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Associate Director, Reinsurance Associate

Selby Jennings, Chicago, IL, United States


We are partnered with a fast‑scaling, tech‑forward financial services platform operating across the life, annuity, and broader insurance ecosystem. The organization combines institutional stability with a modern, innovation‑first mindset. The team hiring for this role functions like an internal structured finance and strategy group-lean, analytical, and directly responsible for driving new business initiatives and balance‑sheet optimization.

Role Overview We are seeking an Associate‑level Structurer to help design and execute reinsurance, capital markets, and other risk‑transfer transactions. This is a highly visible position working closely with actuarial, investments, legal, risk, accounting, and senior decision‑makers. The role blends financial modeling, deal execution, market analysis, and cross‑functional leadership.

This is an exceptional seat for someone who thrives in fast‑paced environments, enjoys solving complex problems, and wants the chance to directly influence business growth. Prior insurance experience is not required-strong analytical ability and intellectual curiosity are what matter.

Desired Skills and Experience Key Responsibilities

Leading end‑to‑end structuring and execution of reinsurance, capital markets, and risk‑transfer transactions

Building and refining financial models, scenario analyses, and transaction evaluations

Creating decision‑ready materials and presenting insights to internal stakeholders

Identifying opportunities informed by market trends, regulatory shifts, and competitive dynamics

Supporting active transactions and contributing to ongoing infrastructure and process optimization

Distilling complex quantitative and legal information into clear, practical deal recommendations

Skills

Strong financial modeling and analytical background

Ability to operate across multiple concurrent projects

Clear communication skills and sound commercial judgment

3-5 years in investment banking, consulting, structured finance, or similar

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