Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, identifies Vic Yeh’s adoption thesis as a design decision made long before rollout. When a technology enters a regulated legacy industry, Vic Yeh, co-founder and CEO of Cara and previously co-founder of the digital insurance brokerage Oyster through its acquisition by the McGowan Companies, holds that approaching product creation from an angle of empowerment rather than replacement changes the design itself, with consequences that run through go-to-market messaging, customer adoption, and product usage. Cara automates the mundane and manual work insurance professionals face daily so they can concentrate on relationship building, and Vic Yeh credits that framing as a strong reason for the growth behind Cara’s $8 million seed round.
This episode is for founders and executives selling technology into regulated, relationship-driven industries where the people expected to use the product suspect it was built to eliminate them.
Key Takeaways
- Adoption resistance is designed in or out at the product stage. Vic Yeh, co-founder and CEO of Cara, states that approaching a product from empowerment rather than replacement fundamentally changes how it is built, with ramifications for go-to-market messaging, customer adoption, and usage.
- The contrarian position is that people are the product in insurance. Vic Yeh names as a common misconception the belief that AI will eventually replace insurance agents, and holds the opposite as someone who built and sold a brokerage.
- Automate the manual work and protect the work that defines the profession. Vic Yeh’s design target at Cara is automating 99 percent of mundane manual workflows so professionals can focus on relationship building and delivering coverage.
- Compliance is a constraint on how innovation enters, not a reason to slow it. Vic Yeh holds that a solution in a regulated industry must be compliant and must plug into existing workflows rather than breaking the regulated framework already in place.
- Domain focus is the defense against a general model. Vic Yeh competes with large language models on workflow fit, accuracy, compliance, and auditability, which he says a generic large model does not necessarily prioritize.
Product Teams Decide Adoption at the Design Stage, Not at Rollout
Vic Yeh, co-founder and CEO of Cara, treats the empowerment question as structural rather than as positioning. His statement of the mechanism is specific: approaching product creation with the angle of empowerment versus replacement fundamentally changes how the product is designed, and carries ramifications across go-to-market messages, customer adoption, and product usage.
The order in that sentence is the point. Messaging is downstream of design, which means a product built to replace the user cannot be messaged into acceptance. The people being asked to adopt it will read the product’s actual behavior, and in an industry where the professionals have decades of pattern recognition about vendors, they will read it quickly.
Vic Yeh’s underlying position is a contrarian one he states as such. The common misconception, in his view, is that technology or AI will eventually replace insurance professionals and agents. Having built his career in the industry and taken Oyster from founding through acquisition by the McGowan Companies, he holds instead that insurance is fundamentally about people, which makes human-first product design critical rather than optional.
Glenn Gow, The Scaling Executive Coach, named the practical consequence for a vendor: a user will lean into empowerment framing, but the company has to prove it quickly, because success depends on end users actually plugging in and using the tool.
Founders Separate the Work to Automate From the Work That Defines the Profession
Vic Yeh, co-founder and CEO of Cara, designed the product around a split that makes the empowerment claim operational rather than rhetorical. Cara was built with a human-in-the-loop approach that automates the mundane and manual work insurance professionals encounter daily, so those professionals can concentrate on what Vic Yeh calls what makes insurance special: the relationship building component.
His stated ambition on the automation side is aggressive. Vic Yeh describes the daily question at Cara as how to help insurance organizations automate 99 percent of the mundane manual workflows they deal with, so they can focus on relationship building and delivering coverage to customers.
The outcome he describes for the professional is a change in role rather than a reduction in work. Insurance professionals are moving from what was often a task processor role toward a risk advisory role, which Vic Yeh characterizes as a shift toward a higher leverage advisory profession rather than pushing paper around. He notes that this is what most insurance professionals are excited about, and identifies himself as a licensed insurance agent who shares that excitement.
That is why the split works as an adoption strategy. A professional who believes the tool is coming for the part of the job they are proud of will resist it. A professional who sees the tool removing the part of the job they never wanted will pull it in, provided the return is visible, which Vic Yeh says it must be for people to naturally come along.
Founders Innovate Inside a Compliance Framework by Plugging Into Existing Workflows
Vic Yeh, co-founder and CEO of Cara, describes insurance as a trillion-dollar global market with a reputation for being behind on technology, and rejects the assumption that this is simple inertia. Having worked with some of the largest carriers and across the insurance value chain, his read is that many existing processes persist for historical reasons that are real.
The constraint that follows applies to any regulated industry. A solution must be compliant, and it must not break the flow of the regulated paradigm and framework already in place. Vic Yeh names the resulting tension as the main challenge for an entrepreneur building in a legacy industry: a constant balance between pushing the boundary and innovating, while making sure the innovation integrates and embeds neatly into existing workflows.
The design implication is that the product has to arrive as an addition to a workflow rather than as a replacement for it. That is the same principle as the empowerment framing applied one level up: the professional keeps their relationships, and the organization keeps its compliance posture, while the manual work between them changes hands.
Vic Yeh’s argument for accepting that constraint rather than avoiding the industry is the payoff. He describes building in a legacy industry such as insurance as the exciting part, because the impact is tremendous when it is done right.
Vertical AI Companies Beat General Models on Workflow, Accuracy, and the Team Behind Them
Vic Yeh, co-founder and CEO of Cara, was asked directly by Glenn Gow how a domain-specific company competes with large language models that an insurance agent or broker could arguably use instead. His answer has three parts, and none of them is model capability.
| Defense | What Cara does | Why a general model does not match it |
| Workflow design | Cara’s platform is tailored to the common workflows insurance agencies and brokerages encounter daily | A general tool requires the professional to construct the workflow themselves, every time |
| Accuracy, compliance, and auditability | Cara pairs the model with a harness and infrastructure built for higher accuracy and for the compliance and auditability the insurance industry requires | Vic Yeh’s assessment is that a generic large model might not necessarily care about those requirements |
| The team | Cara staffs AI engineers alongside insurance professionals who understand the language and the daily pain points of brokerages | A model vendor cannot speak the customer’s language or grow alongside them over the long run |
Vic Yeh puts the third row first in importance, connecting it to the view he formed as a Sequoia Capital ambassador while in college: ideas change, and the team is the most important part of building any organization. His description of what a company actually is follows from that: a set of people building together toward the same mission. He names the team as a key reason customers choose Cara, specifically people who speak the language, build a product that works for those customers, and are willing to grow with them over the long run.
Principles Founders Will Apply From This Episode
| Principle | Practice | Named outcome evidence |
| Adoption is designed, not messaged | Choose empowerment or replacement at the product design stage, knowing the choice propagates into go-to-market, adoption, and usage | Vic Yeh credits the empowerment framing at Cara with the strong growth behind the company’s $8 million seed round to expand AI research and scale the team |
| Automate the work nobody defends | Draw the line at the activity the profession takes pride in, automate everything below it, and leave the rest untouched | Cara targets automating 99 percent of mundane manual insurance workflows, moving professionals from a task processor role toward risk advisory work |
| Enter the regulated workflow, do not replace it | Build the product to embed inside the existing compliance framework rather than requiring the customer to change it | Vic Yeh applies this from direct experience across the insurance value chain, having built and sold Oyster to the McGowan Companies before founding Cara |
| Defend a vertical with the harness, not the model | Compete on workflow fit, accuracy, compliance, and auditability rather than on model capability | Cara pairs its model with purpose-built infrastructure for the accuracy and auditability the insurance industry requires, which Vic Yeh says a generic large model does not necessarily prioritize |
| Staff the domain, not only the technology | Hire practitioners from the industry alongside engineers so the company speaks the customer’s language | Cara’s team of AI engineers and insurance professionals is what Vic Yeh names as a key reason customers choose the company over alternatives |
Quotes from This Episode
- “Insurance is fundamentally about the people.” Vic Yeh, Co-Founder and CEO, Cara
- “When you’re approaching creating a product with the angle of empowerment versus replacement, it fundamentally changes how the product is being designed.” Vic Yeh, Co-Founder and CEO, Cara
- “Ideas can change. But team is what really the most important part of building any organization.” Vic Yeh, Co-Founder and CEO, Cara
- “You can never predict the future … there’s a lot of unknowns.” Vic Yeh, Co-Founder and CEO, Cara
- “What a company really is, is … a set of people building together towards the same mission.” Vic Yeh, Co-Founder and CEO, Cara
Frequently Asked Questions
How do you get professionals in a legacy industry to adopt AI?
Vic Yeh, co-founder and CEO of Cara, told Glenn Gow, The Scaling Executive Coach and a CEO for 25 years, that adoption is determined at the product design stage rather than at rollout, because approaching a product from empowerment rather than replacement fundamentally changes how it is built and carries ramifications for messaging, customer adoption, and usage. At Cara that meant a human-in-the-loop design automating the mundane and manual work insurance professionals face daily while leaving relationship building to them. Glenn Gow’s addition is that the vendor must prove the value quickly, since success depends on end users actually plugging in.
What makes building in a regulated industry different?
Vic Yeh, co-founder and CEO of Cara, describes insurance as a trillion-dollar global market where many existing processes persist for real historical reasons rather than through simple inertia. The constraint on any new solution is that it must be compliant and must not break the flow of the regulated framework already in place, which means the product has to embed into existing workflows rather than replace them. Yeh names that balance between pushing the boundary and integrating cleanly as the main challenge for an entrepreneur in a legacy industry, and the impact when it is done right as the reason to accept it.
How does a vertical AI company compete with general large language models?
Vic Yeh, co-founder and CEO of Cara, competes on three fronts, none of them raw model capability. Cara’s workflows are tailored to what insurance agencies and brokerages encounter daily, its harness and infrastructure are built for the accuracy, compliance, and auditability the industry requires, and the company staffs AI engineers alongside insurance professionals who understand the customer’s language and pain points. Yeh identifies that team as a key reason customers choose Cara, since a general model vendor cannot speak the language or grow with the customer over the long run.
Founders Work With Glenn Gow to Scale Their Companies and Their Own Capability
Glenn Gow is The Scaling Executive Coach. He coaches ambitious executives into the CEO seat and CEOs into successful exits, drawing on 25 years as a CEO and 5 years in venture capital. If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
