Senior E2E Product Designer

Zen Educate•Chicago, IL

About The Position

Zen Educate is seeking a Senior Product Designer to help evolve design into an end-to-end, product-building discipline. The role spans problem framing, discovery, research, flows, prototypes, and shipped product, with an emphasis on understanding users, owning how solutions work, reducing handoffs, and contributing to implementation. The designer will work on complex challenges across Zen’s UK and growing US platform, which supports educators finding work, schools managing staffing needs, and internal teams matching supply and demand. The position covers the full product lifecycle. The designer will learn from educators, school staff, internal teams, data, and product usage; synthesize findings; shape and validate problems and solutions; and iterate through prototypes, conversations, experiments, and real-world feedback. They will collaborate closely with product managers and engineers, and may help shape or write production code using tools such as Claude. The role also includes mentoring designers, sharing insights across the team, and helping shape Zen’s evolving design practice and design system. Zen describes its working style as lean, iterative, collaborative, and focused on shipping and learning. The design team is small, with high ownership and low bureaucracy. The role is Chicago-based and involves collaboration with teams on the West Coast and in Europe. Compensation is listed at $100,000–$130,000 per year, with equity compensation and other benefits.

Nice To Haves

  • Motivation to take ideas beyond design and into real, shipped product experiences.
  • Interest in prototyping, technical fluency, and product building.
  • Ability to explore solutions through flows, prototypes, or lightweight builds, sometimes beyond or instead of Figma.
  • Experience using research synthesis tools such as Dovetail and modern tools such as Claude; the posting presents these as examples rather than explicit requirements.
  • Experience shaping or writing production code is relevant, but the posting states that being an engineer is not necessary.

Responsibilities

  • Own problems end-to-end, from discovery through to shipped product.
  • Design simple, scalable, high-quality flows, systems, and interfaces.
  • Build a deep understanding of educators, schools, and internal teams and how they work day to day.
  • Contribute to ongoing research through interviews, observation, data, and real product usage.
  • Use insights to shape problems, validate direction, and inform what gets built.
  • Create fast feedback loops by testing ideas early through prototypes, conversations, and live experiments.
  • Prototype and validate ideas quickly, including with AI-assisted tools.
  • Explore interaction, logic, and behavior in real environments beyond static design.
  • Collaborate closely with engineers and product managers, increasingly contributing directly to implementation.
  • Balance speed and quality, shipping early and iterating often.
  • Synthesize and share learning to build shared understanding across the team.
  • Mentor other designers and help raise the bar across the team.
  • Help shape how design works at Zen as the discipline evolves.
  • Collaborate across the product lifecycle, from customer insight through prototypes and shipped product to continued learning.
  • Help shape Zen’s evolving design system and product-building practices.

Benefits

  • Equity compensation
  • 20 paid vacation days
  • 10 paid company holidays
  • Comprehensive medical insurance
  • Dental insurance
  • Vision insurance
  • 401(k) retirement plan with no match (not offered in Canada)
  • Sick leave
  • Paid biweekly
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