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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 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.
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.
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.
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.
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.