Most fintech CEOs arrived from banking or venture. Shawn Lane arrived from a Procter & Gamble manufacturing floor in 1994, BS in Industrial Engineering from NC State in hand, watching physical production lines and asking himself one persistent question: why is this still manual?
He spent four years at P&G learning how real operations work - the kind of unglamorous, thousand-invoice-a-day reality that most finance software is designed for in theory and fumbles in practice. Then he moved to i2 Technologies, a supply chain software company that was helping Fortune 500 companies do for procurement what Lane would eventually help Ottimate do for payments: replace human bottlenecks with automated logic.
The next two decades were a masterclass in picking companies at inflection points. Servigistics, which became part of PTC. RedPrairie, which became Blue Yonder. Mitratech. E2open. At each stop, Lane took on more scale - VP of Sales for Europe, VP of Sales Consulting, eventually General Manager. The pattern held: a company with real technology underserving an under-automated market, Lane building the go-to-market motion to close the gap.