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Welcome to another episode of Category Visionaries — the show that explores GTM stories from tech’s most innovative B2B founders. In today’s episode, we’re speaking with Paul Monasterio, co-founder of Kalepa, an insurance underwriting platform that has raised $16 million in funding.

  • Paul’s diverse background spans nuclear physics, data science at Applied Predictive Technologies (APT), and stints at Mastercard and Facebook before founding Kalepa.
  • Kalepa’s platform, Copilot, helps insurance underwriters assess risk and “bind with confidence” by recommending the most suitable opportunities and providing insights into a business’s exposures and controls.
  • The company leverages vast amounts of data, visual intelligence, and machine learning to drive better underwriting decisions at scale.
  • Paul was drawn to insurance by its complexity and centuries-long history of using data seriously to understand and price risk, seeing parallels to the analytical challenges in physics and data science.
  • Kalepa has more than doubled its customer base in the last six months, benefiting from both a hardening insurance market and advancements in its product’s ability to deliver value quickly.
  • The company aims to be the platform that transforms the $1 trillion commercial insurance industry, with the vision of enabling half to two-thirds of premiums to run through Copilot within five years.


Combine Outsider Perspective with Industry Humility:

Paul's journey illustrates the power of bringing an outsider's lens to an industry, drawing on patterns from adjacent domains to spot opportunities for innovation. However, he balances this with deep respect for the institutional knowledge within insurance. Founders should embrace their fresh perspectives while maintaining humility for what industry veterans have gotten right. This balance of naivete and deference can yield potent insights.

Tie AI Advances to Measurable Business Impact:

In an era of generative AI hype, Kalepa differentiated itself by rigorously linking its machine learning models to concrete improvements in underwriting decisions. Paul emphasizes the importance of explainability, allowing users to understand and refine the AI's recommendations. Founders applying AI should prioritize measurable outcomes over opaque models, ensuring solutions tangibly advance business metrics.

Deliver a "Minimum Unit of Value" to Accelerate Adoption:

Kalepa shifted its go-to-market approach to focus on delivering rapid time-to-value, aiming to demonstrate a clear "wow moment" for clients within days, not months. By structuring offerings around a "minimum unit of value," founders can shorten sales cycles, build trust quickly, and create evangelists. This approach seeds the market for future expansion while mitigating adoption friction.

Choose Co-Founders and Early Customers Wisely:

Reflecting on his journey, Paul stresses the immense value of having a co-founder to weather the ups and downs of entrepreneurship. Solo founders should carefully consider partnering to bolster resilience. Similarly, he advises founders to be highly strategic in selecting early customers, seeking those who share their vision and can provide valuable product feedback. The right early partners create ripple effects that shape the venture's trajectory.

Frame Your Vision in Terms of Societal Impact:

Paul articulates Kalepa's vision in terms of insurance's role as an enabler of innovation and risk-taking in the broader economy. By framing the startup's success as a catalyst for unlocking societal benefits, he provides a unifying narrative that transcends dry metrics. Founders should strive to connect their mission to a larger purpose that energizes both internal and external stakeholders. Anchoring your vision in meaningful impact inspires evangelism and persistence.

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