About Us

Our Spark: Rosen Hotels is the spark behind Apostrophe. Rosen’s team was able to cut so much waste from their healthcare spending that they were able to offer a new benefit: free college tuition for their employees and their children. Our mission is to make it what Rosen did plug-and-play for any employer. If you haven’t heard about them, learn more here.

Our Values: This is how we roll.

How We Work: Apostrophe works hand-in-hand with your trusted benefits consultant. If you are new to self-insurance and don’t have a trusted benefits consultant, we’ll be happy to connect you with one of our trusted partners.

Who We Are

Cheryl Kellond

Cheryl Kellond | CEO + 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.

Julia Hutchins

Julia Hutchins | COO + Co-Founder

Julia is committed to making health care cost less and work better for people. Prior to founding Apostrophe, Julia was Chief Executive Officer of Colorado HealthOP, a consumer-run health plan that she helped establish and grew to 85,000 members in three years. She has also held leadership positions at private Medicaid and Medicare health plans in Colorado and California, where she led government and commercial insurance business lines. Julia holds a BA from Washington University in St. Louis, MO and Master’s degrees in Public Health and Public Policy from the University of California, Berkeley.

Kathy Keating

Kathy Keating | CTO + 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.


Brett Schklar | CMO

Brett is a brand-focused growth strategist. He has spent most of his career helping emerging technology companies develop into powerful brands that achieve their vision.  Brett has built brand and marketing programs for some of the most successful B2B brands, running innovative marketing teams and most recently for his clients at his branding firm.  Brett has an MBA from Georgia Tech and an undergraduate degree from the University of Tennessee, Knoxville.  He’s an avid cyclist, professional joker and an overall family man.

Cheryl Wooster

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.

Apostrophe is backed by