CALEB SIMA

Caleb Sima is a distinguished General Partner at Boldstart Ventures, an early-stage venture capital firm renowned for backing the next generation of enterprise technology companies. At Boldstart, Caleb leverages his extensive operational and technical expertise to identify and support innovative founders building solutions in B2B SaaS, cybersecurity, developer tools, and cloud infrastructure. His investment philosophy is deeply rooted in his firsthand experience as an serial entrepreneur, focusing on companies with strong technical foundations and clear market potential.

Before transitioning to venture capital, Caleb Sima built an impressive career as a serial entrepreneur and a recognized leader in cybersecurity. He co-founded and served as CEO of CloudPassage, a pioneer in cloud security posture management, which was later acquired by Cohesity. Prior to CloudPassage, Caleb co-founded SPI Dynamics, a web application security company that was acquired by HP. His leadership roles also include serving as Chief Security Officer at ServiceNow and holding a Vice President of Security position at HP, where he oversaw critical security initiatives. This journey from ethical hacker to founder to CSO has provided him with an unparalleled understanding of the challenges and opportunities within the enterprise technology landscape.

Caleb's unique blend of technical acumen and entrepreneurial drive makes him an invaluable partner to the startups he backs. He is particularly passionate about companies that are disrupting traditional markets with innovative software solutions, especially those that address complex security and infrastructure needs. His notable investments and contributions at Boldstart Ventures include early support for companies like Snyk, a leader in developer security, and BigID, a data intelligence platform. He also played a role in the success of Kustomer, a customer service platform acquired by Meta, and has backed promising firms such as Superhuman, FireHydrant, and Replicated, among others. Through Boldstart, Caleb continues to shape the future of enterprise software by empowering visionary founders with capital, strategic guidance, and a wealth of operational experience.