Seth A. Ravin built Rimini Street around a question software buyers rarely get to ask: what if we kept what already works? Two decades, a public listing and a long legal fight later, he is asking it again in the age of AI.

For nearly four decades, Kevin Maddock has worked the quiet machinery of enterprise software - renewals, support and the patient arithmetic of keeping customers. His career is a study in why the second sale can matter more than the first.