We at Security Compass are on a mission to create a world where we can trust technology by enabling organizations to shift left and build secure applications by design. Our flagship product, SD Elements, helps organizations to reduce cyber risks by taking an automated, developer-centric approach to threat modeling, secure development, and compliance. This, combined with our industry-leading e-Learning offerings, allows us to support our customers in accelerating software time-to-market without sacrificing security.

We’re hiring a Lead Software Architect to lead one of our most important engineering challenges: simplifying a complex monolithic application at the heart of our product ecosystem, while supporting growth across SaaS and on-prem deployments.

Reporting to the VP of Engineering, this is a role for someone with both strategic and technical depth - a pragmatic architect who partners with engineers, has a deep knowledge of building and scaling enterprise software products, and is comfortable owning architectural direction across multiple systems, not just a single codebase. You’ll be a guide, mentor, and catalyst for change as we evolve our platform without unnecessary disruption.

We are open to candidates across Canada/North America. We are a remote-first company with a head-office in Toronto. We don’t mandate team members to come in on a particular schedule, however we encourage team members to come into the office to foster connection with their colleagues on a schedule that works for them personally.

What you’ll do

• Own the architectural vision for Security Compass’ software products, evolving our core application monolith with care while creating paths toward cleaner separation, reuse, and long-term sustainability across the portfolio
• Support cross-application architectural reuse, helping define and deliver functionality from SD Elements into adjacent systems when needed
• Drive a mission-focused backlog for non-functional needs—performance, security, scalability, and operational simplicity—translating them into product-aware conversations and working with business stakeholders to prioritize
• Work closely with senior engineers and tech leads to turn architectural strategy into clear delivery milestones and measurable outcomes
• Lead conversations around platform deployment, ensuring alignment across AWS (EKS), on-prem environments, and our CI/CD tooling
• Build momentum through influence, clarity, and credibility—mentoring and partnering with engineers to move forward together
• Act as a technical voice at the table in planning sessions and stakeholder discussions, helping weigh trade-offs and prioritize what matters
• A well-rounded perspective grounded in hands-on experience building and operating software in production environments, ideally spanning both application development and platform infrastructure

What you’ll need to succeed

• Experience leading architectural direction for complex, real-world systems, especially those balancing SaaS and on-prem delivery
• Deep understanding of monolithic and distributed systems, including service decomposition patterns and experience in significant re-writes of those complex enterprise systems/platforms is a must
• Demonstrated experience leveraging AI in software development or architecture, whether through tooling, process automation, or integrating AI capabilities into real-world systems
• Experience extending or replicating core functionality across multiple applications or systems, while maintaining architectural clarity and minimizing duplication
• Fluency in Python/Django, AWS, Kubernetes, and modern DevOps practices, along with React and Postgres
• Track record of mentoring senior individual contributors, collaborating with product and operational teams, and framing architectural decisions clearly
• Comfort with getting into the details when needed—helping unblock teams, validate approaches, and support delivery

Why Security Compass?

• Meaningful Work. We contribute towards making technology in the world more secure and our vision is one of a world where we can trust technology.
• Trust. It’s important to us that you trust those you work with and are empowered to be yourself. To build this trust and transparency, we encourage open, respectful communication.
• Innovation. We encourage you to explore ideas and test new theories, both in your work and in your individual career development plan.
• Growth. We make your growth and learning a priority by allocating all our employees with a dedicated learning & growth budget. We give our team members tools and support to be the drivers of their careers and encourage knowledge sharing.
• Life-Work Integration. We create an environment where you can integrate your work with life in a way that makes sense for you with our hybrid or remote working model, flexible work hours, and unlimited vacation!
• Fun. We could not have good culture without good fun, and we don’t underestimate its importance. Our casual atmosphere promotes camaraderie, fun and helps bring people together.
• Embracing Diversity, Inclusion and Equity. We speak up for inclusion and celebrate diversity in thought. Our goal is to create a safe, equitable workplace where everyone feels like they belong.

What does the interview process look like?

• Phone Interview You’ll start with a 15–20-minute phone screen with someone from our Recruitment team to learn more about your background and goals for your next role
• Technical Interview You'll be meeting our Director, Engineering and one of our Staff Software Engineer for an in-depth technical interview
• Hiring Manager Interview You’ll meet with the Hiring Manager for a deeper conversation about the role expectations, team dynamics, and how you can make an impact
• Practical Assessment You’ll work through a two-part exercise — one strategic, one technical — giving you the opportunity to showcase your skills and how you approach real-world problems
• Culture-Add Interview – This is a 30-minute virtual meeting with either our Chief People & Culture Officer or CEO to learn how your values align with our CCOAR values of Customer Focus, Collaboration, Ownership, Authenticity and Respect.

This posting is for an existing vacancy. Click here to start imagining your future at Security Compass!

Security Compass is an equal opportunity employer. We are committed to meeting the accessibility needs of all individuals in accordance with the Accessibility for Ontarians with Disabilities Act (AODA) and the Ontario Human Rights Code (OHRC). Should you require any accommodation, please inform hr@securitycompass.com so that an inclusive and barrier free process can be provided for candidates taking part in all aspects of the hiring process. All information provided will be addressed confidentially.