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Upwork
looking for an experienced and certified Ethical Hacker / Penetration Tester to perform a comprehensive security assessment of our IT infrastructure and email environment.
The primary objective is to identify security weaknesses, validate existing security controls, simulate real-world attack scenarios, and provide a practical remediation roadmap that strengthens our overall security posture.
This is not a one-time assessment. We are looking for a security expert who can partner with us through the complete lifecycle of Assessment → Remediation → Validation → Continuous Security Improvement, making this a long-term engagement.
Project Budget: Up to USD 20,000 based on experience, approach, and scope.
Scope of Work
You will be responsible for performing comprehensive infrastructure security testing, including:
External and internal penetration testing
Assessment of servers, firewalls, VPNs, switches, routers, and network devices
Cloud infrastructure security review (Azure, AWS, OCI, or GCP)
Identification of vulnerabilities, misconfigurations, and security gaps
Authentication and authorization testing
Privilege escalation testing
Remote access security validation
Active Directory / Entra ID security review
Microsoft 365 / Exchange Online
Google Workspace
On-Premise Exchange (if applicable)
SPF validation
DKIM validation
DMARC review
Email spoofing assessment
Phishing resilience testing
Business Email Compromise (BEC) risk assessment
Email gateway configuration review
Anti-spam and anti-malware controls
MFA implementation review
Conditional Access policy assessment
Vulnerability scanning
Infrastructure penetration testing
Public attack surface assessment
Exposed services identification
Web application testing (where applicable)
API security testing
SSL/TLS configuration review
Security headers validation
Password policy assessment
Identity and access management review
Expected Deliverables
Executive Summary
Detailed Vulnerability Assessment Report
Risk Classification (Critical / High / Medium / Low)
Technical Findings with Evidence
Proof of Concept (where applicable)
Business Impact Analysis
Prioritized Remediation Roadmap
Best Practice Recommendations
Security Hardening Checklist
Final Validation Report after remediation
Knowledge Transfer / Walkthrough Session with our technical team
Minimum 5+ years of hands-on Ethical Hacking or Penetration Testing experience
Strong expertise in Infrastructure Security
Strong experience with Microsoft 365 / Email Security
Experience performing enterprise security assessments
Kali Linux
Burp Suite
Metasploit
Nessus
Nmap
OWASP Testing Methodology
Active Directory & Entra ID Security
VPN & Firewall Security
MFA & Identity Security
Cloud Security (Azure / AWS / OCI / GCP)
Ability to produce executive-level and technical security reports with actionable remediation recommendations is essential.
Preferred Certifications
Candidates holding one or more of the following certifications will be preferred:
CEH (Certified Ethical Hacker)
CompTIA PenTest+
Security+
Technical Evaluation
To evaluate practical expertise, shortlisted candidates may be requested to participate in a live technical discussion or demonstration.
Demonstrating a real-time infrastructure security assessment approach
Identifying email security vulnerabilities in a controlled environment
Explaining attack methodologies and remediation strategies
Reviewing sample penetration testing scenarios
Discussing previous enterprise engagements
This evaluation is intended to verify practical experience and technical depth.
Engagement Details
Project Type: Fixed Price with Long-Term Opportunity
Budget: Up to USD 20,000
Experience Level: Expert
Regular progress meetings and technical walkthroughs
Potential for ongoing security assessments and remediation projects
NDA and Confidentiality Agreement required before project commencement
Proposal Requirements
Brief introduction and relevant experience
Similar infrastructure and email security assessments completed
Security certifications
Sample or redacted assessment report (if available)
Testing methodology and tools you will use
Estimated project duration
Fixed project cost and milestones
Availability to start
Why you are the right fit for this engagement
Important Notes
This engagement is strictly for authorized and ethical security testing.
All assessments will be performed only against systems for which written authorization has been provided.
The successful consultant should be capable of identifying vulnerabilities, recommending practical remediations, assisting with implementation, and validating that remediation activities effectively strengthen the organization's security posture.
If you have a proven track record in enterprise infrastructure security, email security, penetration testing, and remediation, we would like to hear from you.
Verified Listing
This role has been verified for authenticity, market-rate compensation, and remote eligibility.