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Caleb Sima is a General Partner at Boldstart Ventures and a highly respected serial entrepreneur and cybersecurity expert. He is known for co-founding successful security companies like SPI Dynamics and CloudPassage before transitioning to venture capital.
Caleb Sima primarily invests in early-stage B2B SaaS, cybersecurity, developer tools, and cloud infrastructure companies through Boldstart Ventures. He focuses on innovative enterprise technology solutions.
Caleb Sima works as a General Partner at Boldstart Ventures, an early-stage venture capital firm based in New York City, known for its investments in enterprise software.
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.
Caleb Sima is a General Partner at Cyberstarts and Managing Partner at Sima Ventures, based in the San Francisco Bay Area, California. Previously, he served as Chief Security Officer at Robinhood, Vice President of Information Security at Databricks, and Managing Vice President at Capital One. As a serial entrepreneur, he founded the web application security firm SPI Dynamics, which was acquired by Hewlett-Packard, and the mobile security startup Bluebox Security, which sold to Lookout. He holds multiple patents in application security and has personally invested in more than 20 early-stage technology startups throughout his career. In late 2023, he also launched and began chairing the Cloud Security Alliance AI Safety Initiative to help shape emerging industry standards. Sima currently focuses on early-stage venture capital investments across the cybersecurity, artificial intelligence, and enterprise software sectors.
