Penetration Tester

ISA Cybersecurity•Toronto, ON

4d•CA$75,000 - CA$90,000•Remote

About The Position

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. 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 2026-2027. 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 townhalls and social events throughout the year to encourage teambuilding and collaboration.

Requirements

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
Familiarity with tools such as Burp Suite, Nmap, Metasploit, Nessus, or equivalent
Strong communication and interpersonal skills

Nice To Haves

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

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

Benefits

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 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
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