Product Manager

We're looking for a Product Manager with a design background who can own a problem from the first conversation with a user through a finished product experience.

Willow currently has four full-time team members: our CEO, Chief Product and Technology Officer, Chief Academic Officer, and this role, alongside a small number of part-time and contract contributors. You will make up the product team alongside our CPTO and work closely with our CAO, who leads curriculum and customer success. There are very few layers between understanding a problem, making a decision, and building something better.

We're looking for a Product Manager with a design background who can own a problem from the first conversation with a user through a finished product experience.

The core of the job is understanding users, identifying the right problems to solve, developing and testing solutions, and designing the experience that gets built.

This is not a traditional PM role where you write requirements and hand them to a designer. You will be responsible for the design work yourself and have full responsibility for the overall UI/UX and aesthetic quality of Willow.

• Conduct research with students, educators, counselors, and school leaders.
• Identify opportunities to improve existing experiences and build new ones.
• Turn ambiguous problems into clear product solutions.
• Explore, prototype, and test multiple approaches with real users.
• Design polished, production-ready product experiences.
• Make decisions about workflows, interaction patterns, information architecture, hierarchy, and usability.
• Run product-based experiments to identify opportunities and strengthen outcomes.
• Work closely with engineering from early exploration through implementation.
• Maintain and improve the consistency, usability, and visual quality of Willow across the product.

AI is core to how we work at Willow.

You will be expected to use AI every day to research problems, explore ideas, analyze feedback, design solutions, and build coded prototypes.

We believe product ideas should be experienced, not just described in documents or static mockups. You should be comfortable using modern AI development tools to turn ideas into working prototypes that users and teammates can interact with.

You do not need to be a software engineer, but working and coding with AI is a requirement for this role.

You will have a lot of autonomy here. You will also have a lot of responsibility.

We care far more about the quality and impact of your work than whether you were online for a particular number of hours. This is not a clock-in, clock-out role where completing assigned tasks means the work is done.

If you own something, you own the outcome, and usually the process to drive it.

We expect you to notice when something is not good enough, figure out why, and keep working the problem until it is. In return, you will have substantial freedom to make decisions, challenge assumptions, and shape the product.

You are exceptional at:

• User research and customer discovery
• Product thinking and problem definition
• UX and interaction design
• Prototyping and usability testing
• Turning complex workflows into simple experiences
• Creating polished product interfaces
• Making good product decisions with incomplete information
• Working directly with engineers
• Taking a product from an ambiguous problem through a shipped solution

We are not looking for a PM who creates rough concepts and expects a designer to take over. You should have a strong design eye and be comfortable owning the quality of the experience yourself.

You should also be comfortable setting your own direction, making big decisions without waiting for permission, and operating in an environment…