Senior Penetration Testing Consultant

Posted Yesterday
Be an Early Applicant
Hiring Remotely in Toronto, ON, CAN
In-Office or Remote
Senior level
Information Technology • Professional Services • Consulting • Cybersecurity
The Role
Lead and execute penetration tests across networks, applications, APIs, and cloud environments. Conduct red team, purple team, social engineering, and detection capability assessments. Identify vulnerabilities and misconfigurations, develop exploits and scripts, document risk-rated findings, and provide remediation guidance. Mentor junior consultants, contribute to security methodologies, and communicate findings effectively with clients and stakeholders.
Summary Generated by Built In

About Us: 

AprosSyber is a true first-responder Cybersecurity organization enabling clients to return to business rapidly, the right way, following a cyber-attack. We are a global market leader in ransomware post-breach remediation and cyber-attack first response. We deliver results that far surpass market statistics for cyber-extortion and ransomware events. Our team of cybersecurity professionals works with prominent global insurance carriers, leading law firms, and Fortune 1000 businesses.


We are seeking an experienced Senior Penetration Testing Consultant to join our offensive security team. In this role, you will lead and execute penetration testing engagements, assess complex environments, and provide actionable security recommendations to protect our clients against evolving threats. You will work closely with stakeholders to identify vulnerabilities, misconfigurations, exploit weaknesses, and recommend appropriate actions to mitigate the findings.


Key Responsibilities      

  • Conduct penetration tests on networks, applications, APIs, and cloud environments.
  • Perform red team & purple team exercises, social engineering, detection capability assessments.
  • Document detailed reports with findings, risk ratings, and remediation guidance.
  • Stay current on emerging threats, tools, and techniques in offensive security.
  • Mentor junior team members and contribute to methodology development.

Required Qualifications

  • 5+ years of hands-on penetration testing experience, preferably in professional services.
  • Strong knowledge of network protocols, web application security, and cloud platforms (AWS, Azure, GCP).
  • Proficiency with tools such as Burp Suite, Cobalt Strike, and custom scripts.
  • Ability to develop custom exploits and scripts in Python, PowerShell, or Bash.
  • Knowledge of the MITRE ATT&CK framework and OWASP Top 10.
  • Certifications such as OSCP, OSCE, OSEP, or equivalent highly preferred.
  • Team player: you collaborate with your colleagues for peer review and to help them.
  • Excellent report writing and client communication skills.

 


AprosSyber is an equal opportunity employer. If you need any accommodations or adjustments throughout the interview process and beyond, please let us know. We celebrate our inclusive work environment and welcome members of all backgrounds and perspectives to apply.


We thank you for your interest in joining the AprosSyber team! While we welcome all applicants, only those who are selected for an interview will be contacted.






Skills Required

  • 5+ years of hands-on penetration testing experience
  • Strong knowledge of network protocols and web application security
  • Experience with cloud platforms including AWS, Azure, and GCP
  • Proficiency with Burp Suite, Cobalt Strike, and custom scripts
  • Ability to develop custom exploits and scripts in Python, PowerShell, or Bash
  • Knowledge of the MITRE ATT&CK framework and OWASP Top 10
  • OSCP, OSCE, OSEP, or equivalent certification
  • Excellent report writing and client communication skills
  • Collaborative team-oriented approach, including peer review and mentoring
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The Company
HQ: Toronto
140 Employees
Year Founded: 2019

What We Do

CYPFER is a global leader in cybersecurity, specializing in cyber-attack incident response and ransomware post-breach recovery. The firm provides a comprehensive suite of services, including ransomware remediation, digital forensics, and cyber risk management, aimed at delivering 'Cyber Certainty™.' Their in-house team of experts supports organizations worldwide 24/7, helping them recover from cyber-extortion incidents and strengthen their overall digital resilience.

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