Offensive Security · Threat Hunting · Vulnerability Management

Massimo Stifano

I help organisations find, understand and reduce cyber risk through realistic attack simulation, disciplined vulnerability management and proactive threat hunting across IT and OT/ICS environments.

Profile

Cybersecurity specialist focused on offensive security, vulnerability management and threat hunting, with experience spanning information technology and operational technology (OT/ICS).

Across my career I have supported organisations ranging from government entities to Fortune Global 500 enterprises. In healthcare, banking, insurance, energy, telecommunications, industrial and automotive sectors, identifying, assessing and reducing cyber risk through realistic attack simulations, security assessments and practical remediation strategies.

My work runs the full vulnerability-management lifecycle: from discovery and prioritisation to validation and remediation. It spans penetration testing across web applications, APIs, networks, infrastructure, mobile, IoT and OT/ICS; red team operations and adversary simulation to evaluate detection and response; threat hunting and purple teaming; application security and dynamic application security testing (DAST); and security consulting. Increasingly I combine offensive expertise with automation and AI-driven solutions to improve efficiency, accuracy and scale, strengthening cybersecurity posture without adding operational friction.

Areas of Expertise

  • Offensive Security & Red Team

    End-to-end penetration testing and full-scope adversary simulation across web, network, infrastructure and firmware. From black-box to white-box, evaluating real-world detection and response.

  • Vulnerability Management

    The complete lifecycle: identification, risk assessment, prioritisation, remediation coordination and continuous exposure reduction across complex enterprise ecosystems.

  • Threat Hunting & Purple Team

    Proactive hunting and CSIRT support to uncover sophisticated attacker techniques before exploitation, and purple-team collaboration that matures detection engineering.

  • Application Security & DAST

    Dynamic application security testing programmes, source-code security review and performance stress testing, embedded into development and delivery.

  • OT / ICS & IoT Security

    Assessment of critical infrastructure, SCADA/ICS environments, connected devices and firmware, where safety, availability and security meet.

  • Consulting & AI-driven Automation

    Executive-level advisory, remediation planning and reporting. Increasingly augmented with automation and AI to scale security operations reliably.

Selected toolkit

  • Kali / Parrot / Arch Linux
  • Burp Suite
  • Metasploit
  • Nmap
  • Nessus
  • OpenVAS
  • Wireshark
  • OWASP ZAP
  • SQLmap
  • Aircrack-ng
  • Hydra
  • Hashcat / John
  • Bash & Python
  • Security Onion / SIEM
  • Snort
  • OSINT · SIGINT · FININT

Experience

  1. Senior Security Analyst — Advanced Attacks & Readiness Operations

    Vulnerability Management, Threat Hunting & AI Security Engineering

    • Lead end-to-end vulnerability management across government and critical-infrastructure environments including healthcare. Identification, risk assessment, prioritisation, remediation and continuous exposure reduction.
    • Perform advanced exposure analysis in complex enterprise ecosystems, translating technical findings into business and operational risk to strengthen posture in high-impact environments.
    • Conduct proactive threat hunting and support CSIRT operations to identify attacker techniques, validate detections and improve monitoring and response.
    • Develop and apply AI-driven and automation-based solutions to enhance efficiency in vulnerability analysis, threat detection, reporting workflows and large-scale security data processing.
    • Partner with technical and executive stakeholders to drive remediation, improve governance and ensure security alignment across regulated, mission-critical systems.
  2. Security Analyst — Advanced Attacks & Readiness Operations

    Penetration Testing · Red Team · Purple Team · DAST Lead

    • Conducted advanced penetration tests across banking, insurance, energy, telecom and industrial sectors, covering web applications, infrastructure and firmware.
    • Executed comprehensive red team operations for major conglomerates, simulating advanced adversarial tactics and evaluating detection and response capabilities.
    • Delivered large-scale penetration testing engagements for a major telecommunications provider.
    • Served as a core member of the internal CSIRT with proactive threat hunting and purple-team exercises that matured detection engineering and response.
    • Led and coordinated the security team overseeing DAST activities, and managed the organisation's vulnerability-management programme; mentored junior analysts.
  3. Senior Associate — Cybersecurity & Privacy

    Penetration Testing & Red Team

    • Led multiple assessments for national and international clients across the retail, consumer and automotive sectors.
    • Executed black-box and white-box vulnerability assessments and penetration tests on enterprise networks, systems and web applications.
    • Delivered performance stress testing and in-depth source-code security reviews.
  4. Cybersecurity Consultant & Penetration Tester

    • Conducted vulnerability assessments and penetration testing for Europe's largest water-industry conglomerate, covering data centres, network infrastructure, web applications and SCADA/ICS environments.
    • Provided strategic guidance on security best practice and co-authored remediation plans and executive reports for the Board of Directors.
  5. Bug Bounty Hunter

    • Performed web penetration testing on applications and databases, discovering and validating server- and client-side security vulnerabilities.
    • Delivered clear technical findings and remediation recommendations to developers and management.
  6. Founder & Director

    • Founded a marketing and management-services agency for hospitality companies, retailers and distributors. Successfully sold in 2019.
  7. Graphic Designer & Marketing Specialist

    • Designed web pages, logos, signage, books, magazine covers, annual reports and advertising. Contributing to marketing campaigns and brand communication.

Selected Highlights

CVE-2024-20906

Credited new vulnerability discovery

Identified a new security vulnerability in Oracle software, formally assigned a CVE identifier and indexed by the U.S. National Institute of Standards and Technology (NIST).

Recognition

#1 Hacker of the Month

Ranked first on the TryHackMe leaderboard, a community of hundreds of thousands of security practitioners.

Critical Infrastructure

Europe's largest water utility

Led penetration testing across data centres, network infrastructure, web applications and SCADA/ICS for Europe's largest water-industry conglomerate.

Credentials

Certifications

  • OSCPOffensive Security Certified Professional
  • eCPPTCertified Professional Penetration Tester
  • eJPTJunior Penetration Tester
  • PSM IProfessional Scrum Master I
  • CCNA CyberOpsCisco — Cyber Security Operations (1st of class)
  • ArmisArmis Certified Partner
  • Drone A1–A3EASA / ENAC remote pilot licence

Education & Training

  • PWK / PEN-200Offensive Security — OSCP course
  • PTP v5eLearnSecurity — Penetration Testing Professional
  • PTv4eLearnSecurity — Penetration Testing
  • CCNA CyberOpsCisco Networking Academy
  • IoT SecuritySevenShift bootcamp · RomHack Training
  • ATT&CKBlack Hills Information Security & MITRE ATT&CK

Languages

  • ItalianNative · C2
  • EnglishFull professional · C1
  • SpanishIntermediate · B1–B2
  • FrenchElementary · A2–B2