At 25 he was chief technology officer of pioneering Lombard Brokerage, which was acquired in 1996 by Dean Witter for a then-princely $40 million. (For a while, the Lombard founders fretted that they had sold out too early -- then dot-com paper fortunes began to shrink.) MacIlwaine went on to become CTO of Morgan Stanley Dean Witter’s retail brokerage arm before working briefly as CTO of MyHomeKey.com, an online commerce site serving homeowners that’s currently winding down operations. Now the 33-year-old MacIlwaine is back in the financial business, having just signed on as chief tech maven for Chicago-based EnvestnetPMC, which provides technology for separate-account management. Flashy it’s not. But a hopeful MacIlwaine insists that the opportunities are “frighteningly similar to online brokerage in 1995'96.”
