About the role
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, our agentic HR platform that helps managers become better leaders, 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
You are a hands-on engineering leader who builds great teams and ships great software. As Software Development Manager, you'll build a new team from the ground up focused on modernizing ShareGate's architecture: setting the technical direction, staying close to the code, and earning the trust of your engineers. This is not a purely people-management role — we expect you to lead from the front.
Your impact:
- Build and shape a new team from the ground up, hiring, onboarding, and developing the engineers who will own modernization work;
- Define and drive the technical direction for re-architecting and modernizing ShareGate's platform, staying hands-on across code, design, and quality;
- Raise engineering excellence across testing, security, observability, reliability, and performance, while optimizing delivery flow through CI/CD, automation, and tooling standards;
- Manage technical debt pragmatically by setting clear expectations and communicating trade-offs transparently with stakeholders;
- Grow team members through technical challenges, 1:1s, performance reviews, and a culture of continuous learning and knowledge sharing;
- Partner closely with Product and Design to frame, scope, and deliver high-value solutions while anticipating risks, and contribute to departmental strategic planning.
Your team
a) The team's mandate is modernization: tackling the architectural work that sets ShareGate up for the next chapter of its growth — legacy migration, re-architecture, and meaningful technical debt reduction at scale.
b) You'll be building this team from scratch, which means you'll have a direct hand in shaping its culture, technical standards, and ways of working from day one. You'll also be part of a broader engineering leadership group, collaborating on shared challenges and departmental goals.
What you'll bring
- 3+ years as a Software Development Manager, with a strong background as a software developer;
- Bachelor's degree in computer science or a related field, or equivalent experience (bonus: a background in leadership or management training);
- Proven experience leading modernization efforts, including legacy migration, re-architecture, or meaningful technical debt reduction at scale;
- Deep engineering fundamentals: able to set standards, review work credibly, and raise the bar across a team;
- Experience building teams, not just managing them, hiring, onboarding, and developing engineers from the ground up;
- A track record of developing engineers, influencing peers and directors, and collaborating effectively with Product and Design;
- Comfortable with Agile, whether Scrum, Kanban, or Lean, and pragmatic about how you apply it.
Most of this sounds like you? Apply.
What the job comes with
- Base salary: $145,000 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.
- Annual bonus program.
- 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 gathering 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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