Derek Szeto, Co-Founder of Walnut Insurance: $7 Million Raised to Lead the Embedded Insurance Revolution

Walnut Insurance is pioneering embedded insurance solutions, making it easier for platforms and businesses to offer relevant insurance products at the right moment in the customer journey. With over $7 million in funding, Walnut has partnered with major brands like Neo Financial, Tim Hortons, and Atco to create seamless insurance experiences. In this episode of Category Visionaries, I spoke with Derek Szeto, Co-Founder of Walnut Insurance, about the company's journey from its inception within RBC to becoming a leading embedded insurance enabler, working behind the scenes to power insurance solutions that appear naturally within customer experiences.

Topics Discussed:

• The three buckets of embedded insurance: fully embedded into products, data-driven implementations, and contextual offerings
• How embedded insurance benefits all parties: customers get needed coverage, platforms enhance stickiness and revenue, and insurers receive better risk profiles
• Walnut's origin story discovering insurance as an "unrecognized subscription" in consumer spending
• Finding the right customer touchpoints for offering insurance products
• Establishing Walnut as a technology-first enabler for partners wanting to offer insurance
• The challenge of market education in an emerging category
• The shift from life insurance to property and casualty products for better conversion rates
• Creating one-click insurance journeys that drive strong conversion rates

 

GTM Lessons For B2B Founders:

• Start by recognizing untapped market patterns: Derek identified insurance as an "unrecognized subscription" in consumer spending data—a significant expense that didn't get the attention of typical subscriptions like Netflix or Spotify. B2B founders should look for similar overlooked patterns in consumer behavior that indicate market opportunities.
• Focus on required rather than optional products: Walnut found significantly higher conversion when focusing on insurance products that are required in customer journeys (like tenant insurance when signing a lease) rather than optional ones. Derek explains, "Life insurance in its very end is a much harder product to embed because life insurance is always optional." B2B founders should prioritize solutions that address mandatory needs over discretionary ones.
• Use data signals to drive contextual offerings: The strongest conversion happens when insurance is offered at moments of high relevance. Derek shares, "Thinking about geolocation and travel insurance—an airport is a very good signal, or better yet if you can get them while they're using the Wi-Fi on the plane, that's an even better signal that they might be traveling." B2B founders should identify and leverage precise contextual signals that indicate heightened receptivity to their solution.
• Run fundraising like a sophisticated sales process: Derek learned that fundraising requires the same rigor as enterprise sales. "It became much more of a CRM-driven process, more pre-work. So trying to identify the most likely investors... Are they going to be interested in that category? Are they going to be interested in that geography? Are they writing checks of the size that are relevant to their fund?" B2B founders should approach fundraising with the same systematic process and qualification criteria used in sales.
• Industry conferences drive disproportionate results: For B2B companies in established industries like finance and insurance, conferences remain highly effective for business development. "We've had a lot of success with conferences like the Money 2020s of the world where folks are all together in one place and we can meet with a lot of different clients, whether that's net new or to meet with existing partners." B2B founders should prioritize high-concentration industry events, especially in traditional sectors.

 

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