The company says it has supported more than one million employees and managed over 204,000 qualifying events for Fortune 50 and Fortune 500 employers.
Source postingMore employers
When is hiring. 5 roles are open right now.
Browse the openings below to see requirements, locations, and pay where available. You can also set up alerts for new roles that match your search.
Posted (30d)3
[01] HIRING NOW
See When's current openings.
We update these listings as we find new roles and learn that others have closed.
Open roles
5
Posted (30d)
3
Posted (7d)
1
Posted range
—
Roles with the most current openings
Channel / Partner Sales
1 role
Growth Marketing
1 role
Human Resources / People Ops
1 role
Marketing
1 role
Operations
1 role
[02] OPEN ROLES
Apply to When now.
Live roles pulled from When's career page. Open one to see the full description, location, and pay, then apply or set an alert for the next match.
Work mode
5 open roles
[03] WHERE THEY'RE HIRING
Where When is hiring.
The current listings include remote roles, although they may still require you to live in a particular place.
Remote: 5 positions
[04] FROM THE POSTINGS
What the job postings tell us.
These details come from the linked postings. Benefits and working arrangements can differ by role and location.
The Head of Insurance Operations role leads a small group of full-time licensed agents who carry the core member experience.
Source postingSources reviewed 2026-10-19.
[05] ABOUT
What When does.
When is an enterprise platform for guided health insurance decisions at qualifying life events. It combines decision-support software with licensed, non-commissioned agents through When Choice, When Medicare, and When ICHRA.
[06] INTERVIEW PREP
Going through their loop?
Review the skills in When's job descriptions, practice relevant exercises, and explore any available candidate-reported questions.
[07] HOW TO APPLY
Your resume lands in Ashby.
When uses Ashby for applications. Follow the job link to complete the employer’s form and review its requirements.
Scoutify checks When's career page for new listings. You can set alerts for roles that match your search.
Ashby is one of the career sites where Scoutify's AI auto apply works, so Sniper can submit your application to a matching When role minutes after it posts. Sniper sends one application per posting, and the employer's confirmation email for most applications lands in Scoutify Mail.
ATS identified from the application URLs on When's recent postings
[09] FAQ
Questions people ask about When.
Not covered here? Email support@scoutify.com.
Is When hiring?
Scoutify currently lists 5 open roles at When. Follow the job links to check requirements and apply on the employer's career site.
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