Senior Product Designer - ShareGate

OpenKrill; United States; On-site; USD 88,000 - 112,000; Full time

Benefits offered by this job

Annual bonus

LTIP

RRSP + health insurance

Wellness budget

Flexible vacation

Remote work + Montreal office

In-person gatherings

Claude access

Job summary

ShareGate is seeking a seasoned designer to own a product area end-to-end, collaborating with product and engineering leads to ship tangible solutions. You’ll design flows where AI does the heavy lifting while users stay in control, turning complex, high-stakes workflows into simple, trustworthy experiences.

You’ll bring 6+ years designing software for businesses, a systems mindset, and the ability to defend design choices with clear rationale.

Qualifications

• 6+ years designing complex software for businesses with shipped work from start to finish.
• Systems-minded designer who plans the end-to-end journey and anticipates next steps.
• Judgment to make hard design decisions and defend them.
• Weekly habit of talking to real customers and letting insights guide direction.
• Defend design rationale to designers, engineers, and executives.
• Fluent with using AI in your workflow and knowing its limits.
• Own the last mile: refine in the real product and push to production.
• Comfort working without a clear brief and learning in the open.

Responsibilities

• Own a product area end-to-end, from framing the problem with your team to shipping the solution.
• Design AI-first flows where the product does the work while users stay in control.
• Explain complex situations clearly so users can act with confidence.
• Put bold bets in front of customers early, measure outcomes, and adapt plans.
• Incorporate AI into your working method and test with customers.

Skills

Complex software design

Systems thinking

AI in workflow

Customer interviews

Design rationale

AI in workflows

Production polish

Cross-functional collaboration

Tools

Claude access

Job description

About ShareGate

ShareGate is the leading Microsoft 365 migration and governance platform, trusted by over 100,000 IT pros for its unmatched simplicity.

It offers the simplest, most reliable, and most affordable way to move business data to Microsoft 365.

Whether migrating from Google Workspace, file shares, Exchange Online, SharePoint On-Premises, or tenant-to-tenant, ShareGate gets the job done, without surprises. From cloud transformation to M&A integration, it keeps things just damn simple.

ShareGate also helps organizations stay in control once their data is migrated. Its powerful governance features let users assess environments, uncover issues, and apply fixes on the spot, so everything stays clean, secure, and optimized. It lays the groundwork for safe Microsoft Copilot deployment within organizations.

ShareGate is developed by Workleap Technologies, a Montréal‑based software company.

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.

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

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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