Today, I sit down with Joe Chernov, a three-time CMO, seasoned startup advisor, and Executive in Residence at Battery Ventures, widely recognized as a leader in B2B marketing. Joe, who previously led global marketing at Pendo and oversaw significant growth and acquisitions, shares his circuitous career path from aspiring federal law enforcement to building high-performing teams and launching top-ranked content programs at companies like HubSpot and Eloqua.

Joe talks about the power of finding someone who believes in you and will champion you, emphasizing that your job is to make that person look good by being a strong culture fit, consistently saying “yes” to projects, and trusting that recognition will come.

We also hear about Joe’s “golden era” and how to identify it: by recognizing where your mind truly wanders. That internal motivation that drives success, as he experienced at Eloqua where all his thoughts revolved around the company’s triumph. Joe also candidly discusses the pitfalls of getting “too big for your britches,” sharing how demands for more can turn a collaborative relationship transactional, advising instead a collaborative process with leadership and the wisdom of a famous haiku for building a reputation.

He also reveals his favorite leadership qualities: those who genuinely get to know their people, provide thoughtful, critical feedback, and are constantly “trying to be a good leader” who motivates on a personal level. This episode offers invaluable lessons on career growth, leadership dynamics, recognizing capable versus great leadership, understanding when “winners quit bad matches,” and the importance of a personal inventory to align with the right company culture, whether it’s a fast-paced startup or a more structured large organization.