Episode 87: High Performance, Human Leadership with Cosimo Maiolo

“As you progress in your career, success as a leader is less about what you can achieve as an individual, and more about what you can achieve through others

.”

Cosimo Maiolo, Actuary and Senior Leader.

Nominated as one of the greatest actuarial leaders in 2026, experienced actuary and senior leader Cosimo Maiolo shares his leadership lessons.

In this interview Cos shares: 

  1. Why Cos describes his first leadership role as a "baptism of fire" - managing former peers, losing his manager after two weeks, and navigating one of the most commercially challenging periods in the group insurance market, all at the same time,

  2. What moving overseas to the UK taught him about humility, influence, and why success as a leader has less to do with what you know and more to do with what you can achieve through others,

  3. Why the "compliment sandwich" approach to feedback can do more harm than good, and the performance management experience that reshaped the way he has direct, honest conversations with his team ever since, and

  4. His top tip for actuaries stepping into leadership roles for the first time.

Cosimo is the Chief Actuary & Product Officer at Teachers Health, an Australian-based not-for-profit private health insurer.

His team oversees Actuarial, Pricing, Business Intelligence, Product, and emerging member health initiatives, with a focus on delivering meaningful, sustainable value for Teachers Health members.

A Fellow of the Institute of Actuaries of Australia, Cosimo brings over 15 years of experience across life insurance, superannuation, and health insurance. He has more than a decade of leadership experience, having led diverse teams across Australia, the UK, and Ireland.

Connect with Cos on LinkedIn.

Connect with Julia on LinkedIn.

Views and opinions expressed by guests on this podcast are their own and do not represent the views of their places of work.

Listen now: Apple Podcasts | Spotify | Google Podcasts

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Episode 88: High Performance, Human Leadership with Kriti Khullar

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Episode 86: High Performance, Human Leadership with Jessica Lilley