Years from now, when Castlight Health CFO Will Bondurant reflects back on the varied chapters of his finance career, he may title the current one “The Turnaround”—that is, if he and Castlight CEO Maeve O’Meara are able to achieve what the firm’s previous management team had not been able to: a strategy transformation. Like his CEO, Bondurant is not an outsider: After joining the firm in 2013, he was assigned a variety of strategy and financial planning duties that led to more influential product strategy and operational roles of the type that many aspiring CFOs eagerly seek out. As Bondurant shared with us his cross-functional journey, he mentioned few titles or promotions but instead drew our attention to a variety of experiences that has led us to conclude that Castlight’s future CFO first emerged as one of the company’s foremost problem-solvers. Says Bondurant: “If everything is working, you don’t always get the opportunity to fix something. The reason that I was able to have these opportunities is that we had challenges—and from where I sit now, they certainly benefited my own personal development.” Then, in 2017, came a $135 million acquisition, a transaction that management told investors would transform Castlight but instead ended up leaving a trail of merger snags and glitches that ultimately led to the formation of a new management team. At the time, Bondurant no doubt may have appeared to certain investors and outsiders to be a dark horse candidate for the firm’s CFO role. Still, it appears likely that his Castlight colleagues viewed things differently.   Having spent many hours with Castlight customers before becoming CFO, Bondurant was familiar with certain external facing aspects of the role, but not all. “Investor relations was a new area for me—I had been external in my previous roles but principally with customers and partners and the like,” explains Bondurant, who recalls several unpleasant calls with investors after stepping into the CFO role.   “I recall asking myself in the first week, ‘Do these people just hate me? Am I just really disliked by these people?,’” comments Bondurant, who notes that he now enjoys the calls with investors and very often views them as being more productive than his engagements with customers.  –Jack Sweeney Leave rating & review   Signup for our Newsletter GET MORE: Order now The CFO Yearbook, 2021