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Mr. Montgomery joined Pillar in 2022 as Senior Actuary, and following a series of promotions assumed the Chief Reserving Actuary role in 2025. Mr. Montgomery is a fully qualified actuary with 10+ years’ insurance, reinsurance and banking experience across multiple international jurisdictions, having worked in South Africa, the UK and Bermuda.
Prior to joining Pillar in 2022, Mr. Montgomery was a Senior Manager at KPMG in Bermuda. At KPMG, he acted as lead independent valuation agent reviewer for some of the largest ILS funds globally and audited several other funds in Bermuda, including those of Pillar. Prior to that, Mr. Montgomery worked as a consultant at a global actuarial and analytics firm where he was involved in the development, implementation and validation of capital allocation, reinsurance optimization, reserving and personal and commercial pricing models. He also played a fundamental role in the implementation of predictive modelling and automation solutions amongst some of the largest players in the insurance and banking space.
Mr. Montgomery is a Chartered Enterprise Risk Actuary ("CERA"), a Fellow of the UK Institute and Faculty of Actuaries (“FIA”) and a Fellow of the Actuarial Society of South Africa (“FASSA"). He also holds the Certified Extreme Event Modeler (“CEEM”) designation from Verisk. Mr. Montgomery earned his BSc (cum laude) and Honours BSc degrees in Actuarial Science from North-West University in South Africa.
Wesley Montgomery
Chief Reserving Actuary
Prior to joining Pillar in 2022, Mr. Montgomery was a Senior Manager at KPMG in Bermuda. At KPMG, he acted as lead independent valuation agent reviewer for some of the largest ILS funds globally and audited several other funds in Bermuda, including those of Pillar. Prior to that, Mr. Montgomery worked as a consultant at a global actuarial and analytics firm where he was involved in the development, implementation and validation of capital allocation, reinsurance optimization, reserving and personal and commercial pricing models. He also played a fundamental role in the implementation of predictive modelling and automation solutions amongst some of the largest players in the insurance and banking space.
Mr. Montgomery is a Chartered Enterprise Risk Actuary ("CERA"), a Fellow of the UK Institute and Faculty of Actuaries (“FIA”) and a Fellow of the Actuarial Society of South Africa (“FASSA"). He also holds the Certified Extreme Event Modeler (“CEEM”) designation from Verisk. Mr. Montgomery earned his BSc (cum laude) and Honours BSc degrees in Actuarial Science from North-West University in South Africa.