Sharon Rodriguez, CEO at HighPeak

Personal Background
Can you tell us a little about your background before starting your company?

After spending the majority of my career in big corporate, I took a step into entrepreneurship almost 8 years ago.  I have never looked back!  The truth is that my time in corporate – solving big problems across different businesses across many geographies -these experiences certainly prepared me for  addressing the challenges of starting and scaling a new business

Company Journey
How did you start your company? What were the first steps you took to get it off the ground and how did you identify the need for your product/service in the market? 

HighPeak was formed before I joined just under 2 years ago.  I took the helm as the first employee – and took on every role from CEO, to CFO  to CPO.  I leaned into listening to the market signals and meeting customers with a product that addressed one of the biggest unknowns in retirement – the future cost of healthcare and long term care.  

Innovation & Impact
What innovations or unique features set your company apart from others in the industry?

Prudential is our investor, and with that comes not only a breadth of resources but also access to the proprietary data of the business.  That data is one of our biggest differentiators in market.   Leveraging these inputs our data scientist have developed some incredible IP and delivered unique personalized insights for use by advisors with their clients.  

Growth and Strategy
What has been the most effective strategy for scaling your business?

Everything we build is right for us at a certain point of our journey, we don’t try to over engineer any process or system.  BUT we do always build with the end in mind which means recognizing that there are building blocks that lay the foundation for the organization we aspire to become.  

Advice & Insights
Looking ahead, what are your goals for the future of your company
?

We aspire to be the solution of choice for healthcare and longterm care cost estimations that advisors use to support their customers as they navigate n their retirement planning journey.

Vic Yeh, Co-Founder & CEO at Cara

Company Overview

Vic Yeh is Co-Founder & CEO at Cara, a domain-specific AI platform purpose-built for insurance—a modular system that enables agencies, brokerages, and MGAs to automate servicing, accelerate sales, and scale operations with a 24/7 digital workforce. Learn more at getcara.ai.

Can you tell us a little about your background before starting your company?

Before starting Cara, I was an early engineer at Blend ($BLND), a fintech platform powering digital banking experiences for institutions like Wells Fargo and US Bank, across mortgages, account opening, and insurance. At Blend, I helped launch multiple product lines and scale the platform to handle billions of dollars in transaction volume.

Alongside that, I was investing in early-stage software and fintech startups at Polymath Capital, where I had the opportunity to witness startups growing from zero to venture scale.

Those experiences gave me a deep appreciation for the complexity of financial services and the opportunity to use technology to transform legacy industries. The lessons ultimately led me to team up with Nikhil and Jon—friends from Stripe and Strategy&—to build Cara.

What inspired you to become a founder, and how did you identify the need for Cara in the market?

I’ve always believed that when applied thoughtfully, technology can be one of the most powerful forces for improving society. Yet insurance—one of the largest and most critical industries—has historically lagged in adopting modern tools.

At Blend, I had my first glimpse into the outdated, manual workflows that still dominate the insurance space. My co-founders, Nikhil and Jon, brought deep experience from Stripe and Strategy&, and together we saw a unique opportunity to use our backgrounds in financial technology to bring innovation to insurance.

How did you start your company? What were the first steps you took to get it off the ground?

We started by building a next-generation insurance brokerage, previously known as Oyster. As we scaled to thousands of policyholders, it became clear that revenue growth in insurance requires overcoming labor-intensive, repetitive workflows—without dramatically increasing headcount.

To address that, we built the world’s first AI Copilot for commercial insurance agents, powered by large language models. Initially deployed within our brokerage, the Copilot quickly proved its value by delivering measurable ROI and streamlining agent workflows. That internal success sparked strong demand from other agencies and brokerages. What began as an internal tool has since grown into something much bigger.

We call it Cara.


What innovations or unique features set your company apart from others in the industry?

Cara is a domain-specific AI platform purpose-built for insurance—a modular system that enables agencies, brokerages, and MGAs to automate servicing, accelerate sales, and scale operations with a 24/7 digital workforce.

As the industry’s first Agency Intelligence System, Cara is designed to automate back-office and manual workflows—allowing staff to focus on generating premiums and building client relationships.

What sets Cara apart is its built-in deep insurance knowledge and customizability. Each insurance firm configures Cara to fit its unique needs—whether that’s automating coverage comparisons, handling inbound calls through Voice AI, or building custom workflow automations. And because Cara learns from every interaction, it becomes more effective over time.


What has been the most effective strategy for scaling your business?

Word of mouth has been our most powerful growth engine. Many of our customers hear about Cara from industry peers—agencies and brokerages that have experienced firsthand how it transforms back-office operations and drives business results.

We believe that for AI to succeed in a high-barrier, heavily regulated industry like insurance, it must be domain-specific and vertically integrated. That’s why we’ve purpose-built Cara to align deeply with how insurance agencies and brokerages actually operate.

We stay close to our customers—constantly learning from their workflows and evolving use cases. As we continue to deliver measurable outcomes, our customers become our strongest advocates for growth.