Ep 32 | Building Tomorrow’s Insurer | Automate and Elevate: Skye Theodorou on Redesigning Insurance for SMEs
Podcast: Building Tomorrow's InsurerPublished On: Fri Jun 20 2025
Description: SMEs make up 97% of businesses—but they’re often underserved, misunderstood, or stuck in analog experiences. Can insurance meet them where they are?In this episode of Building Tomorrow’s Insurer, host and Kanopi CEO Nigel Fellowes-Freeman sits down with Skye Theodorou, Co-founder and CEO of upcover, to talk about building a digital-first insurance platform that empowers small business owners through speed, simplicity, and deep operational empathy.From founding upcover via Antler, to scaling nationally with a multi-niche strategy, Skye shares the hard-won lessons of raising capital, hiring globally, and automating 20% of her business every few months.Tune in as Skye shares:How upcover is using automation and AI to simplify SME insuranceWhat it takes to deliver both compliance and speed in regulated marketsWhy trust, transparency, and customer understanding are non-negotiablesHow she’s scaling a remote-first team—and changing lives along the wayWhat the future holds for SME insurance, data, and embedded experiencesIf you’re building in insurtech, distributing SME cover, or just want to hear how real impact meets smart innovation—this one’s for you.
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