Jeremy Krienke, founder and CEO of Sidewalk Security Advisors, shares his journey from early threat intelligence work alongside federal partners to leading security programs in banking and fintech—and ultimately launching his own advisory firm.

In this episode, Jeremy and Greg explore what it really means to serve as a fractional CISO, how to uncover and align to a company’s true risk appetite, and why many organizations misunderstand executive-level security leadership. Jeremy also discusses the entrepreneurial leap, lessons learned in the first year of business ownership, and his vision for improving third-party risk and incident transparency in regulated industries.

A candid conversation about strategy, storytelling, and building security programs that actually fit the business.