In an effort to feature more insurtechs, Digital Insurance has modified the format of our Meet the insurtech series.
Sam Henry, co-founder and CEO of
What's the origin story of the company?
It started with three lifelong friends: Sam Henry and Andrew Kass, two Silicon Valley nerds, and Wendi Henry, an independent financial services agency owner and spouse of Sam Henry. They noticed that distribution for the
They created WealthSmyth AI with the mission of making it fast and easy to buy and sell life insurance and annuities.
The focus with WealthSmyth AI was to help carriers and distributors collaborate in a whole new way. The sales platform is built first for independent agency teams, delivering a consumer-quality web and mobile experience. The tool enables agents to find their ideal clients, collaborate with team members, run their playbook consistently at scale, manage deals across multiple carriers and build their book of business.
When was it founded and when was the product launched?
It was founded in early 2024 and the product launched November 2024.
Can you tell me about the founders/founding team?
Sam Henry, co-founder and CEO, brings over 25 years of software leadership experience. He was one of the original Microsoft .NET product managers. He played a key role in scaling visual studio into a multi-billion-dollar business. Sam Henry later drove venture capital-backed Xamarin. Sam Henry also led the financial services platform success teams at Salesforce and ran SalesSmyth, a consultancy specializing in growth, marketing and sales for VC-backed software startups.
Andrew Kass is the co-founder and chief product officer at WealthSmyth AI. A seasoned tech leader with two computer science degrees from MIT, Kass has spent over 30 years pioneering software innovations at Tableau, Elastic, Oracle, PeopleSoft, Microsoft and various enterprise software startups. At WealthSmyth, he is leading the effort to build the AI-first platform for the future of life insurance and annuities distribution.
Wendi Henry is the president of WealthSmyth Agency, an independent financial services brokerage dedicated to helping families build and preserve generational wealth. While separate from WealthSmyth AI, the two companies share a common brand and mission.
Any meaning behind the company name?
The name symbolizes our mission of skillfully crafting and shaping robust financial strategies. Like a skilled blacksmith, we empower agents to forge personalized solutions, shaping brighter financial futures for their clients.
How many employees?
8
Where is the company based?
Colorado Springs, Colorado.
What pain points is the technology trying to solve?
1. Maximize
2. Differentiate through buyer-aligned sales processes and create competitive advantage by aligning sales processes directly to buyer journeys—
3. Reduce high failure rate and agent turnover of new agents.
4. Driving faster innovation through an industry distribution platform and AI-first tech stack.
What funding rounds has the company had?
$750K bootstrapped.
What's ahead?
Working closely with our charter agencies and early adopters to help shape WealthSmyth AI for the real-world productivity needs of independent brokerages. Today, we're focused on our first phase, AI as Copilot, building the infrastructure and reengineering workflows to lay the foundation for predictable, AI-driven growth.
As we expand beyond invite-only this summer and launch our integrations, we'll move into our second phase, AI as Autopilot, helping agents find the right clients and products faster, with less friction. We're automating lead generation, finding agent–market fit and eliminating time-consuming pre-sales tasks like product comparisons and illustration design.
Ultimately, we're building toward the third phase, AI as Autonomous Producer, where AI operates not just alongside agents, but as one. This is a test for life insurance and annuities distribution: Can AI imitate—and eventually outperform—a top licensed producer? To pass, our AI "Penny" must source and qualify prospects, guide clients with empathy and accuracy, handle paperwork and compliance, and dynamically define each agent's ideal client profile. The future of distribution isn't just assisted—it's autonomous.
