We have spent many hours in discussion with finance leaders about the intersection of finance and sales as we try to better understand the professional collaboration required to achieve successful outcomes in these domains. Still, few of our talks have pushed us to ponder the human elements and relationships that point to such success more than that with finance leader Kent Kelley. From the very start of our discussion, we quickly typecast Kelley and brashly concluded that here was a mild-mannered voice of reason that had sat across the table from some of the software industry’s most energetic sales titans. To be clear: Kelley—a 15-year Oracle veteran whose finance career had spanned operations, sales, and marketing—had never been a bookkeeper, and his consistent willingness to assume career risks along the way set him apart even more from his more traditional finance peers. It was just such a risk attached to a challenging new role that finally led Kelley to move outside of Oracle’s wide-body finance function altogether to join the management team of one of Oracle’s standalone business units dedicated to industry applications. “I moved out of my office overlooking the Oracle pond to a smaller office in San Francisco—I’m sure that some of my friends in finance thought that I was crazy, but I was stepping out of my comfort zone and really challenging myself,” explains Kelley, whose move to the business unit also led to a fateful collaboration with an executive by the name of John Andrus. Andrus, a passionate and seasoned sales leader who had been given global responsibility for the business unit, made it clear that his plans involved broadening Kelley’s responsibilities. “This was someone who had enough faith in me to say, ‘Hey, this organization is growing, and I need to focus on growing the rest of the world, so I need you to be my guy in North America,” comments Kelley. This would not be the last time that Andrus included Kelley in his future plans. A number of years into his new role, Andrus was recruited to be CEO of a company known as PowerPlan, and he asked Kelley to join the firm as CFO. After a “thorough” interviewing process with the company’s board, Kelley was named CFO in 2011.   “We doubled the size of the company within our initial tenure,” says Kelley, whose CFO career took a dramatic turn when Andrus was diagnosed with stage four brain cancer and then shortly thereafter passed away. “I was suddenly leading the company,” recalls Kelley, who was named interim CEO of PowerPlan in late 2014. “Having to interact with the other executives at a level on which I had never interacted before led me to understand their respective challenges in a way that I had never experienced.” Kelley would continue as interim CEO until the sale of the company to private equity firm Thoma Bravo in 2015, at which time he reassumed his CFO position. Reflecting on his dynamic collaborator, Kelley remarks: “John was an experienced leader and a great mentor as well as friend to me.” While Kelley does not recall for us the first time that he sat down across a table from John Andrus, we can assume that the dynamics of the gathering would have been much the same as those at any other meeting between Oracle finance and sales professionals, representing a confluence of both mild-mannered and passionate voices resounding together in pursuit of a successful outcome. –Jack Sweeney