Robert Fly

Experienced Cybersecurity Executive and Entrepreneur

Professional Overview
Robert Fly is an accomplished cybersecurity executive and entrepreneur with a proven track record of driving innovation and growth in the technology industry. As the CEO and Co-founder of System Two Security, he leverages his extensive expertise in security engineering, risk management, and technology leadership to guide his company's strategic vision and execute on its mission to provide cutting-edge security solutions.

Experience Summary

Current Role
As the CEO and Co-founder of System Two Security, Robert is responsible for setting the company's strategic direction, overseeing all business operations, and fostering a culture of excellence and innovation. Under his leadership, System Two Security has established itself as a prominent player in the cybersecurity market, delivering innovative solutions that help organizations protect their critical assets from evolving cyber threats.

Career Progression
Prior to co-founding System Two Security, Robert served as the CEO and Co-founder of Elevate Security, a security startup that was acquired in 2024. He also held various leadership roles at Salesforce, including Vice President of Security Engineering, Vice President of Trust Labs, and Vice President of Trust Technology. Earlier in his career, Robert was a Senior Software Security Lead at Microsoft, where he played a key role in developing secure software products.

Academic Background
Robert holds a Bachelor of Science degree in Computer Science from a leading university, where he graduated with distinction.

Areas of Expertise

• Cybersecurity strategy and risk management

• Security engineering and infrastructure design

• Cloud security and DevSecOps

• Incident response and threat intelligence

• Building and scaling security startups

• Effective leadership and team management

Professional Impact
Throughout his career, Robert has been recognized for his contributions to the cybersecurity industry. He has served as an investor, advisor, and board member for several security-focused companies, leveraging his deep industry knowledge and strategic vision to help drive their growth and success. Robert is also a frequent speaker at industry events, where he shares his insights on emerging security trends and best practices.

Conclusion
With his extensive experience, technical expertise, and entrepreneurial spirit, Robert Fly is poised to continue driving innovation and growth in the cybersecurity industry. As the CEO and Co-founder of System Two Security, he is committed to developing cutting-edge security solutions that empower organizations to stay ahead of evolving cyber threats and protect their most valuable assets.