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Added 50 mins ago
KC
Senior Embedded Software Designer
Kepler Communications Inc.
Toronto, ON
- Full-time
We're on the hunt for a top-tier Senior Embedded Software Engineer. Your focus will be on software development and maintenance required for both space and ground-based assets for a growing…
Added 50 mins ago
N
Senior Software Developer - Networking (Flow)
Nutanix
Vancouver, BC
- $151,000 to $227,000 CAD / year
- Full-time
…in enterprise cloud, is looking for an outstanding Software Developer to join our Software Defined Security product team, Nutanix…
Added 50 mins ago
WS
Vice President, Human Resources
Wolf Steel Ltd
Barrie, ON
- Full-time
Serve as an active member of the Senior Leadership Team, contributing to enterprise strategy and business decision-making.
Added 51 mins ago
D
Talent Acquisition Specialist (12m FTC)
DEPT®
Toronto, ON
- $65,000 to $70,000 CAD / year
…this ‘In-House’ recruitment. You will work closely with our Senior Talent Acquisition Specialist, Client Partner, Delivery teams and directly with our clients, you will effectively source…
Added 1 hour ago
SH
Registered Social Worker
SE Health
Red Deer, AB
- Part-time
Added 1 hour ago
AI
Lead React Native Developer
AI Interviews
Toronto, ON · Greater Toronto Area, Canada
- Full-time
We are seeking a Senior/Lead React Native Engineer with 8+ years of mobile engineering and 5+ years of production React Native experience.Strong expertise in React Native 0.76+, New…
Added 1 hour ago
TW
Senior Support Engineer
Town Web
Remote, Canada
- Full-time
- Remote
This is the senior seat on our Client Success team. We are hiring you to raise the standard of our support: fix what is broken, write down how it should work, and show what great looks like.
Added 1 hour ago
C
Senior Application Security Researcher
CommIT
Toronto, ON
- Full-time
…vulnerabilities at the source. The Security Research group is hiring a senior, hands-on Application Security Researcher to push modern AppSec forward - working with engineers, researchers…
Added 2 hours ago
J
Director Sales Experience
Jobgether
Canada
- Full-time
This senior leadership role will shape national sales strategy while elevating customer and broker experiences across the organization.
Added 2 hours ago
J
Director Sales Experience
Jobgether
Canada
- Full-time
This senior leadership role will shape national sales strategy while elevating customer and broker experiences across the organization.
Added 3 hours ago
CC
Pharmacy Assistant (Training Provided) - Casual
CareRx Corporation
Peterborough, ON
- $18.5 to $20 USD / hour
- Full-time
At CareRx, we are shaping the future of senior care through pharmacy services that make a real difference. As Canada's trusted leader in specialty pharmacy services for long-term care,…
Added 3 hours ago
CC
Pharmacy Assistant, L1
CareRx Corporation
Victoria, BC
- $19 to $21 USD / hour
- Full-time
At CareRx, we are shaping the future of senior care through pharmacy services that make a real difference. As Canada's trusted leader in specialty pharmacy services for long-term care,…
Added 3 hours ago
A
Intermediate Software Engineer
AltaML
Toronto, ON
- $90,000 to $110,000 CAD / year
- Full-time
Technical Autonomy: Resolves the large majority of technical blockers independently, without routinely escalating to senior engineers.
Added 3 hours ago
CC
Pharmacy Assistant, L1
CareRx Corporation
Victoria, BC
- $19 to $21 USD / hour
- Full-time
At CareRx, we are shaping the future of senior care through pharmacy services that make a real difference. As Canada's trusted leader in specialty pharmacy services for long-term care,…
Added 3 hours ago
J
Senior Manager, Technical Architecture
Jobgether
Canada
- Full-time
This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Senior Manager, Technical Architecture based in Canada.
Added 3 hours ago
J
Senior Data Scientist
Jobgether
Canada
- Full-time
This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Senior Data Scientist based in Canada.
Added 3 hours ago
J
Enterprise Customer Success Manager
Jobgether
Canada
- Full-time
Added 3 hours ago
AI
Analyst, Total Rewards (Non-Union)
Alectra Inc.
Woodbridge, ON
- Full-time
Ability to build and maintain collaborative relationships with internal and external stakeholders, including senior leadership.
Added 4 hours ago
P
Senior Backend Engineer .NET & Python
PosiTrace
Vancouver, BC
- Full-time
We're migrating toward MACH (Microservices, API-first, Cloud-native, Headless) and need a senior backend engineer to co-own that evolution.
Added 4 hours ago
Director of Software Development R&D - AI
Siemens
Saskatoon, SK
Strategic Customer Engagement: Serve as a senior technical leader and trusted AI advisor for strategic Siemens EDA customers, including hyperscalers, fabless semiconductor companies, IDMs,…
Added 4 hours ago
FO
Senior Manager, Client and Funding Services - Net Zero Acceleration
Federation of Canadian Municipalities
Ottawa, ON · Greater Ottawa Metropolitan Area
- Full-time
Reporting to the Director, Client and Funding Services (CFS), the Senior Manager, CFS is responsible for functional and strategic leadership, planning activities and management of all…
Added 5 hours ago
M
Front of House - Supervisor
Moxies
Barrie, ON
- Full-time
Actively lead shifts, in support of senior leadership team members while helping to manage budgetary goals
Added 5 hours ago
M
Senior Data Analyst I, Product
Mistplay
Toronto, ON
- Full-time
Au sein du service des données de Mistplay, l'analyste de données sénior I, Produit jouera un rôle crucial dans l'amélioration de la performance commerciale de Mistplay grâce à une analyse…
Added 5 hours ago
PS
Product Owner / Senior Product Owner, GenAI and Digital Workplace (Temporary – 12 months)
Public Sector Pension Investment Board
Montreal, QC
- Full-time
The Product Owner / Senior Product Owner plays a key role within the agile GenAI & Digital Workplace team to maximize the value delivered by the Technology, Data and Operations (TDO) group…
Added 5 hours ago
Community Relations Consultant
Hydro One Networks Inc
Sudbury, ON
Assist senior staff in implementing community/municipal relations programs. Prepare supporting documents and materials for discussions and meetings with key audiences (e.g., council…

Stingrai

Penetration Tester

Toronto, ON, Canada

Contract

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Applications open in a new tab.

Job details

Job type: Contract
Apply by: Apr 2, 2027
Experience: 2 to 3 years of hands-on experience in web application, API, and network penetration testing
Posting language: English
Posted: Oct 4, 2026

Original job description

ABOUT STINGRAI

Stingrai is a CREST-accredited premier offensive security firm specializing in expert-led penetration testing. Headquartered in Toronto, Canada, with a European hub in London, UK, we serve a global client base across Canada, the US, and Europe, from high-growth SaaS and fintech startups to large enterprises.

We are on a mission to transform offensive security. Alongside a team of experienced penetration testers, we operate an agentic penetration testing as a service (PTaaS) platform that delivers autonomous penetration testing, powered by Snipe, our AI pentesting agent, along with expert human pentesters. The result is world-class, real-world security validation that keeps pace with how fast modern environments change.

We are a team of security researchers, exploit developers and penetration testers. Our team holds the industry's most rigorous certifications, including OSCE³, OSCP, OSWE, and OSEP, has published dozens of CVEs, and presents research at conferences including DEF CON, BSides, and NATO Locked Shields.

THE ROLE

We are hiring a Penetration Tester on a 6 month contract, with potential to convert to a permanent full-time position within 3 to 6 months. This is a hands-on role for someone who already have experience in web application, API, and network penetration testing.

The role is hybrid and based in Toronto, with 2 to 3 days per week in our office. Roughly 10 to 20 percent of engagements also require onsite presence at client sites in the Greater Toronto Area.

WHAT YOU'LL DO

Plan and execute penetration tests across web applications, APIs, and internal and external networks
Dig into every finding until you have proven real, exploitable impact, then document it with clear, prioritized remediation guidance
Validate and triage findings from Snipe, our AI pentesting agent, applying human judgment to separate real risk from noise
Where it matters, chain application flaws into adjacent areas such as cloud or Active Directory to demonstrate full impact
Write professional reports and debrief findings to both technical teams and executives
Work directly with clients through our PTaaS platform, including live support during active engagements
Keep current with new attack techniques, tooling, and disclosed vulnerabilities, and bring what you learn back to the team
Participate in our research and development (R&D) initiatives to further enhance our offensive security solutions, publish security blogs, and contribute back to the community

WHO YOU ARE

You think like an attacker. You are not satisfied flagging a vulnerability. You prove its impact.
You communicate clearly and on time, with clients, project leads, and teammates alike.
You take ownership of your work. Your name is on every report you deliver, and it shows.
You go toward hard problems, not around them, and you adapt fast in client environments.
You keep learning, because offensive security changes constantly.
You leave the ego at the door. The strongest finding wins, whoever surfaces it.

MINIMUM REQUIREMENTS

OSCP certification
2 to 3 years of hands-on experience in web application, API, and network penetration testing
Strong grasp of OWASP Top 10 and common attack techniques across web, API, and network
Based in Toronto, Canada, and available for onsite presence at client sites for certain engagements
Legally authorized to work in Canada without restrictions

We do not offer sponsorship for this role.

PREFERRED QUALIFICATIONS

These are not required, but will strengthen your application:

Experience in a consulting or client-facing role
Red teaming and adversary simulation
Physical perimeter security
Wi-Fi security testing
Social engineering and phishing
Cloud security across AWS, Azure, or GCP
Secret clearance, or eligibility to obtain one
A bug bounty track record
Published security research, such as CVEs or conference talks

WHY STINGRAI

A clear path from contract to permanent, with real room to grow your craft
Work alongside an elite team of top bug bounty hunters, OSCE³ certified senior penetration testers, dozens of published CVEs, and talks at DEF CON, BSides, and NATO Locked Shields
Test real targets for a global client base across Canada, the US, and Europe, from high-growth startups to large enterprises
Use and help shape our agentic PTaaS platform and Snipe, our AI pentesting agent, instead of grinding through checklists
A clear path from contract to permanent for the right person
Competitive compensation and real room to grow your craft

COMPENSATION

Conversion to a permanent full-time position with salary and benefits within 3 to 6 months, based on performance during the contract term

HOW TO APPLY

Apply through LinkedIn with your resume. A cover letter is optional. Applications sent by email will not be reviewed.

We use AI-assisted tools, including LinkedIn's AI interview, to help screen and assess applications. A human reviews every shortlisted candidate.

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More about this job

Responsibilities

Plan and conduct penetration tests across web applications, APIs, and internal and external networks, validating vulnerabilities and demonstrating their real-world impact. Document and present prioritized remediation guidance, support clients through the PTaaS platform, and contribute to security research and product development.

Requirements

Requires OSCP certification, 2 to 3 years of hands-on web application, API, and network penetration testing experience, and a strong understanding of OWASP Top 10 and common attack techniques. Candidates must be based in Toronto, legally authorized to work in Canada without restrictions, and available for some client-site work; visa sponsorship is not offered.

Skills

Web Application Penetration Testing
API Penetration Testing
Network Penetration Testing
OWASP Top 10
Vulnerability Validation
Exploit Development
Report Writing
Client Communication
Red Teaming
Adversary Simulation
Cloud Security
Active Directory
Wi-Fi Security Testing
Social Engineering
Phishing
Security Research

Visa sponsorship

Not detected in the job text

Keywords

Penetration Testing
Web Applications
APIs
Internal Networks
External Networks
OSCP
OSCE³
OSWE
OSEP
OWASP Top 10
PTaaS
Snipe
AI Pentesting Agent
Vulnerability Triage
Exploit Development
Active Directory
Cloud Security
AWS
Azure
GCP
Red Teaming
Adversary Simulation
Physical Perimeter Security
Wi-Fi Security Testing
Social Engineering
Phishing
Bug Bounty
CVEs
Security Research
CREST

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