Find your next opportunity
Browse fresh openings from leading companies and apply with a resume tailored to the role.
Browse expert rolesBrowse expert rolesBrowse fresh openings from leading companies and apply with a resume tailored to the role.
Browse expert roles13954 openings
7593-7600 of 13954When
Free to start · No card · 5 credits the moment you sign up
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.
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.
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.
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.
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.
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.
Start with a role or skill you want to use in your next job. Use the location and role filters to narrow the results, then open a listing to review the description. A title alone rarely explains the level of responsibility, working arrangement, or experience a team needs. Compare those details before deciding which opportunities deserve a tailored application.
Employers use different titles for similar work. If an exact phrase produces no results, try a shorter title, a core skill, or an alternative name for the role. Remove one filter at a time to understand which requirement is narrowing your search. A broader search can reveal suitable work without asking you to change your actual qualifications.
For each promising listing, read the responsibilities and separate essential requirements from preferences. Note the location, schedule, employment type, and compensation when provided. Missing details are questions to confirm with the employer. A remote opening may still require a particular country, work authorization, or time-zone overlap, so check the full posting before treating it as a location-independent opportunity.
Choose a few examples that demonstrate the skills this employer names. Explain your contribution and its outcome, using accurate numbers where available. Put the most relevant experience first and keep your resume easy to scan. Avoid adding technologies, qualifications, or achievements simply because they appear in a description. Your application should make your existing strengths easier to understand.
Follow the employer’s instructions for resumes, cover letters, work samples, and screening questions. Review the exported file before submitting it: confirm that contact details are correct, text can be selected, and links reach the intended pages. A resume check can help you spot unclear writing before you apply. Its feedback is advisory and does not predict a hiring decision.
Listings are collected from external sources and may change after they appear here. The employer or recruiting destination controls whether applications are open. If an original link is unavailable, check the company’s careers page for the title or move to another opening. An employer website link is a place to check current vacancies, rather than confirmation that a particular job is still accepting applications.
Keep a simple record of the company, role, job reference, application date, and documents you sent. Record any follow-up instructions and the next action you plan to take. This makes it easier to prepare for interviews, compare opportunities, and avoid applying repeatedly to the same opening through different boards. Review your shortlist as employers update their listings and prioritize opportunities with clear requirements that match the work you want to do.