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 insurance
What it takes to deliver both compliance and speed in regulated markets
Why trust, transparency, and customer understanding are non-negotiables
How she’s scaling a remote-first team—and changing lives along the way
What the future holds for SME insurance, data, and embedded experiences
If you’re building in insurtech, distributing SME cover, or just want to hear how real impact meets smart innovation—this one’s for you.
