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Andrew Ostashen

Cybersecurity Expert, Entrepreneur & Virtual CISO

Protecting organizations for 17+ years • 385+ clients served globally • $4M+ in cybersecurity sales • AI/LLM Security Pioneer • Quantum-Safe Security Innovator

Founder of CISO Marketplace & QSai LLC • Eagle Scout • 40 Under 40 Winner • US Marine Cyber Auxiliary • Serving Fortune 100 enterprises to innovative startups worldwide

Eagle Scout 40 Under 40 Winner Marine Cyber Auxiliary AI Security Pioneer Quantum Security Expert
Andrew Ostashen - Cybersecurity Expert
385+
Global Clients
$4M+
Sales Generated
17+
Years
325K+
Miles

My Cybersecurity Journey

From Eagle Scout to cybersecurity entrepreneur - a 17+ year journey of protecting digital assets, pioneering AI security, and building innovative security solutions for organizations worldwide.

My cybersecurity journey began at Rochester Institute of Technology, where I earned my Bachelor of Science in Information Security and Forensics with minors in Business Administration and Psychology. Starting with early IT experience at Gerber Scientific during high school, I've built a career protecting organizations from evolving digital threats.

At Redspin Inc., I conducted 350+ client assessments over three years, generating $2.25M in sales while specializing in HIPAA, FFIEC, NERC, and PCI compliance. This experience provided deep insights into enterprise security challenges and laid the foundation for founding CISO Marketplace with my brother Peter.

Today, as Founder and vCISO of CISO Marketplace and founder of QSai LLC, I'm at the forefront of AI and cybersecurity convergence. I specialize in LLM security, automated red-teaming using PyRIT, Garak, and Giskard, and quantum-safe security solutions that prepare organizations for tomorrow's threats.

385+
Clients Served
$4M+
Sales Generated
Cybersecurity expertise AI Security leadership
17+
Years Experience

Education

BS Information Security & Forensics, RIT
Minor: Business & Psychology
Howell Cheney Technical High School

Recognition

40 Under 40 Award Winner (2016)
U.S. Cyber Challenge (2011)
AccessData Certified Examiner

Service

US Marine Cyber Auxiliary Member
FBI Infragard Contributor
BSidesLV Volunteer

Community

Eagle Scout
OWASP Contributor
ISSA New England Member

Featured in Media & Publications

Expert insights on cybersecurity challenges and emerging threats featured in industry publications.

"Open source: Big benefits, big flaws"

Featured article discussing the cybersecurity implications of open source code adoption, highlighting both benefits and vulnerabilities in enterprise environments.

"Surgical robots - smart but insecure"

Analysis of cybersecurity risks in medical robotics, examining vulnerabilities in surgical robots and remote surgery capabilities.

Professional Journey

A comprehensive timeline of cybersecurity leadership, AI security innovation, and entrepreneurship across 17+ years in the industry.

2023 - Present

Founder - QSai LLC (QuantumSecurity.AI)

Founded quantum-resistant security solutions company addressing emerging threats from quantum computing. Pioneering AI/LLM security with automated red-teaming methodologies using PyRIT, Garak, and Giskard. Specializing in OWASP LLM/Agentic vulnerabilities and prompt engineering security assessments.

Quantum Security AI/LLM Red Team Innovation
2015 - Present

Founder & vCISO - CISO Marketplace

Founded as Vulsec LLC, evolved into CISO Marketplace - a premier platform connecting CISOs and security professionals. Generated $1.79M in sales over four years while serving 35 clients and managing 17 partners. Now integrating AI-driven threat intelligence using OpenAI, Claude, and Perplexity models with voice and chat bot automation platforms.

Entrepreneurship vCISO Services AI Integration
2012 - 2015

Principal Security Engineer & Sales Engineer - Redspin Inc.

Dual role structure: Led security assessments as Principal Security Engineer and Internal Team Lead while serving as Cybersecurity Sales Engineer. Conducted 350 client assessments across 3 years, generating $2.25M in sales. Specialized in HIPAA, FFIEC, NERC, and PCI compliance assessments. Played intricate role in Redspin's acquisition by Auxilio in April 2015.

Key Expertise: Penetration Testing, Social Engineering, Red Team Exercises, Wireless Security, Physical Security Assessments
Penetration Testing Team Leadership Sales Engineering Compliance
2010 - 2012

IT Director - PMI Industries, Inc.

Led comprehensive IT infrastructure modernization for 35+ users. Migrated Windows 2003 to fault-tolerant Windows Server 2008 R2 environment, implemented Fortinet UTM firewall, and migrated email to Microsoft Office 365. Managed technical projects within budget while supervising junior administrators.

IT Leadership Infrastructure Cloud Migration
2010

College Intern - Storage/SAN/Server Engineering - Aetna

Contributed to enterprise-level infrastructure projects including Windows 2008/R2 MDT 2010 deployment image development, ESXi lab environment upgrades, and software distribution scheduling solutions. Member of Aetna Get Youth Moving (G.Y.M) community initiative.

Enterprise Systems VMware Community Service
2006 - 2009

Network Administrator & Desktop Support - Gerber Scientific

Progressed from Desktop Support Engineer to Network Administrator Intern over 3+ years. Managed Active Directory, Microsoft Exchange 2003, McAfee ePolicy Orchestrator, and Checkpoint firewall maintenance. Provided global support for remote users and deployed Microsoft Deployment Toolkit 2008.

Active Directory Exchange Global Support
2008 - 2012

Rochester Institute of Technology

Bachelor of Science in Information Security and Forensics with minors in Business Administration and Psychology. Participated in SPARSA, ISTS, CCDC competitions. U.S. Cyber Challenge Regional Camp participant (2011). Built foundational expertise while gaining early IT experience at Gerber Scientific.

Information Security Digital Forensics Competitions
385+
Clients Served
$4M+
Sales Generated
17+
Years Experience
325K+
Flight Miles

Compliance & Regulatory Expertise

Extensive experience across multiple compliance frameworks and regulatory standards.

HIPAA
Healthcare Compliance
FFIEC
Financial Institutions
PCI DSS
Payment Card Industry
NERC
Electric Reliability
SSAE16
Attestation Standards

Cybersecurity & AI Security Services

Comprehensive cybersecurity solutions backed by 17+ years of experience, proven results across 385+ client engagements, and cutting-edge AI security expertise.

Virtual CISO (vCISO) Services

Strategic cybersecurity leadership and program development with AI-driven threat intelligence. Get executive-level security expertise without the full-time cost, backed by experience serving 385+ clients globally.

Custom Engagement
Tailored to your organization's needs

AI/LLM Security & Red Teaming

Cutting-edge AI security assessments using automated red-teaming methodologies (PyRIT, Garak, Giskard). Identify OWASP LLM vulnerabilities, strengthen AI system guardrails, and secure your AI implementations.

Starting at $200/hour
Leading-edge AI security expertise

Penetration Testing & Security Assessments

Comprehensive security testing including external/internal penetration testing, vulnerability assessments, and OSINT evaluations. Leveraging enterprise-grade tools and 350+ assessments of experience.

Starting at $5,000
Proven methodology and results

Quantum-Safe Security Solutions

Future-proof your organization with quantum-resistant security assessments and implementations through QSai LLC. Prepare for the quantum computing era with next-generation cryptographic solutions.

Consultation Required
Future-ready security solutions

Compliance & Risk Management

Expert compliance assessments across HIPAA, FFIEC, NERC, PCI DSS, and SSAE16 frameworks. Risk quantification, regulatory alignment, and automated policy generation to streamline your compliance efforts.

Starting at $150/hour
Multi-framework expertise

DevSecOps & Application Security

OWASP-based web application assessments, secure development lifecycle integration, and DevSecOps implementation. Includes social engineering and physical security assessments for comprehensive protection.

Starting at $175/hour
Full-stack security integration

Industries Served Across 17+ Years

Trusted by organizations across diverse sectors with specialized security requirements, from Fortune 100 enterprises to innovative startups.

Healthcare
HIPAA Compliance
Banking
FFIEC Standards
Power Plants
NERC Compliance
Legal
Law Firms
Financial
Private Equity
Enterprise
Fortune 100

Global Reach & Experience

5
Countries Served
USA, Canada, China, UK, Australia
42
U.S. States Visited
Extensive travel experience
325K+
Flight Miles
Global client service
7+
Cross-Country Drives
Coast-to-coast experience
5
States Lived In
Diverse regional experience
Schedule Your Security Consultation

Emergency security consultations available 24/7

Cybersecurity & AI Security Insights

Thought leadership on AI/LLM security, quantum-safe security, automated red-teaming, and the evolving cybersecurity threat landscape from 17+ years of hands-on experience serving 385+ clients globally.

AI and LLM security automated red teaming
June 25, 2025

The Evolution of AI Red-Teaming: From PyRIT to Production-Ready Security

After conducting 350+ security assessments and serving Fortune 100 enterprises, I've witnessed the critical gap between traditional penetration testing and AI system security. This comprehensive analysis explores how automated red-teaming methodologies using PyRIT, Garak, and Giskard are revolutionizing OWASP LLM vulnerability identification. Drawing from real-world implementations across healthcare, banking, and critical infrastructure clients, we examine the practical challenges of securing AI systems at scale. Key insights include the emergence of prompt injection attacks in production environments, the critical importance of guardrail testing, and how organizations can build robust AI security programs that protect against both current and emerging threats. This piece also covers the integration of AI security into existing DevSecOps pipelines and the regulatory implications for HIPAA, FFIEC, and PCI DSS compliance frameworks.

Read Full Analysis
Quantum computing security threats and post-quantum cryptography
June 20, 2025

Quantum-Safe Security: Preparing for the Post-Cryptographic Era

As quantum computing advances accelerate, traditional encryption methods face unprecedented existential threats. Through QSai LLC's research and Fortune 100 enterprise consulting, this deep-dive analysis examines the current state of quantum-resistant security solutions and their practical implementation challenges. We explore NIST's post-quantum cryptography standards, the timeline for quantum supremacy in cryptanalysis, and the critical steps organizations must take today to protect their digital assets tomorrow. The piece covers real-world case studies from power plant NERC compliance assessments, banking FFIEC implementations, and healthcare HIPAA environments where quantum-safe security is becoming mission-critical. Special focus on the intersection of AI and quantum security, including how machine learning algorithms can both accelerate quantum attacks and enhance quantum-resistant defenses. This analysis also addresses the economic implications of quantum transition, vendor risk management, and the strategic roadmap for CISOs navigating this paradigm shift.

Read Full Analysis
Virtual CISO leadership and AI-enhanced security programs
June 15, 2025

The AI-Enhanced vCISO: Transforming Cybersecurity Leadership Through Intelligent Automation

Drawing from 385+ client engagements and $4M+ in cybersecurity sales across diverse industries, this comprehensive analysis explores how virtual CISO services are evolving through AI integration. The traditional vCISO model is being revolutionized by intelligent automation platforms, AI-driven threat intelligence, and automated policy generation systems like GeneratePolicy.com. This piece examines real-world implementations across casinos, law firms, private equity, and hedge funds, demonstrating how AI-enhanced security programs deliver superior outcomes while reducing costs. Key topics include the integration of OpenAI, Claude, and Perplexity models for threat analysis, the role of voice and chatbot automation in security operations, and how CyberAgent.Exchange is creating new paradigms for collaborative security intelligence. The analysis also covers the human element - how AI augments rather than replaces cybersecurity expertise, the critical importance of Human Perception Analysis in security decision-making, and the strategic advantages of combining 17+ years of hands-on experience with cutting-edge AI capabilities. Special attention to compliance automation across HIPAA, FFIEC, PCI DSS, and NERC frameworks.

Read Full Analysis

🎙️ CISO Insights: Voices in Cybersecurity Podcast

Listen to in-depth conversations with cybersecurity leaders, AI security experts, and industry pioneers. Featuring insights from 17+ years of experience and interviews with top CISOs from Fortune 100 companies.

Subscribe to stay updated on the latest cybersecurity trends, AI security developments, and expert insights from the field.

Featured Publications & Media

Industry insights and expert commentary on emerging cybersecurity threats and technologies from 17+ years of hands-on experience.

"Open source: Big benefits, big flaws"

Featured analysis on the cybersecurity implications of open source adoption in enterprise environments, discussing both advantages and vulnerabilities based on Fortune 100 consulting experience.

Industry Publication • Cybersecurity Analysis

"Surgical robots - smart but insecure"

Expert commentary on cybersecurity vulnerabilities in medical robotics and the risks associated with remote surgical capabilities, drawing from healthcare HIPAA compliance assessments.

Healthcare Security Analysis • Medical IoT

Cybersecurity Platforms & Resources

Access comprehensive cybersecurity resources through our platforms including AI-driven solutions, threat intelligence, and industry insights developed through 385+ client engagements.

CISO Marketplace Resources

Compliance frameworks, breached company database, secure IoT resources, and AI-driven security solutions based on real-world implementations

Explore Blog →

DigitalWealthShield.com

Real-time threat intelligence, privacy insights, and global cyber warfare analysis from 325K+ miles of global client service

Visit Platform →

AI Security Tools

CyberSecurityGPT.Store, automated red-teaming solutions, and GeneratePolicy.com for AI-driven compliance automation

Access Tools →

Latest from CISO Marketplace Blog

Cybersecurity Workforce Development

Addressing the critical skills gap through innovative training programs and mentorship initiatives based on 17+ years of industry experience.

Read More →
Emerging Threat Landscape 2025

Analysis of evolving cyber threats including AI-powered attacks, quantum computing implications, and nation-state activities.

Read More →

Let's Secure Your Future

Ready to strengthen your cybersecurity posture? Let's discuss how 17+ years of experience, proven results with 385+ clients, and cutting-edge AI security expertise can protect your organization.

Get in Touch

Email

hello@andrewostashen.com

LinkedIn

linkedin.com/in/andrewostashen

Service Area

The Woodlands/Houston, TX & Austin, TX
Global Remote & On-site Services Available
Serving clients across 5 countries

Professional Recognition

• US Marine Cyber Auxiliary Member

• FBI Infragard Contributor

• Eagle Scout Achievement

• Cape & Plymouth Business 40 Under 40 Winner (2016)

• OWASP Contributor & ISSA New England Member

• AccessData Certified Examiner

Response Time & Availability

I typically respond to cybersecurity inquiries within 24 hours. For urgent security incidents or AI/LLM security assessments, please indicate urgency in your message.

Emergency Security Services

Available 24/7 for critical security incidents, breach response, and urgent AI/LLM security assessments.

Proven Track Record

385+
Clients Served
$4M+
Sales Generated
350+
Security Assessments
17+
Years Experience

Request a Consultation

Trusted by 385+ clients globally • $4M+ in proven cybersecurity sales

Emergency security consultations available 24/7

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