870: Amped Up at the Deep End | John McCauley, CFO, Calendly

John McCauley is the first finance leader to tell us that his path to the CFO office began in a pool.

Back in high school, McCauley relates, he was a rebellious student with less than impressive grades when a stubborn and no-excuses-allowed water polo coach knocked him from his wayward track.

According to McCauley, the coach’s philosophy was rooted not so much in winning or losing but in whether the team had done everything in its power to succeed.

Recalls McCauley: “This meant 4:30 a.m. practices before school began and 3-hour practices after class, 300 days a year—and if you were sick, you were allowed to skip practice, but you still had to sit on the pool deck and watch.”   

These experiences wed McCauley to a lifetime mantra that has forever filled his tank with the power of preparation.

McCauley’s next pivotal career moment arrived a decade deep into his finance career, when he joined one-time start-up ServiceNow in 2011—the same year that saw the dynamic tech duo of Frank Slootman and Michael Scarpelli take up residence as CEO and CFO, respectively, in the ServiceNow C-suite.

“I found my people,” comments McCauley, who notes that the two business leaders ultimately provided him and others with a “new framework” within which to advance and complete their work.

“It’s all about not simply just raising a problem when you see it, but going ahead and fixing it,” explains McCauley, who adds that fixing problems had always been a natural inclination for him, despite the fact that a string of earlier experiences at different companies hadn’t always supported this approach.       

In light of his high regard for ServiceNow’s veteran leadership team, it’s perhaps no surprise that when asked for a book selection, McCauley recommends Amp It Up, Slootman’s 2022 text that argues that the best way for leaders to improve company performance is to raise expectations.

Slootman and a certain high school coach have something in common.

Says McCauley: “At the last four Olympics, there’s been someone from my high school on our team.” –Jack Sweeney