EP 80 – Skye Theodorou and Anish Sinha – UpCover – Unbundling of the Traditional Workspace


Michael Waitze worked in Global Finance for more than 20 years, employed by firms like Citigroup, Morgan Stanley and Goldman Sachs, primarily in Tokyo.  Michael lived and worked in Tokyo from February 1990 until December 2011.  Michael always maintained a particular focus on how technology could be used to make businesses more efficient and to drive P/L growth. Michael is a leader in the digital media space, building one of the biggest and fastest-growing podcast listener bases in the region.  His AsiaTechPodcast.com show has listeners in more than 170 countries and his company, Michael Waitze Media produces some of Asia’s most popular podcasts.

Skye is Cofounder & CEO of upcover. Skye is passionate about helping small business' manage their own risk. She has worked with hundreds of SMEs at Zurich Insurance, across multiple functions. As a certified lawyer, she has also worked to help SMEs in regulatory reform at the state Government in Australia.

Anish Sinha

Anish is Cofounder & COO of upcover. Prior to upcover, Anish was a part of core team at nearbuy.com (8M+ customers in 32 cities, raised $37M+ from Sequoia etc), leading business & product. He has worked across UK & India office of Goldman Sachs, as a lead equities analyst.

This episode is brought to you by:

In this episode, we talked to the two co-founders of Australian InsurTech Upcover, Skye Theodorou, who is the CEO, and Anish Sinha, the COO. UpCover is an InsurTech building tailored, simple, and pay-as-you-go insurance protection and benefits products for the gig economy, the fastest growing workforce in the world. The way we work is changing and with the rise of micro-entrepreneurship the traditional employee benefits approach needs to change as well to give people working in the gig economy access to affordable insurance solutions. 

Skye and Anish met when both participated in the Antler program. Founded in Singapore in 2017, Antler is a global early-stage VC enabling and investing in people and building tech startups. Skye and Anish are sharing their experience with the program and the support they received.

Skye, Anish, and their team have extensively researched the gig economy landscape in Australia. What they found was that the gig economy not only consists of food-delivery drivers but many well educated, white-collar workers who have been working in a corporate environment before but are now working as contractors. As part of their distribution strategy, the UpCover team is building not only insurance solutions for the gig economy but a community to connect with their clients which also helps them better understand their needs.

Other companies mentioned in this episode: Buckle

If you would like to learn more about insuring the gig economy, listen to our episodes with GigaCover and Grab.

Episode 111