673: Advancing Down the Transformation Path | Will Bondurant, CFO, Castlight Health

Published: Feb. 10, 2021, noon

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 \u201cThe Turnaround\u201d\u2014that is, if he and Castlight CEO Maeve O\u2019Meara are able to achieve what the firm\u2019s 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\u2019s future CFO first emerged as one of the company\u2019s foremost problem-solvers.

Says Bondurant: \u201cIf everything is working, you don\u2019t always get the opportunity to fix something. The reason that I was able to have these opportunities is that we had challenges\u2014and from where I sit now, they certainly benefited my own personal development.\u201d

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\u2019s CFO role. Still, it appears likely that his Castlight colleagues viewed things differently. \xa0

Having spent many hours with Castlight customers before becoming CFO, Bondurant was familiar with certain external facing aspects of the role, but not all.

\u201cInvestor relations was a new area for me\u2014I had been external in my previous roles but principally with customers and partners and the like,\u201d explains Bondurant, who recalls several unpleasant calls with investors after stepping into the CFO role. \xa0

\u201cI recall asking myself in the first week, \u2018Do these people just hate me? Am I just really disliked by these people?,\u2019\u201d 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.\xa0\xa0\u2013Jack Sweeney


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