Robert Fly is an accomplished executive with extensive experience in cybersecurity and technology leadership. Currently serving as CEO and Cofounder of detections.ai since June 2025 and leading the rebranded System Two Security as CEO and Cofounder, Robert has a strong track record in building communities for Detection Engineers. As an Investor, Advisor, and Board Member for various successful companies, Robert has guided firms through acquisitions and IPOs while contributing expertise in go-to-market strategies, recruiting, and fundraising. Previously, Robert was the CEO and Co-Founder of Elevate Security, where achievements included developing the first Human Risk Management platform and significant reductions in security incidents. Robert's background also encompasses a significant tenure at Salesforce, with roles ranging from VP of Security Engineering to VP of Trust Technology, along with early experience at Microsoft as a Senior Software Security Lead.
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