Penetration Tester

Company: Stingrai
Location: Toronto, Ontario, Canada
Work Arrangement: Fully remote, with occasional on-site client engagements in the Greater Toronto Area
Employment Type: 6-month contract, with potential to transition to permanent full-time employment within 3 to 6 months
Experience Level: 2 to 3 years of hands-on experience

About the Role

Stingrai is seeking a Penetration Tester to join its offensive security team. This hands-on role focuses on identifying, validating, and demonstrating security vulnerabilities across web applications, APIs, and internal and external networks.

The successful candidate will work alongside experienced security researchers, exploit developers, and penetration testers to deliver security assessments for clients ranging from high-growth startups to large enterprises. The role also involves working with Stingrai's AI-powered penetration testing platform to validate findings, investigate potential vulnerabilities, and strengthen security testing capabilities.

The position begins with a 6-month contract, with the potential to transition to a permanent full-time role within 3 to 6 months, based on performance.

Key Responsibilities

• Plan and conduct penetration tests across web applications, APIs, and internal and external networks.

• Investigate vulnerabilities to confirm their exploitability and demonstrate real-world security impact.

• Prepare professional penetration testing reports with clear findings and prioritized remediation recommendations.

• Review and validate findings generated by Snipe, Stingrai's AI-powered penetration testing agent, using human expertise to distinguish genuine risks from false positives.

• Investigate how application vulnerabilities may affect connected systems, including cloud environments and Active Directory.

• Present assessment findings to technical teams, project leads, and executive stakeholders.

• Work directly with clients through Stingrai's Penetration Testing as a Service (PTaaS) platform, including providing support during active engagements.

• Stay current with emerging attack techniques, security tools, and newly disclosed vulnerabilities.

• Contribute to research and development initiatives that improve offensive security solutions.

• Support the cybersecurity community through technical blog posts, security research, and knowledge sharing.

Required Qualifications

• Offensive Security Certified Professional (OSCP) certification.

• Two to three years of practical experience in web application, API, and network penetration testing.

• Strong understanding of the OWASP Top 10 and common attack techniques affecting web applications, APIs, and networks.

• Residence in the Greater Toronto Area and availability for occasional on-site client engagements.

• Legal authorization to work in Canada without restrictions.

Note: Stingrai does not offer employment sponsorship for this position.

Preferred Qualifications

The following qualifications are beneficial but not mandatory:

• Experience in cybersecurity consulting or other client-facing roles.

• Experience in red teaming and adversary simulation.

• Knowledge of physical security and perimeter testing.

• Experience conducting Wi-Fi security assessments.

• Familiarity with social engineering and phishing assessments.

• Cloud security experience across AWS, Microsoft Azure, or Google Cloud Platform.

• Existing security clearance or eligibility to obtain one.

• A demonstrated bug bounty track record.

• Published security research, including CVEs, technical articles, or conference presentations.

About Stingrai

Stingrai is a CREST-accredited offensive security firm headquartered in Toronto, Canada, with a European hub in London, United Kingdom. The company serves clients across Canada, the United States, and Europe, providing expert-led penetration testing and AI-powered security validation.

Stingrai combines experienced human penetration testers with its agentic Penetration Testing as a Service platform, powered by Snipe, an AI penetration testing agent. Its team includes security researchers and exploit developers with advanced industry certifications, published CVEs, and research presented at conferences such as DEF CON, BSides, and NATO Locked Shields.

Why Join Stingrai?

• Career growth: An opportunity to transition from a contract position to permanent full-time employment, with room to develop technical expertise.

• Expert collaboration: Work alongside experienced penetration testers, security researchers, and exploit developers.

• Global client exposure: Assess real-world security risks for clients across Canada, the United States, and Europe.

• AI-powered security: Help shape the future of offensive security by working with an AI-powered penetration testing platform.

• Research and innovation: Contribute to security research, product development, and the wider cybersecurity community.

Compensation and Employment

The position begins as a 6-month contract, with the potential to convert to permanent full-time employment within 3 to 6 months, depending on performance. Salary and benefits are associated with the permanent full-time position.

How to Apply

Interested candidates can apply through LinkedIn by submitting a resume. A cover letter is optional.

Apply here: View the Penetration Tester position on LinkedIn

Applications submitted by email will not be reviewed.

Stingrai uses AI-assisted tools, including LinkedIn's AI interview, to support application screening and assessment. A human reviewer evaluates every shortlisted candidate.