When Flock Freight CFO Pat Dillon thinks back to his investment banking days at Morgan Stanley and considers the variety of CFOs from whom he once sat across, the banking veteran is struck by how at times the CFOs seem to have had little in common with one another. “What I saw was that their roles could be very different from one to the next,” explains Dillon, who notes that he came to view the CFO position as not one but many roles along a continuum across which that finance leaders migrate as their companies mature. “It wasn’t like a split, where this person was an accounting CFO and that person was a strategic CFO, but really more about the mix of responsibilities and where the CFO was allocating their time,” recalls Dillon, who observes that it was during conversations with CFOs that he would seek to make the finance leaders aware of where along the continuum they would need to begin allocating more of their time. Reports Dillon: “It’s no longer just about a good technology or about acquiring market share. You have to have predictable results. You have to understand that the role of the CFO and of the finance team is going to change and the requirements are only going to go up.“ Asked whether as a banker he had ever had to coax a finance leader to make finance team staff changes or beef up the company’s FP&A team, Dillon remarks: “I think that you have to tread lightly when it comes to making a particular staff recommendation. As an advisor, we have exposure to senior members of the finance team—but not enough to make a judgment regarding operations day to day.” Still, Dillon says, “You make very clear what kind of output and results the finance team is now going to have to produce as the company is evolving. Whereas it used to be just kind of providing information, you now have to hit your results.” Undoubtedly, every banking relationship has its own unique challenges, and certain finance leaders are better listeners than others. Comments Dillon: “The best relationships that I had as an investment banker were where I could talk about that evolution and say, “Hey, I can’t tell you how to run your organization, but I can help to preview where you’re going to start confronting a higher set of requirements and where you could experience pain points with investors if you don’t make certain changes.’” –Jack Sweeney