Senior Product Designer - ShareGate

Workleap Inc.; United States; Hybrid; USD 88,000 - 113,000; Full time

Benefits offered by this job

Annual bonus

LTIP

Health insurance

Remote work

Office access Montreal

Wellness budget

Claude access

Job summary

Workleap Inc. is seeking a senior designer to own a product area end-to-end, shaping problems with the team and delivering solutions customers actually use.

You will design AI-first flows that automate real work while keeping customers in control, and translate complex scenarios into clear, actionable insights. You’ll partner with product and engineering leads, work across two Microsoft 365 security/organization tracks, and move fast in a culture that values craft, ownership, and rapid feedback.

Qualifications

• 6+ years of designing complex software for businesses.
• Ability to design the full journey, not just one screen.
• Judgment to make design decisions that are hard to reverse.
• Regularly talk to real customers and incorporate feedback.
• Ability to defend design rationale aloud to diverse stakeholders.
• fluency using AI in workflows with appropriate boundaries.

Responsibilities

• 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 outcomes, adjust plans accordingly.
• Bring AI into your workflow and testable iterations quickly reach customers.
• Raise the bar through critique and clear thinking that guides the team when you’re not in the room.

Skills

Design experience

Systems thinking

Decision making

Customer interviews

Rationale defense

AI in workflow

Ship to production

Ambiguity handling

IT/Security design

Job description

Company Description

The company 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 company Agent, our newest solution 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

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?

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 the company'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 the company, 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

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.