47 – Digital Doorways: Lessons in Market Disruption from a Serial Entrepreneur w/ Sam Pollaro, Co-CEO of PicassoMD

Welcome to Digital Doorways, where we explore the strategies, stories, and bold moves behind transformational change. I’m your host, Jason Siegel⁠, founder of Bluetext — a branding and marketing agency that helps high-growth companies win at moments of inflection. Today, I’m joined by an entrepreneur who’s proven that great innovation transcends industry. Sam Pollaro is a master builder — whether in hospitality, healthcare, or any vertical in between. From launching a hospitality CRM that was ultimately acquired by Booking.com and integrated into the OpenTable platform, to his latest venture at the intersection of care delivery and technology, Sam has a proven eye for solving big, complex problems.

As the co-founder and Co-CEO of PicassoMD, Sam is tackling one of the most urgent challenges in healthcare: enabling real-time collaboration between primary care physicians and specialists. Today, we’ll unpack how he spotted a powerful gap in the market, what it took to build trust in a complex industry, and how smart positioning and clear brand values can drive both adoption and impact. Whether you’re in tech, healthcare, or anything in between, this is a conversation about innovation under pressure — and how to win by staying focused on the people you serve.

QUESTIONS WILL INCLUDE....

Innovation & Disruption

What pain point in the healthcare system was PicassoMD originally built to solve, and how did that shape your product innovation?

How did you identify the whitespace in the crowded telehealth and virtual care market?

What were the biggest marketplace assumptions you had to challenge—or break—to innovate effectively?

In healthcare, innovation often runs into bureaucracy. How did you overcome friction in scaling PicassoMD’s model?

How do you know when your innovation is truly disruptive vs. just incrementally better?

Market Positioning

What was your original brand positioning for PicassoMD, and how did it evolve over time?

How did you position PicassoMD differently for physicians vs. health systems vs. investors?

What messaging helped you earn trust in a market that is often skeptical of new tech and platforms?

What were the key brand pillars you leaned into to stand out in a noisy digital health space?

How do you define success in positioning—not just in terms of market share, but customer and partner perception?