Benefits Manager

Perennial Services Group is a private equity-backed platform building a national home services business across landscaping, turf, pest control, arbor, plant healthcare, and irrigation. Backed by Brentwood Associates and Tenex Capital Management, we partner with 35+ regional companies and growing. Our HR team supports roughly 1,800 employees across that network, much of which is a field-based, seasonal workforce.

This is a hands-on, operational Benefits Manager role inside a small, fast-moving corporate HR team. You will own the day-to-day benefits function end-to-end, including administration, compliance, vendor management, employee support, and integration of newly acquired companies, with strategic input on plan design and renewals in partnership with our broker.

If you are looking to administer programs someone else designed and ride a steady annual cycle, this is not the seat. We are looking for an experienced benefits practitioner who is energized by getting their hands on the work in a complex, multi-entity, growing platform.

You will report directly to the VP of Human Resources and partner closely with our broker (Alliant), corporate HR teammates, partner company HR contacts, and our finance and payroll team. You will be the recognized benefits expert across PSG and the named go-to for every partner company in our network.

1. Seasonal Workforce Benefits
PSG runs a heavily seasonal field workforce of 300 to 400 employees. You will own the process for measuring eligibility, communicating with crews who do not sit at corporate email addresses, and collecting premiums during off-season periods. There is no off-the-shelf playbook for this. You will build, run, and iterate on it.

2. M&A Integration
PSG acquires 5 to 10 partner companies per year. You will lead the benefits workstream of every integration: comparing legacy plans to PSG plans, modeling cost impact, building gross-up scenarios where needed, coordinating with the broker and target company leadership, setting up ADP for the new company, and running benefits orientation for incoming employees. Expect to travel on-site for roughly two days per integration.

Benefits Administration and Plan Management
• Manage day-to-day administration of all health and welfare benefits: medical, dental, vision, STD, LTD, life, HSA, FSA, COBRA, and voluntary benefits
• Partner with Alliant on plan design, annual renewals, and funding mechanism decisions (fully insured, level funded, self-funded)
• Lead annual open enrollment end-to-end: communications, ADP configuration, system readiness, employee questions, issue resolution
• Manage carrier relationships, EDI data connections, and billing reconciliation with a zero-disruption standard for employees

Compliance and ACA
• Own ACA end-to-end including lookback methodology, measurement period tracking, 1094/1095 reporting, and remediation
• Maintain compliance with ERISA, COBRA, HIPAA, FMLA, state leave laws, and applicable federal and state benefits regulations
• Proactively flag regulatory risk before it lands; partner with outside counsel and the broker on complex compliance questions

Seasonal Workforce Premium Management
• Design, document, and operate the process for collecting premiums from seasonal employees during off-season periods
• Balance employee experience, administrative simplicity, and compliance across approaches such as advance collection, installment plans, or pre-season prepayment
• Partner with payroll and partner company HR contacts to make the process work in the field, not just on paper

M&A Integration (Benefits Workstream)
• Lead benefits integration for every new partner company: plan comparison, cost impact analysis, gross-up modeling, ADP build, communication, and orientation
• Travel on-site to each integration (typically 2 days per acquisition, 5 to 10 acquisitions per year)
• Build and maintain a repeatable, documented benefits integration playbook that scales with PSG's growth

Employee and Partner Company Support
• Be the recognized, approachable expert for employees and partner company HR contacts on every benefits question
• Run new hire benefits orientations and keep plan documentation clear, current, and accessible
• Provide high-touch support on complex or sensitive employee situations across benefits, leave, and coverage
• Collaborate with HR teammates and partner company administrators on STD, FMLA, and state leave processes

Financial and Systems Administration
• Oversee benefits-related financial processes including HSA funding, payroll deductions, carrier payment accuracy, and self-bill calculations
• Partner with payroll and finance to keep deductions, funding, and reporting clean and on time
• Manage benefits configuration in ADP; drive data integrity across ADP, carriers, and payroll
• Build SOPs, documentation, and process improvements that scale as PSG grows

Required
• 5 to 7 years of hands-on benefits administration experience, ideally in a multi-entity, multi-location, or multi-state environment
• Deep ACA expertise, including lookback methodology, measurement period tracking, and 1094/1095 reporting you have personally owned
• Direct experience managing broker relationships and running annual renewal cycles
• Strong working knowledge of self-funded and level-funded plans, stop-loss, and carrier management
• Demonstrated experience integrating benefit plans during M&A, divestitures, or organizational change
• Proficiency with HRIS and benefits administration platforms; ADP experience strongly preferred
• Exceptional organization, follow-through, and ability to juggle priorities in a fast-moving environment
• Comfortable being the technical expert on the team. You are the bench, not a layer above one.

Strongly Preferred
• Experience supporting a seasonal, field-based, or hourly workforce
• Experience in a PE-backed, high-growth, or platform-rollup environment
• Field, service, or trade industry background (landscaping, pest control, HVAC, restoration, construction, restaurants, healthcare, retail multi-unit)
• CEBS, GBA, or equivalent benefits credential

• Open Enrollment for 2027 lands clean, with strong employee engagement, minimal carrier disruption, and no rework
• ACA reporting is fully buttoned up with no surprises
• Seasonal premium collection process is documented, tested, and demonstrably improving each cycle
• Every partner company integration has followed a repeatable, well-documented benefits playbook
• Employees and partner company HR contacts know who to call and trust they will get an answer
• You have built credibility with the VP HR, the CEO, and the partner company GMs as the person who owns this function

• Remote, with a workspace suited to confidential HR work and reliable high-speed internet
• Travel: 5 to 10 trips per year, primarily for partner company integrations (roughly 2 days each), plus occasional HR team meetings and partner company support
• Collaborative across time zones with a bias toward action and direct, honest communication
• Small corporate HR team supporting a much larger field organization. We move quickly, we trust each other, and we do not hand off work to find a layer to do it.

Competitive base salary commensurate with experience, plus bonus eligibility. Full benefits package including medical, dental, vision, HSA/FSA, 401(k) with company match, life and disability coverage, PTO and much more.

You will own an end-to-end function that directly touches thousands of employees across one of the fastest-growing platforms in our industry. You will work alongside a small, capable HR team that values smart action over polish, and partner with field operators who genuinely appreciate the function. If you want to build something that scales, own the work, and see your decisions improve people's lives every day, this is your seat.

Apply and tell us why this is the right next chapter for you. We read every application.

Perennial Services Group is an Equal Opportunity Employer. We celebrate diversity and are committed to 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 law.

PSG participates in E-Verify to confirm the identity and employment eligibility of all newly hired employees. Candidates must be legally authorized to work in the United States.