Principal Product Designer, LearnWith.AI (Remote) - $200,000/year USD

Crossover

fulltime

Design, Product Management, and Strategy/Planning

5+ years

About the role

You'll be joining a proven educational model that has already delivered measurable results at Alpha School. LearnWithAI powers the platform beneath it and is scaling rapidly across the United States and internationally. Students complete their core academics in two hours daily and achieve top national percentile scores. The approach is validated. What's required now is someone who thinks constantly about the people within the system.

You will establish design excellence, create foundational standards, and develop the capability. Your focus encompasses our learning platform and its associated applications, serving multiple audiences both within and beyond Alpha.

A five-year-old who cannot yet read is learning to count through a system that must transform novelty into something that feels like play. A teenager performing two grade levels below is reconstructing confidence after repeated academic setbacks, where a single unclear interaction could reverse progress. A parent gains visibility into their child's actual learning process. That transparency reduces worry and transforms them into a capable advocate. An academic coach overseeing a multi-age classroom requires insight into progress without information overload. You must develop sufficient understanding of each to make meaningfully distinct design decisions for every audience.

Your domain is the experience layer: conduct thorough research into each audience, translate findings into actionable design principles that engineers implement directly, and deliver functional code-based deliverables ready for immediate deployment rather than static mockups awaiting review. You collaborate with product leaders accountable for results and engineers responsible for implementation. You challenge requests that compromise user experience. You maintain complete ownership.

You will apply AI as a multiplier to accelerate iteration and expand coverage, though your discernment—not the model's initial output—determines what gets released. Primary emphasis is our education platform, supplemented by occasional work in other areas.

What You Will Be Doing

Conduct research across fundamentally distinct user audiences and develop design principles that reflect that understanding
Establish and sustain design systems within each product's native UI framework, enabling faster engineering delivery and cumulative rather than fragmented design value
Develop functional prototypes that enable product leaders to validate decisions within days rather than weeks
Evaluate existing products through the user lens: identify experience failures, quantify engagement costs, determine high-impact improvements
Establish design culture: define feedback mechanisms, articulate trade-off evaluation methods, identify non-negotiable standards
Collaborate with product leaders and engineers, challenge requests that degrade user experience

What You Won’t Be Doing

Determining product strategy; that belongs to product leaders, you ensure experience aligns with it
Creating static mockups requiring code translation
Concentrating on a single product; your scope spans the entire portfolio
Executing against a design brief; you synthesize context from ambiguous inputs and begin designing with partial information
Waiting for approval; you possess authority to surface and resolve UX issues independently

Basic Requirements Principal Product Designer key responsibilities

Minimum 5 years in product design or UX positions, demonstrating complete ownership from research through production release
Clear evidence of user empathy and research rigor with audiences substantially different from yourself
Established design excellence in interaction and visual design, portfolio demonstrating audience-tailored decisions over generic solutions, combined with articulated design convictions
Confirmed AI-native working style: rapid iteration, evaluative judgment, and capacity to challenge initial AI outputs instead of defaulting to them
Capability to implement designs in code leveraging AI tools and contemporary frameworks
Prepared to construct a design function and culture from the ground up, not operate within existing structures

About LearnWith.AI LearnWith.AI is an edtech startup that leverages AI and subject matter experts to cultivate a new way of learning. Our unique approach leverages 50+ years of learning science, cutting-edge data analytics and AI-powered coaching. In doing so, we can help students learn more, learn faster, and learn better - and have fun while doing it. We are a remote-first company that hires globally via Crossover.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help\-and\-faqs for more details on this topic.

Crossover Job Code: LJ-5747-GB-COUNTRY-PrincipalProdu

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