Product Designer, Connect

📍 Job Overview

Job Title: Product Designer, Connect

Company: Chess.com

Location: Remote (Global, with 3-hour overlap with US working hours)

Job Type: Full-Time, Salaried

Category: Product Design, User Experience (UX) Design

Date Posted: September 04, 2026

Experience Level: Mid-Level (2-3 years required, 2-5 years estimated)

Remote Status: Fully Remote

🚀 Role Summary

• Design and iterate on high-impact user experiences for critical Chess.com features like Home, Profile, Notifications, Widgets, Friends, Messages, and Sharing.

• Craft polished, production-ready interfaces across web, iOS, and Android platforms for a global user base of millions.

• Collaborate closely with Product Managers, Engineers, and fellow Product Designers to define requirements, explore design directions, and ensure seamless design-to-code implementation.

• Leverage AI-assisted tools such as Cursor and Claude for rapid prototyping and idea iteration, alongside established design systems and patterns.

• Contribute to a remote-first, globally distributed team environment, emphasizing proactive communication and constructive feedback.

📝 Enhancement Note: This role is focused on Product Design with a strong emphasis on UI (User Interface) design and UX (User Experience) principles. The "Connect" aspect suggests a focus on social features and user engagement within the Chess.com platform. The requirement for AI tool proficiency is a significant differentiator.

📈 Primary Responsibilities

• Own the end-to-end design process for specific features within the "Connect" domain, from initial problem definition and user research to final implementation and post-launch iteration.

• Develop high-fidelity, production-ready UI designs for web, iOS, and Android applications, ensuring consistency with Chess.com's design system and brand guidelines.

• Create and maintain detailed design documentation, including user flows, wireframes, mockups, and interactive prototypes, to effectively communicate design intent to cross-functional teams.

• Collaborate with engineering teams to ensure accurate implementation of designs, providing clear specifications and conducting design reviews to maintain design integrity.

• Utilize AI-powered design tools (Cursor, Claude) to accelerate the design process, experiment with new interaction models, and prototype complex ideas efficiently.

• Actively participate in design critiques and team discussions, providing and receiving constructive feedback to elevate the overall quality of design work.

• Contribute to the evolution of Chess.com's design system by identifying opportunities for new components, patterns, and best practices.

• Conduct user research and analyze user feedback to inform design decisions and identify areas for improvement in user engagement and satisfaction.

📝 Enhancement Note: The responsibilities emphasize ownership, cross-functional collaboration, and a strong understanding of UI fundamentals within a multi-platform environment. The inclusion of AI tools suggests an expectation for designers to be at the forefront of new design methodologies.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong foundation in design principles is expected, often gained through formal education (e.g., Bachelor's degree in Design, HCI, or related field) or equivalent practical experience.

Experience: 2-3 years of professional experience as a Product Designer, with a proven track record of designing for consumer-facing products or games.

Required Skills:

• Proven experience in UI design with a strong command of visual design fundamentals: typography, color theory, layout, visual hierarchy, alignment, contrast, and interactivity.

• Demonstrated ability to design polished, production-ready user interfaces for web, iOS, and Android platforms.

• Experience working with and contributing to established design systems, including the use of design tokens, components, and established patterns.

• Proficiency in creating interactive prototypes to communicate complex ideas and iterate rapidly.

• Familiarity with frontend development principles and how design translates into code.

• Experience utilizing AI-assisted design and prototyping tools, specifically Cursor and Claude.

• Excellent written and verbal communication skills, essential for a remote, globally distributed team.

• Strong collaboration, ownership, and follow-through capabilities. Preferred Skills:

• A genuine passion for chess and familiarity with the Chess.com platform and its user experience.

• Experience designing social features for mobile games or consumer products.

• Motion design skills, complementing a strong foundation in product and UI design.

• Experience in design engineering or frontend development for web, iOS, or Android.

📝 Enhancement Note: The experience requirement is mid-level, indicating a need for designers who can operate with a degree of autonomy. The explicit mention of AI tools is a key differentiator, suggesting that candidates with this experience will be highly valued.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A comprehensive portfolio showcasing polished UI designs for both web and mobile applications.

• Clear demonstration of the candidate's personal contribution to each project, detailing their role and impact.

• Examples of how design decisions were informed by user insights, product context, and business objectives.

• Visual evidence of strong UI design fundamentals, including typography, color, layout, and visual hierarchy.

• Case studies that illustrate the design process from problem definition through to implementation and iteration. Process Documentation:

• Demonstrations of how designs were created and iterated upon using AI-assisted tools like Cursor and Claude.

• Examples of how design systems and tokens were utilized to ensure consistency and efficiency.

• Evidence of collaboration with engineering teams to ensure design-to-code alignment.

• Prototypes that effectively communicate complex interactions and user flows.

📝 Enhancement Note: The portfolio is critical for this role, needing to clearly articulate the candidate's design craft, process, and collaborative abilities, especially highlighting experience with AI tools and design systems.

💵 Compensation & Benefits

Salary Range: For a mid-level Product Designer with 2-3 years of experience in a remote, global role requiring US working hour overlap, typical salary ranges can vary significantly by region. Based on industry benchmarks for similar roles in tech, a competitive range could be between $90,000 - $130,000 USD annually.

Benefits:

• Full-time employment with competitive salary.

• Fully remote work environment, allowing for global flexibility.

• Opportunity to work on a highly visible product with millions of users.

• Collaborative and dynamic team culture.

• Potential for professional growth and development within a leading online chess platform.

• [Specific benefits such as health insurance, paid time off, retirement plans, etc., would typically be provided by Chess.com and should be confirmed directly.]

Working Hours: 40 hours per week, with flexibility, but requiring at least 3 hours of overlap with U.S. working hours to facilitate collaboration with the globally distributed team.

📝 Enhancement Note: Salary is an estimate based on general industry standards for remote, mid-level Product Designers in tech companies. Specific compensation will depend on the candidate's experience, location, and the company's compensation philosophy. The 3-hour US overlap requirement is a key consideration for global applicants.

🎯 Team & Company Context

🏢 Company Culture

Industry: Online Gaming, Technology, E-commerce (Chess Platform). Chess.com is a leader in online chess, providing a platform for players of all levels to play, learn, and connect.

Company Size: Chess.com is a significant player in the online gaming space, operating with a sizable, globally distributed team. While the exact number isn't provided, their description as a "100-person virtual team" from their blog link suggests a well-established, mature organization.

Founded: Chess.com was founded in 2007, giving it over a decade of experience in building and scaling its platform and community. This history implies a stable and experienced organization.

Team Structure:

• The Product Design team is likely integrated within product squads, working closely with Product Managers and Engineers.

• The "Connect" team focuses on social and engagement features, indicating a specialized area within the broader product organization.

• Collaboration is heavily reliant on remote tools like Slack, suggesting an asynchronous communication style with scheduled synchronous touchpoints. Methodology:

• Data-driven decision-making, leveraging user analytics and feedback to inform product development.

• Agile development methodologies are common in tech companies, likely applied to design and engineering processes.

• Emphasis on iterative design and rapid prototyping, especially with the integration of AI tools.

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

📝 Enhancement Note: Chess.com's culture is defined by its remote-first, global nature and its focus on building a world-class platform for chess enthusiasts. The "Connect" team specifically focuses on fostering community and interaction, which is a key aspect of their growth strategy.

📈 Career & Growth Analysis

Operations Career Level: This role is classified as a mid-level Product Designer. Candidates are expected to have a solid grasp of core design principles and processes and be capable of owning significant features with moderate supervision. They are beyond junior-level tasks and are expected to contribute independently to design strategy and execution.

Reporting Structure: The Product Designer will likely report to a Design Lead or Head of Product Design. They will work within cross-functional product teams, reporting operationally to the Product Manager of their specific feature area for project alignment.

Operations Impact: The "Connect" features are vital for user retention and engagement. Successful design in this area directly impacts user satisfaction, community growth, and ultimately, the overall success and revenue of Chess.com. Designers here have a direct line of sight to how their work influences user behavior and platform health.

Growth Opportunities:

• Skill Specialization: Deepen expertise in social features, mobile design, or AI-assisted design workflows.

• Leadership Potential: Progress to Senior Product Designer roles, leading larger initiatives or mentoring junior designers.

• Cross-Functional Exposure: Gain experience in product strategy, user research methodologies, and A/B testing through close collaboration with Product Managers and data analysts.

• Platform Expansion: Contribute to the design of new features or even new product lines within the Chess.com ecosystem.

📝 Enhancement Note: The growth path for a Product Designer at Chess.com is likely tied to increasing scope of responsibility and design leadership, with opportunities to specialize in areas critical to user engagement.

🌐 Work Environment

Office Type: 100% Remote. This means no physical office location is required for this role. The work is conducted from the employee's chosen location.

Office Location(s): Global. Candidates can work from anywhere, provided they can maintain at least 3 hours of overlap with U.S. working hours. This implies a need for self-discipline and effective time management.

Workspace Context:

• Collaborative Environment: Heavily reliant on digital collaboration tools like Slack for real-time and asynchronous communication. Virtual whiteboarding and design review sessions are standard.

• Tools & Technology: Access to industry-standard design software (e.g., Figma, Sketch), prototyping tools, and the specified AI tools (Cursor, Claude).

• Team Interaction: Regular virtual meetings, design critiques, and team syncs to foster connection and alignment within the remote setting.

Work Schedule: Full-time, 40 hours per week. While remote, adherence to core overlap hours with U.S. teams is essential for effective collaboration. This may require adjusting personal schedules to accommodate these overlap periods.

📝 Enhancement Note: The remote-first nature is a key aspect of the work environment. Candidates must be comfortable with asynchronous communication and possess strong self-management skills. The US overlap requirement is critical for ensuring seamless teamwork across time zones.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter or hiring manager will review applications and portfolios. Candidates with strong portfolios and relevant experience will be invited for a first-round interview.

• Design Challenge/Portfolio Review: This stage typically involves a deeper dive into the candidate's portfolio. They may be asked to present specific projects, discuss their design process, and explain their rationale. A take-home design challenge or a live design exercise may also be part of this stage, focusing on problem-solving and UI execution.

• Cross-functional Interviews: Interviews with Product Managers and Engineers to assess collaboration skills, technical understanding, and ability to work within a team.

• Final Interview: Often with a senior leader (e.g., Head of Design or Product) to assess cultural fit, strategic thinking, and overall suitability for the role and company.

Portfolio Review Tips:

• Highlight "Connect" Features: Showcase projects that demonstrate experience with social, community, or engagement-focused features if possible.

• Emphasize AI Tool Usage: Clearly articulate how AI tools like Cursor and Claude were used in your design process, what benefits they provided, and what your personal contribution was.

• Showcase Design System Proficiency: Include examples of how you've used or contributed to design systems, demonstrating an understanding of tokens, components, and consistency.

• Detail Your Process: For each project, clearly explain the problem, your approach, the tools you used, your specific contributions, the challenges you faced, and the outcomes.

• Quantify Impact: Whenever possible, use data or metrics to demonstrate the impact of your design decisions on user behavior or business goals.

Challenge Preparation:

• Understand the Product: Familiarize yourself deeply with Chess.com, its features, and its user base. Play games, explore profiles, and use the "Connect" features.

• Prepare for AI Tool Integration: Be ready to discuss how you would leverage AI tools in a design context for Chess.com, or be prepared for a challenge that may involve using them.

• Focus on UI Craft: Practice creating clean, polished UI mockups and prototypes for web and mobile interfaces, paying close attention to detail.

• Articulate Rationale: Be prepared to clearly and concisely explain the "why" behind your design decisions, linking them back to user needs and business objectives.

📝 Enhancement Note: The interview process will likely be rigorous, with a strong emphasis on portfolio quality, practical design skills, and an understanding of how to work effectively in a remote, AI-augmented design environment.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (or similar industry-standard tools like Sketch, Adobe XD) for UI design and prototyping.

• AI-Assisted Design: Cursor and Claude are explicitly mentioned for prototyping and idea iteration.

• Collaboration: Slack for day-to-day communication and team interaction.

• Project Management: Tools like Jira, Asana, or Trello may be used by product teams.

Analytics & Reporting:

• User Analytics: Tools like Google Analytics, Mixpanel, or Amplitude for tracking user behavior and feature adoption.

• Data Visualization: Potentially tools like Tableau or Looker for reporting and dashboard creation, though less direct for a designer.

CRM & Automation:

• While not directly a designer's tool, understanding how CRM and automation platforms (e.g., Salesforce, HubSpot) integrate with user-facing features can be beneficial for context.

📝 Enhancement Note: Proficiency in Figma and a willingness to adopt and experiment with AI design tools like Cursor and Claude are paramount. Familiarity with collaborative platforms like Slack is also essential.

👥 Team Culture & Values

Operations Values:

• Craftsmanship: A high standard for polished, intuitive, and visually appealing user interfaces.

• Collaboration: Proactive engagement with product, engineering, and design peers, valuing feedback and shared ownership.

• Curiosity: A desire to understand user needs, explore innovative solutions, and learn new tools and methodologies (including AI).

• Impact-Driven: Focusing on designing features that demonstrably improve user experience, engagement, and platform growth.

• Remote-First Mindset: Emphasizing clear communication, asynchronous workflows, and mutual respect in a distributed team.

Collaboration Style:

• Cross-functional Integration: Designers are integral members of product teams, working hand-in-hand with PMs and Engineers from concept to launch.

• Open Feedback Culture: Encourages constructive critique and open dialogue within the design team and with stakeholders.

• Knowledge Sharing: Active participation in Slack channels, design reviews, and potentially internal knowledge-sharing sessions to disseminate best practices and learnings.

📝 Enhancement Note: Chess.com's culture values a blend of individual craft and collaborative teamwork, adapted for a remote environment. The emphasis on "craft-focused" and "curious" designers suggests a team that values both technical skill and a proactive, learning-oriented approach.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Innovation with Consistency: Integrating new AI-driven design approaches while adhering to established design systems and brand guidelines.

• Remote Collaboration Complexity: Effectively communicating and collaborating across multiple time zones and diverse cultural backgrounds.

• Designing for Scale: Creating experiences that are intuitive and engaging for millions of users with varying levels of chess expertise and technical proficiency.

• Rapid Iteration: Adapting to fast-paced product development cycles and quickly iterating on designs based on feedback and data.

Learning & Development Opportunities:

• AI Design Tool Mastery: Becoming an expert in leveraging AI tools for design, potentially shaping how Chess.com approaches future design workflows.

• Social Feature Design Expertise: Developing deep insights into designing engaging social and community features for a global audience.

• Cross-Disciplinary Learning: Gaining exposure to product strategy, user research, and front-end development through close collaboration.

• Mentorship: Opportunities to learn from experienced designers and potentially mentor junior team members as the role progresses.

📝 Enhancement Note: The role presents opportunities to be at the cutting edge of design technology with AI tools, while also developing expertise in critical user engagement features for a massive online platform.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you used AI tools to accelerate your design process. What were the challenges and benefits?" (Prepare to discuss your experience with Cursor/Claude or similar tools, focusing on efficiency and innovation.)

• "How would you approach designing a new notification system for Chess.com's 'Connect' features to increase user engagement without causing notification fatigue?" (Focus on user-centric design, iterative process, and understanding of notification best practices.)

• "Walk us through a challenging UI design project from your portfolio. How did you define the problem, explore solutions, and ensure successful implementation?" (Be ready to detail your process, decision-making, and collaboration.) Company & Culture Questions:

• "What interests you about Chess.com and the 'Connect' features specifically?" (Research Chess.com's mission, user base, and the role of social features.)

• "How do you approach collaboration in a remote, globally distributed team?" (Highlight your communication skills, proactivity, and experience with tools like Slack.)

• "How do you balance adhering to a design system with exploring new design directions?" (Demonstrate an understanding of design system principles and innovation.) Portfolio Presentation Strategy:

• Structure Your Narrative: For each project, clearly outline the problem, your role, the design process, your specific contributions (especially with AI tools), the challenges, and the outcomes (quantified if possible).

• Highlight AI Tool Impact: Explicitly show where and how AI tools like Cursor and Claude were used and what tangible benefits they provided (e.g., faster prototyping, novel idea generation).

• Demonstrate UI Craftsmanship: Ensure your presented designs are polished, well-organized, and showcase a strong understanding of visual hierarchy, typography, and interaction design.

• Be Ready for Deep Dives: Anticipate questions about your design decisions, trade-offs made, and how you would iterate on the presented work.

📝 Enhancement Note: Interview preparation should heavily emphasize practical design skills, a clear understanding of the design process, and specific experience with AI design tools and remote collaboration.

📌 Application Steps

To apply for this Product Designer position:

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

• Customize Your Portfolio: Tailor your portfolio to highlight relevant projects, especially those involving UI design for consumer products, social features, or demonstrating the use of AI design tools. Clearly articulate your contributions and the impact of your work.

• Optimize Your Resume: Ensure your resume emphasizes your years of experience, key skills (UI Design, Prototyping, Design Systems, AI Tools), and relevant achievements in product design. Use keywords from the job description.

• Prepare Your Presentation: Practice walking through 2-3 key portfolio pieces, focusing on your process, decision-making, and how you leveraged tools like Cursor and Claude. Be ready to explain your rationale clearly and concisely.

• Research Chess.com: Understand the company's mission, its user base, the "Connect" features, and its remote-first culture. Be prepared to articulate why you are a good fit for Chess.com and this specific role.

⚠️ 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.