Senior Product Designer (AI-First Flows) at ShareGate

Your Role

Almost every company now runs on Microsoft 365, and almost nobody has it fully under control. Work has to be moved into it and around it, through mergers, acquisitions, and reorganizations that touch millions of files and can’t afford to lose a single one. ShareGate is what IT professionals use to manage these complex and consequential tasks. Your impact will include:

• Own a whole product area end-to-end, from framing the problem with your team to shipping the solution customers actually use, and monitoring for learnings after.
• Design AI-first flows where the product does the real work for customers while they stay fully in control.
• Turn genuinely complicated situations into something a busy person can understand at a glance and feel confident acting on.
• Put bold bets in front of real customers early, measure what happens, and let the result change the plan, including when it proves you wrong.
• Bring AI into your own way of working so you can go from a question to something real and testable in days, and put it in front of customers while it’s still rough.
• Raise the bar for everyone around you through critique, standards, and making your thinking clear enough that the team can carry a decision without you.

Your Team

You’ll join ShareGate’s design team and partner with a product lead and an engineering lead on every project you own, from first idea to launch. ShareGate focuses on two main areas: migrating companies into and around Microsoft 365, and keeping it secure and organized once they’re there. Both areas are big, high-stakes problems.

ShareGate values builders who care about craft and taste, expect ownership of work, and prioritize genuine customer benefit over safe versions. AI is integrated into daily workflows to accelerate progress and experimentation. Work is shared early, feedback is direct, and decisions are made quickly and revisited as needed.

The people you design for are IT experts who handle critical issues. Your job is to earn their trust and simplify complex, high-stakes workflows.

What You’ll Bring

• 6+ years designing complex software for businesses, with shipped work you owned from the first question to the last detail.
• A systems mind: you design the whole journey and think about what happens next, not one screen at a time.
• The judgment to make design decisions that are hard to take back: what people see first, what they confirm, what they can reverse.
• A weekly habit of talking to real customers, and the discipline to let what they actually do change your direction.
• Design rationale you can defend out loud to designers, engineers, and executives alike: the problem, the options you turned down, the trade-off you made.
• Real fluency using AI in your own workflow, with the judgment to know where it helps and where it gets in the way.
• The drive to take your work the last mile yourself: refining and polishing in the real product and pushing those changes straight to production.
• Comfort working without a clear brief: you name the assumption, pick a direction, and learn in the open.
• Bonus: experience designing for IT, security, data, or any audience where the user is an expert and a wrong move is expensive.

What the Job Comes With

• Base salary: $125,000 - $160,000 (Canada-wide compensation scale, adjusted based on region).
• 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 the Montreal office.
• In-person gatherings twice a year.
• Claude access for everyone.