Head of Technology, Transformation Full-Stack Builder

Company Description

Workleap is a Montreal-based tech company on a mission to make work simpler.

Since 2006, we’ve been building game-changing products that tackle HR and IT’s biggest challenges.

Workleap operates two distinct product lines:

• The Workleap Platform , an AI-powered HR solution designed to drive team performance and boost employee engagement.


• ShareGate , the leading Microsoft 365 migration and governance solution, trusted by IT professionals worldwide for its unmatched simplicity.

Today, more than 20,000 companies rely on Workleap products to grow, lead, and operate with confidence.

We’re builders at heart, with a clear purpose: to craft the simplest products that deliver exceptional value for our customers. Period.

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;


• Based in Montreal or able to travel regularly.

 

Who we are

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.

Additional Information

At Workleap, we build together, we trust each other, and we support each other in success or failure. You will be able to express yourself, evolve and develop your creativity in an environment that will adapt to your daily life and your needs.

We strive to create a healthy and inclusive work environment. This is everyone’s business. 

Our Candidate Experience Flow at Workleap: 
Phone Screen - Virtual Interview using Microsoft Teams - Work Sample - Job Offer

As a tech-forward company, we leverage AI tools to enhance our recruitment process, while ensuring all hiring decisions remain human-led.

We are looking forward to getting to know you! 

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