Product Designer, Courses

📍 Job Overview

Job Title: Product Designer, Courses

Company: Chess.com

Location: Remote (Significant overlap with US Eastern Time zone required)

Job Type: Full-Time, Salaried

Category: Product Design / User Experience Design

Date Posted: 2026-07-28

Experience Level: Mid-Senior (3-5 years)

Remote Status: 100% Remote

🚀 Role Summary

• Design and own the user experience for the Courses product at Chess.com, a leading online chess platform.

• Collaborate closely with Product Managers, Engineers, Copywriters, and leadership to define problems and deliver effective product solutions.

• Craft high-fidelity, engaging interfaces for web and mobile platforms, adhering to established design patterns and a comprehensive design system.

• Develop interactive learning experiences that incorporate habit-forming principles like spaced repetition and gamification to enhance user engagement and skill mastery.

• Leverage AI-assisted tools and rapid prototyping techniques to iterate on design concepts and test user flows efficiently.

📝 Enhancement Note: This role is specifically focused on the "Courses" product, implying a need to understand educational design principles, user learning journeys, and engagement strategies within a digital learning context. The emphasis on habit formation and spaced repetition suggests a deep dive into behavioral design and motivational psychology as applied to product.

📈 Primary Responsibilities

• Take full ownership of the design lifecycle for the Chess.com Courses product, from initial concept to final implementation.

• Partner cross-functionally to conduct user research, analyze user insights, and apply heuristics to inform design decisions.

• Design intuitive and interactive course content, practice modules, and progress tracking features for both web and mobile platforms.

• Create polished, pixel-perfect UI designs that align with Chess.com's brand guidelines and existing design system, ensuring consistency and a high-quality user experience.

• Build interactive prototypes using tools like Figma, Cursor, and Claude Code to effectively communicate design ideas and facilitate rapid iteration and testing.

• Ensure seamless design-to-code handoff and collaborate with engineering teams to maintain design integrity throughout the development process.

• Proactively identify opportunities for product improvement, proposing and designing innovative solutions to enhance user engagement, learning efficacy, and overall product delight.

• Provide constructive design feedback to fellow designers and contribute to a culture of continuous improvement within the design team.

📝 Enhancement Note: The responsibility to "Own the design of the Courses product experience" indicates a significant level of autonomy and strategic input expected from the designer. The mention of "agentic tools like Cursor, Claude Code, and Figma Make" suggests an expectation for proficiency in leveraging AI to accelerate design and prototyping workflows, which is a key emerging skill in product design.

🎓 Skills & Qualifications

Education: Not explicitly stated, but a Bachelor's degree in Design, HCI, or a related field, or equivalent practical experience, is typically expected for this level of role.

Experience: 3-5 years of experience as a Product Designer, with a strong focus on consumer-facing products or games.

Required Skills:

• Proven experience in UI design fundamentals, including typography, color theory, layout, visual hierarchy, alignment, contrast, and interactivity.

• Demonstrated ability to design responsive and interactive user interfaces for both mobile applications and web platforms.

• Strong portfolio showcasing exceptional UI/UX design work, with clear examples of problem-solving and user-centered design thinking.

• Proficiency in industry-standard design and prototyping tools, with a specific emphasis on Figma.

• Familiarity with frontend development principles and an understanding of how design translates into functional code.

• Experience designing for engagement, habit formation, and user retention.

• Excellent collaboration and communication skills, with the ability to articulate design decisions clearly and effectively.

• Experience working effectively in a remote, globally distributed team environment. Preferred Skills:

• Experience working with and contributing to a large, established design system.

• Direct experience designing educational products, online courses, or learning platforms.

• Familiarity with AI-assisted design and prototyping tools such as Cursor, Claude Code, and Figma Make.

• Experience with user research methodologies and translating user insights into design solutions.

• A strong sense of ownership, pride in craftsmanship, and accountability for design outcomes.

📝 Enhancement Note: The inclusion of specific AI tools like Cursor and Claude Code, alongside Figma Make, indicates a progressive approach to design tooling and an expectation for candidates to be at the forefront of leveraging AI for productivity and innovation in design. The "3-5 years" experience level, coupled with the "Courses" focus, suggests a need for a designer who can operate semi-autonomously and has a solid foundation in user-centered design for engaging digital products.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A comprehensive portfolio showcasing a minimum of 3-5 distinct product design projects, with at least one project specifically related to educational content, gamified learning, or habit-forming products.

• Each project should clearly articulate the problem statement, your role and contributions, the design process followed (research, ideation, prototyping, testing, iteration), and the final design solutions.

• Demonstrate a deep understanding of UI/UX principles through high-fidelity mockups, interactive prototypes, and visual design examples.

• Showcase your ability to design for both web and mobile platforms, highlighting responsive design considerations.

• Include examples of how you've used design systems or contributed to design patterns. Process Documentation:

• For each portfolio project, clearly outline the design methodology employed, emphasizing user-centered approaches.

• Document your process for leveraging AI tools (Cursor, Claude Code, Figma Make) in your workflow, detailing how they aided in prototyping or iteration.

• Provide insights into your collaboration process with Product Managers and Engineers, including examples of design handoffs and feedback loops.

• If applicable, include case studies demonstrating how your designs have led to improved user engagement, retention, or learning outcomes.

📝 Enhancement Note: The emphasis on AI tools in the required skills and expected portfolio content suggests that candidates should be prepared to demonstrate their experience and proficiency with these technologies. The portfolio should not just be a collection of visuals but a narrative of problem-solving, process, and impact, particularly within the context of learning and engagement.

💵 Compensation & Benefits

Salary Range: Based on typical compensation for mid-senior Product Designers in fully remote roles within the US tech industry, and considering Chess.com's standing, an estimated annual salary range would be between $120,000 - $170,000 USD. This range can vary based on specific experience, location (though fully remote, some companies adjust for cost of living), and negotiation.

Benefits:

• Full-time employment with competitive salary and potential for performance-based bonuses.

• Comprehensive health, dental, and vision insurance plans.

• Generous paid time off (PTO) and holidays.

• Opportunities for professional development, including courses, conferences, and certifications.

• Access to cutting-edge design tools and technology.

• Contribution to a globally recognized brand with a massive user base.

• A collaborative and supportive remote work environment.

Working Hours: This is a full-time role, typically requiring approximately 40 hours per week. The company emphasizes flexibility within a remote setting, with the caveat that significant overlap with the US Eastern Time zone is necessary for effective collaboration.

📝 Enhancement Note: The salary estimate is based on industry benchmarks for similar roles in the US tech market, adjusted for a fully remote position and the experience level required. The "significant overlap with US Eastern Time zone" requirement is a key factor for remote candidates, as it implies a need for availability during core US business hours, which can influence work-life balance considerations.

🎯 Team & Company Context

🏢 Company Culture

Industry: Online Gaming & Education Technology. Chess.com is a dominant player in the online chess space, bridging competitive gaming with educational content delivery. This dual focus creates a unique environment demanding both engaging entertainment design and effective learning experience design.

Company Size: Chess.com is a rapidly growing company, with a significant global team. While exact numbers fluctuate, it's understood to be a medium to large-sized organization with a substantial engineering and product development footprint. This size suggests established processes but also opportunities for impact.

Founded: Chess.com was founded in 2007. Its long history in the digital space means it has a mature platform and a well-understood user base, yet it continues to innovate and expand its offerings, particularly in areas like educational content.

Team Structure:

• The design team at Chess.com is likely structured to support various product verticals, including Courses. Designers will work within cross-functional product teams, reporting to design leadership.

• The reporting structure will likely involve a direct manager (e.g., Head of Product Design) and close collaboration with Product Managers and Engineering Leads for specific product areas.

• Cross-functional collaboration is a cornerstone, with designers working intimately with Product, Engineering, Copywriting, and potentially Marketing/Content teams to ensure cohesive product development. Methodology:

• Data-driven decision-making is paramount, with an emphasis on user analytics, A/B testing, and user feedback to inform design iterations and strategy.

• Agile development methodologies are likely employed, requiring designers to be adaptable and responsive to iterative development cycles.

• A strong focus on user empathy and understanding the nuanced motivations of chess players, from beginners to advanced, is critical for designing effective learning and engagement experiences.

Company Website: https://www.chess.com/

📝 Enhancement Note: Chess.com's unique position at the intersection of gaming and education means the design culture likely values both playfulness and pedagogical effectiveness. The emphasis on a "100% remote" culture suggests a need for strong asynchronous communication skills and self-discipline, alongside a commitment to virtual team cohesion.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned at a mid-senior level (3-5 years of experience). It requires a designer who can operate with a significant degree of autonomy, take ownership of a product area, and contribute strategically to product development, rather than just executing design tasks. The "Courses" product focus indicates a specialization opportunity within the broader product design discipline.

Reporting Structure: The Product Designer will report to a Design Lead or Head of Product Design and will work closely with Product Managers and Engineering Leads within the Courses product team. This structure allows for both design mentorship and deep integration with product strategy and development.

Operations Impact: The Product Designer's work will directly influence user acquisition, retention, engagement, and learning outcomes within the Courses product. Successful designs will contribute to increased user satisfaction, longer session times, greater course completion rates, and ultimately, the growth and revenue of Chess.com. The impact is measurable through user behavior analytics and direct feedback.

Growth Opportunities:

• Specialization: Deepen expertise in educational design, gamification, and behavioral psychology applied to learning products.

• Leadership: Potential to lead design initiatives for larger product features or new product areas as experience grows.

• Skill Development: Opportunities to master new design tools, including AI-assisted technologies, and refine skills in user research, prototyping, and cross-functional collaboration.

• Mentorship: Contribute to mentoring junior designers and participate in design critiques, fostering a culture of learning and improvement.

• Company Growth: As Chess.com continues to expand, there will be opportunities to move into more senior design roles or explore related fields within the product organization.

📝 Enhancement Note: The role offers a clear path for specialization in educational technology design, a growing and impactful field. Growth opportunities are framed around both individual skill enhancement and potential leadership within the design team, aligned with the company's expansion.

🌐 Work Environment

Office Type: Chess.com operates as a 100% remote company. This means there is no central office, and employees work from their chosen locations. The "office" is virtual, relying heavily on digital collaboration tools.

Office Location(s): Fully remote, with the requirement for significant overlap with the US Eastern Time zone. This implies candidates should be located in regions that facilitate this overlap (e.g., North America, parts of South America, or Europe depending on specific hours).

Workspace Context:

• The virtual workspace is characterized by asynchronous communication (Slack, email, project management tools) and synchronous meetings (video conferencing).

• Access to a wide array of digital tools for design, communication, and project management is standard.

• Collaboration is fostered through structured design reviews, team meetings, and open communication channels.

• The environment encourages self-discipline, time management, and proactive communication to ensure seamless teamwork across different time zones.

Work Schedule: While the role is full-time (approx. 40 hours/week), there is a degree of flexibility inherent in remote work. However, the requirement for significant Eastern Time zone overlap means that core working hours will need to accommodate team meetings, collaborative sessions, and real-time problem-solving with colleagues in that time zone.

📝 Enhancement Note: The 100% remote nature necessitates a high degree of self-management and communication skill. The "significant overlap" with ET is crucial for candidates to understand, as it dictates a portion of their available working hours.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio to assess qualifications and alignment with the role requirements.

• Hiring Manager Interview: A discussion about your experience, design philosophy, and approach to product design, with a focus on your understanding of learning and engagement.

• Design Challenge/Portfolio Presentation: You will likely be asked to present your portfolio, walking through key projects, explaining your design process, and demonstrating how you've solved user problems. A specific design exercise or case study related to educational products might be assigned.

• Cross-functional Team Interview: Meet with Product Managers, Engineers, and potentially other designers to assess your collaboration skills, communication style, and ability to integrate into a team.

• Final Interview: Potentially with senior leadership to discuss strategic fit and long-term vision.

Portfolio Review Tips:

• Highlight Relevant Projects: Prioritize projects that showcase your UI/UX skills, experience with consumer products/games, and any work related to learning or habit formation.

• Tell a Story: For each project, clearly articulate the problem, your unique contribution, the process, the challenges faced, and the outcomes achieved. Use visuals effectively to support your narrative.

• Showcase Process: Detail your design thinking, research methods, and iteration strategies. Demonstrate how you use user insights and data.

• Demonstrate Tool Proficiency: If you've used AI tools like Cursor or Claude Code, highlight these in your projects and be ready to discuss how they accelerated your workflow.

• Be Concise and Clear: Aim for clarity and impact. Prepare a concise overview and be ready to dive deeper into specific areas as requested.

Challenge Preparation:

• Understand the Domain: Familiarize yourself with Chess.com and its existing Courses product. Think about how users learn chess and what makes an educational experience engaging.

• Practice Articulation: Be prepared to clearly explain your design decisions, rationale, and trade-offs. Practice presenting your portfolio and any assigned case studies.

• Prepare for Collaboration Questions: Think about how you collaborate with product managers and engineers, handle feedback, and resolve design disagreements.

• Research Chess.com: Understand their mission, target audience, and any recent product updates or news.

📝 Enhancement Note: The emphasis on AI tools in the job description strongly suggests that candidates should be prepared to discuss their experience with these tools during interviews, potentially even in a design challenge. The portfolio review will likely focus heavily on how candidates approach educational design and habit formation.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The core tool for UI design, prototyping, and collaboration. Mastery is essential.

• Cursor: An AI-first code editor that can assist with design implementation and understanding code. Proficiency is preferred.

• Claude Code: An AI assistant that can help with code generation and design-related tasks. Experience with this or similar AI coding assistants is beneficial.

• Figma Make: A feature within Figma that allows for quick iteration and prototyping. Familiarity is expected.

Analytics & Reporting:

• While not explicitly listed, experience with analytics platforms (e.g., Google Analytics, Mixpanel, Amplitude) for tracking user behavior and measuring design impact is highly valuable.

• Familiarity with A/B testing frameworks and how to interpret results to inform design decisions. CRM & Automation:

• Not directly applicable to a Product Designer role, but understanding how user data is managed and how product features impact user journeys within the broader platform is beneficial.

📝 Enhancement Note: The explicit mention of Cursor, Claude Code, and Figma Make indicates a strong leaning towards candidates who are early adopters and proficient users of AI-assisted design and development tools. This is a key differentiator for this role.

👥 Team Culture & Values

Operations Values:

• Player-First Design: A deep commitment to understanding and serving the needs of chess players, balancing competitive play with learning and enjoyment.

• Data-Driven Innovation: Utilizing analytics and user feedback to guide design decisions and drive continuous improvement.

• Collaboration & Transparency: Open communication and mutual respect among team members, fostering a supportive and productive remote work environment.

• Craftsmanship & Quality: A dedication to producing polished, high-quality designs that elevate the user experience and brand.

• Learning & Growth: A culture that encourages continuous learning, skill development, and embracing new technologies and methodologies.

Collaboration Style:

• Cross-functional Integration: Designers are expected to be integral members of product teams, working hand-in-hand with Product Managers and Engineers throughout the development process.

• Constructive Feedback: A culture of giving and receiving design feedback openly and constructively to elevate the quality of work.

• Asynchronous Efficiency: Proficiency in asynchronous communication tools and practices to ensure smooth collaboration across time zones, complemented by effective synchronous meetings when needed.

📝 Enhancement Note: The emphasis on "playfulness" and "serious learners" suggests a unique blend of fun and educational rigor in the company's values. The remote nature underscores the importance of proactive communication and a strong sense of shared purpose.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Gamification and Education: Designing experiences that are both fun and effective for learning, integrating habit-forming mechanics without compromising pedagogical integrity.

• Scalability of Design: Ensuring designs are scalable and maintainable across web and mobile platforms for a massive, global user base.

• Remote Collaboration: Navigating the complexities of distributed teamwork, ensuring effective communication and alignment across different time zones.

• Adopting New Technologies: Staying current with and effectively integrating emerging AI tools into the design workflow.

Learning & Development Opportunities:

• Specialized Skill Development: Deep dive into UX for educational technology, behavioral design, and gamification principles.

• AI Tool Mastery: Become an expert in utilizing AI-powered design and coding tools to enhance productivity and creativity.

• Cross-functional Exposure: Gain in-depth understanding of product management, engineering workflows, and data analytics.

• Mentorship: Opportunities to learn from and contribute to a talented team of designers and product professionals.

📝 Enhancement Note: The primary challenge lies in mastering the unique intersection of gaming, education, and behavioral psychology to create truly sticky and effective learning experiences. The growth opportunities are tied to becoming a leader in this niche, empowered by cutting-edge AI tools.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you designed a product experience focused on habit formation or user retention. What were your key design decisions and what was the outcome?"

• "How would you approach designing an interactive chess course for absolute beginners? What key learning principles would you incorporate?"

• "Walk us through your process for designing a new feature for a mobile app, from initial concept to handoff to engineering. How do you ensure design quality and consistency?"

• "How do you leverage user research and data to inform your design decisions? Can you provide an example?" Company & Culture Questions:

• "What interests you about Chess.com and our mission to make chess accessible and engaging for everyone?"

• "How do you approach collaboration in a fully remote environment? What are your strategies for effective communication with distributed teams?"

• "How do you stay up-to-date with the latest trends in product design, particularly in areas like AI-assisted design?"

• "Describe a time you received constructive criticism on your design work. How did you handle it, and what did you learn?" Portfolio Presentation Strategy:

• Structure: Organize your presentation logically, typically starting with an overview of Chess.com and the Courses product, then diving into 2-3 key projects.

• Narrative: For each project, tell a compelling story: Problem -> Your Role -> Process -> Solution -> Outcome -> Learnings.

• Visuals: Use high-quality mockups, prototypes, and flow diagrams. Ensure they are clear and easy to understand.

• Tool Discussion: Be prepared to discuss your use of Figma and specifically how you've leveraged AI tools like Cursor or Claude Code in your workflow to accelerate your design process or prototyping.

• Q&A: Anticipate questions about your design choices, trade-offs, and how your work aligns with Chess.com's goals.

📝 Enhancement Note: Candidates should be ready to discuss their understanding of educational design principles and their experience with AI-powered design tools. Demonstrating an ability to connect design solutions to user learning and engagement metrics will be crucial.

📌 Application Steps

To apply for this Product Designer position:

• Submit your application through the provided link on the Chess.com careers page.

• Portfolio Customization: Ensure your portfolio prominently features relevant projects, especially those demonstrating UI/UX expertise, consumer product design, and ideally, experience with educational content or habit-forming features. Tailor your project selection and descriptions to highlight your fit for designing learning experiences.

• Resume Optimization: Craft a resume that clearly articulates your 3-5 years of experience, highlighting key skills such as UI/UX design, responsive design, Figma proficiency, and any experience with AI design tools. Quantify achievements where possible (e.g., "improved user engagement by X%").

• AI Tool Familiarity: Be prepared to discuss your experience with AI tools like Cursor, Claude Code, and Figma Make in your application materials or during interviews. If you don't have direct experience, show a willingness and aptitude to learn them quickly.

• Company Research: Thoroughly research Chess.com, its mission, its existing Courses product, and its remote culture. Understand the unique blend of gaming and education.

• Interview Readiness: Prepare to articulate your design process, present your portfolio compellingly, and answer questions about educational design, habit formation, and remote collaboration.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.