Software Development Manager - ShareGate

Company Description

Workleap is a Montreal-based tech company, founded in 2006. We're builders at heart, making simple products that actually matter to the people who use them. We have two product lines: Workleap, built to make every manager more effective, and ShareGate, the world's leading solution for Microsoft 365 migration and governance. More than 15,000 companies worldwide trust us to do exactly that.

Your Role

Microsoft 365 keeps getting bigger, busier, and harder to keep under control. ShareGate helps more than 100,000 IT pros move, understand, and govern their Microsoft 365 environments with confidence. AI now lets us build faster than ever, so the real question is whether we're building the right things. We're looking for a Software Development Manager to bridge the two: someone who moves fast with every tool available and keeps the team focused on what makes a difference for customers.

Your Impact

• Drive customer value: Ensure what the team ships improves the customer experience and challenge work that doesn't.
• Leverage AI: Build faster, raise quality, and simplify maintenance while keeping squads focused on key priorities.
• Build autonomous squads: Lead squads that fully own their part of the product, from design to production.
• Align roadmap & delivery: Collaborate with Product and Design so delivery speed translates into customer value.
• Raise engineering standards: Coach team members and hire top-tier developers who make the team stronger.

Your Team

Our developers already use AI agents to design, build, test, and maintain the product. The next challenge is making sure that speed turns into more value for customers: better experiences, sharper insights, and problems solved proactively. Under the hood, a data ingestion platform continuously reads Microsoft 365 environments so customers always see what's really going on.

You'll lead 12 developers organized in 3 squads, each owning its part of the product. We're remote-first, with access to our Montreal office.

What You'll Bring

• Experience managing a software team of 5+ developers, including hiring, coaching, direct feedback, and performance management.
• A strong product mindset focused on customer problem-solving.
• Solid knowledge of modern software development practices and architecture to constructively challenge technical decisions.
• Proven track record of improving team workflows using AI and automation.
• Comfort with ambiguity and fast, reversible decision-making.

What the Job Comes With

• Base Salary: $155,000 to $185,000 CAD (Canada-wide scale, adjusted based on local market conditions).
• Annual bonus program + LTIP program (share in long-term growth).
• RRSP matching, family health insurance, telemedicine, and annual wellness budget.
• Flexible vacation policy.
• Remote work with access to the Montreal office.
• Twice-yearly in-person gatherings.
• Claude AI access for everyone.

How We Hire

1. Initial call with a recruiter.
2. Virtual interview with the hiring manager.
3. Take-home case study.
4. Peer discussion meeting with future colleagues.