Benefits Analyst

About SimpliSafe

We’re a high-tech home security company that’s passionate about protecting the life you’ve built and our mission of keeping Every Home Secure. And we’ve created a culture here that cares just as deeply about the career you’re building. Ours is a no ego culture of collaboration and innovation where those seeking their next challenge can find big opportunities and make a huge impact on the lives of all those who we protect. We don’t just want you to work here. We want you to grow and thrive here.

We’re embracing a hybrid work model that enables our teams to split their time between office and home. Hybrid for us means we expect our teams to come together in our state-of-the-art office on two core days, typically Tuesday, Wednesday, or Thursday – working together in person and choosing where they work for the remainder of the week. We all benefit from flexibility and get to use the best of both worlds to get our work done.

Why are we hiring?

Well, we’re growing and thriving. So, we need smart, talented, and humble people who share our values to join us as we disrupt the home security space and relentlessly pursue our mission of keeping Every Home Secure.

About the Role

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.

What You’ll Do

• Benefits Operations
• 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.
• Compliance & Reporting
• 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.
• Leave & Accommodations
• 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.

• Cross-Functional Partnership
• 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.

What You’ll Bring

• 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 Have (Preferred)

• 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.

Work Style & Travel

• Boston-based hybrid role (on-site expectations can be tailored to team norms).
• Ability to travel 5–10% for orientations, training, vendor meetings, or site visits.

What Success Looks Like (First 6–12 Months)

• 100% on-time and accurately reconciled monthly invoices; clear audit trail for adjustments.
• <2% error rate on enrollments and EDI files; recurring exception reports in place.
• Positive employee feedback on benefits, education, and responsiveness (e.g., <1-business-day SLA).
• ACA forms filed accurately and on schedule; no corrective filings required.
• Documented SOPs for core processes; measurable cycle-time reductions for everyday transactions.

What Values You’ll Share

• Customer Obsessed - Building deep empathy for our customers, putting them at the core of our work, and developing strong, long-term relationships with them.
• Aim High - Always challenging ourselves and others to raise the bar.
• No Ego - Maintaining a “no job too small” attitude, and an open, inclusive and humble style.
• One Team - Taking a highly collaborative approach to achieving success.
• Lift As We Climb - Investing in developing others and helping others around us succeed.
• Lean & Nimble - Working with agility and efficiency to experiment in an often ambiguous environment.

What We Offer

• 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 (For more information on our total rewards please click here)
• 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.

The target annual base pay range for this role is $83,500 to $122,500.

This target annual base pay range represents our good-faith estimate of what we expect to pay for this role. We use a market-based compensation approach to set our target annual base pay ranges and make adjustments annually. We carefully tailor individual compensation packages, including base pay, taking into consideration employees’ job-related skills, experience, qualifications, work location, and other relevant business factors.

Beyond base pay, we offer a Total Rewards package that may include participation in our annual bonus program, equity, and other forms of compensation, in addition to a full range of medical, retirement, and lifestyle benefits. More details can be found here.

We’re committed to fair and equitable pay practices, as well as pay transparency. We regularly review our programs to ensure they remain competitive and aligned with our values.

We wholeheartedly embrace and actively seek applications from all individuals, no matter how they identify. We are committed to cultivating a diverse and inclusive workplace, and we believe our work is enriched when we incorporate a multitude of perspectives, backgrounds, and experiences. We want everyone who works here to thrive and contribute to not only our mission of keeping every home secure, but also to making our workplace safe and supportive for others. If a reasonable accommodation may be needed to fully participate in the job application or interview process, to perform the essential functions of a position, or to receive other benefits and privileges of employment, please contact [email protected].