Senior Application Security Engineer II

Relay; Toronto; On-site; CAD 180,000 - 220,000; Full time

Job summary

Relay is seeking an Senior Application Security Engineer II to own a defined slice of our platform end-to-end, testing services, identifying exploitable gaps, and fixing issues alongside our senior engineers who maintain the auth system and build DAST tooling. You will threat model designs, run white-box tests, triage bug reports, and coordinate fixes with owners, writing patches when appropriate.

You’ll use Datadog security, Burp Suite, and in-house tools, while leveraging AI tooling like

Qualifications

• 5 to 6 years of professional security experience.
• Shipped production code with security in mind.
• Deep understanding of OWASP Top 10 and mitigations.
• Experience with AI tooling in daily work.
• Clear communicator and collaborator with developers.
• Ownership and mentorship mindset.
• Familiar with security testing in cloud environments.

Responsibilities

• Threat model technical designs and run white-box tests.
• Triage bug bounty reports and coordinate fixes with owners.
• Contribute patches to Relay’s codebase when appropriate.
• Work with Datadog security, secrets scanning, Burp Suite, and in-house tools.
• Build with AI as a default using Claude Code and Cursor.

Skills

Threat modeling

Penetration testing

Product security engineering

AI tooling in security

Communication

Mentorship

Ownership

Tools

Burp Suite

Datadog

CI/CD tooling

Job description

Relay is a digital banking platform that gives self-made business owners the tools and know-how to be great with money—bringing clarity, confidence, and control to every dollar earned, so they can turn hard work into lasting success. We do this by replacing financial guesswork with real visibility, transforming cash flow from a constant source of stress into a clear signal owners can use to run stronger, more resilient businesses.

We’re looking for an Senior Application Security Engineer II who thrives on autonomy, curiosity, and impact. You'll join an Application Security team that is deliberately moving away from the advisory model most AppSec functions are stuck in. You’ll work across our stack (from TypeScript and Node.js, to Postgres and AWS cloud infrastructure) ensuring our applications are secure from design to deployment. You’ll blend technical depth with systems thinking, working across teams to identify risks, build guardrails, and evolve our security practices as Relay scales.

That coverage number is where you come in. Right now, most of Relay's platform has never been properly tested — and closing that gap is the single highest-leverage thing our team can do this year. Your mission is to own a defined slice of it end to end: testing the services in scope, working out what's actually exploitable, and fixing what you can yourself.

This is a role with room to grow. You'll be working next to senior engineers who are maintaining our auth system and building our DAST tooling from scratch. The Relay AppSec team genuinely enjoys Application Security and is looking to make an impact on the field.

What You'll Be Doing

• Threat modeling & offensive testing: Threat model technical design documents (TDDs) and run white-box penetration tests on our testing environment to identify vulnerabilities from an attacker’s point of view.

• VDP & bug bounty: Triage researcher reports, reproduce/assess impact, coordinate fixes with owners, and close the loop with clear comms and durable controls.

• Shipping the fixes you can: Contributing directly to Relay’s code base when it makes sense — writing the patch, not filing the ticket.

• Working in our security tooling and extending it: Datadog security, secrets scanning and logging, Burp Suite, and in-house tools you'll be expected to modify rather than just operate.

• Building with AI as a default: Claude Code and Cursor are daily drivers on this team, not a pilot program.

• Joining the team's rhythms: Two weekly standups, a biweekly security champions session with product engineers, and a weekly Hack The Box session.

• Software supply chain: Enforce provenance: SBOM on every build, dependency pinning/owner verification, private registries/proxies, and runtime SCA detections.

Who You Are

• You have 5 to 6 years of professional security experience. Application security, penetration testing, or product security engineering or similar roles.

• You’ve shipped production code: Production-level software real users depended on. And you can read an unfamiliar codebase well enough to fix something in it, which is most of this job.

• Security fundamentals: Deep understanding of OWASP Top 10 and real-world exploitation/mitigation techniques.

• You build with AI. You use AI tooling in your daily work and you've built something with it. You can talk about where it gets things wrong, not just that it's fast.

• Clear communicator & collaborator: you are a collaborator who loves to partner with developers to bring value to customers in the most secure way possible.

• Ownership: You have a sense of responsibility towards problems and take ownership over them making sure nothing is forgotten and stakeholders stay informed.

• Mentorship: You are comfortable mentoring team members and members of other teams on security best practices.

The Interview Process

• Stage 1: A 60-minute Google Meet video call with the Hiring Manager

• Stage 2: A 60-minute live session with the team

• Stage 3: A 60-minute Secure Code Review and Coaching session with two members of our Customer Experience team

• Stage 4: A 45-minute Google Meet video call with a member of our leadership team

Our Compensation Approach

We believe Relayers should feel rewarded for the impact they have on our mission and growth. Compensation follows impact. As impact increases, compensation grows, and we do not limit compensation changes to a once-a-year review cycle.

The annual salary range for this role is $180,000 CAD to $220,000 CAD.

For candidates who demonstrate full readiness for the defined scope of the role, the typical starting salary is $200,000 CAD. Offers below this point reflect candidates we believe can grow into the full scope of the role with support and development. Offers above this point reflect impact that meaningfully exceeds the role’s defined expectations or an expanded scope from day one.

We encourage you to have a conversation with your recruiter and ask questions about compensation throughout the hiring process. For more information on our compensation philosophy and perks and benefits, visit our Candidate Hub.

Why Relay Might Be the Perfect Fit For You

• You push relentlessly for reinvention: You're always asking "how can this be better?" -- in your work, in your craft, in yourself. Comfort is a signal to push harder, not coast. You'd rather build something better than defend something familiar.

• You crave autonomy: We trust our team with big challenges and the freedom to solve them. If you’re someone who takes initiative, is comfortable taking risks, and seeks input when needed, you’ll find the freedom here empowering.

• You own your work: You take pride in your work, follow through on commitments, and feel a deep sense of responsibility for outcomes, not just tasks.

• You build with AI, not just use it: You're actively embedding AI into how you work, pushing what's possible, and bringing your team along with you.

• You care about impact, not noise: You care deeply about the substance of your work. You measure success by results, not recognition, and you let your work speak for itself.

• You’re energized by complexity and ambiguity: You enjoy tackling problems that don’t come with a playbook. You’re comfortable building from scratch, iterating as you go, and collaborating to shape the best path forward.

• You seek out feedback: You see directness as respect, not criticism. You actively seek input, sit with hard truths, and use feedback as fuel for improvement.

• Small businesses are why we're here: Relay exists to help them thrive -- and that mission has to resonate with you.

Join Us

We're looking for people who are relentless, curious, and care deeply about the work. You're encouraged to apply even if your experience doesn't perfectly match the job description -- your perspective and drive matter more. We welcome diverse backgrounds and people who think critically, challenge the status quo, and want to help small businesses thrive.

If you require accommodations at any stage of the hiring process, please reach out to your Talent Partner.

Disclaimer: For compliance reasons, all offers of employment at Relay are conditional upon a successful background check and employment verification through Certn.