Boardroom Series EP06 - Insurance Coffee House: Career Risk, Leadership Transitions, AIG Transformation & CEO Perspective - Elaine Rocha, Former CIO (AIG) & CEO (Madison Square Boys & Girls Club)

On this episode of the Insurance Coffee House, Nick Hoadley is joined by Elaine Rocha, former Chief Investment Officer at AIG and current CEO of the Madison Square Boys & Girls Club of New York City. Elaine brings a career that spans law, insurance, investments, and executive leadership, shaped by a series of deliberate career moves and transitions across the industry.

Elaine shares how she first entered the insurance industry through private legal practice, working on complex insurance coverage matters in the London market. She reflects on the early years of her career, where she developed deep technical expertise by working through large-scale claims, litigation, and policy structures, and how that foundation shaped her approach to problem-solving and learning.

The conversation explores her move into AIG in the aftermath of the financial crisis. Elaine discusses the decision to leave private practice, the risks involved in joining a company undergoing significant change, and how she approached building credibility in a new environment. She explains how she navigated a large and complex organisation by focusing on learning quickly, asking questions, and developing strong relationships across the business.

Nick and Elaine discuss how her role evolved within AIG, moving from legal into broader leadership responsibilities. Elaine reflects on the importance of saying yes to new opportunities, even when they sit outside your core expertise. This included stepping into roles such as Chief of Staff, moving into the investments division, and eventually becoming Chief Investment Officer, overseeing complex operations, transformation programmes, and large-scale strategic initiatives.

The discussion highlights the breadth of experience required to operate at senior executive level within a global organisation. Elaine describes how working across insurance, investments, operations, and finance gave her a unique perspective across the value chain, including asset liability management, technology transformation, outsourcing strategies, and regulatory engagement.

The conversation then turns to her transition into her current role as CEO of the Madison Square Boys & Girls Club. Elaine shares how her experience at AIG prepared her to lead an organisation undergoing transformation, and how many of the same leadership principles apply in a nonprofit environment. This includes building alignment across teams, introducing new operating models, leveraging technology, and worki