Most investment banks are staffed with professionals with a large amount of transactional experience. Many senior M&A advisors have been part of hundreds of transactions and have gained valuable experience through them. You should consider the types of transactions (sell-side representation, capital raise, buy-side representation, ESOPs, and more) in which the banker has experience compared to your anticipated transaction. It is also useful to consider what experience the banker has outside of managing transactions. Seller (or buyers) often find it beneficial if their advisor has operational, strategic, or specialized experience. For example, a banker with a degree in science, who was an executive in a technology company, and has deep transactional expertise might be the ideal representative in the sale of a technology-enabled business.