Alex Tosheff

Board Member | Advisor | Investor | 3x CSO/CISO

San Diego Metropolitan Area

About

With 30 years of experience in cybersecurity and technology, I have led global security initiatives that align with business objectives and drive innovation. As the former Senior Vice President and Chief Security Officer at VMware, I oversaw cybersecurity, physical security, and enterprise resiliency, contributing to the company’s strategic direction and operational excellence. My career includes serving as Chief Information Security Officer at PayPal, where I developed and implemented security strategies to protect critical assets and support business growth. I also held leadership roles at BillMeLater and SAIC, focusing on technology integration and security operations. Currently, I serve on the Board of Directors for Tenable, Inc.(NSDQ:TENB), contributing to audit and cybersecurity risk management committees. I am also an independent board member for AIceberg and a venture partner with SYN Ventures, where I focus on supporting early-stage cybersecurity investments. Additionally, I advise organizations like Zoom, RegScale, and Material Security, guiding them through the evolving cybersecurity landscape. In 2023, I was honored to be appointed to the Cybersecurity and Infrastructure Security Agency (CISA) Advisory Board, reflecting my commitment to national and global cybersecurity strategies. My approach is pragmatic and results-driven, focusing on aligning security initiatives with business goals to foster innovation and resilience. Specialties: Cybersecurity operations and strategy, crisis management, technology integration, investment due diligence, venture capital, enterprise resilience, application and workload security, operational security, high-performing team development, advisory board service, and board governance.

Experience

  • Independent Board Member at RegScale
    Feb 2025 - Present · 1 yr 6 mos

  • Venture Partner at SYN Ventures
    Jan 2025 - Present · 1 yr 7 mos

  • AIceberg (1 yr 8 mos)
    • Board Member
      Jan 2025 - Present · 1 yr 7 mos

    • Strategic Advisor
      Dec 2024 - Present · 1 yr 8 mos

  • Tenable (9 yrs 3 mos)
    • Board Member
      Sep 2022 - Present · 3 yrs 11 mos

      Independent Director serving on Audit and Cyber committees

    • Executive Advisory Board Member
      May 2017 - Sep 2022 · 5 yrs 5 mos

  • CEO Advisory Board Member at Zoom
    Mar 2020 - May 2025 · 5 yrs 3 mos