Back in the 1990s, Dilip Upmanyu sat in a room filled with servers as he pieced together a homegrown database of costs and SKUs. His employer at the time couldn’t tell which products paid the bills; by dawn, the young financial analyst could. That improvised profitability model, he tells us, still informs his investment mindset today.Upmanyu never mistook rows of numbers for the whole story. Later joining IBM, he moved from product analytics to revenue accounting in a single year, then volunteered to face Wall Street. Preparing earnings decks, he practiced fielding questions until he could anticipate three out of four before the line opened. “Data matter only when you can explain the ‘why,’ ” Upmanyu tells us.A misstep—a brilliant job wrapped in toxic politics—taught him culture diligence. From then on he evaluated environments as rigorously as balance sheets. That instinct paid off when NetIQ sold to Attachmate: suddenly he was steering a global integration that tripled his team and required fresh capital. He treated the chaos as a practicum in fundraising and leadership, logging the final credit hours for his CFO ambition.By the time Cloudera called in 2023, Upmanyu had stitched together every major finance discipline. Today he pushes growth by leading with the firm’s public‑cloud platform and embedding AI into forecasting.