Penetration Tester

About the Role: ISA is seeking a motivated Penetration Tester to join our cybersecurity team. In this role, you will play a key part in identifying and exploiting security vulnerabilities across networks, systems, and applications, applying your experience in offensive security methodologies. This is an excellent opportunity for cybersecurity professionals looking to take on more complex engagements and further develop their expertise in penetration testing.

About Us: We are proud to be recognized as a top employer for multiple years in a row, we currently hold the distinctions of Canada’s Top Small and Medium Employers 2025, Greater Toronto’s Top Employers 2025 and are Certified Great Place to Work 2025-2026.

ISA Cybersecurity is a proudly Canadian cyber and AI services and solutions provider. Trusted by over 500 clients from SMB to global enterprises, we empower organizations to safeguard their most critical assets and adopt AI securely. Through our highly customizable Cyber 360 and AI 360 offerings, we deliver a comprehensive range of governance, assurance, engineering protection, detection, and response services for the public and private sectors. Backed by over three decades of operational experience and a vast network of highly specialized and certified experts, we leverage cutting‑edge technologies and AI to ensure that clients achieve their privacy, security, and business goals.

We operate in a remote‑first environment. Office presence is typically less than 20% of the time, varying by role and work requirements. Our office space, located at Bloor and Islington, is a collaborative space designed for in‑person meetings and drop‑ins. We enjoy hosting in‑person quarterly town halls and social events throughout the year to encourage teambuilding and collaboration.

Responsibilities:

Conduct penetration tests on web applications, networks, systems, and cloud environments

Perform vulnerability assessments and validate identified issues

Document technical findings in clear, concise, and professional reports

Lead remediation efforts by communicating findings and recommendations to technical and non‑technical stakeholders

Stay up to date with the latest security threats, tools, and techniques

Execute and contribute to red team exercises and security testing engagements

Collaborate with team members across security operations, engineering, and compliance

Qualifications:

2+ years of professional experience in cybersecurity, including areas such as Offensive Security, Vulnerability Management, Incident Handling, Security Analysis, or other related security roles

Hands‑on experience with penetration testing, vulnerability assessments, and vulnerability management

Strong understanding of common vulnerabilities (OWASP Top 10, CWEs, CVSS, etc.)

Ability to write clear, detailed technical reports with remediation steps

Having one or more offensive security certifications, such as OSCP, CompTIA Pentest+, GIAC GCIH, or similar, would be considered an asset

Familiarity with tools such as Burp Suite, Nmap, Metasploit, Nessus, or equivalent

Strong communication and interpersonal skills

Why Join Us? At ISA Cybersecurity we lead with our "Why". Our Why is to make people feel safe. This not only applies to the result of services that we provide to our clients, but how people feel when interacting with us. Whether you're an employee of ISA or a client we want you to feel safe and supported. Each one of our team members is expected to uphold this leadership quality and embrace it through consistent demonstration of our core values of Explore, Persevere, Adapt and Uplift.

We are proud to offer a variety of employee friendly programs that enable our team to perform at their best.

Highlights of our programs and policies include:

Flexible sick and personal days for all employees

Generous health plan with enhanced mental health resources and programs

Professional development opportunities and education reimbursement up to $2,000 annually for all employees

Maternity and parental leave top‑up

Employee referral bonus of $2,000

Competitive salaries complemented with RRSP matching and bonus programs

Distance remote working policy

LinkedIn Learning access for all team members

Service recognition programs:

Service anniversary recognition and generous five‑year milestone service awards

President’s Club recognizing special achievement awards: Team Member of the Year for Sales, CIOC and Cyber Services, the Rich Uhrich Founder’s Award that is nominated on by all employees and four President’s Awards (Risk Taker, Lost Without You, Money Maker and On the Rise)

Spot rewards providing opportunities for instant peer recognition

Information‑sharing and team‑building initiatives include:

Annual kick‑off meeting to communicate our strategic priorities

Quarterly town hall meetings

Regular team get togethers and client events

Scheduled employee feedback surveys and goal setting focus groups

Thank you for your interest in joining ISA Cybersecurity. Our team looks forward to reviewing your application. We will be reaching out to you directly if your experience matches our needs.

Vacancy Status: This posting is for an existing vacancy.

AI Disclosure: ISA Cybersecurity does not currently use artificial intelligence tools as part of our recruitment process.

Accessibility: ISA Cybersecurity is committed to providing accommodations for applicants with disabilities. If you require specific accommodation because of a disability or medical need, please inform ISA's Human Resources team (peopleoperations@e-isa.com) so arrangements can be made for appropriate accommodation to be in place during the recruitment process.

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