Workleap En

Your role

Workleap's engineering organization is at an inflection point. We have two ambitious product lines, teams that ship, and a real window to change how we build. What's needed now is someone who can move engineering from a support function to a true velocity engine - more autonomous, more AI-enabled, and capable of delivering end-to-end value without the dependencies that slow everyone down. As Head of Technology, reporting directly to the CPTO & Co-Founder, you'll lead the Shared Tech group (~20 people), spanning Product Ops, Data, and Security & Infrastructure - the foundation on which both product lines run. Your mandate: stabilize, clarify, and accelerate.

Your impact:

• Increase engineering velocity and impact by enabling teams to ship end-to-end value with minimal dependencies;
• Improve delivery performance through stronger deployment frequency, shorter lead times, and sustained production reliability;
• Reduce organizational friction by increasing team autonomy, simplifying workflows, and clarifying ownership;
• Accelerate delivery cycles and reduce manual effort through AI and automation embedded across development workflows;
• Increase the leverage of product teams through scalable platform capabilities across Product Operations, Data, and Security & Infrastructure;
• Strengthen accountability by aligning teams around production outcomes, customer impact, and end-to-end ownership;
• Elevate organizational performance by building strong technical leadership and high-performing teams.

Your team

Over the next 6 to 12 months, your mandate is clear: transform engineering into a faster, more autonomous, and more reliable delivery engine. Concretely, that means enabling end-to-end delivery with fewer dependencies, embedding AI and automation across the full development lifecycle, strengthening engineering systems and platform foundations to durably increase impact per builder, and reinforcing ownership and accountability across teams.

The challenge is as much organizational as it is technical - building systems that scale while changing how teams collaborate and deliver value. You'll take charge of the Shared Tech group (~20 people), where we build the standards, platforms, and enabling infrastructure that serve both product lines.

The team spans three pillars: Product Ops (builder tooling, AI SDLC, observability, analytics, billing), Data (single trusted AI-ready analytics backbone, governance, shared data science capability, AI quality foundations), and Security & Infrastructure (security architecture, compliance, incident response, infrastructure operations). You'll work in partnership with the heads of each product line - they own the product outcomes, your mission is to make delivery dramatically faster.

What you'll bring

• +8 years of experience in engineering leadership within a scaling or large-scale SaaS environment;
• Hands-on experience in transformation contexts, with a focus on improving team velocity, efficiency, and overall impact;
• Strong technical credibility with a hands-on mindset: ability to go deep, understand systems, and contribute to technical decisions;
• Experience managing and developing leaders within engineering organizations of approximately 20-30 people;
• Strong ability to influence in matrix environments and quickly build credibility with senior stakeholders;
• Proven ability to improve execution while maintaining high standards of quality, reliability, and judgment;
• Sound judgment to navigate trade-offs between speed, quality, security, and innovation;
• Strong interest in modern engineering practices, particularly in AI-influenced development environments;
• Experience with the Microsoft / .NET ecosystem, or strong ability to ramp up quickly;
• Good understanding of French (written and spoken) required;
• Based in Montreal or able to travel regularly.

What the job comes with

• Annual bonus program.
• LTIP program, share in Workleap's long-term growth.
• RRSP + Family health insurance + telemedicine + annual wellness budget.
• Flexible vacation policy.
• Remote work, with access to our Montreal office.
• In-person gathering twice a year.
• Claude access, for everyone.