You in? Good. We've got work to do.
We’re hiring mavericks, not middle managers.
We’re not your typical insurance company, mostly because we’re not an insurance company at all. We’re a fast-moving team of builders, dreamers, and doers who got tired of watching freelancers and independents get left behind.
At Lolly, titles don’t matter; impact does. We care less about org charts and more about ideas that make things better. If you see something broken, fix it. If you have a wild idea that could help millions of self-employed people get the coverage they deserve, say it out loud.
We move fast, question everything, and spend our time building real stuff, not sitting in endless meetings. Politics don’t fly here; progress does.
Our team is warm, sharp, and scrappy. We celebrate individuality but win as a group. Everything we do directly improves real people’s lives: the freelancers, gig workers, and creators powering the new economy.
If that sounds like your kind of chaos, come join us.
Let’s fix health insurance and have fun doing it.
Benefits that don’t make you roll your eyes.
Competitive Pay
We don’t reward job titles, we reward results. Bring your A-game and get paid like it.
Paid Time Off
We’re all for hustle, but burnout? Not our vibe. Take your time off, disappear for a bit, and come back fired up. Life first, work second (that’s how great work happens anyway).
In Office or Remote
Office or hammock? Your call. We’re a remote-friendly crew who believes great work doesn’t need fluorescent lighting.
Health Insurance
Our team gets the same badass coverage we sell, the kind that actually works when you need it.
Lolly’s Annual
“Freedom Bonus”
Get $1,500 every year to travel, recharge, or chase that passion project to learn harmonica.
Get Smarter Bonus
$1,000+ yearly learning budget for courses, certifications, or conferences.
We're not posting job listings,we're starting conversations.
If you’re one of the best at what you do (technical or not), drop us a line. We’re always looking for sharp minds, bold thinkers, and people who give a damn. You never know where it might lead.
© Lolly Tech, Inc. 2026. All right reserved.
This website is operated by Lolly Tech, Inc. and is not the Health Insurance Company or Health Insurance Marketplace® website. In offering this website, Lolly, as a Division of Lolly Tech, Inc., is required to comply with all applicable federal law, including the standards established under 45 CFR §§155.220(c) and (d) and standards established under 45 CFR §155.260 to protect the privacy and security of personally identifiable information.