Director of Legal Affairs

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.

So, what will your new role look like?

As Director of Legal Affairs, you will lead Workleap's legal department and play a critical role in enabling the company's continued growth. Reporting to the CFO, you will be responsible for shaping our legal strategy and operations, supporting commercial scale, and ensuring compliance across multiple jurisdictions. You will be a key partner to business stakeholders, continuing to shift the perception of legal from gatekeeper to enabler. Your work will directly contribute to building organizational resilience and driving smart, strategic decisions.

Responsibilities:

• Lead and mentor the in-house legal team, promoting a collaborative and solution-oriented culture.
• Act as the primary legal advisor to the executive team and cross-functional business leaders.
• Oversee commercial legal operations, including contract negotiation, vendor agreements, and partnership support.
• Provide guidance on data privacy, compliance, and regulatory frameworks across multiple regions.
• Support strategic corporate initiatives, including M&A and corporate governance matters.
• Continuously improve internal legal processes, templates, and knowledge sharing.
• Build strong internal relationships to promote a proactive and business-oriented legal function.

What does your future team look like?   

You'll join a dynamic legal function working closely with multiple departments, from product to sales to finance. The team is evolving to meet the demands of a fast-scaling tech company. You'll report to the CFO and collaborate closely with Workleap's leadership team.

What are the next challenges awaiting your team?  

The legal team is at the heart of several key initiatives: scaling our commercial operations, strengthening privacy and compliance, and supporting strategic growth across new markets. A top priority is positioning the legal team as a proactive, business-savvy partner helping to drive Workleap's mission forward.

• Law degree (LL.B. or J.D.) and active membership in the Barreau du Québec or another Canadian provincial Bar.
• Strong experience in corporate law; 
• 10+ years of progressive legal experience, with at least 5 years in a senior in-house role preferably within a technology or SaaS company;
• Strong ability to go beyond the law to provide pragmatic, business-first advice;
• Autonomous and able to make decisions with confidence;
• Excellent communication skills; able to simplify complex legal matters clearly and concisely;
• Ability to communicate fluently in both French and English, written and spoken;
• Knowledge of privacy laws such as GDPR and other global regulations, and IP considerations, a plus;
• Experience supporting executive teams and corporate strategy.

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.

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

We are looking forward to getting to know you 

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