When
When Insurance is a technology platform that helps individuals and employers navigate health insurance options during transitions such as job loss or retirement. It connects users with a marketplace of health plans from third-party providers and offers tools to compare and apply for coverage alternatives to COBRA, including personalized guidance and reimbursement options for premiums. The platform
7 open roles
Roles are read from When’s Ashby every hour and disappear here as soon as they close there.
When hiring insights
Counted from every role read from its board, compared with every startup listed on firsthires.live.
Key findings
- When has the 1025th most open roles of 2,950 startups hiring on firsthires.live.
- 7 open roles is 0.7× the average Series A startup here (10.4).
- 43% of openings are in Operations, then Marketing (29%).
- Most roles are mid level (43%). None are tagged for graduates or interns.
- With a team of about 50, these openings would grow headcount by up to 14%.
- Median posted pay of $83k is 50% below the Series A startup median ($165k).
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- Operations pay here (median $75k) is 42% below the market median for Operations ($130k).
- 71% of its roles post pay, against 42% across all listed startups.
- 86% of its roles are fully remote (market: 24%).
- 57% of postings mention equity.
- 7 roles added in the last 30 days; 0 closed in the last 90.
- A typical open listing here is 24 days old, against 2 months across the site.
Hiring momentum
50 is flat. Blends the 4-week change, the 12-week trend and net roles added.
- Added, last 4 weeks
- 00%
- vs 0 in the 4 weeks before
- Added last week
- 00%
- Week before: 0
- Weekly trend
- +0.00
- Roles/week, per week · R² 0.00
- Net roles, 4 weeks
- +0
- 0 added − 0 closed
- Forecast this week
- 0
- Holt exponential smoothing
- Average week
- 0.0
- σ 0.0 · CV —
- 4-week refresh rate
- 0%
- New roles ÷ open roles
- 4-week churn
- 0%
- Closed roles ÷ open roles
- Median time listed
- >90 days
- 0% close within 30 days
Momentum, explained
- When hasn’t added enough roles in the last few months to read a trend yet.
Hiring history
- Roles ever listed here
- 7
- Roles added in 30 days
- 7
- Roles added in 90 days
- 7
- Roles closed in 90 days
- 0
- Tracked since
- Oct 2026
- Rank by open roles
- #1,025
- of 2,950 hiring startups
- Openings per current employee
- 0.14
Volume and freshness
- Open roles
- 7
- Listed in the last 7 days
- 0
- 0% of open roles
- Listed in the last 30 days
- 4
- 57% of open roles
- Typical listing age
- 24 days
- Oldest: 43 days
Pay
- Median posted pay
- $83k
- Annual USD, range midpoint
- Middle half of pay
- $75k–$145k
- 25th to 75th percentile
- Roles that post pay
- 71%
- 5 of 7
- Mention equity
- 57%
Work, level and access
- Fully remote
- 86%
- Say they sponsor visas
- 0
- Graduate and intern roles
- 0
- Median experience asked
- 5 yrs
Breakdowns
- 1Operations343%
- 2Marketing229%
- 3Engineering114%
- 4People114%
- 1Mid level343%
- 2Executive229%
- 3Manager114%
- 4Senior114%
- 1Remote686%
- 2Not stated114%
- 1USA571%
- 2United States229%
- 1Full-time7100%
- 1Agency Operations343%
- 2Sales & Marketing229%
- 3Administrative & Executive114%
- 4Engineering114%
Pay is each role’s posted range converted to annual US dollars, midpoint. See every When role.