Design Strategist, Stealth Start-Up Company

About the Organization: 

We’re a Seed-Funded Startup developing an AI-native platform that converts messy human business intent into production-ready software. We tackle the gaps where current tools fall short in real-world enterprise environments, moving quickly to turn ideas into working systems.

About the Role: 

You'll help shape a 0→1 product alongside a small, deeply experienced team — influencing foundational decisions while nothing is set in stone. You'll be supported by colleagues with decades of experience in product, design, AI, and enterprise software. The work happens in a bright, calm Montreal office designed for both heads-down flow and creative collaboration, as part of an intentionally diverse and inclusive team.

Key Responsibilities:

• Partner tightly with engineering, ML, product, and design to define how users collaborate in — and with — the product
• Facilitate shared understanding across engineering, ML, product, and design — be the person in the room who makes everyone else think better
• Frame problems before solving them; turn ambiguous signals into clear problem statements and decision frameworks
• Lead and synthesize research from scattered sources: users, transcripts, Slack threads, docs, wherever insight lives
• Prototype to learn — and to ship: validate novel interactions across the requirements → generation → verification loop (e.g., conflict resolution, validation, evaluation) to inform direction and de-risk bets
• Shape the interaction model for how humans and AI collaborate in the product (make the hard feel easy)
• Design experiences that help users and the team see the value of the product quickly and clearly

Qualifications: 

• 8+ years of experience designing software products, ideally in complex or technical B2B domains
• Strong facilitation skills — you design and run workshops, alignment sessions, and collaborative exercises that unlock teams
• Proven research and synthesis ability — you find patterns in chaos and turn them into clarity
• Systems thinker who sees flows, dependencies, and tradeoffs, not just screens
• Exceptional communicator across modes: written, verbal, and visual
• Comfortable with AI as a design material — you have evolving workflows and a clear point of view on where it helps and where it fails
• 0-to-1 energy, comfortable from early problem framing through final direction
• Strong product thinking — you ask "why" as often as "how"

Nice to Have:

• Visual design sensibility, interaction design craft, or service design background
• Experience designing developer tools, AI systems, or collaborative/workflow-heavy products; startup or early-team experience a plus

At AppDirect, we believe that innovation thrives in an environment that houses diversity of excellence, experience and thought. We respect each AppDirector as their own fingerprint; unique with no one alike. We foster an environment of inclusion without regard to race, religion, age, sexual orientation, or gender identity enabling AppDirectors to embrace their uniqueness to do their best work. As such, we strongly encourage applications from Indigenous peoples, racialized people, people with disabilities, people from gender and sexually diverse communities, and/or people with intersectional identities.

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