# Skye Theodorou

> Skye Theodorou is the Sydney-based co-founder and CEO of upcover, a digital commercial insurance business founded in 2019. A lawyer with experience at Zurich and in New South Wales government, she drew inspiration from her father’s small businesses. She led upcover through its move from delivery-worker insurance to a broader business offering; the company announced A$19 million in equity and debt financing in 2025 and won InsurTech Company of the Year at the 2026 Finnies.

- **Role:** Co-founder & CEO at upcover
- **Organizations:** upcover, Zurich Financial Services Australia, New South Wales Government, Antler, Australian Insurance Law Association
- **Education:** Bachelor of Business and Bachelor of Laws (LLB), University of Technology Sydney, Bachelor of Business (Management, Honours), University of Technology Sydney
- **Known for:** Co-founded upcover in 2019., Led upcover through its change from delivery-worker insurance to a broader SME offering., Pitched at Antler’s inaugural Sydney Demo Day before more than 1,000 people.

## Career timeline

- **Before 2019** — Worked at Zurich across insurance functions and in NSW government on innovation and regulatory reform for startups and small businesses.
- **2014** — Solicitor of the Supreme Court qualification recorded in January.
- **2015-2016** — Completed further UTS study with a dissertation examining emerging cybersecurity risk for Australian SMEs.
- **2019** — Met Anish Sinha through Antler’s first Sydney cohort and co-founded upcover.
- **2020** — upcover launched its delivery-insurance product in November with EASI and Agile Underwriting Services.
- **2021** — Closed the original delivery platform and relaunched with an SME offering backed by ProRisk.
- **2025** — upcover announced A$11 million equity funding and an A$8 million debt facility.
- **2026** — upcover won InsurTech Company of the Year at the Finnies; Theodorou was a Female Fintech Leader of the Year finalist.

## Achievements

- Co-founded upcover in 2019.
- Led upcover through its change from delivery-worker insurance to a broader SME offering.
- Pitched at Antler’s inaugural Sydney Demo Day before more than 1,000 people.
- Co-led a business that announced A$19 million in combined equity and debt financing in February 2025.
- Female Fintech Leader of the Year finalist at the 2026 Finnies.

## Latest updates

- **2026-06** — upcover won InsurTech Company of the Year at the Finnies; Theodorou was a Female Fintech Leader of the Year finalist.
- **2026-06** — upcover reported approximately 70,000 businesses assisted, around 7,000 active customers and more than 10,000 policies across its platform.
- **2025-12** — Joined Anish Sinha and Antler’s Bede Moore on the Further, Faster Podcast to discuss building upcover.
- **2025-08** — Publicly discussed a startup-secondaries webinar and opportunities for early investors and team members to participate.
- **2025-02** — upcover announced A$19 million in combined equity and debt financing.

## Links

- Website: https://www.upcover.com/
- LinkedIn: https://www.linkedin.com/in/skye-theodorou/

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Profile page: https://yespress.io/skye-theodorou
Published by YesPress — https://yespress.io
Last updated: 2026-10-14