Team Lead, Design

About Stay
22

Based in Montreal, Stay
22 helps ambitious creators and intent-rich digital platforms turn their existing traffic into incremental revenue, with technology that works quietly in the background.

Today, more than 6,500 creators and platforms rely on Stay
22, with over $1 billion in annual transactions flowing through the platform. Originally built for travel, the company now supports partners across retail, lifestyle, publishing, events, and transport as it expands its monetization infrastructure for the modern creator economy.

At Stay
22, the Team Lead, Design is both a leader and a builder — someone who gets as much energy from growing people as from shaping pixels. This role leads a growing design team of three Product Designers and a UX Researcher, guiding them to deliver intuitive, elegant, and effective experiences across our platform.

You’ll partner closely with the Head of Product to shape where our products — and our Hub ecosystem — are headed, balancing the day-to-day needs of your squads with a real point of view on where design should be in 1-2 years. You're someone who's genuinely excited about AI, and who sees agents and modern tools as a way to multiply your team's craft and speed.

You're also an outward-looking leader who keeps one eye on the competitive landscape at all times, and who's comfortable moving between qualitative insight and quantitative data to make the call.

• Lead, mentor, and grow a team of three Product Designers and a UX Researcher, fostering a culture of ownership, curiosity, and continuous improvement.
• Maintain and evolve Stay
  22's design principles, systems, and best practices, keeping our design system alive, scalable, and genuinely used across squads.
• Lead design work on key product initiatives on your squad from discovery to delivery, partnering closely with Product, Engineering, and Leadership on strategy and execution.
• Think beyond the sprint: help shape the future of our products and the Hub hierarchy, balancing short-term delivery needs with a compelling long-term vision.
• Champion the use of AI tools, skills, and agents across the design workflow, helping the team work smarter and ship faster.
• Bring both qualitative and quantitative data into design decisions, from user research to product analytics, to ground your team's work in evidence.
• Proactively benchmark competitors and stay outward-focused, bringing fresh market and industry perspective back into how we design and prioritize.
• Raise the quality bar for user experience, design craft, and product thinking across the team.

• 10+ years of experience in product design, including 3+ years in a design leadership or Team Lead role.
• Strong product design expertise across UX, UI, interaction design, and information architecture, with proficiency in modern tools.
• Experience designing, maintaining, and scaling design systems, with a genuine interest in continuing to evolve ours.
• A real enthusiasm for AI tools, skills, and agents in the design workflow, and excitement about what they unlock for the team.
• Experience managing or leading designers; experience managing or closely partnering with a UX Researcher is a strong asset.
• Background in the ad, e-commerce, or travel industry is a strong plus.
• Comfort moving fluidly between qualitative and quantitative data to make and defend design decisions.
• A track record of proactively benchmarking competitors and staying outward-focused rather than heads-down internally.
• Strategic thinking that balances short-term execution with a long-term vision for the product and its underlying architecture (including how the Hub evolves over time).
• Strong leadership, coaching, and mentoring abilities, with excellent communication and stakeholder management skills.
• An ownership mindset, comfort navigating ambiguity, and a bias toward action in a fast-moving environment.

We know your time’s valuable, so here’s the quick rundown of what to expect.

• Screening call with our Talent Acquisition Partner (30min)
• Hiring Manager call (45min)
• In-person panel Interview and presentation with cross-functional team members (75-90min)
• Final interview with our CEO (30min)

Prime Montreal

Location:

Work from our vibrant Little Italy HQ with a cafeteria allowance, full gym access, and a rooftop terrace complete with a seasonal basketball/pickleball court & hockey rink.

Comprehensive Benefits:
Health & dental coverage, RRSP matching, fully paid STM pass’, and regular team socials, events, and retreats.

Flexibility That Works:
Flexible schedules, work-from-anywhere opportunities, year-end shutdown, and flex days.

Stay
22 is an equal-opportunity employer.

All qualified applicants are given consideration.

If you have a disability or particular need that requires accommodation, please contact us at