Host: Martin Rowinski, CEO of Boardsi
Guest: Drew Shockley, Co-Founder at Move Health
Reimagining Healthcare Planning with Drew Shockley
On this episode of Boardsi Leadership Talks, Martin Rowinski, CEO of Boardsi, sits down with Drew Shockley, the Co-Founder of Move Health, to discuss the power of innovation at the intersection of healthcare, retirement planning, and leadership. Drew brings over two decades of experience in health insurance and Medicare markets and shares how his company is solving one of the most overlooked issues for early retirees: healthcare planning.
From Coach to Entrepreneur Drew’s journey began far from the tech startup world. Growing up playing sports and aspiring to be a coach, he developed a passion for people early on—an inspiration he credits to his grandfather. This people-first mindset became central to his career as he navigated the healthcare space and now leads Move Health in helping retirees transition with confidence and clarity.
Why Move Health Exists Move Health is not your typical healthcare platform. It’s designed specifically for financial advisors to guide clients in estimating and planning for health insurance during retirement. With millions wanting to leave the workforce but unsure about healthcare options, Move Health fills that critical gap—enabling better decisions with real financial impact.
The Healthcare Landscape: Where Are We Now? Drew breaks down the current U.S. healthcare structure:
50% get insurance through employers
15% rely on Medicare
Over 20% use Medicaid
6-7% purchase private insurance
9-10% remain uninsured
The shift toward more personalized and flexible models is evident. Programs like ICHRA (Individual Coverage Health Reimbursement Arrangements) are enabling smaller employers to transition employees to the individual market—an evolution Move Health is helping to lead.
Tech-Enabled, Human-Driven Despite growing reliance on digital tools, Drew emphasizes the irreplaceable value of human connection. “You might start the journey with a platform, but the final decision on something as crucial as health coverage should be guided by a real person,” he notes. That’s why Move Health pairs its tech tools with licensed professionals who provide personalized support.
Leadership Lessons from the Trenches From founding his first company at 23 to leading successful exits and navigating corporate acquisitions, Drew shares the hard truths of startup leadership. One major takeaway: founders must learn to delegate authority and trust others to lead. “You don’t scale a company by doing everything yourself,” he says.
Building a Winning Team When it comes to hiring, experience in healthcare isn’t the top priority. Drew looks for communication skills, empathy, and integrity—character traits that can’t be taught. “I can teach deductibles and copays,” he says, “but not kindness and drive.”
From Small Cap to Scaling Giants Having worked in everything from small startups to $400M public companies, Drew sees leadership principles as universal: show up, work hard, be kind. Whether managing a team of seven or seventy, he believes integrity and consistency are the keys to sustained growth.
Giving Back: Service Beyond Business Drew also serves on the board of trustees at Oakland City University and co-leads PAC Haiti, an organization that ships backpacks and educational supplies to children in need. These roles keep him grounded and fuel his commitment to mission-driven work.
Advice for Corporate Leaders For executives overseeing wellness strategies without a healthcare background, Drew advises seeking out innovation, mandating PTO, and integrating holistic wellness—including stress and sleep support. “It’s not just about cutting costs—it’s about building healthier, happier teams,” he adds.
Closing Thoughts For Drew, success is rooted in purpose. Whether it’s helping retirees transition confidently or delivering school supplies to kids in Haiti, leadership is about creating impact where it matters most.
