Senior Product Manager, AI-Driven Prototyping & Roadmaps

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Product Management Regular Full-Time CA

30+ days ago Requisition

Salary Range: CA$ To CA$ Annually

Role Overview:

Win Zip is one of the world’s most recognized software brands, used by millions of people, businesses, and governments worldwide to manage, encrypt, compress, and share files.

We are transforming the Win Zip portfolio, and we are hiring a Senior Product Manager in Canada to help lead that shift.

You will own product areas end-to-end: roadmap, execution, and results. This is an AI-fluent role. AI and agentic workflows are your primary way of working, not a side interest: you will use them to inform strategy, pressure-test roadmap decisions, run discovery, and build working prototypes yourself, then codify what works so the team can repeat it, on a faster cycle than traditional product management allows.

You will report to the Senior Director of Product Management and work daily with Engineering, UX Design, Product Marketing, and Sales.

One thing to know before you apply: this is not the role for you if AI is something you reach for occasionally to draft a document. We work through agents daily, and we will ask to see what you have built. Beyond that, we want a partner who challenges our thinking, proposing alternatives when we disagree, and moving forward with what customers need without waiting to be asked.

If you want to own a roadmap, from research to execution, this is the right role for you.

What success looks like in your first 12 months:

• You have put several working prototypes in front of real customers, not just in front of us.
• You have taken at least one 0-to-1 product from problem to launch.
• The AI workflows you built are being used by the rest of the product team.
• This is a fast-paced environment. You will be measured on what shipped, not on what was planned.

Responsibilities:

• Be the customer’s voice: consolidate customer feedback, understand their pain points, and turn qualitative and quantitative signals into decisions, and decisions into shipped product.
• Own the roadmap and outcomes for products within the Win Zip portfolio, from discovery through launch and iteration.
• Help shape the portfolio transformation: question existing workflows, rethink them from first principles with AI as a design assumption rather than an add-on, and design the product around where customers are going.
• Make AI the default in planning and execution: use AI and agentic tools daily for research, analysis, prototyping, writing, and decision support, build repeatable AI workflows the team can adopt, and raise the bar for how the whole team works.
• Write crisp PRDs, EPICS/User Stories, and business cases that Engineering and Product Marketing can act on.
• Partner with Engineering on technical trade-offs and sequencing, and with Product Marketing on positioning, pricing, and launch.
• Contribute to the business side of the product: packaging, pricing, and monetization.
• Communicate progress, risks, and disagreements openly to stakeholders, up to the executive level.

Required qualifications:

• 5+ years of product management experience, including owning a commercial software product or major product area end to end.
• Daily, hands-on use of agentic AI tools, not a chat assistant alone. You run agents, build your own workflows and tooling, and have shipped work that would not have been possible without them. Come ready to share concrete examples of what you have built, automated, or shipped with it, and how AI changed the way you made product decisions.
• A track record of shipping: products or features you took from problem to launch, and what happened after.
• Strong…