“Steal Your Boss's Job”: Calendly CFO John McCauley on Leadership, Ownership & Growth

In this episode, CJ sits down with John McCauley, the CFO of Calendly. From his learnings under the leadership of Frank Slootman and Mike Scarpelli at ServiceNow to his first CFO role at Seismic, and his current position, John shares valuable insights from his career. He gives advice on hiring and getting promoted, why you should consider your value prop to your company, the benefits of seeking healthy confrontation, and why the CFO should take responsibility for overall company performance. From tracking product-led growth in your metrics to debunking the myths of benchmarking, John offers profound insights into what it takes to excel as a CFO in today's evolving software climate. He also explains the role of loyalty in software organizations and why businesses are teams, not families.

If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

—

SPONSORS:

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

NetSuite provides financial software for all your business needs. More than 37,000 thousand companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:02) Sponsor - Mercury | NetSuite

(04:49) What John Learned Under Frank Slootman and Mike Scarpelli

(10:30) A Big Mistake That John Made at ServiceNow

(15:54) John’s Mindset Going Into His First CFO Role

(18:23) Sponsor - Maxio

(21:22) A Lesson on Hiring and Getting Promoted

(24:48) Brand Equity and Calendly’s Viral Coefficient

(28:22) Tracking Product-led Growth in Your Metrics

(32:36) The Changing Climate of Software

(36:16) Creating Value as a Privately Held Tech Company in M&A

(39:12) The Truth About Benchmarking

(42:17) What Makes a Great CFO

(44:41) John on “Moving Slow to Move Fast” 

(47:01) The Role of Loyalty in Business: Team Versus Family

(50:49) The Long-ass Lightning Round: John’s Advice to His Younger Self

(52:20) John’s Finance Software Stack

(53:35) The Craziest Thing Someone Tried to Expense