Benefits Analyst

SimpliSafe • Boston, MA

1d • Hybrid

About The Position

We’re seeking a Benefits Analyst to own day-to-day benefits operations and help us deliver an exceptional employee experience. You’ll reconcile and audit benefit invoicing, lead new-hire benefit orientations, manage enrollments and eligibility, and serve as a trusted resource for employee questions. The ideal candidate is proactive, detail-obsessed, comfortable working with minimal supervision, and eager to learn. Experience with large enterprise HRIS platforms and analytical skills for business operations will help you thrive in this role.

Requirements

• 4+ years of progressive experience in benefits administration, with direct ownership of billing reconciliation, enrollments, and employee support.
• HRIS experience required; large enterprise HRIS platforms (reporting, approvals, audits, eligibility, and EDI monitoring).
• Demonstrated experience with ACA reporting , LOA/accommodations (FMLA/ADA), and benefits compliance (ERISA, HIPAA, COBRA).
• Proven ability to multitask with minimal supervision in a fast-paced environment while maintaining exceptional accuracy and confidentiality.
• Strong Excel/Google Sheets skills (v-lookups, pivot tables) and comfort learning new systems.
• Clear, empathetic communicator with a positive attitude and service mindset; skilled at explaining complex topics simply.

Nice To Haves

• Bachelor’s degree in HR, Business, or related field (or equivalent experience).
• Professional certifications (CEBS, PHR/SPHR, SHRM-CP/SCP).
• Experience with multi-state benefits and leave laws (including MA Paid Family and Medical Leave).
• Prior vendor/carrier management and open enrollment project leadership.

Responsibilities

• Reconcile and audit monthly benefit invoices; research and resolve discrepancies; track credits and adjustments.
• Approve and audit benefit enrollments, life event changes, and terminations; ensure data integrity across HRIS, carrier portals, and EDI feeds.
• Conduct engaging new-hire benefit orientations and open enrollment sessions; create clear employee communications and job aids.
• Respond to employee benefit inquiries with timely and accurate guidance; escalate complex issues as needed.
• Maintain carrier relationships; navigate insurance vendor and enrollment websites to resolve eligibility, claim, and billing issues.
• Support/lead ACA reporting (1094-C/1095-C) and related compliance activities; assist with nondiscrimination testing and required notices (HIPAA, COBRA, SBCs, etc.).
• Partner with HRIS to monitor EDI files and troubleshoot file errors; run and schedule routine and ad-hoc reports.
• Maintain thorough documentation, SOPs, and audit logs for internal and external compliance reviews.
• Oversee leave of absence (LOA) and accommodations at a high level (FMLA, ADA, paid family/medical leave, state programs); coordinate with employees, managers, payroll, and vendors.
• Collaborate closely with Payroll on deductions, arrears, retro adjustments, and year-end reconciliations.
• Process and audit limited payroll data on a biweekly basis, and act as payroll processing backup when needed.
• Work in UKG Ready to process timesheets and calculate payroll, as well as perform various audits to ensure accuracy.

Benefits

• A mission- and values-driven culture and a safe, inclusive environment where you can build, grow and thrive
• A comprehensive total rewards package that supports your wellness and provides security for SimpliSafers and their families
• Free SimpliSafe system and professional monitoring for your home.
• Employee Resource Groups (ERGs) that bring people together, give opportunities to network, mentor and develop, and advocate for change.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 1,001-5,000 employees