H
HeyAutofill

Staff/Senior Product Designer

Toronto, Canada Posted 2026-06-04
Type
Full-time
Experience
6+ yr
Source
Ashby
STAFF/SENIOR PRODUCT DESIGNER

Location: Toronto, San Francisco
Work model: Hybrid (2 days/week in office)
Reports to: Head of Product

WHY YOU'LL LOVE THIS

- Trailblazing: We’re building a product that hasn’t existed before. Real, production-grade AI agents you can actually see think and work in real time. It’s ambiguous, occasionally scary, and incredibly rewarding.

- Collaboration: We work shoulder-to-shoulder with PMs and engineers who care deeply about craft. No design-by-handoff. Real problem solving, together.

- We have fun: We take the work seriously, not ourselves. If belly laughs in standup matter to you, you’ll fit right in.

- Impact: Your work helps hundreds of thousands of patients get care insanely faster. This isn’t abstract UX. It’s real-world impact at scale.

- Ownership: You’ll own projects end-to-end and shape the design system and product direction, not just push pixels.

- No decks: We never touch slides to show our work internally.

ABOUT MAGICAL THE COMPANY

- Magical is an AI agentic automation platform bringing production-grade AI to healthcare, one of the most complex and operationally broken industries in the world.

- We build AI agents that automate repetitive, high-stakes workflows. Unlike most AI products, our systems actually run in production, at scale, with real customers relying on them every day.

- We’re backed by Greylock, Coatue, and Lightspeed, with $41M raised. Our founder is a second-time founder who previously sold his company to LinkedIn.

ABOUT THE ROLE

This role is for a designer who is fully self-sufficient. You’ll be one of 3 designers on the team and will be expected to run projects end-to-end with minimal direction, from problem framing through execution and delivery.

If you’re looking for heavy coaching, tight briefs, or constant design reviews, this role is probably not a fit. If you enjoy owning complex problems, shaping direction, and shipping high-quality work independently, it likely is.

WHAT YOU’LL DO

- Own design projects end-to-end: discovery, problem framing, solution design, and delivery

- Translate ambiguous product and business goals into clear, user-centered solutions

- Lead or run lightweight user research to inform decisions when needed

- Partner closely with product and engineering to ship thoughtful, scalable solutions

- Design high-craft interfaces for complex, technical, enterprise workflows

- Contribute to and evolve our design system

- Balance multiple workstreams and move projects forward without constant oversight

- Use prototyping to explore ideas, align stakeholders, and de-risk solutions

- Help shape the longer-term product direction, not just execute what’s handed to you

WHAT YOU BRING

- 6+ years of experience as a product designer

- A portfolio demonstrating end-to-end ownership of real, shipped products

- Experience designing enterprise or complex B2B products

- Strong product thinking and comfort operating in high ambiguity

- Ability to understand technical concepts and collaborate deeply with engineers

- High bar for visual design, interaction design, and craft

- Experience contributing to or maintaining a design system

- Proven ability to work independently and manage competing priorities

NICE TO HAVE

- Healthcare or regulated-industry experience

- Early-stage or fast-growing startup experience

- Experience designing developer tools or internal tools

- Strong prototyping skills

- Prior use of AI tools to accelerate or enhance design workflows

WHY THIS ROLE

- High ownership, high trust, and real impact

- Work on genuinely hard problems with real-world consequences

- Small team, low process overhead, high agency

- Competitive compensation, equity, and benefits

- Adventure: epic team offsites (Past trips: Iceland, Lisbon, Dominican Republic, Mexico)

- Rest: Unlimited PTO, because burnout is not in our vocabulary.

- Wellness: annual wellness credit to keep you healthy and happy.

- Productivity stipend: to supercharge your work setup.
HeyAutofill is hiring for the staff/senior product designer role. NewJob aggregates active openings directly from HeyAutofill's applicant tracking system, so this listing is current. More jobs at HeyAutofill →
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