Looking back at the early years of his finance career, David Bedell recalls being frustrated when a business unit leader remained leery about the merits of a potential deal. “I had done all of the analysis and was convinced that it would make a lot of money for the company, but I just couldn’t figure out how to convince him,” explains Bedell, who spent the balance of his early career years at software developer Intuit, where he advanced from running the gauntlet of FP&A projects to serving in multiple CFO business unit roles. “Finally, I bet my entire bonus for the year on it—I told the leader that if the deal failed, he could keep it, but if it was a win, I would appreciate my bonus being doubled,” explains Bedell, who notes that his confidence in his own analysis of the deal compelled him to break what he refers to as the “glass wall.” Says Bedell: “If we in finance limit ourselves to only making recommendations and choose to keep that wall between us, it’s just not pers...