COMPANY DESCRIPTION

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 [https://workleap.com/], our agentic HR platform that helps managers become better leaders, and ShareGate [https://sharegate.com/], the world's leading solution for Microsoft 365 migration and governance. More than 15,000 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.

JOB DESCRIPTION

So, what will your new role look like?

As Head of Technology, your mission is to evolve Workleap’s engineering organization toward a more autonomous, efficient, and AI-enabled model. You will lead the Shared Tech group and help accelerate the organization’s execution by aligning and evolving key teams. The role spans three core functions, Product Ops, Data, and Security & Infrastructure, with a clear mandate: stabilize, clarify priorities, and increase velocity without compromising quality. You will shape the systems, platforms, and practices that enable product teams to deliver faster, with greater autonomy and impact, by leveraging AI and automation.

Responsibilities:

• 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.

What does your future team look like?   

You'll lead the Shared Tech group (~20 people): where we build the standards, the platforms, and the enabling infrastructure that serve both product lines (ShareGate and Workleap HR). You'll partner with the heads of each product line who own the product outcomes, and your mission is to make delivery dramatically faster.

The three pillars of your scope:

• Product Operations: Builder tooling, AI SDLC, observability, analytics, billing and subscription. Turn product activity into decisions and improve developer velocity.
• Data: Single trusted, AI-ready analytics backbone. Shared data models, governance, data science as a shared capability, AI quality foundations.
• Security & Infrastructure: Enterprise-grade trust without killing speed. Security architecture, compliance, incident response, infrastructure operations.

Your role will be to evolve this group from a support function into a true engine of engineering velocity and impact.

What are the next challenges awaiting your team?

Your mandate is clear: transform engineering into a builder organization that can deliver faster without compromising quality or trust. In the next phase, the team will need to:

• Enable more autonomous, end-to-end product delivery with fewer dependencies and handoffs;
• Embed AI and automation throughout the development lifecycle to reduce manual work and accelerate execution;
• Strengthen the engineering systems and platform foundations that increase impact per builder over time;
• Replace manual processes with scalable, automated platform capabilities;
• Reinforce ownership and accountability across teams.

The challenge is both technical and organizational: building systems that scale while changing how teams collaborate, operate, and deliver value. Success means creating an engineering organization that operates as a high-leverage system, where small teams can deliver outsized customer impact at market speed.

QUALIFICATIONS 

• +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 DRIVES US

At Workleap, we build software that sits at the center of how people experience work, every day, at every level.

We move fast. Priorities shift, decisions get made with the information we have, and we iterate. If you thrive on intensity and ambiguity doesn't slow you down, you'll feel right at home. We're builders. We do what it takes to move forward. AI is part of our toolkit. We use it to go faster and decide smarter, not to replace judgment.

If you want real impact and a place where your decisions matter, this is it.

HOW WE HIRE 

Transparency is how we hire — for you and for us.

Your journey starts with a recruiter conversation, followed by a virtual interview with the hiring manager and one additional interviewer. Next, you'll complete a take-home case study and meet potential teammates to discuss and collaborate on your work. If it's a match on both sides, we move to an offer. Some positions follow a slightly different path — your recruiter will walk you through it on the call if that's the case.

In the spirit of transparency: we use AI to support parts of the process, but every hiring decision remains firmly human.

We're committed to making this an inclusive and thoughtful experience for every candidate. We're looking forward to showing you that.

By applying, you confirm you've read and agree to our privacy policy [https://workleap.com/trust-center/privacy].

#LI-Remote