Human Resources Generalist
When
When Human Resources Generalist Remote · Full time
HR
About When
Description
When is a U.S.-based, venture-backed company partnering with employers to deliver an AI-driven health insurance and benefits marketplace. Our platform helps individuals navigate key life events, including job changes, retirement, Medicare eligibility, and ICHRA, with personalized, affordable coverage options.
The Opportunity
We’re looking for an experienced HR Generalist to join our growing team as we scale from approximately 25 employees to 50+. Reporting to the CFO, this is a foundational role responsible for building and running the core HR infrastructure that supports our people and our growth.
As an early hire, you’ll partner closely with leadership, finance, sales, and operations to ensure payroll, benefits, compliance, and people processes run smoothly today, while helping design scalable systems for the future. This role is ideal for a hands-on HR professional who thrives in a fast-moving environment and enjoys building structure where it doesn’t yet fully exist.
What You’ll Do
Own Core HR Operations
- Serve as the primary point of contact for employee HR questions and support
- Maintain employee records and HR systems
- Ensure HR policies, documentation, and processes are consistent, compliant, and scalable
Manage Payroll & Payroll Tax Execution
- Administer biweekly payroll through our payroll provider, ensuring accurate processing of salaries, bonuses, commissions, and changes
- Register with agencies and coordinate payroll tax filings, reconciliations, and year-end reporting through vendors
- Resolve payroll issues and employee inquiries promptly and accurately
Lead Benefits Administration
- Administer employee benefits including medical, disability, retirement, and any future benefits
- Manage new hire enrollments, life events, and annual open enrollment
- Act as liaison with brokers, carriers, and benefits vendors
- Support benefits renewals and plan evaluations in partnership with leadership
Own Onboarding and Offboarding
- Manage end-to-end onboarding for new hires, including documentation, orientation, and system access coordination
- Ensure compliant and smooth offboarding, including final payroll, benefit notices, and exit interviews
- Maintain and improve onboarding/offboarding workflows and checklists
Support Recruiting, Hiring, and Compensation
- Coordinate job postings, interview scheduling, and candidate communication
- Partner with hiring managers to support interview processes and offers
- Maintain applicant tracking system and manage background checks and offer documentation
- Support annual reviews, promotions, and compensation analysis
Ensure Compliance and Manage Risk
- Ensure compliance with federal, state, and local employment laws
- Maintain employee handbook and HR policies
- Support leave administration
- Assist with employee relations matters and performance documentation
- Coordinate required trainings
Who you are
- Empathetic and employee-centric with the ability to make employees feel supported, heard, and welcomed while balancing business and compliance needs
- 3-6+ years of HR experience, ideally in a small to mid-sized company or startup environment
- Hands-on experience with payroll administration, benefits, onboarding/offboarding, and HR operations
- Familiarity with HRIS and payroll platforms and ability to learn quickly
- Working knowledge of employment law with the ability to research, interpret, and apply regulations when answers are not immediately known
- Highly organized, detail-oriented, and comfortable managing multiple priorities
- Strong communicator with the ability to work effectively with employees and leadership
- Self-starter who thrives in a fast-paced, evolving environment where processes are still being built
- Comfortable taking ownership and operating independently with minimal oversight
Compensation & Perks
- Competitive base salary
- 100% company-paid health insurance
- Opportunity to build and scale the HR function from an early stage
- Collaborative, mission-driven team
Travel Requirement: When is a fully remote company but occasional travel for in-person presence at meetings may be required
Salary
$65,000 - $80,000 per year