James Drew

Jim Drew is a senior healthcare marketing executive who helps innovators design, position, and scale products and services that drive meaningful impact. With more than two decades of experience across both startups and enterprise organizations, he brings a rare blend of strategic insight, creative execution, and commercial discipline to every engagement.

Jim has led marketing, growth, and product strategy efforts for organizations spanning captives, stop loss, reinsurance, employee benefits, healthtech, and insurtech. He’s worked on both sides of the industry—building from scratch inside emerging startups, and modernizing legacy systems and strategies within established payers and platforms. His experience spans captives, stop loss, reinsurance, ancillary benefits, healthcare administration, and cost management—giving him a 360-degree view of the evolving healthcare landscape.

He has held senior leadership roles at companies backed by Blue Cross Blue Shield, Allianz, and venture investors. Most recently, he served as SVP of Marketing for a next-generation captive benefits platform, CGO for a healthtech startup focused on specialty care access, and President of a joint venture bringing embedded insurance and digital distribution to regional health plans.

In 2023, Jim launched drew.health, where he provides executive-level marketing and advisory leadership to founders, executive teams, and boards seeking to align strategy, story, and growth.

For more information, visit me on LinkedIn.