Director, Security & Infrastructure

Workleap is a Montreal-based tech company, founded in 2006. We're builders at heart, we make simple products that actually matter to the people who use them. We have two product lines: The Workleap Agent, our agentic HR platform that helps managers become better leaders, and ShareGate, the world's leading solution for Microsoft 365 migration and governance. More than 20,000 companies worldwide trust us to do exactly that. We're intentional about who joins us. If you're the kind of person who gets excited by a hard problem and wants to help shape what comes next, there's a place for you here.

So, what will your new role look like?

As Director, Security & Infrastructure, your role is to create the conditions for product and engineering teams to move faster with confidence. You will lead the infrastructure, security operations, and governance, risk, and compliance functions across Workleap and ShareGate, ensuring our environment remains reliable, scalable, and secure as the organization evolves. You will play a key role in supporting Workleap’s shift toward a Full-Stack Builder model, where small teams own the full journey from insight to production. This means building a platform and security foundation that reduces friction, strengthens trust, and helps teams ship quickly without compromising reliability, security, or compliance.

Responsibilities:

• Improve platform reliability and scalability so product teams can ship with confidence across Workleap and ShareGate;
• Reduce security and compliance risk through guardrails embedded directly into delivery workflows;
• Increase engineering autonomy by reducing dependency on centralized infrastructure support;
• Increase system resilience and minimize service disruption through stronger observability, incident response, and proactive capacity planning;
• Elevate team impact and organizational leverage by building a high-performing infrastructure and security function;
• Improve executive decision-making with clear, business-relevant visibility into security, compliance, and risk posture.

You will lead a platform-focused team spanning infrastructure, security operations, and GRC, supporting both Workleap and ShareGate. This team is evolving from a traditional support function into a platform enablement team, one that helps product teams move faster by providing reliable, secure, and easy-to-use foundations. Your role is to position this team as a force multiplier for engineering: reducing friction, increasing autonomy, and making security and infrastructure feel invisible to builder teams.

What are the next challenges awaiting your team?   

Your mandate is clear: transform infrastructure and security into silent foundations, robust in the shadows, transparent in everyday use, so that product delivery is smooth and the entire company stands on solid ground.

In the next phase, the team must:

• Enable true self-service so teams can build, deploy, and scale independently;
• Embed security directly into delivery workflows, eliminating manual gates;
• Strengthen platform reliability to support faster and more frequent releases;
• Shift governance from static control to continuous, automated assurance.

Beyond the systems, the real challenge is cultural: turning infrastructure and security into enablers of speed, not constraints. Success means product teams can ship faster with confidence and never have to slow down for infrastructure or security.

• 8+ years of experience across infrastructure and security leadership in technology organizations;
• Experience leading technical teams through transformation in fast-paced, evolving organizations;
• Strong expertise in cloud-native environments such as Azure or GCP;
• Hands-on experience with Kubernetes, infrastructure as code, and platform automation;
• Deep understanding of security frameworks, such as SOC 2, NIST CSF, ISO 27001, and CIS Controls;
• Proven ability to build secure, scalable, high-availability environments for SaaS products;
• Strong ability to communicate risk, priorities, and tradeoffs to executive and board-level stakeholders;
• CISSP, CISM, or equivalent credentials are considered an asset;
• Based in Montreal, or able to travel there a few times per quarter.

We’re a team of curious minds and bold builders, brought together by a shared drive to make work simpler - and better - for everyone. Challenges fuel our creativity, fast-paced environments keep us sharp, and pushing boundaries is just part of how we operate. We believe the best ideas come from experimentation, rapid learning, and even the occasional discomfort - that’s where growth happens.

Since 2006, we’ve been rethinking the way teams work, blending creativity and tech to solve real problems in IT and HR. We move quickly, we learn constantly, and we always keep our customers at the center of what we do. If you're a proactive thinker who takes ownership, loves to collaborate, and isn’t afraid to leap into the unknown - you’ll fit right in.