In episode 200 of Fintech Chatter, host Dexter Cousins chats to Simon Schwartz, Co-Founder and CEO of FreightInsure, about his journey from fintech to insurtech.
Simon shares how his career from investment banking, to fintech, to insurtech (working with SocietyOne, Zip and BizCover along the way) has shaped his current scaleup, FreightInsure.
We take a deep dive into Simon’s strategy to build FreighInsure and how the MGA (Managing General Agent) model has enabled the distribution of embedded insurance products.
Simon reflects on the dual responsibilities as Co-Founder and CEO, and his life hacks for balance and well-being.
Simon is the Co-Founder and Managing Director of FreightInsure, Australia’s leading platform for embedded freight insurance.
He started his career at Investec Bank in Australia, holding roles as Head of Investments, Head of Credit and Head of Board Risk and Capita. Simon has sat on boards as a Non-Executive Director and Chairman at several investee companies. He has also acted on advisory boards at Zip Co and Middle, and is a Board member of Insurtech Australia and the Regulatory and Compliance Working Group.
Simon is a graduate of the Australian Institute of Company Directors, holds an MBA (Exec), Masters of Applied Finance, and is the recipient of the University Medal for pure mathematics from the University of Sydney. He was an Honorary Fellow at Macquarie University’s Applied Finance Centre and a member of the Menzies School of Health Research Development Committee.
FreightInsure offers embedded goods-in-transit insurance directly from a transport company's booking platform. Shippers no longer need to buy annual marine insurance policies, but can simply purchase insurance on a needs basis, when booking their freight, within less than a minute.
00:00 Introduction
05:54 The Birth of FreightInsure
12:01 Innovation in Distribution
17:57 Future Innovations and AI Applications
25:15 Identifying Market Opportunities
30:54 The Dual Role of Founder and CEO
39:00 The InsurTech Landscape in Australia
Peter Jones used to be the CEO he now sells to. It's helped him bootstrap a core banking platform that now holds 20% market share in Australia's mutual banking sector, without a dollar of outside capital. We are celebrating the World Credit Union Conference coming to Sydney. Dexter Cousins will be bringing you interviews from […]
Andy Taylor is Co-Founder of Stakk an embedded finance infrastructure solution. On 6 July 2026, ASX-listed Stakk Limited signed a definitive agreement to acquire US document intelligence firm ParaScript for US$63 million. I've interviewed Andy more than once over the past decade, way back when he was just starting to build Douugh out of Tank […]
When QED Investors, Blackbird, Square Peg and Airtree all back the same early-stage Australian AI startup, the funding round is news. What matters more for anyone hiring or being hired in fintech right now is why they all said yes, and what the founder behind it says about building and hiring in an AI native […]
Looking to scale your fintech leadership team? Start at tieronepeople.com Clayton Howes is the co-founder and CEO of MONEYME (ASX: MME), a Sydney-based non-bank lender that has originated over $5 billion in consumer credit since 2013 and manages a $1.9 billion loan book today. In this conversation, Clayton covers the full arc: bootstrapping without external […]
