Sr. Product Designer

📍 Job Overview

Job Title: Sr. Product Designer

Company: Chalkboard

Location: New York, New York, United States

Job Type: FULL_TIME

Category: Product Design / GTM Operations

Date Posted: February 26, 2026

Experience Level: 5-10 Years

Remote Status: Hybrid (Remote within the United States)

🚀 Role Summary

• This Sr. Product Designer role is pivotal in shaping the user experience for a cutting-edge sports gaming platform, focusing on intuitive design for complex gaming mechanics.

• The position requires end-to-end ownership of the design process, from initial product discovery and user research to polished UI and successful feature launches.

• Collaboration is key, involving close partnerships with Product, Engineering, Growth, and Leadership teams to drive engagement, retention, and revenue through user-centered design.

• A significant aspect of this role involves contributing to and evolving a scalable design system, ensuring consistency and efficiency across all product surfaces.

📝 Enhancement Note: While the role is for a "Sr. Product Designer," the emphasis on driving engagement, retention, and revenue, along with close collaboration with Growth and Product teams, strongly indicates a significant GTM (Go-To-Market) operations component. The role requires not just aesthetic design but also a deep understanding of user journeys that lead to conversion and sustained user activity. The "play to win" and "insight into action" language further suggests a focus on how design directly impacts business outcomes within the sports gaming context.

📈 Primary Responsibilities

• Lead product discovery initiatives by collaborating with Product and Engineering to gain a deep understanding of user behaviors, motivations, and pain points within the sports gaming landscape.

• Translate user insights and business requirements into well-structured UX flows, wireframes, interactive prototypes, and high-fidelity visual designs that enhance the Chalkboard user experience.

• Own the end-to-end design process for key product surfaces, ensuring a seamless and intuitive user journey from initial concept through to shipped features.

• Continuously refine, evolve, and contribute to the company's design system to maintain consistency, improve scalability, and accelerate design and development velocity.

• Design and iterate on mobile-first experiences, prioritizing clarity, usability, performance, and overall user delight in a competitive market.

• Partner with the Growth team to design and implement experiments (A/B tests) aimed at optimizing onboarding flows, engagement loops, and monetization strategies.

• Present design rationale and solutions clearly and confidently to cross-functional teams and leadership, grounding decisions in user needs, business objectives, and available data.

• Champion product quality and user experience standards across the organization, acting as a key advocate for the user.

📝 Enhancement Note: The responsibilities highlight a blend of strategic design thinking and tactical execution, typical of senior roles in fast-paced tech environments. The emphasis on "revenue," "engagement," and "monetization" directly ties this design role into GTM operations by focusing on how design contributes to business performance metrics. The requirement to "simplify complex sports gaming mechanics" is a core GTM challenge, ensuring product adoption and user retention.

🎓 Skills & Qualifications

Education:

Experience:

• 5-10 years of proven experience designing consumer-facing digital products, with a strong preference for mobile-first experiences.

• Demonstrated experience working cross-functionally with Product Managers, Engineers, and Growth teams in agile, fast-paced environments.

• Experience in the gaming, sports, betting, or Daily Fantasy Sports (DFS) industries is highly advantageous.

Required Skills:

• Portfolio: A strong portfolio showcasing end-to-end product thinking, from UX strategy and user research to polished UI design and shipped features.

• Design Tools: Fluency in modern design and prototyping tools, with specific emphasis on Figma.

• UX Strategy: Proven ability to define user journeys, conduct user research, and translate findings into intuitive product experiences.

• Interaction Design & IA: Deep understanding of interaction design principles, information architecture, and visual hierarchy to create clear and effective user flows.

• Cross-functional Collaboration: Ability to effectively partner with Engineering, Product, and Growth teams, ensuring seamless design implementation and iteration.

Preferred Skills:

• Design Systems: Experience contributing to or building scalable design systems.

• Experimentation: Familiarity with experimentation frameworks and A/B testing methodologies for product optimization.

• Sports/Gaming Domain: Experience designing for gaming, sports, betting, DFS, or other high-engagement consumer products.

• Startup Environment: Proven ability to thrive in ambiguous, fast-paced startup settings.

📝 Enhancement Note: The "Pro Points" section strongly suggests a need for candidates who can not only design but also understand the business implications of their designs, particularly in driving user acquisition, engagement, and monetization. This aligns with GTM operations, where design directly influences market performance.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• End-to-End Product Thinking: Showcase a minimum of 2-3 comprehensive case studies demonstrating ownership of the entire design lifecycle, from problem definition and user research to iterative design solutions and final UI.

• UX Strategy & User Flows: Clearly articulate the problem, your strategic approach, user research findings, and how these informed the creation of intuitive UX flows and wireframes.

• UI Design & Polish: Present high-fidelity mockups and interactive prototypes that highlight attention to detail, visual hierarchy, and a strong sense of aesthetic appeal consistent with a modern consumer product.

• Impact & Iteration: Demonstrate how your designs addressed specific user needs or business goals, ideally with examples of how data, user feedback, or A/B testing informed iterations and improved outcomes.

Process Documentation:

• Design System Contribution: If applicable, showcase examples of how you've contributed to or utilized design systems to ensure scalability and consistency.

• Cross-functional Workflows: Briefly describe your process for collaborating with Product Managers and Engineers, including how you hand off designs and iterate based on technical feasibility and feedback.

• Experimentation Design: If you have experience with A/B testing, illustrate how you designed variations for experiments and what metrics were used to evaluate success.

📝 Enhancement Note: For a Sr. Product Designer role with GTM implications, the portfolio should not just be a showcase of visual design but a testament to problem-solving, strategic thinking, and measurable impact. Demonstrating how designs directly influenced user acquisition, engagement, or revenue is crucial.

💵 Compensation & Benefits

Salary Range: $180,000 - $200,000 per year

Benefits:

• Health Coverage: Employee-sponsored medical, dental, and vision coverage starting within 30 days of employment. Chalkboard covers 80% for employees and 70% for dependents.

• Retirement Savings: 401(k) plan with a company match.

• Daily Meals: Corporate DoorDash account for daily lunch.

• Office Refreshments: Access to protein shakes, energy drinks, and a snack buffet in the office.

• Flexible Time Off: Generous flexible time off policy.

• Holidays: 10 company holidays, with work-from-home flexibility during the holiday period.

• Potential for Bonus & Equity: While not explicitly detailed, roles at this level in high-growth startups often include performance-based bonuses and/or equity options.

Working Hours:

• Standard 40 hours per week, with flexibility offered through the PTO policy.

📝 Enhancement Note: The salary range is competitive for a Sr. Product Designer in New York City, especially for a high-growth startup. The benefits package is robust, with a strong emphasis on employee well-being and daily perks that are attractive to team members. The inclusion of "WFH during the holidays" points to a culture that balances work with personal time, even within a demanding startup environment. The potential for bonus and equity is a standard expectation for senior roles in this sector and should be clarified during the interview process.

🎯 Team & Company Context

🏢 Company Culture

Industry: Sports Gaming / Technology / Entertainment

Company Size: Small to Medium-sized (Likely between 50-200 employees, given the "early-stage or high-growth startup" preference)

Founded: Chalkboard was founded to innovate in the sports gaming space, aiming to create a more immersive and social experience than traditional betting apps. The company values clarity, fairness, and enabling fans to translate their insights into winning actions.

Team Structure:

• The design team likely operates within a lean, cross-functional pod structure, working closely with dedicated Product Managers and Engineers.

• Designers are expected to be highly autonomous, taking ownership of product areas and driving initiatives from conception to launch.

Methodology:

• Data-Driven Design: Decisions are informed by user research, data analytics, and A/B testing, rather than solely relying on intuition.

• Agile Development: The company operates in a fast-paced environment, requiring rapid iteration and adaptation.

• User-Centricity: A strong focus on understanding and solving user problems within the sports gaming context.

• Iterative Improvement: A culture that embraces shipping quickly, learning from results, and continuously refining features.

Company Website: https://chalkboard.io/

📝 Enhancement Note: The company's mission to "blur the line between watching and playing" and create a "social, immersive experience" suggests a product that is both functional and highly engaging. The emphasis on "sports-obsessed builders" and "fans who play to win" indicates a culture that deeply understands its target audience, which is critical for GTM success.

📈 Career & Growth Analysis

Operations Career Level: Senior Individual Contributor (IC) in Product Design. This role is expected to operate with a high degree of autonomy, lead significant product initiatives, and mentor junior designers if the team grows. The "Play Like a Captain" section implies leadership in driving projects and raising the bar for quality.

Reporting Structure: The Sr. Product Designer will likely report to a Head of Product, Design Lead, or a senior Product Manager, depending on the current organizational structure. Close daily collaboration with Product Managers and Engineering leads is expected.

Operations Impact: This role has a direct and significant impact on key business metrics such as user acquisition, activation, engagement, retention, and revenue. By simplifying complex gaming mechanics and designing effective monetization and engagement loops, the designer directly contributes to Chalkboard's GTM success and overall business growth.

Growth Opportunities:

• Design Leadership: Opportunity to shape the future of the design function and potentially lead a growing design team as the company scales.

• Product Strategy Influence: Deep involvement in product discovery and strategy, allowing for significant influence on the product roadmap.

• Domain Expertise: Develop deep expertise in the rapidly evolving sports gaming and real-money gaming industry.

• Cross-functional Skill Development: Enhance skills in areas like growth experimentation, user research, and stakeholder management through close collaboration.

• Startup Experience: Gain invaluable experience in a high-growth startup environment, learning to navigate ambiguity and drive impact rapidly.

📝 Enhancement Note: The "Sr." title and emphasis on ownership, minimal oversight, and raising the bar suggest significant growth potential. The company's focus on "winning as a team" and the growth of its members implies that opportunities for advancement into leadership or specialized product roles will be available as Chalkboard scales.

🌐 Work Environment

Office Type: The role is listed as "TELECOMMUTE" and "remote_derived": true, with a primary location in New York. This suggests a hybrid work model where employees can work remotely within the United States, potentially with occasional in-office collaboration in New York. The "Lunch on us everyday with a corporate DoorDash account" and "Refuel in the office with protein shakes, energy drinks, and a snack buffet" imply a physical office space that is utilized and designed to support employees.

Office Location(s): Primary focus on New York, New York, United States, but with remote flexibility for candidates within the US.

Workspace Context:

• Collaborative Environment: The need for daily collaboration with Product, Engineering, and Growth teams suggests a dynamic, interactive work setting, whether in-person or virtual.

• Tech-Enabled: Access to modern design tools (Figma) and likely other collaboration platforms (Slack, etc.) is standard. The physical office likely has amenities to support focused work and team interaction.

• Team Interaction: Opportunities for design critiques, brainstorming sessions, and knowledge sharing are encouraged, fostering a strong design culture.

Work Schedule:

• A standard 40-hour work week is expected, aligning with the "FULL_TIME" employment type.

• The "Flexible time off policy, plus 10 company holidays, WFH during the holidays" indicates a culture that values work-life balance and offers flexibility where possible.

📝 Enhancement Note: The hybrid nature of the role, coupled with the strong emphasis on in-office perks (lunch, snacks, drinks), suggests that while remote work is supported, the company culture likely encourages some level of in-person interaction for team building and collaborative sessions, especially for key strategic discussions or design sprints.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screen: A brief call with a recruiter to assess basic qualifications, interest, and cultural fit.

• Portfolio Review & Design Challenge: Presentation of your portfolio, focusing on end-to-end product thinking and impact. This is often followed by a design exercise or case study, either take-home or live, to assess problem-solving skills and design process.

• Cross-functional Interviews: Interviews with Product Managers, Engineers, and potentially Growth team members to evaluate collaboration skills, technical understanding, and strategic thinking.

• Leadership Interview: A final interview with a senior leader (e.g., Head of Product, CEO) to discuss vision, strategic alignment, and overall fit within the company.

Portfolio Review Tips:

• Tell a Story: Structure your case studies to clearly articulate the problem, your role, the process you followed, the solutions you designed, and the impact achieved.

• Focus on Impact: Quantify results whenever possible. Highlight how your designs contributed to user engagement, retention, revenue, or other key business metrics.

• Showcase Process: Demonstrate your thought process, including user research, ideation, wireframing, prototyping, and iteration.

• Highlight Collaboration: Mention how you worked with Product, Engineering, and other stakeholders.

• Tailor to Chalkboard: Emphasize any experience with consumer-facing products, mobile design, gaming, or high-growth environments. Show how you've simplified complex systems.

Challenge Preparation:

• Understand the Domain: Familiarize yourself with sports gaming, betting, and DFS mechanics. Think about common user pain points and opportunities for innovation.

• Practice Design Exercises: Be prepared for exercises that might involve ideating on a new feature, redesigning an existing flow, or solving a specific user problem within the sports gaming context.

• Articulate Your Rationale: Be ready to explain the "why" behind every design decision, linking it back to user needs and business goals.

• Consider Constraints: Understand that startup environments often require balancing speed with craft, so be prepared to discuss how you prioritize and make trade-offs.

📝 Enhancement Note: Given the emphasis on GTM impact, be prepared to discuss how your design decisions directly influence user acquisition, activation, retention, and monetization. Showcasing how you've used data and experimentation to drive these metrics will be critical.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (primary tool, fluency required).

• Collaboration: Slack, Zoom, Google Workspace (or similar).

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

Analytics & Reporting:

• User Analytics: Tools like Amplitude, Mixpanel, or Google Analytics are likely used to track user behavior and product performance.

• A/B Testing Platforms: Familiarity with tools like Optimizely, VWO, or in-house experimentation frameworks.

• Data Visualization: Potentially tools like Tableau or Looker for deeper data analysis.

CRM & Automation:

• While not directly used by designers, understanding how CRM (e.g., Salesforce, HubSpot) and marketing automation tools function can provide context for user journeys and growth initiatives.

📝 Enhancement Note: Proficiency in Figma is explicitly required. Experience with analytics and A/B testing tools is highly preferred and essential for demonstrating the impact of design decisions, particularly in a GTM context. Understanding how design integrates with growth marketing efforts is key.

👥 Team Culture & Values

Operations Values:

• Clarity & Fairness: Core tenets of the company, implying transparent communication and equitable user experiences.

• Thrill of Helping Fans: Focus on empowering users and enhancing their sports gaming experience.

• Teamwork & Accountability: Emphasis on winning as a team, collective responsibility, and delivering results.

• Building from Scratch: A culture that embraces innovation, iteration, and tackling new challenges.

• Speed & Craft: Balancing the need for rapid execution with a commitment to high-quality design.

Collaboration Style:

• Cross-functional Integration: Daily collaboration with Product, Engineering, and Growth is expected, fostering a tightly integrated team dynamic.

• Constructive Critique: An environment where feedback is openly shared and incorporated to improve designs and processes.

• Transparency: Open communication about goals, challenges, and decisions.

• Agile & Iterative: A willingness to adapt, experiment, and learn quickly from both successes and failures.

📝 Enhancement Note: The company culture appears to be fast-paced, results-oriented, and highly collaborative, with a strong emphasis on user-centricity and teamwork. The "play to win" mentality extends beyond the users to the internal team, suggesting a driven and competitive spirit.

⚡ Challenges & Growth Opportunities

Challenges:

• Simplifying Complexity: Translating intricate sports gaming mechanics and real-money betting rules into intuitive and user-friendly interfaces.

• Balancing Speed and Craft: Delivering high-quality designs rapidly in a fast-paced startup environment where priorities can shift quickly.

• Driving Engagement & Monetization: Designing features that not only attract users but also keep them engaged and encourage spending in a competitive market.

• Building Scalable Design Systems: Ensuring the design system can support rapid feature development and evolving product needs without becoming a bottleneck.

• Navigating Ambiguity: Thriving in a startup environment where not all processes are established and requirements can evolve.

Learning & Development Opportunities:

• Deep Domain Expertise: Become a specialist in the sports gaming and real-money gaming industry, understanding user psychology and market dynamics.

• Product Strategy Impact: Gain significant experience in shaping product strategy and roadmaps at a growing company.

• Growth Experimentation: Develop expertise in designing and interpreting A/B tests to optimize user acquisition, engagement, and monetization funnels.

• Design Leadership: Opportunity to grow into a leadership role, guide design direction, and potentially manage a team.

• Startup Acumen: Acquire broad experience in building a company from the ground up, understanding various facets of business operations beyond design.

📝 Enhancement Note: The challenges are typical of a senior role in a high-growth tech startup, particularly in a regulated and competitive industry like sports gaming. The growth opportunities are substantial, offering a path for both design and product leadership.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you simplified a complex user flow. What was the problem, your approach, and the outcome?" (Focus on sports gaming context if possible).

• "How do you balance user needs with business objectives (like revenue and engagement) in your designs?"

• "Walk us through a challenging cross-functional collaboration experience. How did you ensure alignment and successful delivery?"

Company & Culture Questions:

• "What excites you about Chalkboard's mission and the sports gaming industry?"

• "How do you contribute to a positive and productive team culture, especially in a remote/hybrid setting?"

• "Describe your experience working in a fast-paced startup environment."

Portfolio Presentation Strategy:

• Structure: Use a clear narrative for each case study: Problem -> Research -> Solution -> Impact.

• Quantify: For each project, highlight the business impact (e.g., "increased conversion by X%", "reduced drop-off by Y%", "improved engagement metrics by Z%").

• Process Emphasis: Clearly show your design process, including user flows, wireframes, and iterations.

• Collaboration: Mention how you worked with Product, Engineering, and Growth teams.

• Tailor: For Chalkboard, emphasize projects that demonstrate experience with mobile-first design, consumer products, simplifying complex systems, and driving engagement/monetization.

📝 Enhancement Note: Be prepared to discuss how your design work directly influences GTM outcomes such as user acquisition, activation, retention, and monetization. Demonstrating an understanding of growth loops and experimentation is crucial for this role.

📌 Application Steps

To apply for this Sr. Product Designer position:

• Submit your application through the provided link on Ashby.

• Portfolio Customization: Ensure your portfolio prominently features 2-3 strong case studies that showcase end-to-end product thinking, with a clear emphasis on user impact and business results relevant to consumer-facing digital products.

• Resume Optimization: Tailor your resume to highlight experience in mobile-first design, cross-functional collaboration, working in fast-paced environments, and any relevant domain experience (gaming, sports, betting). Use keywords from the job description.

• Interview Preparation: Practice articulating your design process, rationale, and the impact of your work. Prepare specific examples for behavioral questions and be ready to walk through your portfolio with confidence.

• Company Research: Thoroughly research Chalkboard, its mission, target audience, and the sports gaming industry. Understand their competitive landscape and identify potential design opportunities.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions based on the provided data. All details, particularly regarding team structure, specific processes, and exact interview steps, should be verified directly with the hiring organization during the application process.