[All remote jobs](https://jobicy.com/jobs.md)[![Workleap logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/b84329e1-221.png)](https://jobicy.com/company/workleap.md)[Workleap](https://jobicy.com/company/workleap.md) # Senior Product Designer – ShareGate Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/workleap.md)ShareRemote from[Canada](https://jobicy.com/job-region/canada.md)SalaryCAD 125k–160k / yrDepartment[Web, UI & UX Design](https://jobicy.com/categories/web-app-design.md)EmploymentFull TimeExperienceSeniorPublished16 Oct 2026Apply before15 Nov 2026Listing views46Application actions4Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. AI Summary ## The role, at a glance. Workleap is hiring a Senior Product Designer to own complex ShareGate product areas serving IT professionals managing Microsoft 365 migration, governance, and security workflows. The designer will lead discovery through launch, simplify high-stakes enterprise workflows, test bold concepts with customers, and monitor outcomes after release. The role requires strong systems thinking, direct customer research, polished production execution, and close partnership with product and engineering leads. AI-first product design and practical use of AI tools in the design workflow are core expectations. This remote Canada role offers a base salary range of CAD 125,000 to CAD 160,000 plus bonus and long-term incentive programs. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a senior, end-to-end role in a complex enterprise domain where design decisions can affect high-stakes migration, governance, and security workflows. Success requires independent judgment, rapid experimentation, customer-facing research, and the ability to align designers, engineers, product leaders, and executives. ## Salary analysis Estimated compensation compared with the broader CA market for similar roles. Estimated job median (per year)Market rateC$142,500CA market range (per year)C$120k–C$170k0C$187.00k AI insightThe yearly pay period is inferred from the job context; it was not explicitly stated by the employer. The employer discloses a base salary of CAD 125,000–160,000 per year; the yearly cadence is inferred from the senior full-time Canadian role context because the posting does not explicitly state a pay period. The midpoint is CAD 142,500 annually. A reasonable estimated Canadian market range for a senior enterprise product designer is CAD 120,000–170,000 per year. ## Core skills Skills and capabilities most closely associated with this opportunity. [Product design](https://jobicy.com/jobs?search_keywords=Product%20design.md)[UX design](https://jobicy.com/jobs?search_keywords=UX%20design.md)[Enterprise software](https://jobicy.com/jobs?search_keywords=Enterprise%20software.md)[Design systems](https://jobicy.com/jobs?search_keywords=Design%20systems.md)[User research](https://jobicy.com/jobs?search_keywords=User%20research.md)[Usability testing](https://jobicy.com/jobs?search_keywords=Usability%20testing.md)[Interaction design](https://jobicy.com/jobs?search_keywords=Interaction%20design.md)[Information architecture](https://jobicy.com/jobs?search_keywords=Information%20architecture.md)[Prototyping](https://jobicy.com/jobs?search_keywords=Prototyping.md)[AI product design](https://jobicy.com/jobs?search_keywords=AI%20product%20design.md)[Systems thinking](https://jobicy.com/jobs?search_keywords=Systems%20thinking.md)[Stakeholder management](https://jobicy.com/jobs?search_keywords=Stakeholder%20management.md)[Design critique](https://jobicy.com/jobs?search_keywords=Design%20critique.md)[Cross-functional collaboration](https://jobicy.com/jobs?search_keywords=Cross-functional%20collaboration.md)[Microsoft 365](https://jobicy.com/jobs?search_keywords=Microsoft%20365.md) Sample interview questionsTell us about a complex B2B workflow you redesigned from discovery through launch.I would explain the customer problem, the research methods used, the key workflow risks, and how I partnered with product and engineering. I would show how the shipped solution improved usability or business outcomes and describe what I changed after observing real usage. How do you design for expert users when a wrong action can be costly or difficult to reverse? I make system state, consequences, and recovery options explicit. I use progressive disclosure for complexity, provide clear confirmations for irreversible actions, and validate designs with representative expert users before release. How do you decide whether an AI-powered feature is genuinely useful rather than simply novel? I start with a specific customer task where AI can reduce effort or improve understanding while preserving user control. I prototype the experience early, define measurable success criteria, test failure states and trust signals, and iterate based on observed behavior. Describe a time customer research caused you to change direction on a design decision. I would share a case where customer behavior or feedback challenged an initial assumption. I would explain how I synthesized the evidence, communicated the trade-off to stakeholders, adjusted the design, and measured the result after launch. How do you maintain quality while working quickly in an ambiguous environment? I clarify the highest-risk assumptions, establish a decision-making framework, and ship the smallest testable version that preserves the core experience. I keep work visible through frequent critique and use feedback and outcomes to refine rather than waiting for perfect certainty. Opportunity details ## About this 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: [Workleap Agent](https://workleap.com/), our newest solution built to make every manager more effective, and [ShareGate](https://sharegate.com/), 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 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. And once it’s there it sprawls faster than anyone can track, with people sharing things they shouldn’t and no clear view of what’s actually going on. ShareGate is what IT professionals use to do both jobs. Taking something this complex and this consequential and making it feel simple and trustworthy is what we’re here to do. Your impact: * 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, through the standards you hold, and by making your thinking clear enough that the team can carry a decision without you in the room. ### Your team You’ll join our design team at ShareGate and partner with a product lead and an engineering lead on every project you own, from first idea to launch. We’re hiring across two sides of the product right now: one focused on moving companies into and around Microsoft 365, one focused on keeping it secure and organized once they’re there. Both are big, high-stakes problems, and we’ll work out together which one fits you best. We’re builders. We care a lot about craft and taste, we expect people to own their work rather than wait to be handed it, and we’d rather take a big swing on what’s genuinely best for customers than ship the safe version. AI is part of how we work every day; it helps us move faster and try more ideas, not think less. Work gets shared early and often, feedback is direct, and decisions get made quickly and revisited just as quickly when we learn something new. The people we design for run IT at their companies. They’re experts who get the call when something breaks. Our job is to earn their trust and make complex, high-stakes workflows feel simple. ### 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. Most of this sounds like you? Apply. ### What the job comes with * Base salary: $125 000 – $160 000. 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 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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