People Operations and Compliance Generalist

Assured • ,

10d • $110,000 - $140,000 • Remote

About The Position

Assured is seeking an organized, detail-oriented People Operations and Compliance Generalist to keep the administration and compliance of its people operations function running smoothly. The role serves as a go-to resource for employee benefits and administrative questions, and ensures payroll compliance requirements and state filings are completed accurately and on time. It works closely with an external benefits broker, payroll provider, insurance companies, payroll compliance vendors, government agencies, and internal teams.

The role administers benefits, payroll and multi-state employment compliance, HRIS updates, leave coordination, company mail and registered-agent relationships, employee records, policies, and people reporting. It also supports audits and builds employee-facing automation for common questions, while helping employees and managers use Lattice for documentation and reviews. The position requires discretion with sensitive information, independent work, and effective collaboration as Assured grows.

Requirements

• Two to five years of experience in benefits administration and multi-state payroll tax compliance.
• Knowledge of benefits administration and employment compliance.
• Exceptional attention to detail and strong organizational skills.
• Ability to manage multiple priorities and meet payroll and compliance deadlines.
• Excellent verbal and written communication skills, including the ability to explain benefits and policies in plain language.
• Strong customer-service orientation and interpersonal skills.
• Ability to handle sensitive information confidentially and with discretion.
• Ability to work independently and collaborate effectively with internal teams and external partners.

Nice To Haves

• Bachelor’s degree; equivalent work experience will be considered.
• Experience with Rippling, Assured’s HRIS and payroll systems.

Responsibilities

• Answer employee questions about health, dental, vision, retirement, and other benefit programs.
• Coordinate benefits enrollment, life-event changes, 401(k) plans through Betterment, COBRA, and annual open enrollment.
• Serve as the primary contact for Sequoia, Assured’s benefits broker, and work with it to administer benefit plans.
• Ensure compliance with federal, state, and local benefits regulations, including ACA filings, nondiscrimination testing, and required notices.
• Monitor and maintain state and local employment compliance, including withholding and unemployment registrations, account maintenance, paid family leave and disability programs, workers’ compensation, and responses to jurisdictional notices.
• Own AbstractOps, including reviewing mail received through the tool and mail forwarded by executive assistants.
• Manage incoming company mail, distribute correspondence, respond to routine inquiries, and maintain the relationship with CT Corporation as registered agent.
• Maintain HRIS updates and administer benefits and leave coordination, including FMLA and parental leave, entering changes in Rippling.
• Support audits by gathering documentation and maintaining organized records, notices, and legally required documentation.
• Manage and update the employee handbook and company policies, keeping them current and compliant, and distribute communications about benefits and policy updates.
• Administer Lattice, train employees to use it, follow up with managers on regular documented one-on-ones, and help administer annual reviews once a company-wide review cycle is established.
• Help employees use Lattice features, including its Slack integration, AI agent in one-on-ones, and MCP connection with Claude.
• Produce current headcount, turnover, and hiring reports.
• Partner with IT to set up automated replies and playbooks for common questions about benefits, PTO, and handbook topics, using Console or another ITSM vendor.
• Take on ad hoc requests and additional tasks as the role evolves.

Benefits

• Competitive salary and equity packages for all employees.
• Platinum medical, dental, and vision plans.
• Free life insurance, including long-term and short-term disability.
• Unlimited PTO and paid holidays.
• Maternity and paternity leave.
• Assured 401(k) contribution of 3% of income, even if the employee does not contribute.
• Work-from-home benefits, including lunch twice a week, a monthly phone stipend, and other home-office perks.
• Health FSAs and HSAs for pre-tax out-of-pocket medical expenses.
• Team events and offsites.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level