Jason Gross is an award-winning technology, strategy, and innovation leader with more than 25 years of experience driving transformation across the insurance and financial services industries. As Chief Strategy Officer at TruStage, Gross leads enterprise-wide strategic initiatives that advance TruStage’s mission to “make a brighter financial future accessible to everyone,” guiding the organization through innovation, competitive insight, and long-term growth in a rapidly evolving market.
Before joining TruStage, Gross served as a Vice President at a leading InsurTech and FinTech-focused venture capital firm, where he helped accelerate engagement between established carriers and emerging startups, bringing new digital solutions and strategic partnerships into mainstream industry adoption. Previously, he also held senior strategy, innovation, and business transformation roles at a top property and casualty insurance carrier, shaping corporate vision and operational excellence.
Recognized for his leadership and forward-thinking approach, Jason Gross has held prominent industry roles including Co-Chair of the Global Insurance Symposium and Vice Chair of the Global Insurance Accelerator, where he contributed to thought leadership and ecosystem development in insurance innovation.
Gross’s deep expertise spans corporate strategy, innovation management, ventures, and business transformation — making him a sought-after speaker on topics such as digital disruption in insurance, enterprise strategy execution, and the future of financial services. His experience uniquely bridges traditional carrier perspectives with startup-driven innovation models, delivering insights that resonate with executive audiences, entrepreneurs, and investors alike.
At industry conferences, Jason Gross is known for his engaging presentations on how organizations can harness strategy, technology, and innovation to unlock competitive advantage and create sustainable value.
