“Those numbers will be explosive”: How Upcover is providing insurance for the workforce of the future


Anish Sinha with Upcover co-founder Skye Theodorou. Source: supplied.

At less than six months old, startup Upcover has carved out a niche in the super-traditional insurance industry, and co-founders Skye Theodorou and Anish Sinha now have their eyes on funding, and on international growth.

Having met through the inaugural Antler startup generator program in Sydney, co-founders Theodorou and Sinha paired up quickly, seeing the potential in combining Theodorou’s passion and experience in insurance solutions with Sinha’s financial know-how and business experience.

Initially, they worked on a prototype for a Tinder-style platform allowing Millenials to choose what they wanted covered by contents insurance.

“They could just swipe yes or no as to whether or not you liked something … and if you loved something enough to protect it,” Theodorou tells StartupSmart.

But, after doing some market research and customer surveys, they identified a much bigger gap in the insurance space: the gig economy sector.

“We very quickly went over which were the fastest-growing segments, which were the under-insured or over-insured segments,” Sinha explains.

Gig economy workers are effectively operating as ‘nano-businesses’, he says.

“They were the ones who needed support and benefits and protection,” he says.

The platform provides pay-as-you-go insurance, designed to be flexible and to bring a nimble startup approach to insurance.

As one of the final 12 startups in the Antler program, Upcover secured $100,000 in investment to start developing the business. Theodorou then took to the stage at the program’s inaugural Demo Day, pitching to more than 1,000 people.

An international outlook

Since the Demo Day event last month, Upcover has already seen some significant traction from potential strategic investors.

“We’re still working through first, second or third conversations with a few of them,” Theodorou says.

“Some of them … I believe they’ll be on our cap table in the not-too-distant future.”

In fact, the founders could be looking at closing their first funding round this side of Christmas.

At the moment, they’re focusing on a beta market in Australia — creating the product for the mobility segment of the gig economy.

Then, once they’re established here, they plan to take Upcover overseas.

They will be looking to countries with similar regulatory regimes to Australia, but they also have their sights set on the enormous Indian market — one in which Sinha has significant experience.

“That market is really, really underpenetrated,” he says.

“It’s big, it’s growing really fast, there are insurance needs … that are not being tapped into. There’s a big, growing gig economy,” he adds.

“Those numbers will be explosive in the near future.”

Having worked in India for three years, and across various states, Sinha has an idea as to how Upcover will have to approach it.

“When most people talk of India they think about one country, one monolith,” he says.

Actually, different cities and states have their own culture, and almost their own market to tackle.

“It’s like a European Union of Indian states,” the founder says.

“It’s incredible.”

The new economy

Gig economy work, as a concept, hasn’t always received the best of press — often portrayed as something that’s not necessarily a good arrangement for the workers themselves.

But, Theodorou says this is a growing workforce — one that didn’t exist even a few years ago, and one that is here to stay.

“There’s a lot of policy and social and political commentary about who these people are and how they should be protected — whether they should be employees or not,” she says.

But, while building Upcover, the co-founders have had many, many conversations with their customers, Theodorou says. A lot of them genuinely value the flexibility the gig economy affords, she says.

At the same time, “they do want to be protected, they are quite risk-averse, and the platforms themselves also want to provide protections”.

Gig economy workers don’t even consider themselves as such, Theodorou says.

“That’s just what the media, or people looking at it from a macro level, call it.”

And, when it comes to the actual work they’re doing, whether that’s jumping on an illustration project on Freelancer or driving a car, “these jobs have always existed”, she adds.

“It’s just adding a greater flexibility and, you could almost say, more power to the individual to go direct to a customer.”

Sinha points to a more general shift in the way people work, and how people’s assets — that is, their time, energy and effort — are valued.

From Airbnb to Uber to Freelancer, people are using platforms to share their skills in their own time and on their own terms. And that will only continue, Sinha says.

“It’s inevitable that people will be able to control their source of income and their time, and have the kind of freedom they would not have had if they were working for one person throughout their life,” he explains.

“The gig economy is definitely here to stay.”

StartupSmart was invited to Antler HQ as the official media partner of Antler Demo Day 2019.

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