Dean Sysman

Husband and Father | Systems/AI @ Columbia | Exec Chair/Co-Founder @ Axonius | Board @ Olakai, Lasso, SecurityScorecard | VA @ BVP

📍 New York, New York, United States🔄 Updated September 2026💼 5 investments📅 10 years investing🗓 Last invested Mar 2026𝕏 @upgrade_to_unlock
VC🌍 United StatesInvested this year
5
Total investments
1
Early stage
1
Mid stage
0
Late stage
10y
Years active

Portfolio

3 investments · sorted by recency
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Board Member
Feb 2026
Howdy fearless cybersecurity explorer! 🤠​ Lasso is the AI Security Platform built for the agentic era. By connecting discovery, AI risk management, automated red teaming, and runtime protection in a single continuous loop, Lasso ensures every agentic application behaves within its intended scope, at every stage of its lifecycle. For more information visit www.lasso.security.
Board Member
Oct 2024
The only Enterprise AI ROI & Governance platform. Enterprise AI is being deployed faster than anyone can prove its working. Olakai shows you the ROI, the productivity, and the risk across every AI deployment in your organization. One platform, three lenses: assistive AI, agentic workflows, and AI coding agents. Governance and Shadow AI included. We provide this. With clear evidence. See it in Action: https://olakai.ai/paul/ Category: Enterprise AI ROI & Governance | HQ: Palo Alto, CA |Backed by: AI Fund and Andrew Ng
Investor
May 2016
Startup Network in London
Experience · 10 entries
All (10)
Investments (5)
Founder (2)
Board (3)
2026
Board Member
Mar 2026
Funded by world-class investors, including Evolution Equity Partners, Silver Lake Partners, Sequoia Capital, GV, Riverwood Capital, and others, SecurityScorecard is the global leader in cybersecurity ratings, response, and resilience, with more than 12 million companies continuously rated. Founded in 2013 by security and risk experts Dr. Aleksandr Yampolskiy and Sam Kassoumeh, SecurityScorecards patented rating technology is used by over 25,000 organizations for enterprise risk management, third-party risk management, board reporting, due diligence, cyber insurance underwriting, and regulatory oversight. SecurityScorecard makes the world a safer place by transforming the way companies understand, improve and communicate cybersecurity risk to their boards, employees, and vendors. SecurityScorecard is listed as a free cyber tool and service by the U.S. Cybersecurity & Infrastructure Security Agency (CISA). Every organization has the universal right to its trusted and transparent Instant SecurityScorecard rating Founded in 2013 by security and risk experts Dr. Alex Yampolskiy and Sam Kassoumeh, SecurityScorecard’s patented rating technology is used by over 25,000 organizations for self-monitoring, third-party risk management, board reporting and cyber insurance underwriting; making all organizations more resilient by allowing them to easily find and fix security risks across their externally facing digital footprint. SecurityScorecard is the only provider of instant cyber risk ratings that automatically map to vendor cybersecurity questionnaire responses - providing a true 360 degree view of risk. SecurityScorecard continues to make the world a safer place by transforming the way companies understand, improve and communicate security risk to their boards, employees and vendors. To receive an email with your company’s current score, please visit instant.securityscorecard.com.
Board Member
Feb 2026
Howdy fearless cybersecurity explorer! 🤠​ Lasso is the AI Security Platform built for the agentic era. By connecting discovery, AI risk management, automated red teaming, and runtime protection in a single continuous loop, Lasso ensures every agentic application behaves within its intended scope, at every stage of its lifecycle. For more information visit www.lasso.security.
Venture Adviser
Feb 2026
Bessemer Venture Partners helps entrepreneurs lay strong foundations from inception to build long-standing companies. With more than 155 IPOs and 450-plus portfolio companies across industries, Bessemer supports founders and CEOs from seed through every stage of growth. Bessemer has backed industry defining companies including Anthropic, Abridge, Canva, LinkedIn, Perplexity, Pinterest, RocketLab, Shopify, ServiceTitan, Toast, and Twilio, and has $20 billion of assets under management. Bessemer invests globally, with investment teams located in San Francisco, Silicon Valley, New York, Boston, London, Bangalore, and Tel Aviv.
2024
Board Member
Oct 2024
The only Enterprise AI ROI & Governance platform. Enterprise AI is being deployed faster than anyone can prove its working. Olakai shows you the ROI, the productivity, and the risk across every AI deployment in your organization. One platform, three lenses: assistive AI, agentic workflows, and AI coding agents. Governance and Shadow AI included. We provide this. With clear evidence. See it in Action: https://olakai.ai/paul/ Category: Enterprise AI ROI & Governance | HQ: Palo Alto, CA |Backed by: AI Fund and Andrew Ng
Venture Advisor
Jun 2024
AI Fund is a venture studio. We collaborate with entrepreneurs, venture funds, and corporate partners to create great companies that move humanity forward. Founded by Andrew Ng, AI Fund is backed by over $370 million. As a venture studio, we work alongside entrepreneurs, venture funds, and corporate partners to build new companies rapidly and increase their odds of success. The studio is supported by top-tier VCs and partners including Sequoia Capital, NEA, Nikkei, and AES.
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Investment activity
2016–2026 · 5 investments
201622024120262
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