12 min read
OffSec's New OSAI+
My experience taking OffSec's OSAI+ course and exam.
- offsec
- osai
- ai-red-teaming
Dmitrii “Zamrax” Strizhkov
Head of Offensive Security. Penetration tester. AI red teamer.
Canada-based ethical hacker focused on practical offensive security, AI security assessment, and helping teams understand their real attack surface.
latest transmissionpublished
AI red teaming · field note
OffSec's New OSAI+
My experience taking OffSec's OSAI+ course and exam.
open field note Continue to experienceExperience in the field
Canada-based penetration tester and ethical hacker focused on helping organizations understand their vulnerabilities, strengthening offensive security practice, and mentoring people entering the field.
Parabellyx Cybersecurity
3 progressive roles
Head of Offensive Security
February 2026 — Present
Scaled the offensive team, implementing a Shadow-to-Lead mentorship program that cut junior onboarding-to-billable time by 40%
Additional evidence
- Engineered a custom LLM-based agent for automated report generation, reducing administrative overhead by 20%
- Architected and deployed an MCP server and gateway, automating 40% of internal engagement execution
- Institutionalized peer-review process, reducing client clarification requests by 15%
Penetration Testing Practice Lead
April 2024 — February 2026
Led strategic planning and execution of the penetration testing practice, aligning security initiatives with business objectives
Additional evidence
- Conducted 50+ web application, 20+ network infrastructure, and wireless penetration tests independently
- Led adoption of the updated OWASP ASVS 5.0 framework for enhanced application security verification
- Reported directly to and assisted the CTO in shaping security strategy
Penetration Tester
February 2022 — April 2024
Conducted testing on 200+ web applications, 40+ network infrastructures, and wireless networks
Additional evidence
- Developed custom Python tooling, reducing testing time by 20% and report writing by 60%
- Produced comprehensive reports for technical and executive audiences with tailored remediation strategies
- Achieved average 60% improvement in client security maturity through personalized recommendations
Digital Defence
consulting role
Information Security Consultant
May 2021 — February 2022
Conducted internal and external penetration tests on networks, operating systems, and databases as part of a 4-member team
Additional evidence
- Utilized NMAP and Nessus for network mapping, resulting in 20% improvement in network hardening
- Authored comprehensive penetration testing reports with vulnerability analysis and remediation strategies
- Assisted in incident response activities including forensic investigations and risk mitigation
University of Toronto
Honours BSc, Specialist in Information Security, Major in Statistics
September 2017 — June 2021
Capabilities with evidence
The tool list matters less than where it has been applied. These are the disciplines that organize the work, with credentials and supporting tooling available for verification.
Primary credentials
OSAIOffSec AI Red TeamerOSCPOffensive Security Certified ProfessionalCRTOCertified Red Team OperatorBSCPBurp Suite Certified Practitioner
Show additional credentials
Application & AI security
Security assessment across modern web, mobile, API, and AI-enabled systems.
- Web application penetration testing
- AI security assessment
- Mobile penetration testing
Supporting tools and platforms
- Burp Suite
- Postman
- SQLMap
Adversary simulation
Internal and external testing that follows realistic attacker paths through infrastructure and identity.
- Internal penetration testing
- External perimeter testing
- Active Directory, OSINT, wireless, and firewall assessment
Supporting tools and platforms
- Nmap
- Nessus
- Impacket
- Metasploit
- BloodHound
- Wireshark
- Covenant
Security engineering
Custom tooling and automation that make testing, evidence collection, and reporting more reliable.
- Python, Go, Rust, and Bash automation
- Windows and Linux operations
- AWS, GCP, and Azure environments
Supporting tools and platforms
- Java
- C
- Assembly
Field notes
Practical observations from offensive security, AI red teaming, and the systems built around the work.