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SimplyInsured
We sell health insurance to small businesses 100% online.
Last verified August 17, 2026 · Updated daily
Open roles at SimplyInsured
Nothing live right now. We re-check SimplyInsured daily and this page updates the moment they post.
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A role stays uncontested for about four days. Here's the window — and where we put you in it.
From $9/month, cancel any time.
Watching SimplyInsured
0 applicantsRole spotted & verified
1You get the alert
1You've applied
~8Hits the job boards
250+Working at SimplyInsured
Since , SimplyInsured has built We sell health insurance to small businesses 100% online.. The team is now <50 people. For a Healthcare, Healthcare Services company this size, the reality is broad remit, direct access to founders, and equity that still means something if the company works out.
The majority of roles are in San Francisco, CA, USA.
How to actually get hired at SimplyInsured
Why applying the normal way doesn't work
At <50 people, SimplyInsured has no recruiting team. Your application lands with a founder who is also running sales, product and payroll. The obstacle isn't a queue or an ATS, it's being seen at all. Cold outreach outperforms the form here, consistently.
Who to contact at SimplyInsured
Contact route not yet verified for SimplyInsured. For a <50-person Healthcare, Healthcare Services company, expect a founder or department head to make the call — but this is a model, not confirmed data.
What SimplyInsured screens for
relevant experience and ability to operate autonomously
Customize your CV for the SimplyInsured role. Matching the job description language helps clear ATS filters.
Mistakes that kill SimplyInsured applications
Generic CVs stand out at a <50-person company — and not in a good way. Fastest path to rejection.
Skip 'I'm looking for...' — start with is growing and your specific angle on solving it.
Applying and waiting = silence. Follow up at day five — it roughly doubles your odds of a reply.
Applying to SimplyInsured? Get the contact, not the form.
The SimplyInsured interview process
3 stages · 7 days typical · take-home: no · modelled from similar companies
We don't yet have verified candidate reports for SimplyInsured. What follows is the typical process for a <50-person Healthcare, Healthcare Services company — treat it as a model, not confirmed detail.
Interview stages
Intro Call
Video call · 30 min
Culture fit and role expectations
Founder or hiring manager
Technical Deep Dive
Video call or in-person · 60 min
Past projects and problem-solving approach
Technical founder or lead
Final Round
In-person or video · 45 min
Team fit and offer discussion
Founding team
SimplyInsured interview timeline
Expect days total. Compared to similar Healthcare, Healthcare Services companies (10 days median), SimplyInsured is faster.
Interviewed at SimplyInsured?
Tell us how it went — stages, questions, timeline. Takes 90 seconds and it's how this page stays accurate for the next person.
Submit your SimplyInsured interview experience →SimplyInsured jobs, frequently asked questions
Is SimplyInsured hiring right now?
We aren't tracking any live SimplyInsured vacancies today. We re-check daily and this page updates as soon as a role appears.
How do I apply for a job at SimplyInsured?
Use the apply links above, or check our guide to getting hired at SimplyInsured.
Does SimplyInsured respond to cold emails?
Response rate data for SimplyInsured not yet confirmed.
Who is the hiring manager at SimplyInsured?
At this size, hiring is usually run by a founder or department head.
What ATS does SimplyInsured use?
SimplyInsured uses Greenhouse.
How competitive is it to get hired at SimplyInsured?
Expect 50-100 applicants in the first two weeks for Healthcare, Healthcare Services roles at this size. Apply within 72 hours for best odds.
How many rounds is the SimplyInsured interview?
3 stages: Intro Call, Technical Deep Dive, Final Round.
Is the SimplyInsured interview hard?
Focus on relevant experience and culture fit, not puzzles. Final Round is reportedly the most challenging round.
Does SimplyInsured give a take-home task?
No, SimplyInsured does not include a take-home stage.
How long does SimplyInsured take to get back to you?
Around 7 days across the full process.
What should I prepare for the SimplyInsured interview?
relevant experience and culture fit is the priority. Show you can work autonomously — that matters more than algorithms at <50 people.
Where is SimplyInsured based?
SimplyInsured is headquartered in San Francisco, CA, USA.
Get SimplyInsured roles before they're posted
A role stays uncontested for about four days. Here's the window — and where we put you in it.
From $9/month, cancel any time.
Watching SimplyInsured
0 applicantsRole spotted & verified
1You get the alert
1You've applied
~8Hits the job boards
250+