Senior Product Designer, Connect

📍 Job Overview

Job Title: Senior Product Designer, Connect

Company: Chess.com

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

Job Type: Full-time, Salaried

Category: Product Design / UX/UI Design

Date Posted: September 04, 2026

Experience Level: 5-10 years

🚀 Role Summary

• Lead the end-to-end design of high-impact user experiences for critical Chess.com features including Home, Profile, Notifications, Widgets, Friends, Messages, and Sharing.

• Drive product and design decisions by identifying opportunities beyond initial briefs and influencing strategic direction.

• Collaborate closely with Product Management, Engineering, and other Designers to ensure a cohesive and engaging user experience across web, iOS, and Android platforms.

• Elevate the overall quality and craft of the design team through strong visual design, thoughtful interactions, and constructive critique.

• Own the design process from problem definition through implementation, ensuring strong design-to-code alignment.

📝 Enhancement Note: This role is positioned as a Senior Product Designer, indicating a need for significant autonomy, strategic thinking, and the ability to mentor or guide other designers without direct people management. The focus on "Connect" features suggests a strong emphasis on social interaction, community building, and user engagement within the Chess.com ecosystem. The mention of "agentic tools" like Cursor and Claude points to an innovative approach to design tooling and rapid prototyping.

📈 Primary Responsibilities

• Spearhead the design strategy and execution for key "Connect" features, delivering polished, production-ready UI designs for web, iOS, and Android.

• Translate complex requirements into intuitive and engaging user experiences that foster connection and community among millions of Chess.com players.

• Proactively identify and champion new product opportunities, leveraging user insights and market trends to drive innovation.

• Collaborate effectively with cross-functional teams, presenting design proposals, articulating rationale, and facilitating alignment on critical decisions.

• Contribute to and uphold the Chess.com Design System, ensuring consistency, usability, and scalability across all product touchpoints.

• Conduct thorough design critiques, providing constructive feedback to peers and contributing to the continuous improvement of design quality and craft.

• Maintain design integrity throughout the development lifecycle, working closely with engineers to ensure accurate implementation and a high-fidelity user experience.

• Utilize advanced design tools, including Cursor and Claude, for rapid prototyping, iteration, and exploration of diverse design solutions.

• Think strategically about the broader product ecosystem, identifying opportunities for cross-feature improvements and enhanced user journeys.

• Actively participate in problem-solving sessions, navigating ambiguity and diverse perspectives to arrive at optimal design outcomes.

📝 Enhancement Note: The responsibilities emphasize leadership in design, strategic influence, and cross-functional collaboration. The mention of "ownership through implementation" highlights the expectation for designers to see their work through to launch and beyond, ensuring quality and impact. The specific focus on "Connect" features and community building suggests a need for designers with a strong understanding of social dynamics and user engagement strategies.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong foundation in design principles is implied through the required skills. Candidates with degrees in Design, HCI, or related fields may have a foundational advantage.

Experience: Minimum of 5 years of experience as a Product Designer, with a preference for candidates with 5-10 years of experience in consumer-facing products or gaming.

Required Skills:

• 5+ years of experience in Product Design for consumer-facing products or games.

• A compelling portfolio showcasing polished web and mobile UI design work, demonstrating strong product thinking and accountability.

• Mastery of UI design fundamentals: typography, color theory, layout, visual hierarchy, alignment, contrast, interactivity, and user experience heuristics.

• Proficiency in using agentic tools like Cursor and Claude for building shareable prototypes and rapid iteration.

• Proven experience owning complex product initiatives from initial problem definition through to successful implementation.

• Strong fluency with Design Systems, including the ability to leverage existing patterns and identify opportunities for enhancement and consistency.

• Demonstrated ability to influence product and design decisions, articulate design rationale clearly, and manage cross-functional disagreements or competing priorities.

• Familiarity with front-end development principles and how design translates into code across web, iOS, and Android platforms.

• Excellent written and verbal communication skills, with a proactive approach to remote collaboration and the judgment to work autonomously in ambiguous environments. Preferred Skills:

• A genuine passion for chess and a deep understanding of Chess.com's product experience.

• Prior experience designing social features for mobile games or other consumer products.

• Experience with motion design, building upon a strong foundation in product and UI design craft.

• Experience in design engineering or front-end development on web, iOS, or Android platforms.

📝 Enhancement Note: The "5+ years" combined with the Senior title strongly suggests a need for candidates who can operate independently and strategically. The emphasis on agentic tools (Cursor, Claude) is a key differentiator, indicating a forward-thinking design team. The "Preferred" section highlights specific domain interest and technical skills that would be advantageous.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase a minimum of 3-5 end-to-end product design case studies, with at least two focusing on complex consumer-facing web and mobile applications.

• Clearly articulate the problem statement, your role and responsibilities, the design process followed, key challenges encountered, and the final outcomes.

• Demonstrate strong UI craft, visual design execution, and interaction design principles through high-fidelity mockups and prototypes.

• Include examples of how you've leveraged or contributed to Design Systems, showcasing consistency and scalability.

• Detail your experience with prototyping tools, specifically mentioning your use of agentic tools like Cursor and Claude, and how they facilitated iteration and decision-making.

• Quantify impact where possible, using metrics to illustrate user experience improvements, engagement increases, or problem resolution. Process Documentation:

• Case studies should clearly outline the design process, including research, ideation, wireframing, prototyping, user testing (if applicable), and final UI design.

• Highlight how you navigated ambiguity, collaborated with cross-functional teams (Product, Engineering), and influenced product direction.

• Showcase your approach to problem definition and how you translated insights into tangible design solutions.

• Demonstrate your understanding of design system implementation and its role in maintaining product consistency.

• Provide evidence of your ability to own design work from conception through to implementation, including collaboration with engineering for design-to-code alignment.

📝 Enhancement Note: Given the Senior title and emphasis on "leading design," portfolios are expected to demonstrate strategic thinking, end-to-end ownership, and the ability to influence product direction. The specific mention of agentic tools implies that candidates should be prepared to discuss their experience with these advanced prototyping methods.

💵 Compensation & Benefits

Salary Range: For a Senior Product Designer with 5-10 years of experience working remotely globally, with an overlap in US working hours, a competitive salary range would typically fall between $130,000 - $180,000 USD annually. This estimate considers the seniority of the role, the demand for skilled product designers, and the global remote nature of the position, which often aligns with US market rates for experienced talent.

Benefits:

• Full-time, salaried position with competitive compensation.

• 100% Remote work environment, offering flexibility and global work opportunities.

• Potential for international team collaboration and exposure to a diverse, global user base.

• Opportunities to work on high-impact features for a leading online platform with millions of users.

• Contribution to a Design System and potential to influence design direction across the product.

• Professional development opportunities, including potential for learning new design tools and methodologies.

• The chance to be part of a company dedicated to connecting people through a shared passion for chess.

Working Hours: This is a full-time position, typically implying around 40 hours per week. The role requires at least 3 hours of overlap with US working hours to facilitate effective collaboration with the US-based teams.

📝 Enhancement Note: Salary is estimated based on industry benchmarks for senior remote product designers in markets that align with US tech compensation standards, considering the company's global reach and the role's seniority. Benefits are inferred from standard offerings for full-time remote positions in tech companies of this caliber, with a focus on flexibility and professional growth.

🎯 Team & Company Context

🏢 Company Culture

Industry: Online Gaming / Community Platform / Technology. Chess.com is a dominant player in the online chess and strategy game space, focusing on community, learning, and competition for a global audience.

Company Size: Chess.com operates as a large, established company within the online gaming sector. While the exact number isn't provided, their significant user base and product breadth suggest a robust operational structure, likely with hundreds of employees. This implies a professional environment with established processes and a significant impact potential for individual contributors.

Founded: Founded in 2007, Chess.com has grown to become the world's largest chess website. This long history indicates a stable company with a proven track record, a deep understanding of its user base, and a culture that values continuous improvement and adaptation.

Team Structure:

• The "Connect" team likely consists of a dedicated Product Manager, Engineering leads, and a group of Product Designers focused on user-facing social and engagement features.

• Designers will report into a Design Lead or Head of Design, working within a cross-functional pod structure alongside Product and Engineering.

• Collaboration is expected to be highly cross-functional, with designers working closely with Product Managers to define strategy and Engineers to ensure faithful implementation across platforms. Methodology:

• Data-driven decision-making, leveraging analytics to understand user behavior and inform design choices.

• Agile development methodologies, with a focus on iterative design and rapid prototyping.

• Emphasis on user-centric design, with a commitment to creating engaging and accessible experiences for a global community.

• A culture that values experimentation and learning, particularly in leveraging new tools like Cursor and Claude for design innovation.

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

📝 Enhancement Note: The company's focus on chess and community suggests a culture that values strategic thinking, continuous learning, and a passion for the product. The remote-first nature implies a strong emphasis on asynchronous communication, clear documentation, and trust.

📈 Career & Growth Analysis

Operations Career Level: This role is a Senior Product Designer. It signifies a level of expertise where the individual is expected to lead significant design efforts, influence product strategy, mentor junior designers (even without direct management), and operate with a high degree of autonomy. They are expected to be comfortable with ambiguity and drive complex projects to successful completion.

Reporting Structure: The Senior Product Designer will likely report to a Design Lead or Head of Design. They will work within cross-functional product teams (pods) alongside Product Managers and Engineers, collaborating closely on feature development.

Operations Impact: The "Connect" features are central to user retention and engagement on Chess.com. A Senior Product Designer in this area has a direct impact on how millions of players interact, socialize, and build community. Their work directly influences user satisfaction, platform stickiness, and overall community health, which are critical KPIs for a platform like Chess.com.

Growth Opportunities:

• Specialization: Deepen expertise in social design, community building, or specific platform design (web, iOS, Android).

• Leadership: Transition into a Lead Product Designer role, taking on more strategic oversight and potentially people management responsibilities in the future.

• Cross-functional Advancement: Move into Product Management or other strategic roles within the company, leveraging their deep understanding of user experience and product development.

• Tool Mastery: Become an expert in advanced design tools like Cursor and Claude, potentially influencing their adoption and best practices within the company.

• Mentorship: Guide and mentor junior designers, contributing to the growth of the design team.

📝 Enhancement Note: The Senior title implies a clear path for growth into leadership positions or specialized expert roles within the design organization. The focus on specific, high-impact features offers significant opportunities to demonstrate influence and drive tangible results.

🌐 Work Environment

Office Type: Chess.com is a 100% remote company. This means there is no central office. All employees work from their chosen locations globally.

Office Location(s): Remote (Global). Applicants must be able to overlap at least 3 hours with US working hours. This requirement is crucial for synchronous communication and collaboration with US-based teams.

Workspace Context:

• Collaborative Environment: Despite being remote, the company emphasizes proactive collaboration. This involves strong reliance on digital communication tools, clear documentation, and scheduled virtual meetings.

• Operations Tools & Technology: Access to industry-standard design software (e.g., Figma, Sketch) and potentially specialized tools like Cursor and Claude for prototyping. Robust communication platforms (e.g., Slack, Zoom) are essential.

• Team Interaction: Opportunities for team interaction will be primarily through virtual meetings, design critiques, and collaborative design sessions using shared digital workspaces.

Work Schedule: Full-time, with flexibility inherent in a remote role, but requiring a minimum of 3 hours of overlap with US working hours. This allows for core working hours where real-time collaboration is possible.

📝 Enhancement Note: The 100% remote nature requires candidates to be self-disciplined, excellent communicators, and comfortable working autonomously. The requirement for US working hour overlap is a critical logistical consideration for remote candidates.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio to assess experience, craft, and alignment with the role's requirements.

• Portfolio Presentation & Design Chat: A session where you present 1-2 key case studies from your portfolio, discussing your process, decisions, and impact. This will be followed by a discussion about your design philosophy and approach to complex problems.

• Cross-functional Interview: An interview with a Product Manager and/or Engineer from the Connect team to assess collaboration skills, understanding of product strategy, and ability to work effectively in a cross-functional environment.

• Design Critique Session: You may be asked to participate in a simulated design critique, providing feedback on a design artifact or discussing your approach to giving and receiving feedback.

• Final Interview: A conversation with a senior leader (e.g., Head of Design) to discuss career aspirations, cultural fit, and overall suitability for the Senior Product Designer role at Chess.com.

Portfolio Review Tips:

• Focus on Impact: Clearly articulate the problem you solved, your specific contributions, the design process, and the quantifiable outcomes or learnings.

• Showcase Craft: Ensure your UI designs are polished, demonstrating strong visual hierarchy, typography, and attention to detail.

• Explain Your "Why": Be prepared to articulate the rationale behind your design decisions, referencing user insights, heuristics, or strategic goals.

• Highlight Collaboration: Detail how you worked with Product, Engineering, and other stakeholders, and how you navigated feedback and disagreements.

• Address Tool Usage: Specifically mention and demonstrate your experience with tools like Cursor and Claude, explaining how they were leveraged to enhance the design process.

• Tailor to Chess.com: If possible, subtly tailor your case studies to reflect an understanding of community-building, engagement, or consumer-facing platforms.

Challenge Preparation:

• Be ready to discuss how you would approach designing a new social feature for Chess.com, considering user motivations, platform constraints, and business goals.

• Prepare to articulate your understanding of design systems and how you would ensure consistency across different platforms.

• Practice presenting your design thinking clearly and concisely, anticipating questions about your process and decision-making.

• Think about how you would handle situations with ambiguous requirements or conflicting stakeholder opinions.

📝 Enhancement Note: The interview process emphasizes practical application of design skills, strategic thinking, and collaborative ability. A strong portfolio that showcases end-to-end ownership and the use of advanced tools will be critical.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (standard for UI design and collaboration), Cursor (AI-powered IDE for design iteration and prototyping), Claude (AI assistant for design ideation, content generation, and rapid prototyping).

• Design Systems: Deep understanding and experience working with established design systems.

• Collaboration: Slack (real-time communication), Zoom (video conferencing for meetings and reviews).

Analytics & Reporting:

• While not explicitly listed, expect to work with tools that provide user analytics (e.g., Google Analytics, Amplitude, Mixpanel) to inform design decisions and measure impact.

• Proficiency in interpreting data to drive design improvements is essential. CRM & Automation:

• Not directly applicable to the Product Designer role, but understanding how user data flows from design implementation into CRM or other systems can be beneficial.

📝 Enhancement Note: The explicit mention of Cursor and Claude is a significant indicator of the team's tooling and workflow. Candidates should be prepared to discuss their experience and comfort level with these AI-assisted design tools. Familiarity with Figma is a given for most UI/UX roles.

👥 Team Culture & Values

Operations Values:

• User-Centricity: A deep commitment to understanding and serving the needs of Chess.com's diverse global player base.

• Craftsmanship: A dedication to high-quality visual design, intuitive interactions, and a polished user experience.

• Collaboration: Proactive, open, and respectful communication and teamwork across remote, cross-functional teams.

• Innovation: Embracing new technologies and methodologies (like AI-assisted design) to push the boundaries of product experience.

• Community: Fostering a sense of belonging and connection among players, reflected in the design of social features.

• Autonomy & Ownership: Empowering individuals to take initiative, drive projects, and make impactful decisions.

Collaboration Style:

• Asynchronous First: Due to the global remote nature, emphasis is placed on clear written communication, detailed documentation, and well-structured asynchronous updates.

• Intentional Synchronicity: Scheduled meetings and focused collaboration sessions are used for critical discussions, brainstorming, and decision-making, ensuring alignment and efficient progress.

• Constructive Critique: A culture of open, honest, and constructive feedback within design critiques to collectively elevate the quality of work.

• Cross-functional Partnership: Designers are integrated into product teams, working as equal partners with Product Managers and Engineers to achieve shared goals.

📝 Enhancement Note: The culture values individuals who are proactive, self-motivated, and adept at remote collaboration. The emphasis on community and craftsmanship aligns with Chess.com's brand and mission.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Scale: Creating engaging social features for millions of diverse users globally requires careful consideration of scalability, accessibility, and cultural nuances.

• Balancing Ambiguity and Structure: Working in a fast-paced, remote environment with evolving product priorities requires comfort with ambiguity and the ability to create structure and clarity.

• Cross-Platform Consistency: Ensuring a cohesive and high-quality user experience across web, iOS, and Android platforms presents ongoing technical and design challenges.

• Leveraging AI Tools Effectively: Integrating new and potentially evolving AI-assisted tools like Cursor and Claude into established design workflows requires adaptation and strategic application.

• Maintaining Design Ownership: Effectively managing design through implementation in a remote setting requires strong communication and partnership with engineering teams.

Learning & Development Opportunities:

• Advanced Tool Mastery: Becoming proficient with cutting-edge AI design tools like Cursor and Claude, potentially becoming a go-to resource for the team.

• Social Design Expertise: Deepening knowledge and practical skills in designing for community, engagement, and social interaction in a digital platform context.

• Strategic Product Influence: Developing skills in influencing product roadmaps and design strategy through data-driven insights and compelling proposals.

• Cross-functional Leadership: Gaining experience leading design initiatives within cross-functional pods, enhancing skills in communication, negotiation, and stakeholder management.

• Mentorship: Opportunities to mentor junior designers, refining leadership and communication skills.

📝 Enhancement Note: The challenges are inherent to a senior role at a large, global, remote company. The growth opportunities are substantial, particularly in areas like advanced tooling and strategic product influence.

💡 Interview Preparation

Strategy Questions:

• "How would you approach designing a new 'Friends' feature for Chess.com, considering user motivations for connection and the platform's existing social elements?" (Focus on problem framing, user needs, and iterative design process.)

• "Describe a time you had to influence product or design decisions when faced with competing priorities or differing opinions from stakeholders. What was your approach, and what was the outcome?" (Highlight communication, negotiation, and strategic thinking.)

• "Walk us through a complex product design challenge you faced. How did you break down the problem, what design process did you employ, and how did you ensure a high-quality outcome?" (Emphasize end-to-end ownership, problem-solving, and process rigor.) Company & Culture Questions:

• "What interests you about Chess.com and our mission to connect players through chess?" (Show genuine interest and research into the company.)

• "How do you approach collaboration in a remote, cross-functional team environment?" (Discuss your preferred communication methods, documentation habits, and proactive engagement strategies.)

• "How do you measure the success of your designs, particularly for features focused on user connection and engagement?" (Discuss key metrics and how you use data to inform design decisions.) Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly define the problem, your role, the process, key decisions, challenges, and outcomes.

• Focus on "Why": Articulate the rationale behind your design choices, linking them to user needs, business goals, or design principles.

• Show, Don't Just Tell: Use high-fidelity visuals and interactive prototypes to demonstrate your UI craft and interaction design skills.

• Highlight AI Tool Usage: Specifically explain how you utilized Cursor and Claude to iterate, prototype, or solve design problems, showcasing innovative workflow.

• Be Concise and Engaging: Practice your presentation to ensure it's clear, engaging, and within the allotted time. Be prepared for follow-up questions.

📝 Enhancement Note: Interview preparation should focus on demonstrating strategic thinking, strong problem-solving skills, excellent communication, and a deep understanding of user-centered design, particularly within a social and community context. Specific preparation for discussing AI tools is crucial.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the provided link on ats.rippling.com/chess/jobs/02e2145b-d211-4b96-a8a8-82abefee0ae4.

• Curate Your Portfolio: Select 2-3 of your strongest case studies that best represent your experience in designing consumer-facing web and mobile products, ideally showcasing social or community features. Ensure each case study clearly outlines your process, contributions, and the impact of your work. Specifically highlight instances where you used advanced tools like Cursor and Claude.

• Optimize Your Resume: Tailor your resume to highlight your 5+ years of relevant experience, focusing on achievements in product design, UI/UX, and cross-functional collaboration. Use keywords from the job description such as "Product Design," "UI Design," "Design Systems," "Prototyping," "Cursor," and "Claude."

• Prepare Your Presentation: Practice walking through your chosen case studies, focusing on clear articulation of your design process, decision-making rationale, and quantifiable outcomes. Be ready to discuss your experience with remote collaboration and AI-assisted design tools.

• Research Chess.com: Familiarize yourself with Chess.com's platform, user base, and existing "Connect" features. Understand their mission and values to better tailor your responses and demonstrate cultural fit.

⚠️ 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.