A bit about us.
Lolly was built by freelancers, for freelancers. We’ve spent years chasing projects, juggling invoices, and trying to piece together coverage that actually worked, and we learned firsthand how broken the system can feel when you don’t have an HR department behind you.
So we decided to fix it.
Lolly makes it simple for independent workers, creators, and gig pros to get real, affordable, quality coverage any day of the year with no open enrollment deadlines, no fine print, and no waiting games.
We’ve partnered with OneHealth, one of the most trusted names in private health networks, to bring you plans from carriers like Cigna, Equitable, and Guardian. These are the same companies Fortune 500s use, but built for people who work for themselves.
Behind the tech, there’s a human touch.
Our AI assistant Alia helps guide you through the process, explaining everything in plain English (no insurance jargon). Whether you’re comparing plans, adding coverage, or just figuring out what you actually need, Alia and our team are here to make sure you never feel lost in the maze.
At Lolly, we believe independence shouldn’t come at the cost of security. You work hard for your freedom and we’re here to help you protect it.
“Lolly exists so independence doesn’t come with risk
—only possibility.”
“If the system wasn’t built for us, we’ll build one that is.”
Kevin Dorry
CEO and Founder
What we value.
We are fueled by passion, anchored by integrity. We chase excellence relentlessly, but never at the expense of our values or our fire.
Take chances: create
what others won’t
We value the maverick and the trailblazer. We support those who don’t take the easy road in search of their goals and dreams. Dare to leap, or forever stand still!
Impossible is
an option
Nothing is truly impossible. The word itself says “I’m possible.” At Lolly, we stand with the people who see “impossible” as just another item on their to-do list.
Leave a mark
on the world
Make a dent in the universe. Leave this world a little better than it was before we existed by supporting the health and wellbeing of our customers and employees.
Excellence in
all things
Never let the perfect be the enemy of the good but let excellence be your north star. Make this your mantra even in the smallest things. Master the small, and the extraordinary will follow.
© 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.