Insurtech | Upcover | Skye Theodorou

Skye Theodorou grew up in Sydney, Australia. Growing up she had many different career ambitions - everything and anything from a singer, to a psychologist.  At one stage, she wanted to be a lawyer but that was always a secret. After working in the NSW Government and the insurer Zurich, she decided to become an entrepreneur and today is the Co-founder & CEO at upcover. upcover is an innovative insurtech start-up providing benefits and insurance for gig economy workers.

Today Skye lives in Coffs Harbour. She says she doesn’t mind frequently travelling to cities. It gives her a great sense of perspective and balance.  We were lucky enough to speak to Skye about her journey and upcover.

Skye Theodorou with co-founder Anish Sinha

What gave you the idea for upcover?

My dad. He’s been operating small businesses my whole life from pizza shops, market stalls, homewares to discount variety stores. Navigating the uncertainty of these businesses has had a big impact on me. It made me passionate about doing something where I can help people like my dad manage risk, and make informed decisions for themselves and their families.

Any key stats, data, reports, research you can provide to give flavor to the opportunity/problem?

upcover is focussed on the gig economy.  By providing insurance and benefits products that empower people that work for themselves. We’re doing this so that they have the peace of mind of knowing they will have a safety net when they really need it. Right now 1 in 10 Australian workers are in the gig economy but this is set to increase to 1 in 5, as we transition to online, virtual and service-based work. 

What does upcover do? Who is the solution for? What problem does it solve?

upcover bridges the protection gap for the fastest growing workforce in Australia. We provide the self-employed and independent contractors of today with the insurance protection and benefits they need. We’re doing this by creating personalised insurance and portable benefits (sick leave, holiday, maternity leave) products that are flexibly and dynamically priced and simple and easy to use.

What is unique about upcover?

We build pay-as-you-go insurance products. These workers can decide how much cover they would like; how much protection they want; and pay on a monthly basis; flexibly being able to cancel whenever they want or need. In the not too distant future, we’ll be making this truly pay-as-you-use by tapping into APIs, so a worker only needs to pay for when they’ve worked too.

 We also have a grassroots approach. We build our products from the ground up for these workers. We engage them so we can understand their needs, wants, hopes, dreams and anxieties. Our financial and insurance products will solve gig workers real problems and needs. I’m not sure that many products are built so closely in connection with the needs of this sector.

Where do you see your proposition in ten years?

In 10 years, we’d like to be an established player supporting large companies and enterprises in bridging the protection gap for their transitory workforce, and doing that across the Asia Pacific region.

If you are not from a Tech background how has that impacted and what do you bring to the table?

Anything great comes from pulling together the skill, passions and diversity of different people. I am super passionate about helping people like my dad. I can really relate to gig economy workers. I work hard, and I want to make a difference. When it comes to tech, I’ve partnered with an extraordinary co-founder, Anish Sinha, who has an incredible background in building and scaling e-commerce products. That’s helped me a great deal in building the upcover products and bringing them to market.

Biggest challenge you have faced so far?

Building an insurance tech company on a shoe-string budget and getting our partnership in three months was a challenge, but something we’ve risen to and accomplished. This wouldn’t have been possible however without so many supporters around us - from being a part of the Antler program, and from securing our insurance partnership with the innovative Agile Underwriting Services team. Everything we have achieved has only been through the combined efforts of so many of us!

What is your focus now? And for the next couple of years?

Through COVID19 our focus and effort hasn’t wavered. If anything, COVID19 has made us more determined. It has highlighted the need for our products more than ever before -  the challenges faced by gig workers in the current climate of COVID-19.  As an early-stage startup,  it’s also made us think forward; to ensure we have a sufficient runway to build out our products over the next year or more.

Looking ahead, we want to protect more than 1,000 delivery riders in our first year of operating and we believe that’s possible - we’ll be the only product in the market.

What tips would you have for female entrepreneurs?

Use your networks, ask to help, and partner with those that can help you. Finally, always put your best foot forward to believe in yourself - you need to before others will.

What are the one or two lessons/principles/ you carry with you into everything you do?

I apply the 5 whys to everything I do. I really hold a high standard for myself and others, believing that we can always improve. I also continue to never be afraid to openly ask if I don’t understand something - the environment we operate in is such that if we don’t think deeply about the problems we are solving, then we likely don’t understand.

Where do you see yourself in 10 years time?

 In ten  years I’m sure my investors will be hoping we have an exit, though I’m interested to see how far we can take the upcover journey beyond the Asia Pacific region. I’d also like upcover to be in a position such that we are ‘thought leaders’ on the future of work, and the gig economy and the protections that exist for this growing workforce.

How do you balance your personal time and your ‘work’ time?

Taking time out is really important as the demands of building a startup can be pretty high. The work is almost akin to a marathon and a sprint, so rest on weekends or on a morning or afternoon is really important.

 To help find balance I love doing yoga and getting out on to my local Sawtell beach as well as cooking for my loved ones whether friends or family! As the weather cools down this often means a red wine and an open fire pit in our backyard and something delicious.

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