Self-Insured Employers 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 employers — and their employees — 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 KELLOND | CHIEF EXECUTIVE OFFICER + CO-FOUNDER


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 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.


KATHY KEATING | CHIEF TECHNOLOGY OFFICER + CO-FOUNDER


Kathy has dedicated her career to using technology to solve some of the most complex business and social challenges facing us. With more than 25 years of experience in the field of software engineering she has led several engineering teams successfully from startup conception through rapid growth. Kathy is very active in the local Colorado tech community and has served since 2014 as the Mentor Liaison to the Colorado Secretary of State’s office for their Go Code Colorado initiative. Kathy has a bachelor’s degree in Computer Engineering from the University of Arizona with an emphasis in Artificial Intelligence and User Experience.


JASON HAGER | SENIOR VP OF OPERATIONS


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.


CHERYL WOOSTER | VP PROVIDER SERVICES


Cheryl has more than 20 years in health care operational leadership roles: health plan compliance, claims and value based contracting, facility and physician practice management and population health management. Cheryl earned a BA from Assumption college in Spanish literature and a MBA with honors at East Carolina University.


CHUCK BOYLE | CHIEF FINANCIAL OFFICER


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).


DAN MARTELLA | VP OF CUSTOMER SUCCESS



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


contact us right away