HR Generalist

🕒 October 29

🇺🇸 United States – Remote

💵 $75k - $90k / year

⏰ Full Time

🟡 Mid-level

🟠 Senior

👩‍👩‍👧‍👦 Human Resources (HR)

👻 Ghost score 5%

What it means: the chance that no one is really hiring for this job.How to read it: 60% or higher means we think this is a ghost. Lower scores are less of a worry.How we score it: age, reposts, open roles vs team size, how fast jobs close, and whether pay is listed.Fine print: an estimate from public data, not a judgment of the company. Real jobs can score high, so treat it as a hint, not a fact.

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When

WebsiteLinkedInAll Job Openings

11 - 50 employees

Founded 2020

🛡️ Insurance

👥 HR Tech

☁️ SaaS

🔥 Funding within the last year

💰 $10.2M Series A on 2026-02

Insurance • HR Tech • SaaS

When is an enterprise platform (When Insurance Agency, Inc. ) that helps employers manage health coverage transitions at qualifying life events. The company provides decision support and guided enrollment for departing employees and other coverage changes—covering COBRA alternatives, Medicare education and enrollment guidance, and broker-aligned ICHRA solutions. When combines technology, licensing, and licensed, non‑commissioned agents to integrate with existing employer benefits workflows, aiming to reduce employer claims exposure and lower renewals. Its products include When Next (decision support), When Medicare Pro (proactive Medicare guidance), and When Choice (ICHRA solution). The platform is positioned for HR and benefits teams at large employers and is licensed in all 50 states.

📋 Description

• Manage onboarding, orientation, and offboarding • Prepare offer letters, new hire paperwork, and employee documentation • Administer benefits and the HRIS, including open enrollment and maintaining accurate employee records • Maintain HR reporting, including headcount, turnover, and benefits enrollment • Coordinate the annual performance review process • Coordinate multi-state HR compliance processes with the PEO • Administer employee leaves and accommodations with the PEO • Draft, update, and maintain the employee handbook and HR policies • Develop and maintain HR templates, checklists, and processes • Serve as the first point of contact for day-to-day employee questions and HR matters • Support managers with routine people matters, feedback, performance conversations, and time-off questions • Help coordinate culture initiatives, employee communications, and team activities • Support engagement programs, including employee surveys and recognition • Turn employee feedback into practical improvements • Report to a co-founder and work closely with the fractional Chief People Officer and PEO

🎯 Requirements

• 4+ years of hands-on HR generalist experience • Experience managing onboarding, offboarding, benefits, and employee records • Experience supporting employees across multiple states • Working knowledge of employment compliance requirements • Experience handling day-to-day employee questions and routine employee relations matters • Hands-on experience with an HRIS and benefits administration • Strong organizational skills and attention to detail • 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 • Experience at a startup or high-growth company (strongly preferred) • Familiarity with multi-state wage and hour requirements and employee leave administration (strongly preferred) • Experience working with a PEO (strongly preferred) • Bachelor's degree or equivalent relevant experience (strongly preferred) • PHR or SHRM-CP certification (strongly preferred) • Authorized to work in the United States

🏖️ Benefits

• 100% employer-paid health insurance • Stock options/equity • Minimal travel for occasional company events • Remote work within the United States

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