self-insured plan sponsors deserve better

health plans

the health plan that’s fixing america

You’re paying too much for health insurance that gets worse every year. Legacy insurance carriers use a business model that operates at a net gain if everyone else is operating at a net loss.

Low-quality, expensive healthcare is keeping America broken. It’s not right, and we’re here to fix it.

We founded Apostrophe to give self-insured plan sponsors — and their members — excellent health plans at a fair price by keeping things simple and transparent. We’ve rewired the payment process between employers, providers and members to cut waste and pass the savings on to you, our customers.

That’s what we call Intelligent Health Benefits.

our values

Everything we do at Apostrophe is guided by

simplicity transparency love

That’s our promise, that’s our purpose and
that’s why we believe in what we do.

our leaders


Cheryl wakes up every day to build the health plan that can fix America. She’s a concept-to-launch product expert who has delivered more than $750M in revenue from version-one hardware, software and internet products at both startups and marquee brands. She grew her last startup, Bia Sport, from a $400K Kickstarter to the #1-rated fitness wearable on Amazon. Cheryl has an MBA from MIT Sloan and an undergraduate degree from the University of Chicago. She’s an ultrarunner, an Ironman, and a mom of four.


Jason brings 25 years of experience working in healthcare technology and operations to Apostrophe. He has held leadership roles with large carriers and has built operations from scratch in two prior health insurance start-ups. He’s overseen enrollment and eligibility, premium billing, member and provider service, provider network development, claims processing and financing, technology integration and end-to-end productization of new lines of business. As a seasoned healthcare executive, Jason thrives in scaling start-up organizations into sustainable growth companies while solving consumers’ biggest gripes with their healthcare experience.


Chuck is a finance executive and co-founder with a demonstrated history of driving growth through organic and inorganic strategies. His expertise is in Corporate Finance, Fundraising, Operational Leadership and Mergers & Acquisitions (M&A).

If you want to learn more about what it is
to bring an intelligent approach to health benefits

contact us right away