Ep. 113 – From CRO to CEO: What Boards Really Look for in Sales Leaders with Jason Baumgarten - Part 2

In Part 2 of this Selling the Cloud conversation, Mark Petruzzi and KK Anderson continue their discussion with Jason Baumgarten, diving deeper into how boards think, govern, and evaluate senior sales leaders once they reach the highest levels of leadership.

Jason unpacks why boards care less about confidence and more about clarity, learning, and diagnosis. He explains how CROs must evolve from operators into enterprise leaders who understand risk, governance, succession planning, and investor expectations.

The conversation also explores what executive vetting really looks like at the senior level, how boards assess integrity and credibility over time, and why understanding context behind results matters more than headline numbers. This episode is essential listening for CROs, CEOs, and revenue leaders aspiring to board seats or the CEO role.

What You’ll Learn:

• Board Governance for CROs: Why sales leaders must understand how boards think and operate
• Investor Empathy: How understanding investor pressure builds trust and credibility
• Learning Over Bravado: Why boards care more about why results happened than confidence alone
• Risk Awareness: How governance thinking changes how CROs evaluate decisions and tradeoffs
• Succession Planning: Why boards expect leaders to plan for a future beyond themselves
• Board Readiness: What boards actually look for when recruiting sales leaders as directors
• Executive Vetting Reality: What senior leadership evaluation really includes
• Integrity Signals: Why honesty about misses builds long-term executive trust

Key Topics:

• Board governance through a sales leadership lens
• Operator mindset vs investor mindset
• Risk management and risk of inaction
• Stakeholder alignment beyond compensation plans
• Succession planning and leadership maturity
• Board selection criteria for sales leaders
• Executive search and forensic referencing
• Ethics, credibility, and long-term reputation
• Contextualizing revenue performance and growth
• Preparing for CEO and board-level roles

Guest Spotlight: Jason Baumgarten

Jason Baumgarten is the Global Head of the CEO and Board Practice at Spencer Stuart, where he advises boards, investors, and executive teams on leadership selection, succession planning, and governance. He has led more than 250 CEO and board transitions and brings deep expertise in evaluating executive readiness, integrity, and long-term leadership impact.

Resources & Mentions:

• Spencer Stuart
• Harvard Business Review: How CEOs Build Confidence in Their Leadership
• Board governance and executive succession best practices

🎧 Listen now and follow Selling the Cloud for deeper conversations on executive leadership, governance, and what it truly takes to move from CRO to CEO.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.