Episode overview

Anish Sinha joins Give It A Nudge to walk through the upcover story: how he met co-founder Skye Theodorou through the Antler program, the sixteen months it took to get their first insurance underwriting partner on board, the challenge of becoming actuaries without actuarial backgrounds, and why the company is now positioned as the one-stop shop for SMB insurance in Australia. The episode is a masterclass in founder persistence and navigating a heavily regulated, relationship-driven industry.

Meeting a co-founder on day one of Antler

Anish arrived in Australia in 2019 knowing almost nobody, having followed his then-girlfriend to Sydney after eight years of long-distance dating across countries. He joined the Antler program where he met Skye Theodorou, who had seven years of insurance industry experience across Zurich and the NSW Government. They paired immediately, what Antler calls cracking out, and combined Skye’s insurance domain expertise with Anish’s background in technology, product, and distribution from scaling nearBuy with Sequoia backing.

The hardest part: sixteen months getting insurance capital

Before upcover could raise venture capital, it needed insurance capital: underwriting partners willing to back the policies. With no balance sheet and no track record running a book of insurance, Anish and Skye spent sixteen months pitching to sixteen different insurance providers. Skye wrote all the policy documents by hand while Anish built actuarial models from scratch, drawing on his mathematics background to hold his own in rooms full of career actuaries. The first partner came on after that sixteen-month process. They now have three.

The product: 90 seconds from quote to cover

upcover launched its first product in 2020 as pay-as-you-go personal accident cover for food delivery riders, delivered inside the delivery company’s mobile app at one dollar per day. The model demonstrated that contextual delivery dramatically increased conversion compared to standalone insurance websites. That insight became the foundation for the SMB product: two questions to get a price, ninety seconds to buy a policy, documents delivered instantly. Upcover has since expanded to allied health professionals, cyber insurance, and commercial motor.

78 engineering interviews to find the right CTO

After securing insurance partners, Anish and Skye spent six months interviewing seventy-eight engineers before hiring their CTO Sajad on the seventy-ninth interview. The deliberate approach reflected the understanding that whoever joined would need to be resilient enough to write software for six months before selling the first policy, agile enough to keep pace with evolving underwriting requirements, and hands-on enough to work in a very small team. Sajad, who had also been interviewing at Google, has been with the business for two years.