Alex Tosheff
InvestorVenture Partner at Syn Ventures Seed Management Llc · Board director at Aiceberg · Board director at Balance Theory
San Diego Metropolitan Area
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About
Alex Tosheff brings decades as a senior security executive at VMware and PayPal plus CISA advisory and Tenable board experience, uniquely guiding national cyber priorities and scalable enterprise security models.
Invests in
AI & Machine LearningCybersecurityDeveloper ToolsEnterprise SoftwareInsurTech
Board director at Aiceberg
Intro paths
In turn, Alex can intro founders to Aiceberg's investors below.
Aiceberg's investors · 2
Co-founders at Aiceberg

Board director at Balance Theory
Intro paths
In turn, Alex can intro founders to Balance Theory's investors below.
Balance Theory's investors · 4
Co-founders at Balance Theory
Experience
- RegScaleIndependent Board Membercurrent2025 — present
- SYN VenturesVenture Partnercurrent2025 — present
- AIcebergBoard Membercurrent2025 — present
- AIcebergStrategic Advisorcurrent2024 — present
- TenableBoard Membercurrent2022 — present
- TenableExecutive Advisory Board Member2017 — 2022
- ZoomCEO Advisory Board Member2020 — 2025
- Cybersecurity and Infrastructure Security AgencyCybersecurity Advisory Commitee2023 — 2025
- VMwareSenior Vice President, Chief Security Officer2022 — 2024
- VMwareVice President, Chief Security Officer2017 — 2022Palo Alto, CA
- VMwareVice President, Chief Information Security Officer2014 — 2022Palo Alto, CA
- vArmourExecutive Advisory Board Member2014 — 2021
- GoSecureExecutive Advisory Board Member2014 — 2020
- PayPalChief Information Security Officer2008 — 2014
- PayPalHead of Global Information Security2008 — 2011San Diego
- Bill Me Later, Inc.Vice President, CISO BillMeLater Inc. (acquired by PayPal)2007 — 2008Washington DC-Baltimore Area
- PivxXCTO2004 — 2007
- St. Paul Venture CapitalVenture Partner2001 — 2004
- Science Application International, CorpCorporate Vice President, CTO1994 — 2001
Skills & more
+12 more
Enterprise SoftwarePaymentsPCI DSSBusiness StrategyVulnerability ManagementComplianceInformation TechnologyComputer SecurityEnterprise Risk ManagementSoftware as a Service (SaaS)Technical LeadershipIntegrationFrom Alex's professional profile.
Deals · 1
AicebergBoard seat
via Syn Ventures Seed Management Llc · filed Feb 2025 · $7.5M raise
Attribution from SEC filings, press coverage, and firm rosters.
Other disclosed investments
Board seats
Per SEC Form D filings.
Colleagues at Syn Ventures Seed Management Llc
Frequently asked questions
- Who is Alex Tosheff?
- Alex Tosheff brings decades as a senior security executive at VMware and PayPal plus CISA advisory and Tenable board experience, uniquely guiding national cyber priorities and scalable enterprise security models.
- Where does Alex Tosheff work?
- Alex Tosheff is Venture Partner at Syn Ventures Seed Management Llc and Board director at Aiceberg and Board director at Balance Theory.
- What does Alex Tosheff invest in?
- Alex Tosheff invests in AI & Machine Learning, Cybersecurity, Developer Tools, Enterprise Software, InsurTech.
- What boards does Alex Tosheff sit on?
- Alex Tosheff holds tracked board seats at Aiceberg, Balance Theory.
- Where did Alex Tosheff go to school?
- Alex Tosheff studied at California State University, Fullerton (BS, Physics).
Founder mafias
PayPal mafia129
Also came through, then founded or led a company.
California State University, Fullerton mafia14
Also came through, then founded or led a company.
Syn Ventures Seed Management Llc mafia4
Also came through, then founded or led a company.
Aiceberg mafia3
Also came through, then founded or led a company.
Regscale mafia2
Also came through, then founded or led a company.
Same school
Also attended California State University, Fullerton49
+ 43 more
Shared employers
Also worked at Tenable28
+ 22 more
Also worked at Zoom39
+ 33 more
Also worked at VMware252
+ 246 more




























































