John McCauley

CFO of Calendly, John McCauley, shares insights on hiring, promotion, confronting challenges, and CFO responsibility. Talks about product-led growth, debunking benchmarking myths, loyalty in software organizations, and the importance of teamwork. Reflects on mentorship, leadership influence, CFO journey, embracing opportunities, navigating challenges in finance leadership, and redefining loyalty in the workplace. Discusses crazy expenses, sales strategies, and memorable CFO experiences.

Joe Euteneuer, seasoned CFO and operator who learned finance through hands‑on ops. John McCauley, finance leader turned COO who credits tough coaching and early CFO wins. Shelagh Glaser, longtime Intel/Synopsys exec who led rapid, people‑centered decisions during market collapse. They discuss leadership forged under pressure, decisive refocusing, CEO–CFO chemistry, and how preparation shapes high‑stakes judgment.