# Justin Holland

> Justin Holland is the co-founder and CEO of HealthJoy, a Chicago-based digital health company that turns the maze of employee benefits into a single AI-guided app. An MIT-trained engineer and serial entrepreneur with two prior exits (OpenInstall to AVG/Avast and FreeCause to Rakuten), he started HealthJoy in 2014 after a personal run-in with the American healthcare system left him unable to find out what his own care would cost. He has led the company for more than a decade, raised roughly $108M in venture financing through a Series D, and built a platform now used by hundreds of thousands of members to navigate care, cut costs, and reach a virtual assistant named JOY.

- **Role:** Co-Founder & CEO at HealthJoy
- **Organizations:** HealthJoy, OpenInstall (acquired by AVG/Avast), FreeCause (now Rakuten Loyalty)
- **Nationality:** American
- **Education:** BS, Mechanical Engineering and Management, Massachusetts Institute of Technology (MIT)
- **Known for:** Co-founded and scaled HealthJoy to hundreds of employees and hundreds of thousands of members, Raised roughly $108M in venture financing across rounds through Series D, Two prior successful startup exits: OpenInstall (AVG/Avast) and FreeCause (Rakuten)

## Career timeline

- **2006** — Graduates from MIT with a BS in Mechanical Engineering and Management
- **Pre-2014** — Founds FreeCause, a loyalty/ad-tech venture later acquired by Rakuten (now Rakuten Loyalty)
- **Pre-2014** — Founds OpenInstall, a cloud-based software installation platform, later acquired by AVG/Avast
- **2014** — Co-founds HealthJoy with Doug Morse-Schindler, initially targeting individual consumers during the Obamacare rollout
- **2016** — Pivots HealthJoy exclusively to B2B, rebuilding the technology platform, service, and marketing
- **2022** — HealthJoy raises a $60M Series D (total funding roughly $108.5M)
- **2024** — HealthJoy marks its 10th anniversary under Holland's leadership

## Achievements

- Co-founded and scaled HealthJoy to hundreds of employees and hundreds of thousands of members
- Raised roughly $108M in venture financing across rounds through Series D
- Two prior successful startup exits: OpenInstall (AVG/Avast) and FreeCause (Rakuten)
- Named to a '40 Under 40' list as a HealthJoy co-founder
- Built JOY, an AI-powered virtual healthcare assistant, into a widely used benefits navigation tool

## Latest updates

- **2024** — HealthJoy celebrated its 10th anniversary under Holland's continued leadership
- **2026-06** — HealthJoy published its 2026 Member Health Goals report analyzing data from over 100,000 members

## Links

- Website: https://healthjoy.com
- LinkedIn: https://www.linkedin.com/in/hollandjustin/
- Twitter/X: https://x.com/jh_healthjoy
- Facebook: https://www.facebook.com/healthjoydotcom/

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Profile page: https://yespress.io/justin-holland
Published by YesPress — https://yespress.io
Last updated: 2026-07-01