Episode #159
Apr 17, 2025
Rethinking Enrollment Strategy in Insurance
with Jason Gross from TruStage
SPONSORED BY
Jason Gross from TruStage joins James at InsurTech NY to share his expertise on rethinking enrollment from the strategy seat. Discover how emerging technologies are reducing friction in the enrollment process, and how those improvements connect to larger goals like access, equity, and long-term customer value.
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A Strategic Shift in Insurance
Enrollment season—a time of decision-making for employees, HR teams, and insurance providers. But what if we reimagined this annual process not just as a routine task, but as a strategic touchpoint for deeper customer connection and value?
In Episode 159 of the InsurTech Geek Podcast, we sit down with Jason Gross, Chief Strategy Officer at TruStage, formerly known as CUNA Mutual. Recorded live at the InsureTech New York Conference, this episode delivers fresh insights on insurance enrollment, digital transformation, and the evolution of strategy in the financial services space.
From Political Campaigns to Insurance Boardrooms
Jason’s journey is anything but traditional. With a background in politics and public policy, and family roots in insurance, Jason eventually found his way to the insurance sector. As he tells it:
“Figure out what type of life you want. Where do you want to live? What’s important to you?”
This practical wisdom led him to Des Moines, Iowa—where insurance isn’t just a career, it’s an ecosystem.
What is TruStage?
Formerly CUNA Mutual, TruStage has deep roots in the credit union world. With a wide array of offerings—including life, annuity, personal lines, and wealth management—TruStage is what Jason calls a “multi-multi-line company.” Their mission-driven model, aligned closely with credit unions, positions them uniquely in the financial services landscape.
“The reason we changed the name was to better reflect our broader vision—serving people at any stage of life.”
Despite being a $4B company, TruStage maintains its mutual ownership structure and continues to evolve to meet the demands of modern consumers.
Enrollment as a Strategic Touchpoint
Enrollment is evolving—from paperwork-heavy drudgery to intelligent, tech-enabled customer experiences. Jason breaks down how automation and data-driven decision-making are changing the game.
“We finally have the tools to summarize these large documents, compare options, and deliver real insurance insights with AI.”
Think embedded insurance within HR platforms, predictive analytics for plan recommendations, and conversational AI guiding users through tough decisions.
Why Brokers Still Matter
In an era of automation, Jason offers a firm defense of brokers:
“I love my broker. Because they help me identify gaps. That’s real value.”
Rather than seeing digital tools as a replacement, Jason views them as enhancers—giving brokers and customers the tools to make smarter, faster choices.
Advice to Startups: What VCs Really Want
Having served in both carrier and VC roles, Jason shares what makes or breaks a startup pitch:
“Don’t tell me what you can do. Tell me what you’re doing.”
Focus, clarity, and relevance to a carrier’s top 1-2 problems are essential. A product that solves a “problem 12” won’t cut it.
Conclusion: What’s Next?
As AI, automation, and mission-driven innovation converge, the insurance industry is on the cusp of a transformation. Leaders like Jason Gross remind us that customer focus, strategic clarity, and tech integration are no longer optional—they’re foundational.
You might also find these posts interesting:
- Improvement Betterments Explained
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A practical guide outlining strategies to streamline claims handling and boost operational efficiency—perfect for teams modernizing legacy processes.