Software Development Manager - ShareGate

Workleap; Montreal; Hybrid; CAD 155,000 - 185,000; Full time

Benefits offered by this job

LTIP program

Health insurance

Remote work with Montreal office

Flexible vacation policy

In-person gatherings twice a year

Job summary

Workleap seeks a Software Development Manager for ShareGate to bridge AI-driven delivery and customer value across multiple squads. You will lead 12 developers in 3 squads, partner with Product and Design, and drive speed without sacrificing quality.

You will mentor engineers, raise engineering standards, hire great talent, and ensure the roadmap aligns with customer impact. This remote-first role offers Montreal office access and biannual in-person gatherings.

Qualifications

• Experience leading a software team of 5+ developers, from hiring to coaching.
• Strong product mindset focusing on customer problems and value.
• Solid knowledge of modern software development practices and architecture.
• Proven track record improving AI/automation usage in development.
• Comfort with ambiguity and fast, reversible decision making.

Responsibilities

• Drive customer value by ensuring what the team ships improves experience.
• Use AI to build faster, improve quality, and simplify maintenance.
• Build squads that own their product areas end to end.
• Collaborate with Product and Design to keep roadmaps aligned with customer value.
• Elevate engineering practices and mentor developers to strengthen the team.

Skills

Team leadership

Product mindset

Software architecture

AI/automation

Decision making under ambiguity

Job description

Software Development Manager - ShareGate

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: 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. 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.

Your role

Microsoft 365 is where work happens. It 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 by making sure what the team ships improves the customer experience, and challenge work that doesn't.
• Use AI to build faster, raise the quality of what we deliver and simplify maintenance, while keeping every squad focused on the right priorities.
• Build squads that fully own their part of the product, from design to production.
• Keep the roadmap ahead of the team by working with Product and Design, so delivery speed turns into customer value.
• Raise the bar on engineering practices and on the people behind them, from coaching to hiring developers who make the team stronger.

Your team

AI is changing how we build software. Our developers already use agents to design, build, test and maintain the product, and we ship faster than ever. The next challenge isn't going faster. It's making sure that speed turns into more value for customers: better experiences, sharper insights and problems solved before they become problems. 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 work closely with Product and Design, decide fast and fix course even faster. We're remote-first, with access to our Montreal office.

What you'll bring

• Experience managing a software team of 5+ developers, from hiring to coaching, with the managerial courage to have the hard performance conversations, give direct feedback and keep standards high so the people around you grow;
• A strong product mindset: you start from the customer problem and you're comfortable saying no to work that doesn't solve it;
• Solid knowledge of modern software development practices and architecture, enough to challenge technical decisions;
• A track record of improving how a team works with AI and automation, and measuring the impact;
• Comfort with ambiguity and with making fast, reversible decisions.

Most of this sounds like you?

What the job comes with

• Base salary: $155 000 to $185 000. This range reflects our Canada-wide compensation scale. Final offers may be adjusted based on the candidate's region to align with local market conditions.
• 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 gatherings twice a year.
• Claude access, for everyone.

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 as much as for us.

Here's how it works: a first call with a recruiter, then a virtual interview with the hiring manager. You'll then complete a take-home case study, followed by a meet with future colleagues to discuss it together. Depending on the role, the process may vary slightly — your recruiter will walk you through it on your first call.

We use AI to support certain steps of the process, but every hiring decision remains human.

We can't wait to meet you.

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