasonal workforce benefit administration — particularly premium collection logistics
• Comfort with technology tools and SOP/documentation development
• CEBS, CBP, or equivalent certification

Additional Requirements

Remote Work Requirements

• Reliable high-speed internet and a dedicated workspace suitable for confidential HR work
• Ability to collaborate effectively across time zones and communicate clearly in a virtual environment

Travel Requirement

• Up to 10% travel, primarily for acquisitions, partner company support, and key HR or benefits-related initiatives

Physical Requirements

• Prolonged periods of sitting at a desk and working on a computer
• Ability to lift up to 15 pounds occasionally (e.g., benefits materials, equipment for presentations)
• Ability to travel by car or plane as needed
• Ability to participate in on-site meetings, presentations, and employee sessions

EEOC Statement

Perennial Services Group is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. All employment decisions are based on business needs, job requirements, and individual qualifications, without regard to race, color, religion, national origin, age, sex, sexual orientation, gender identity or expression, disability, veteran status, or any other protected status under applicable laws.

E‑Verify Participation

Perennial Services Group participates in the E‑Verify program to confirm the identity and employment eligibility of all newly hired employees. Candidates must be legally authorized to work in the United States.

If you'd like, I can also create a shorter job-board version, a LinkedIn post, or a candidate pitch to help recruiters present the role.

Join Our Team

At PSG, you’ll play a pivotal role in shaping a benefits program that directly impacts thousands of employees across a rapidly growing national platform. If you thrive in a dynamic environment, enjoy building scalable processes, and want to contribute to a mission-driven organization in a meaningful way, we’d love to connect. This is an opportunity to bring your expertise to a team that values innovation, collaboration, and continuous improvement.