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 / UX/UI

Date Posted: April 06, 2026

Experience Level: 5-10 Years

Remote Status: Remote (within the United States)

🚀 Role Summary

• Lead the end-to-end product design process for a cutting-edge sports gaming platform, focusing on user engagement and revenue generation.

• Translate complex gaming mechanics and user insights into intuitive, seamless, and high-impact mobile-first user experiences.

• Drive product discovery and iteration through cross-functional collaboration with Product, Engineering, and Growth teams in a fast-paced startup environment.

• Develop and maintain a scalable design system to ensure consistency and efficiency across all product surfaces.

• Utilize data, user research, and experimentation to inform design decisions and optimize key performance indicators like onboarding, retention, and monetization.

📝 Enhancement Note: The role is explicitly for a "Sr. Product Designer" with an estimated 5-10 years of experience, indicating a need for a candidate who can independently own significant product initiatives and mentor others. The focus on "sports gaming," "mobile-first," "revenue," and "growth" suggests a strong emphasis on business impact and user acquisition/retention strategies, common in early-stage consumer tech startups.

📈 Primary Responsibilities

• Own the complete product design lifecycle, from initial concept exploration, user research, and wireframing to high-fidelity UI design and final implementation oversight.

• Conduct in-depth product discovery sessions with Product and Engineering to identify user pain points, motivations, and opportunities within the sports gaming ecosystem.

• Craft clear, intuitive user flows, wireframes, prototypes, and polished visual designs specifically tailored for mobile-first consumer applications.

• Design and evolve a robust design system, ensuring consistency, scalability, and efficient collaboration across the product development team.

• Collaborate closely with Growth teams to design and implement experiments (A/B tests) aimed at optimizing onboarding funnels, engagement loops, and monetization strategies.

• Translate complex sports gaming mechanics and betting logic into easily understandable and actionable user journeys.

• Partner with Engineering to ensure accurate and high-quality implementation of designs, maintaining pixel-perfect execution and optimal performance.

• Champion user-centric design principles, advocating for user needs and leveraging qualitative and quantitative data to validate design decisions.

• Continuously raise the bar for product quality, user experience, and aesthetic appeal across the Chalkboard platform.

• Contribute to building a strong, transparent, and collaborative design culture within the company.

📝 Enhancement Note: The responsibilities emphasize a blend of strategic product thinking (discovery, user behavior, business impact) and tactical execution (UI design, prototyping, design systems). The specific mention of "gaming, sports, betting, DFS" and "monetization surfaces" indicates a need for design expertise in highly engaging, potentially complex, and revenue-driven consumer applications. The expectation to "design experiments" and "leverage user research, data, and testing" highlights the data-informed nature of the role.

🎓 Skills & Qualifications

Education: While not explicitly stated, a Bachelor's or Master's degree in Design, Human-Computer Interaction, or a related field is typically preferred for senior-level product design roles. Equivalent practical experience will also be strongly considered.

Experience: A minimum of 5-10 years of professional experience in product design, with a significant focus on consumer-facing digital products, preferably mobile applications. Experience in gaming, sports, betting, or DFS industries is a strong plus.

Required Skills:

• Proven end-to-end product design experience, demonstrated through a strong portfolio showcasing UX strategy, wireframing, prototyping, and polished UI design.

• Fluency in modern design and prototyping tools, with Figma being a primary requirement.

• Deep understanding of interaction design principles, information architecture, and visual hierarchy for creating intuitive user interfaces.

• Experience designing for mobile-first environments, optimizing for usability, clarity, and performance on smaller screens.

• Demonstrated ability to translate complex concepts and systems into simple, user-friendly flows and experiences.

• Experience collaborating effectively with cross-functional teams, including Product Managers and Engineers, in fast-paced, agile environments.

• Strong presentation skills, with the ability to clearly articulate design decisions and ground them in user needs, business goals, and data insights.

Preferred Skills:

• Experience designing specifically for gaming, sports, betting, daily fantasy sports (DFS), or similar high-engagement consumer products.

• Familiarity with experimentation frameworks, A/B testing methodologies, and data analysis for design optimization.

• Experience contributing to or building scalable design systems.

• A proactive approach to product discovery and user research.

📝 Enhancement Note: The "Pro Points" section clearly outlines preferred qualifications, suggesting that candidates with experience in the gaming/betting sector and familiarity with experimentation will have a distinct advantage. The emphasis on "mobile-first," "Figma," and "end-to-end product thinking" are critical keywords for ATS screening.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase end-to-end product thinking, including the process from initial problem definition and user research through to final UI and shipped features.

• Highlight case studies demonstrating how you translated complex user problems or business requirements into elegant and effective design solutions.

• Include examples of mobile-first design experiences, detailing the specific considerations for mobile platforms.

• Demonstrate proficiency with modern design tools, particularly Figma, showcasing your ability to create detailed wireframes, interactive prototypes, and high-fidelity UIs.

Process Documentation:

• Clearly articulate your design process for at least 2-3 significant projects, detailing the phases: discovery, ideation, design, testing, and iteration.

• For each project, explain the rationale behind your design decisions, supported by user research findings, data insights, or A/B test results where applicable.

• Describe your approach to user research and how you gathered insights to inform your designs.

• Illustrate your experience with design systems, including how you contributed to or utilized them for consistency and efficiency.

• Show how you balanced speed and craft, explaining when you prioritized rapid iteration versus deep design exploration.

📝 Enhancement Note: For a senior design role, especially in a startup, the portfolio is paramount. It needs to prove not just visual design skills but also strategic thinking, problem-solving capabilities, and the ability to drive product outcomes. Emphasizing "end-to-end," "user research," "data," and "collaboration" will be key.

💵 Compensation & Benefits

Salary Range: $185,000 - $200,000 USD per year

Benefits:

• Comprehensive medical, dental, and vision coverage, with the majority of premiums covered by Chalkboard, effective within 30 days of employment.

• 401(k) plan with a company match to support long-term financial planning.

• Daily lunch provided through a corporate DoorDash account, offering flexibility and convenience.

• Well-stocked office with protein shakes, energy drinks, and a snack buffet for employee refreshment and energy.

• Flexible time off (PTO) policy allowing for work-life balance.

• 10 company holidays observed, plus the option to work from home during holiday periods.

• Equity options, reflecting a stake in the company's growth and success.

• Bonus opportunities, tied to individual and company performance.

Working Hours: The role is full-time, and while specific hours aren't mandated, a standard 40-hour work week is expected, with flexibility likely offered due to the remote nature and startup culture. The emphasis on "fast-moving environments" and "shipping and iterating" suggests a need for dedication and adaptability.

📝 Enhancement Note: The salary range is explicitly provided. The benefits list is extensive and includes specific details like "majority of premiums covered" and "within 30 days," which are attractive to candidates. The "corporate DoorDash account" and "snack buffet" highlight perks common in tech startups focused on employee comfort and productivity. Equity and bonus are standard for senior roles in growing companies.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, specifically Sports Gaming & Entertainment. Chalkboard operates at the intersection of sports, technology, and real-money gaming, aiming to create an immersive and social fan experience. This industry is characterized by rapid innovation, high engagement, and a focus on user acquisition and retention.

Company Size: Chalkboard is likely an early-stage startup, given the description of "building from scratch" and "fast-moving environments." This implies a lean, agile team where individual contributions have a significant impact.

Founded: The founding date is not specified, but the company's mission to "build the future of sports gaming" suggests a relatively new venture focused on disrupting the existing market.

Team Structure:

• The design team, while not explicitly detailed in size, will likely be integrated closely with Product Management and Engineering.

• The Sr. Product Designer will report to a Head of Product or Design Lead, and will collaborate daily with engineers and product managers.

Methodology:

• Data-driven decision-making is emphasized, with a requirement to leverage "user research, data, and testing" to inform design.

• Agile development methodologies are implied by the "fast-moving environments" and the need to "rapidly test, iterate, and refine features."

• A strong emphasis on user-centric design and continuous improvement through iteration and experimentation.

Company Website: https://chalkboard.io/

📝 Enhancement Note: The company description positions Chalkboard as an innovative player in the sports gaming space, differentiating itself from traditional betting apps. The culture is described as "sports-obsessed," valuing "clarity, fairness, and the thrill of helping fans turn insight into action," which provides insight into the team's passion and core values. The "MVP" vs. "win as a team" comment suggests a collaborative, not individualistic, high-performance culture.

📈 Career & Growth Analysis

Operations Career Level: This role is designated as "Sr. Product Designer," indicating a senior individual contributor position. It requires significant autonomy, strategic thinking, and the ability to lead design initiatives from conception to launch with minimal oversight. The expectation is to "raise the bar for product quality" and "own major product initiatives."

Reporting Structure: The Sr. Product Designer will likely report to a Head of Product or Design Lead. They will work daily with Product Managers and Software Engineers, forming a core product triad. Collaboration will extend to Growth, Marketing, and company Leadership.

Operations Impact: The Sr. Product Designer will have a direct and substantial impact on user engagement, retention, and revenue through the design of core product features and user journeys. Their work will be instrumental in shaping how users interact with Chalkboard, directly influencing the company's success in the competitive sports gaming market. The role demands balancing user needs with business objectives, particularly monetization.

Growth Opportunities:

• Leadership in Design: Potential to grow into a Design Lead or Manager role as the company scales, mentoring junior designers and shaping the overall design strategy.

• Strategic Influence: Opportunity to significantly influence product strategy and roadmap based on design insights and user feedback.

• Domain Expertise: Deepen expertise in the rapidly evolving sports gaming and real-money gaming industries.

• Skill Development: Continuous learning through working on complex, innovative features, and potentially exposure to new technologies and design challenges.

• Company Growth: Participate in the growth trajectory of an early-stage startup, with potential for significant career advancement and financial reward through equity.

📝 Enhancement Note: The "Sr." title implies a level of mentorship and strategic contribution beyond typical design tasks. Growth opportunities are framed around leadership, strategic influence, and industry specialization, reflecting the potential of an early-stage company.

🌐 Work Environment

Office Type: Chalkboard offers a hybrid work environment, with the explicit mention of a "corporate DoorDash account" and "Refuel in the office" suggesting a physical office space is utilized for collaboration and amenities, even though the role is remote-friendly. The "WFH during the holidays" also points to a hybrid model.

Office Location(s): The primary location is New York, New York. While the role is remote within the United States, the presence of an office in NYC indicates it may serve as a hub for key meetings and collaborative sessions.

Workspace Context:

• A dynamic and fast-paced startup environment where adaptability and quick iteration are key.

• A collaborative atmosphere where designers work closely with Product, Engineering, and Growth teams, fostering a sense of shared ownership.

• Access to office amenities such as daily catered lunches, snacks, and beverages, suggesting a culture that supports employee well-being and productivity.

• A remote-friendly setup for individual work, balanced with potential in-person collaboration opportunities in the New York area.

Work Schedule: While a standard 40-hour work week is assumed, the startup environment often requires flexibility and dedication. The emphasis on "shipping and iterating" and "balancing speed and craft" suggests that successful candidates will be able to manage their time effectively to meet project deadlines, likely with some autonomy over their daily schedule within the remote framework.

📝 Enhancement Note: The "Hybrid" work arrangement implies a need for candidates comfortable with both remote work and occasional in-office collaboration, likely centered around the New York location. The description of office perks suggests a company culture that invests in employee comfort and productivity.

📄 Application & Portfolio Review Process

Interview Process:

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

• Portfolio Presentation: A dedicated session where you will present your portfolio, walking through key projects, your design process, and the impact of your work. This is a critical stage to demonstrate end-to-end product thinking.

• Design Exercise/Challenge: You may be asked to complete a design exercise, either take-home or live, to assess your problem-solving skills, design approach, and ability to work within constraints. This could involve critiquing an existing flow or designing a new feature.

• Cross-Functional Interviews: Interviews with Product Managers, Engineers, and potentially Growth team members to evaluate collaboration skills, communication style, and understanding of technical constraints and business goals.

• Leadership Interview: A final interview with a senior leader (e.g., Head of Product, CEO) to assess cultural fit, strategic alignment, and long-term potential.

Portfolio Review Tips:

• Curate Strategically: Select 3-4 of your strongest projects that best demonstrate end-to-end product thinking, mobile-first design, and ideally, experience in consumer-facing or high-engagement products.

• Tell a Story: For each case study, clearly outline the problem, your role, the process you followed (discovery, ideation, design, testing), your specific contributions, the challenges faced, and the measurable outcomes or impact.

• Highlight Process & Rationale: Don't just show final screens; explain why you made certain design decisions. Reference user research, data, or business objectives.

• Showcase Figma Proficiency: Be prepared to discuss your workflow in Figma, including how you manage design systems, collaborate with others, and create interactive prototypes.

• Quantify Impact: Wherever possible, use data and metrics to demonstrate the success of your designs (e.g., increased conversion rates, improved user satisfaction, reduced friction).

• Tailor to Chalkboard: Research Chalkboard's current product and target audience. Highlight projects that show an understanding of their domain (sports gaming) and user base.

Challenge Preparation:

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

• Practice Whiteboarding/Flows: Be ready to sketch out user flows or wireframes quickly on a whiteboard or digital tool to articulate your thinking process.

• Focus on Strategy: For any design challenge, think about the underlying business goals and user needs first, before jumping into UI solutions.

• Articulate Trade-offs: Be prepared to discuss the trade-offs between different design solutions, considering factors like speed of implementation, user experience complexity, and business impact.

📝 Enhancement Note: The application process suggests a rigorous evaluation, with a strong emphasis on the portfolio as a primary assessment tool. The advice focuses on demonstrating strategic thinking, impact, and collaboration, crucial for a senior role in a startup.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The core design and prototyping tool. Proficiency is mandatory for wireframing, UI design, prototyping, and collaboration. Experience with Figma’s advanced features, including component libraries and design system management, is highly valued.

• Prototyping Tools: While Figma handles much of this, familiarity with other prototyping tools (e.g., InVision, Principle) might be beneficial for specific use cases or if the team uses a mixed stack.

Analytics & Reporting:

• User Analytics Platforms: Familiarity with tools like Amplitude, Mixpanel, or Google Analytics is expected for understanding user behavior, tracking engagement metrics, and informing design decisions.

• A/B Testing Platforms: Experience with platforms like Optimizely, VWO, or built-in experimentation tools within analytics suites is crucial for designing and analyzing growth experiments.

CRM & Automation:

• While not directly a designer's primary tool, an understanding of how CRM systems (e.g., Salesforce, HubSpot) and marketing automation tools might integrate with the user experience or impact growth strategies would be advantageous.

📝 Enhancement Note: Figma is explicitly mentioned as a required tool. The inclusion of analytics and A/B testing tools highlights the data-driven nature of the role and the expectation for designers to contribute to growth metrics.

👥 Team Culture & Values

Operations Values:

• Teamwork & Collaboration: A strong emphasis on working "together" and "winning as a team, not just as an MVP." This indicates a culture that values shared success and mutual support.

• Clarity & Fairness: Core tenets of the company, suggesting transparency in communication and equitable treatment of users and team members.

• Thrill & Insight: A passion for sports and the excitement of turning fan insight into actionable gaming experiences.

• Speed & Craft: The ability to balance rapid iteration and execution ("shipping and iterating") with high-quality design work ("craft").

• Accountability & Ownership: Taking ownership of "major product initiatives" and driving them to completion, fostering a sense of responsibility.

Collaboration Style:

• Cross-functional Integration: Daily collaboration with Product, Engineering, and Growth teams is central to the workflow.

• Constructive Critique: An open culture for feedback and design critique, encouraging continuous improvement.

• Transparency: A commitment to a "strong, transparent design culture."

• Adaptability: Willingness to adapt quickly as product priorities evolve in a dynamic startup environment.

📝 Enhancement Note: The company's core tenets (clarity, fairness, thrill, insight) and the emphasis on teamwork and collaboration paint a picture of a passionate, high-performance, yet supportive environment. The "MVP" vs. "team" distinction is important for understanding cultural fit.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Speed and Craft: In a fast-paced startup, delivering high-quality designs quickly can be a significant challenge. Candidates will need to be adept at prioritizing and making pragmatic design decisions.

• Simplifying Complexity: Translating intricate sports gaming mechanics and betting rules into intuitive user experiences requires significant design skill and deep user understanding.

• Data-Informed Design in Ambiguity: Thriving in an environment with evolving priorities and leveraging limited data (especially early on) to make informed design choices.

• Driving Engagement & Monetization: Designing features that not only delight users but also effectively drive key business metrics like retention and revenue in a competitive market.

Learning & Development Opportunities:

• Product Strategy Influence: Opportunity to gain significant experience in shaping product strategy and roadmap within an early-stage company.

• Industry Specialization: Deepen expertise in the rapidly growing and dynamic sports gaming and real-money gaming sectors.

• Cross-Functional Skill Development: Enhance collaboration and communication skills by working closely with diverse teams (Product, Engineering, Growth, Marketing).

• Design System Growth: Contribute to the evolution and scaling of a design system, a valuable skill for future senior roles.

• Leadership Potential: Develop leadership capabilities by owning major initiatives and potentially mentoring junior team members as the company grows.

📝 Enhancement Note: The challenges are framed around the realities of startup life and the specific domain of sports gaming, offering a realistic outlook for candidates. Growth opportunities are tied to the company's expansion and the inherent learning opportunities of a senior role in a dynamic sector.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to simplify a complex user flow or system. What was your process, and what was the outcome?" (Focus on your methodology, user-centricity, and impact.)

• "How do you approach designing for engagement and retention in a consumer application, especially one with a monetization component?" (Highlight your understanding of growth loops, user motivation, and business goals.)

• "Walk us through a project where you collaborated closely with Product Managers and Engineers. How did you handle disagreements or technical constraints?" (Emphasize your communication, negotiation, and problem-solving skills.)

Company & Culture Questions:

• "What interests you about Chalkboard's mission and the sports gaming industry?" (Research their mission, values, and market position.)

• "How do you incorporate user feedback and data into your design process?" (Provide specific examples of how you've used research and analytics.)

• "Describe your ideal team environment. How do you contribute to a positive and productive design culture?" (Align your response with their values of collaboration, transparency, and teamwork.)

Portfolio Presentation Strategy:

• Structure: Begin with a brief overview of Chalkboard and the role, then present 2-3 key case studies. For each, dedicate time to problem definition, your process, your specific contributions, challenges, solutions, and measurable impact.

• Narrative: Tell a compelling story for each project. Focus on the why behind your decisions and the impact of your work.

• Visuals: Ensure your slides are clean, visually appealing, and clearly showcase your design work. Use high-fidelity mockups and interactive prototypes where appropriate.

• Key Metrics: Quantify results whenever possible. If exact numbers are unavailable, discuss projected impact or lessons learned.

• Q&A Readiness: Anticipate questions about your design choices, trade-offs, collaboration, and how you would apply your experience to Chalkboard's specific challenges.

📝 Enhancement Note: The interview preparation advice focuses on demonstrating strategic thinking, domain understanding, and collaborative abilities, all critical for a senior role. The portfolio presentation strategy emphasizes storytelling and impact measurement.

📌 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 of your strongest end-to-end product design case studies, highlighting mobile-first experiences and any relevant consumer/gaming industry work. Clearly articulate your process, rationale, and measurable impact.

• Resume Optimization: Tailor your resume to highlight experience in product discovery, UX strategy, UI design, Figma proficiency, cross-functional collaboration, and data-informed design. Use keywords from the job description.

• Interview Preparation: Practice articulating your design process, showcasing your portfolio with a focus on storytelling and impact, and preparing thoughtful questions about Chalkboard's product, team, and culture.

• Company Research: Thoroughly research Chalkboard, its mission, target audience, and current product offerings. Understand their position in the sports gaming market and their core values.

⚠️ 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.

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