Senior Product Designer - 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: 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. Job Description So, what will your new role look like? ShareGate Migrate helps IT teams move data, users, and configurations between Microsoft 365 environments during mergers, acquisitions, and restructures. The decisions are high-consequence, the timelines are tight, and the teams running these projects need software that gives them confidence and control — not just visibility into the problem. You'll join a product trio (PM, Tech Lead, Designer) to own the experience end-to-end: framing the problem, shaping the flow, refining the interaction, and owning what actually ships. You'll use AI tools daily to prototype, validate, and explore — and you'll ship AI features into the product that help IT teams plan, assess risk, and make confident decisions. We're looking for a senior designer who combines systems thinking, technical fluency, and high craft standards with a real bias to action. Responsibilities: Own end-to-end design within your trio — from problem framing through shipped interaction — with minimal direction; Ship AI-powered features that materially change how IT teams plan, validate, and execute their most consequential projects. Not concepts. Shipped product; Turn ambiguous, technically complex workflows into experiences that hold up at enterprise scale; Partner with PM and engineering as equals — surface constraints early, hold the experience bar through development, and fix what drifted after release; Validate with prototypes, session recordings, support data, and usage signal — not opinion; Contribute to and evolve the design system: maintain existing patterns and create new ones as the product grows; Own the coherence of the user journey across your surface area, including the seams between your work and adjacent teams'. A typical week? Your weeks blend structured collaboration with focused design time. Here's what that looks like: Review session recordings, support trends, or usage data to proactively identify problems and patterns before they become bigger ones; Prototype multiple directions for a complex flow or edge case, then pressure-test them with your Tech Lead before committing; Present in-progress work at design critique — take the feedback somewhere useful, and push back where you disagree, with reasons; Sync with engineering to validate how your design holds up against real data shapes and technical constraints; Ship something — a refined interaction, a validated prototype, a clearly documented decision — then move to the next challenge. You'll have autonomy, ownership, and a team that values a bias to action. The pace is real, and so is the support. What does your future team look like? A multidisciplinary product, design, and engineering team where designers shape what gets built and why — not just how. Feedback is direct, the bar is high, and craft is non-negotiable. You'll work alongside experienced designers, engineers, and product managers who care deeply about the quality of what ships and how it impacts customers. What are the next challenges awaiting your team? Helping IT teams move business-critical data and access between systems without disruption — even at enterprise scale; AI-native planning and guidance that helps teams anticipate risk before they hit it; Modernizing the core Migrate experience without breaking the trust we've built with the IT community; Evolving the design system to support new patterns, accessibility, and multi-product cohesion across ShareGate. Qualifications Senior-level evidence: shipped enterprise B2B SaaS products, owned outcomes end-to-end, and visibly raised the bar on a team; Experience designing for technical audiences — IT admins, platform tools, infrastructure, or enterprise workflows (required, not a nice-to-have); Shipped AI-powered features in a real product — not prototypes, not explorations, production users; Active AI tooling fluency embedded in your daily workflow (v0, Cursor, Lovable, Claude, or equivalent); Systems thinking: you reason from first principles, anticipate ripple effects, and design for empty, loading, error, and edge states from the start; Clear communicator with strong rationale — you can show three solutions and say exactly why one is better; Microsoft 365 or cloud migration context is a strong asset, not a requirement. Salary range: $120–$145k CAD. 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. Who we are We’re a team of curious minds and bold builders, brought together by a shared drive to make work simpler - and better - for everyone. Challenges fuel our creativity, fast-paced environments keep us sharp, and pushing boundaries is just part of how we operate. We believe the best ideas come from experimentation, rapid learning, and even the occasional discomfort - that’s where growth happens. Since 2006, we’ve been rethinking the way teams work, blending creativity and tech to solve real problems in IT and HR. We move quickly, we learn constantly, and we always keep our customers at the center of what we do. If you're a proactive thinker who takes ownership, loves to collaborate, and isn’t afraid to leap into the unknown - you’ll fit right in. Additional Information At Workleap, we build together, we trust each other, and we support each other in success or failure. You will be able to express yourself, evolve and develop your creativity in an environment that will adapt to your daily life and your needs. We strive to create a healthy and inclusive work environment. This is everyone’s business. Our Candidate Experience Flow at Workleap: Phone Screen - Virtual Interview using Microsoft Teams - Work Sample - Job Offer As a tech-forward company, we leverage AI tools to enhance our recruitment process, while ensuring all hiring decisions remain human-led. We are looking forward to getting to know you! By applying to this job, you are confirming that you have read and agree to the terms of our privacy policy . #LI-Remote