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 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, 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 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.


JESSE GOMEZ | SENIOR VP OF SALES & MARKETING


Jesse is responsible for overall business growth and development, overseeing sales, marketing and strategic partnerships. Jesse brings more than 25 years of healthcare leadership experience having worked closely with self-funded employers, Taft-Hartley plans, payers, providers, brokers and consultants. He specializes in scaling early-stage, high-growth companies and marketing new, complex products and services. Jesse is a graduate of Fresno State University and lives in Denver with his wife and two children.


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


Dan is a results-driven Customer Experience Executive with more than 23 years of success spanning across healthcare, financial services, technology and consulting. He has held leadership roles in both start-up and large organizations. His broad expertise includes business unit development and scalability, change management, leadership, customer engagement strategy, scaling customer and operational support teams and leveraging technology to improve the overall customer experience.


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


contact us right away