Catherine Casazza, Senior Legal Counsel at Fidelity International — From Wall Street to the Buy Side

In this episode, Catherine Casazza shares her remarkable journey from aspiring actor to senior legal counsel at Fidelity International, offering an honest look at life across private practice, international opportunities and the investment management industry.Catherine reflects on growing up in Rhode Island before heading to the University of Southern California, initially pursuing acting before discovering mock trial and later the law. After graduating, she worked as a paralegal at Davis Polk in New York, where she was unexpectedly thrown into the world of derivatives and structured products.The conversation explores her experiences at the SEC, Cahill Gordon & Reindel and Sidley Austin, including relocating to Sydney to practise US capital markets law abroad. Catherine shares what it was really like working in offices overseas, balancing demanding workloads with the opportunity to travel and experience different cultures.Catherine discusses joining Kirkland & Ellis and transitioning from representing banks and financing sources to advising private equity-backed issuers. She reflects candidly on why she decided private practice was no longer the right fit and how she knew it was time to move in-house.A major focus of the episode is her current role at Fidelity International. Catherine provides a fascinating insight into life as buy-side counsel, sitting directly on the trading floor and advising investment teams on debt investments, high-yield bonds and restructurings.The discussion highlights how in-house lawyers often move beyond black-letter law to provide practical, risk-based guidance to internal stakeholders.Catherine also reflects on the cultural differences between private practice and in-house roles, including abandoning the billable hour, adapting to hot-desking and learning to thrive in a collaborative environment where colleagues become both teammates and internal clients.The conversation explores how AI is changing legal practice, with Catherine sharing how she uses Microsoft Copilot and Harvey AI in her day-to-day work. From drafting emails and improving clarity to reviewing lengthy offering memoranda, she explains how these tools are enhancing efficiency while raising important questions about training the next generation of lawyers.Beyond her legal career, Catherine discusses co-founding Muses in the City, a network bringing together women across London's professional community through arts, culture and heritage experiences. She reflects on the importance of finding your tribe, creating leadership opportunities outside the office and building meaningful relationships through shared interests.Finally, Catherine shares thoughtful advice for aspiring lawyers and trainees: stay curious, avoid rigid career plans, embrace opportunities when they arise and approach networking as an extension of friendship rather than a transactional exercise.00:00 Introduction  00:20 Meet Catherine Casazza & Her Route Into Law  01:00 From Acting to Political Science  02:00 Working at Davis Polk as a Paralegal  03:00 Discovering Derivatives & Structured Products  04:00 Studying for the LSAT & Cornell Law School  05:00 The US Route to Qualification Explained  06:00 Summer Associateships & The SEC  08:00 Mock Trial, Acting & Communication Skills  10:00 Early Career Lessons in Authenticity  13:00 Moving to Sydney with Sidley Austin  15:00 Life in a US Satellite Office Abroad  18:00 Returning to New York  19:00 Relocating to London & Joining Kirkland  21:00 Transitioning from Sell Side to Buy Side  22:00 Moving In-House at Fidelity International  23:00 Life as Buy-Side Counsel  24:00 Understanding High-Yield Bonds  26:00 Investor Protections & Covenants Explained  28:00 Trading Floors vs Law Firms  30:00 Building Relationships with Internal Clients  33:00 The Benefits of Going In-House  35:00 Commercial Advice vs Black Letter Law  39:00 Risk Tolerance & Business Judgement  42:00 AI, Copilot & Harvey in Legal Practice  46:00 The Future of Junior Lawyer Training  52:00 Muses in the City & Leadership Outside Work  56:00 Advice for Trainees & Young Lawyers  59:00 Networking as Friendship  01:01:00 Awards, Recognition & Giving Back  01:03:00 What's Next for Catherine?