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The Opportunity Every year, tens of millions of Americans go through a coverage transition: a layoff, a resignation, a move into retirement, a 65th birthday while still working. It is one of the most consequential financial decisions a person makes, and it usually arrives as a twenty-page packet during the worst week of their professional life. Nobody owns it. COBRA makes the event compliant; it does not make it managed. That gap is expensive for employers and genuinely hard on people. When is the enterprise platform for guided health insurance decisions at every qualifying life event. Through When Choice, When Medicare, and When ICHRA, we combine an intelligent decision-support experience with licensed, non-commissioned agents so every person understands their real options and lands somewhere good. We have supported more than one million employees and managed over 204,000 qualifying events for Fortune 50 and Fortune 500 employers, reducing COBRA enrollment by up to 80% while improving the experience for the people leaving. Doing right by employees and taking cost out are usually opposing forces. Here they are the same action. Role Overview We are hiring an HR Generalist to own day-to-day HR operations at When, supporting our employees throughout their experience with the company and helping build the processes that keep a fast-growing, fully remote team running smoothly. This is a hands-on, execution-focused role. You'll manage the daily details of HR, support employees and managers, and help put practical policies and processes in place as we grow. You enjoy being close to the work, take pride in getting things done, and are comfortable both running existing processes and building new ones. You'll work closely with our fractional Chief People Officer, who provides strategic guidance and support on more complex matters, and partner with our PEO on benefits, compliance, and HR administration. Responsibilities HR Operations Manage onboarding, orientation, and offboarding, ensuring a smooth employee experience. Prepare offer letters, new hire paperwork, and other employee documentation. Administer benefits and our HRIS, including open enrollment and maintaining accurate employee records. Maintain HR reporting, including headcount, turnover, and benefits enrollment. Coordinate the annual performance review process, including timelines, communications, and documentation. Compliance and Policy Coordinate multi-state HR compliance processes in partnership with our PEO, including employee documentation, wage and hour requirements, and worker classification. Administer employee leaves and accommodations in partnership with our PEO, including documentation and employee communication. Help draft, update, and maintain When's employee handbook and HR policies. Develop and maintain practical HR templates, checklists, and processes as the company grows. Employee Relations and Manager Support Serve as the first point of contact for day-to-day employee questions and HR matters, escalating complex or sensitive situations as appropriate. Support managers with routine people matters, including feedback, performance conversations, and time-off questions. Help ensure employee issues are addressed promptly, consistently, and thoughtfully. Culture and Communication Help coordinate culture initiatives, employee communications, and team activities. Support engagement programs, including employee surveys and recognition. Help turn employee feedback into practical improvements. Qualifications Required 4+ years of hands-on HR generalist experience. Experience managing core HR processes, including onboarding, offboarding, benefits, and employee records. Experience supporting employees across multiple states, with working knowledge of employment compliance requirements. Experience handling day-to-day employee questions and routine employee relations matters, with good judgment about when to escalate. Hands-on experience with an HRIS and benefits administration. Strong organizational skills, attention to detail, and the ability to manage multiple priorities. Excellent written and verbal communication skills, discretion with confidential information, and sound judgment. Comfortable working in an early-stage environment where processes are still evolving. Strongly Preferred Experience at a startup or high-growth company. Familiarity with multi-state wage and hour requirements and employee leave administration. Experience working with a PEO. Bachelor's degree or equivalent relevant experience. PHR or SHRM-CP certification. Reporting and Team This position reports to one of When's co-founders and works closely with our fractional Chief People Officer, who provides strategic guidance and support on complex HR matters. Compensation, Location, and Travel We offer a competitive salary, we pay 100% of your health insurance, offer stock options, and more. This role is remote within the US, with minimal travel for occasional company events.