About this role
Build and lead Workleap's application security program, transitioning from traditional AppSec tooling to agentic AI-powered security review. You'll architect security guardrails for AI-assisted development, automate SAST/DAST/SCA in CI/CD, and pioneer autonomous security agents that perform first-pass code review. This is a hands-on IC role with real ownership and broad scope across product security, cloud security, and governance.
Must have
Five or more years in application security, DevSecOps, or security focused software development with real engineering background
Deep working knowledge of web application security, OWASP Top 10, and CWE Top 25
Proven experience building security automation into CI/CD pipelines, GitHub Actions preferred
Built and shipped real agent tooling including MCP servers, Claude skills, subagents, and custom tools
Context engineering as a discipline for agent reasoning about codebases
Understanding of security model of agentic systems including prompt injection and tool permission scoping
Proficiency in Python for building tooling, not just scripting
Hands on experience with AI assisted and agentic development workflows
Solid grasp of Azure services, infrastructure security, and deployment patterns
Ability to explain risk tradeoffs to both engineers and executives effectively
Technologies
Responsibilities
Build security guardrails for AI assisted and agentic development so speed and safety stop being a tradeoff
Move security review from human bottleneck to automated first pass with human judgment for ambiguous cases
Achieve near-zero developer friction on security signals by wiring SAST/DAST/SCA into CI/CD with tuned noise
Lead threat modeling on new features and architectural changes
Drive real remediation of application security vulnerabilities measured by risk retired not tickets closed
Harden Azure environments and deployment patterns alongside Infrastructure SecOps
Write code as a hands-on individual contributor
Partner closely with AI SDLC team and product engineering across the organization
Benefits
Amenities
Recruitment process
Join LeapSec team reporting to Director of Infrastructure and Security
Small team with broad reach covering product security, cloud security, and governance across Workleap and ShareGate
Own work end to end and set priorities that matter with real scope and autonomy
Hiring process includes recruiter call, hiring manager interview, take-home case study, and team discussion
AI supports certain hiring steps but every decision remains human
Company uses AI as toolkit to go faster and decide smarter, not to replace judgment
Similar offers
Senior Application Support Engineer (Remote Ontario)
85,000 – 110,000 CAD
/ year
Azure DevOps & Infrastructure Lead
114,400 – 166,400 CAD
/ year
Staff Backend Engineer - Mimir Query, Databases
186,368 – 223,642 CAD
/ year
Senior Migration Engineer - GitLab Dedicated
152,800 – 259,200 USD
/ year
Cybersecurity Operations Architect
191,600 – 249,000 USD
/ year