People Operations and Compliance Generalist - Assured

Assured is on a mission to modernize insurance. Claims processing, while often overlooked, is the foundation of the entire industry. It’s currently highly manual, costing tens of billions of dollars a year. At Assured, we provide large insurers with the software solutions they need to win in a modern, technology-driven world.

We're looking for an organized, detail-oriented People Operations and Compliance Generalist to join our team. In this role, you'll keep the administration and compliance of our people operations function running smoothly. You'll be the go-to person for benefits and administrative questions, ensuring payroll compliance requirements and state filings are completed accurately and on time.

Some of the Work You'll Own

• Benefits Administration: Serve as the primary contact for employee benefit programs (health, dental, vision, 401(k) through Betterment, COBRA). Coordinate enrollments, life events, and annual open enrollment.
• Broker Partnership: Serve as the primary point of contact for Sequoia, our benefits broker. Ensure compliance with federal, state, and local regulations including ACA filings, non-discrimination testing, and required notices.
• Payroll & State Compliance: Monitor and maintain compliance with state and local employment requirements, including withholding, unemployment registrations, paid family leave, disability programs, and workers' compensation.
• Vendor & Mail Management: Own AbstractOps for multi-state business compliance, handle incoming company correspondence, and manage the relationship with CT Corporation.
• HRIS Operations: Run core HR processes in Rippling, managing updates, benefits administration, and leave coordination (FMLA, parental leave, etc.).
• Audit & Documentation: Maintain audit-ready paper trails, proper records, and required employment notices to reduce risk.
• Policies & Handbook: Update and maintain the employee handbook and company policies, ensuring timely distribution of compliance updates.
• Lattice Administration: Administer Lattice, train employees, track manager 1:1s, and help run performance review cycles.
• Reporting: Produce regular headcount, turnover, and hiring reports.
• Process Automation: Work with IT to set up automated workflows and playbooks for recurring employee HR questions.

What You'll Bring

• 2–5 years of experience in benefits administration and multi-state payroll tax compliance.
• Strong working knowledge of employment compliance and benefits administration.
• Experience with Rippling (HRIS/payroll) is preferred.
• Bachelor’s degree preferred, or equivalent practical experience.
• Exceptional attention to detail and ability to handle confidential information with discretion.
• Strong written and verbal communication skills with a service-oriented mindset.
• Proven ability to manage multiple priorities independently and meet strict compliance deadlines.

Benefits

• Competitive Compensation: Base salary and equity packages for all employees.
• Healthcare Plan: Platinum medical, dental, and vision coverage.
• Life & Disability: Free life insurance, long-term disability, and short-term disability.
• Unlimited PTO: Uncapped vacation days and paid holidays.
• Family Leave: Comprehensive maternity and paternity leave.
• 401(k) Match: 3% company contribution, regardless of employee contribution.
• WFH Perks: Lunch stipend twice a week, monthly phone stipend, and home office allowances.
• Pre-Tax Accounts: Health FSAs and HSAs.
• Team Retreats: Regular remote team offsites and company events.