Jerome Upton still remembers the silence that descends just before a game begins. As captain of his college team, he’d scan the huddle, gauge nerves, and ask, “What does winning look like today?” “That’s where I learned the power of shared goals,” Upton tells us. Years later, the Genworth Financial CFO opens staff meetings similarly—then hands teammates room to execute.The first bold play of his career came soon after graduation. At a small insurer, Upton stunned mentors by jumping to KPMG. “I needed wider fields,” he explains. Eight years of audits sharpened his technical vision, yet the move that truly stretched him arrived when GE Capital—Genworth’s predecessor—offered a divisional‑controller seat with global scope. Overnight his “team” expanded ten‑fold, teaching him to win through trust rather than touch‑every‑file oversight.International assignments followed: boardrooms in Europe, investor roadshows in Asia, client visits in Latin America. Hearing customers critique products in real time “made finance feel less like a ledger and more like a heartbeat,” he says. That perspective proved vital during Genworth’s post‑crisis crossroads. Tasked with raising capital quickly, Upton orchestrated a minority IPO of a foreign subsidiary, executed at speed and premium valuation. The deal slashed leverage and revealed hidden asset value.Today his playbook balances share buybacks and debt reduction with growth bets such as CareScout. Multi‑year downside modeling safeguards the core, while his Gretzkyesque mantra—skate where the puck is going—keeps him focused on tomorrow’s opportunity.