Product Designer, Arena (Pittsburgh)

📍 Job Overview

Job Title: Product Designer, Arena

Company: Gray Swan AI

Location: Pittsburgh, Pennsylvania, United States

Job Type: Full-Time

Category: Product Design / UX/UI Operations

Date Posted: May 12, 2026

Experience Level: Mid-Senior Level (4+ years)

Remote Status: On-site

🚀 Role Summary

• Drive end-to-end product design for the Gray Swan AI Arena, focusing on UI/UX improvements across web and mobile platforms.

• Translate intricate technical workflows and AI security concepts into clear, intuitive, and engaging user experiences.

• Champion user-centered design principles, incorporating visual design and persuasive design elements to enhance user engagement and trust.

• Build and maintain a robust design system, including UI components, patterns, and visual standards, to ensure consistency and scalability.

• Foster strong cross-functional collaboration with Product, Engineering, ML Research, and Go-To-Market (GTM) teams to align design solutions with business objectives and user needs.

📝 Enhancement Note: This role is positioned within a high-ownership environment at an early-stage startup, emphasizing initiative and direct impact on product and company trajectory. The "Arena" product suggests a focus on interactive, potentially gamified user experiences for testing and monitoring AI systems.

📈 Primary Responsibilities

• Design and iterate on the user interface and user experience for the Gray Swan AI Arena, covering both web and mobile applications.

• Lead design initiatives from conceptualization through to the delivery of production-ready specifications, ensuring a high standard of craft and user focus.

• Develop clear, intuitive, and trustworthy user experiences that simplify complex technical workflows and AI security concepts for diverse user segments.

• Integrate visual design principles and persuasive design techniques to create engaging, delightful, and effective user journeys.

• Contribute to the development and maintenance of the company's design system, ensuring consistency in UI components, patterns, and visual standards across all products.

• Actively collaborate with product managers, engineers, ML researchers, and GTM teams to gather requirements, provide design expertise, and ensure successful product launches.

• Address ad hoc design needs and contribute to various projects, demonstrating flexibility and a willingness to wear multiple hats in a fast-paced startup environment.

📝 Enhancement Note: The responsibilities highlight a blend of strategic design thinking and hands-on execution, typical of a Product Designer in a growing tech company. The emphasis on "Arena" and "AI security threats" implies a need for designers who can handle complex, technical domains and translate them into user-friendly interfaces, potentially with gamified elements.

🎓 Skills & Qualifications

Education: No specific degree requirements are listed, emphasizing practical experience and demonstrable skills over formal education.

Experience: 4+ years of professional experience in product UI/UX design.

Required Skills:

• Proven experience in product UI/UX design, with a strong portfolio showcasing end-to-end design processes.

• Expertise in designing for both web and mobile platforms.

• Proficiency with modern design and prototyping tools (e.g., Figma, Sketch, Adobe Creative Suite).

• Solid understanding of user-centered design principles, usability testing methodologies, and user research techniques.

• Detail-oriented with experience in managing style guides, component libraries, and design systems.

• Strong ability to translate complex technical workflows into clear, intuitive, and user-friendly experiences.

• Excellent collaboration and communication skills, with a demonstrated ability to work effectively with cross-functional teams.

Preferred Skills:

• Experience in gamified consumer applications, with a focus on creating playful yet functional designs.

• Experience building tooling or chat interfaces.

• Background in early-stage startup environments, demonstrating adaptability and initiative.

• Familiarity with AI safety principles or ethical considerations in AI systems.

• Basic understanding of front-end development principles or practical coding skills (e.g., HTML, CSS, JavaScript).

📝 Enhancement Note: The qualifications emphasize practical skills and a proactive mindset, aligning with the startup's culture of high ownership. The preference for gamified app experience and familiarity with AI safety suggests a unique intersection of consumer-level engagement design and cutting-edge technology.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase a minimum of 4 years of professional product UI/UX design work, with a clear focus on end-to-end project ownership.

• Include case studies that demonstrate the process of translating complex technical workflows into intuitive user experiences, highlighting problem identification, ideation, design execution, and iteration.

• Present examples of designing for both web and mobile platforms, illustrating adaptability to different screen sizes and interaction models.

• Feature projects that involve building or maintaining design systems, component libraries, or style guides, showcasing attention to detail and commitment to consistency.

• Demonstrate experience with user-centered design principles, including evidence of user research, usability testing, and incorporating feedback into design iterations.

Process Documentation:

• Clearly articulate your design process, from initial problem definition and user research to wireframing, prototyping, visual design, and final handoff to engineering.

• Provide examples of how you incorporate user feedback and data from usability testing or analytics into your design iterations.

• Detail your approach to collaborating with product managers, engineers, and other stakeholders throughout the design lifecycle.

• Illustrate your understanding of modern design tools and your ability to leverage them effectively for prototyping and delivering production-ready assets.

• For preferred skills, include examples of how you've navigated the complexities of early-stage startup environments or contributed to AI-related design challenges.

📝 Enhancement Note: The portfolio should not only showcase visual design skills but also a robust, repeatable design process that emphasizes problem-solving, user advocacy, and cross-functional collaboration, particularly in the context of complex technical products.

💵 Compensation & Benefits

Salary Range: $109,000 - $157,169 per year. The provided range is based on the job listing's salary data.

Benefits:

• Competitive equity package, offering significant ownership and potential upside.

• 401k with up to 4% matching, supporting long-term financial planning.

• Comprehensive health, dental, and vision coverage for employees and their dependents.

• Generous annual leave policy of 28 days (inclusive of vacation and holidays), promoting work-life balance.

• Catered lunches provided for employees working at the Pittsburgh office, enhancing the on-site work experience.

• Flexible work arrangements, allowing for a balance between on-site collaboration and personal needs.

• Visa sponsorship is available for exceptional candidates, broadening the talent pool.

Working Hours: While not explicitly stated, a full-time role at a tech startup typically involves around 40 hours per week, with the expectation of flexibility and dedication to project deadlines.

📝 Enhancement Note: The salary range is competitive for a Product Designer role with 4+ years of experience in a major US tech hub. The combination of salary, significant equity, and comprehensive benefits reflects the company's commitment to attracting and retaining top talent in a fast-growing startup environment. The mention of "AI safety" and "early-stage startup" suggests that compensation may also reflect the unique challenges and potential impact of the role.

🎯 Team & Company Context

🏢 Company Culture

Industry: Artificial Intelligence (AI) Security & Safety. Gray Swan AI operates at the forefront of AI security, developing solutions to protect organizations from emerging threats posed by AI systems. This niche industry demands cutting-edge technical understanding and a proactive approach to risk mitigation.

Company Size: Approximately 35 employees. This size indicates a close-knit team where individual contributions are highly visible and impactful. It allows for agility, rapid decision-making, and direct influence on product direction and company culture.

Founded: The founding date is not explicitly stated, but the company's description as "well-funded" and "growing fast" suggests it is a relatively young but established startup with significant traction.

Team Structure:

• The design team is described as "small but mighty," implying a lean and efficient group.

• The Product Designer will work closely with the "Arena Product team," indicating a dedicated product group focused on a specific area of the company's offerings.

• Collaboration is explicitly mentioned with developers, marketing, product, engineering, ML research, and GTM teams, highlighting a cross-functional and integrated approach to product development.

Methodology:

• Data-Driven Design: The company's focus on AI security and real-time threat detection implies a strong reliance on data analysis to inform product decisions and design improvements.

• Agile Development: The emphasis on moving "quickly" and "high-ownership" suggests an agile or lean development methodology, where iterative design and rapid prototyping are key.

• Mission-Focused Innovation: Gray Swan AI emphasizes its mission of practical, high-impact work in AI safety, indicating a culture driven by purpose and a desire to solve critical challenges.

Company Website: https://www.grayswan.ai/

📝 Enhancement Note: The company culture appears to be characterized by rapid growth, high impact, and a strong sense of mission. For a Product Designer, this means being adaptable, proactive, and comfortable working in a dynamic environment where collaboration and initiative are highly valued. The focus on AI security also suggests that a deep understanding of technical concepts and a commitment to ethical AI practices will be crucial.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a mid-level to senior Product Designer, requiring 4+ years of experience. It offers significant ownership and the opportunity to shape product direction, indicating a path towards more senior design leadership or specialized roles within the company.

Reporting Structure: The Product Designer will report into the design team, likely under a UX Lead or Head of Design, and will collaborate closely with Product Managers and Engineering Leads for the Arena product. The "high ownership" aspect suggests autonomy in managing one's own projects and contributing to strategic decisions.

Operations Impact: The Product Designer will have a direct and significant impact on the core "Arena" product, which is central to Gray Swan AI's mission of detecting and defending against AI security threats. Their work will influence how customers interact with and trust AI systems, directly contributing to the company's value proposition and market success. The role also involves contributing to the formalization of design processes as the company scales, offering a chance to build foundational design practices.

Growth Opportunities:

• Design Leadership: As the company grows, there will be opportunities to take on more leadership responsibilities, potentially mentoring junior designers or leading specific design initiatives.

• Specialization: The unique domain of AI security offers a chance to develop deep expertise in a cutting-edge field, becoming a go-to expert in designing for AI-related products.

• Process Improvement: The role explicitly mentions helping to "formalize our design processes," providing an opportunity to shape and optimize how design operates within the company, which is a critical growth area for operations-focused roles.

• Cross-Functional Advancement: Success in this role could open doors to product management, GTM strategy, or even research-oriented roles within the AI safety domain, given the company's multidisciplinary approach.

📝 Enhancement Note: The growth trajectory for this role is strong, particularly for someone looking to make a tangible impact in a fast-growing startup and specialize in a high-demand field like AI security design. The opportunity to influence process and strategy is a key differentiator for experienced operations and design professionals.

🌐 Work Environment

Office Type: The job is listed as "On-site" in Pittsburgh, indicating a physical office location is the primary work environment. The mention of "Catered lunches (Pittsburgh office)" further reinforces the importance of the physical workspace for team cohesion and employee experience.

Office Location(s): Pittsburgh, Pennsylvania, United States. This location is known for its growing tech scene and cost of living relative to other major tech hubs.

Workspace Context:

• Collaborative Environment: Given the small team size and emphasis on cross-functional collaboration, the workspace is likely designed to foster interaction and teamwork. Open office layouts, shared meeting spaces, and informal gathering areas are probable.

• Tools and Technology: Employees will have access to modern design and prototyping tools, likely managed through a company-provided IT infrastructure. Given the AI focus, access to relevant research, data, and potentially specialized hardware or software for AI model interaction might be available.

• Team Interaction: The on-site nature of the role facilitates direct interaction with colleagues across product, engineering, and research teams, promoting quick feedback loops and a shared understanding of project goals.

Work Schedule: The role is Full-Time. While specific hours aren't detailed, a typical tech startup schedule involves standard business hours (e.g., 9 AM to 5 PM) with flexibility to accommodate project needs and deadlines. The emphasis on "high ownership" suggests a results-oriented approach rather than strict adherence to hours.

📝 Enhancement Note: The on-site requirement in Pittsburgh suggests a company that values in-person collaboration and team synergy, particularly important in a startup environment where rapid iteration and close communication are critical. The catered lunches and flexible arrangements indicate an effort to create a positive and supportive on-site work experience.

📄 Application & Portfolio Review Process

Interview Process:

• Application Review: A thorough review of all submitted materials, with particular attention to the portfolio.

• Intro Call (30 min): An initial conversation to assess mutual fit, understand the candidate's background, and introduce Gray Swan AI's mission and culture.

• Portfolio Presentation (60 min): A dedicated session where candidates walk through their portfolio, explaining their design process, problem-solving approach, and impact on previous projects. Expect detailed questions about your methodology and decision-making.

• Live Design (75 min): A practical exercise where candidates demonstrate their design skills and problem-solving abilities in real-time, likely involving a design challenge related to the Arena product or a similar technical domain.

• Reference Checks: Verification of employment and performance through 3-5 provided references.

• Offer: A swift decision-making process if both parties agree on a mutual fit.

Portfolio Review Tips:

• Showcase Process, Not Just Pixels: Emphasize your design thinking, problem-solving steps, user research, iteration, and the rationale behind your design decisions. For Gray Swan AI, highlight how you translated complex technical requirements into user-friendly interfaces.

• Quantify Impact: Whenever possible, use data and metrics to demonstrate the success of your designs (e.g., increased user engagement, improved conversion rates, reduced task completion time). For this role, focus on how your designs contributed to user understanding, trust, or efficiency in the AI security context.

• Tailor to the Role: Highlight projects that align with the requirements, such as experience with gamified apps, tooling, chat interfaces, or complex technical workflows. If you have experience with AI safety or ethical design, make that prominent.

• Be Ready to Discuss: Prepare to discuss your design choices, challenges faced, and how you collaborated with cross-functional teams. Be articulate about your process and your contributions.

• Design System Experience: Clearly present any experience you have with building or contributing to design systems, component libraries, and style guides.

Challenge Preparation:

• Understand the Domain: Research Gray Swan AI, their mission, and the "Arena" product. Understand the basics of AI security threats and the importance of user trust in such systems.

• Practice Problem Solving: Be prepared to tackle a design challenge that requires translating technical concepts into user-friendly solutions. Think about how to make complex information accessible and actionable.

• Demonstrate Collaboration: Consider how you would approach collaborating with engineers and product managers on a real-time design exercise. Think about communication strategies and how to solicit feedback effectively.

• Time Management: The live design session has a strict time limit. Practice working efficiently and prioritizing key aspects of the design challenge.

📝 Enhancement Note: The interview process is rigorous, with a strong emphasis on practical design skills, process understanding, and cultural fit. The portfolio presentation and live design exercise are critical components, requiring candidates to not only showcase their design abilities but also their strategic thinking and ability to articulate their process effectively within the context of AI security.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Proficient use of modern design and prototyping tools is a core requirement. This typically includes industry standards such as:

  • Figma: Highly probable for collaborative design, prototyping, and component management.
  • Sketch: Another common tool for UI design and prototyping.
  • Adobe Creative Suite (Photoshop, Illustrator): Potentially used for asset creation or more advanced visual design tasks.

• Design System Management: Experience with building, maintaining, and utilizing component libraries and style guides is essential for ensuring consistency and scalability.

Analytics & Reporting:

• While not explicitly listed as a primary tool for the designer, understanding how to interpret and utilize data from analytics platforms is crucial for a user-centered approach. This could involve familiarity with tools like:
  • Google Analytics / Adobe Analytics: For understanding user behavior on web platforms.
  • Product Analytics Tools (e.g., Mixpanel, Amplitude): For deeper insights into user interactions within the application.
  • Data Visualization Tools (e.g., Tableau, Power BI): For understanding and presenting performance metrics to stakeholders.

CRM & Automation:

• This role is less likely to directly manage CRM or automation tools, but a foundational understanding of how these systems support the user journey and product lifecycle can be beneficial. Collaboration with GTM and Product teams may involve understanding how user data flows through these systems.

📝 Enhancement Note: The emphasis on "modern design and prototyping tools" and "component libraries" points towards a design workflow that prioritizes efficiency, collaboration, and scalability. Proficiency in Figma is highly recommended given its widespread adoption in fast-paced tech environments. Familiarity with how design impacts data collection and user journeys within CRM and analytics platforms will be advantageous.

👥 Team Culture & Values

Operations Values:

• High Impact & Ownership: The company culture values individuals who take initiative, drive projects forward, and feel a strong sense of responsibility for their work's outcomes. This translates to expecting designers to not just execute but to proactively identify problems and propose solutions.

• Collaboration & Mission Focus: Gray Swan AI fosters a collaborative environment where team members work closely together towards a shared mission of AI safety. This means valuing open communication, constructive feedback, and a collective drive to solve complex challenges.

• Craftsmanship & Quality: While moving quickly is important, there's a deep care for the quality of the work ("craft"). This implies a commitment to high standards in design execution, user experience, and attention to detail.

• Initiative & Proactivity: The description emphasizes needing someone who "can take a problem, run with it... without waiting to be told what to do." This highlights a culture that rewards proactivity, self-direction, and a proactive approach to problem-solving.

Collaboration Style:

• Cross-Functional Integration: The design team is expected to work seamlessly with Product, Engineering, ML Research, and GTM teams. This involves active participation in discussions, sharing design rationale, and incorporating diverse perspectives.

• Feedback-Driven Iteration: The culture likely embraces constructive feedback as a means to improve designs. Designers should be comfortable receiving and giving feedback, viewing it as a collaborative process to achieve the best outcome.

• Agile & Iterative: Given the startup environment and focus on speed, collaboration is likely iterative, with frequent check-ins, quick feedback loops, and an embrace of agile methodologies to adapt to changing requirements.

📝 Enhancement Note: The cultural values at Gray Swan AI are centered around ownership, impact, and a shared mission. For a Product Designer, this means being an active participant in the product development process, contributing ideas, and embodying a proactive, collaborative spirit. The emphasis on both "craft" and "speed" suggests a balance between meticulous execution and agile delivery.

⚡ Challenges & Growth Opportunities

Challenges:

• Translating Complex AI Concepts: A primary challenge will be simplifying highly technical and abstract AI security concepts into understandable and actionable user experiences for potentially diverse user groups.

• Balancing Technical Users with Playful Design: The role requires designing for users who understand complex technical workflows while also incorporating "playful design" elements for engagement, which can be a delicate balance.

• Early-Stage Startup Dynamics: Working in a fast-growing startup means navigating evolving priorities, rapid iteration cycles, and the need to establish processes from scratch, which can be demanding but also highly rewarding.

• AI Safety Nuances: Understanding and ethically representing the complexities of AI safety, threat detection, and automated validation requires continuous learning and careful design considerations.

Learning & Development Opportunities:

• Deep Dive into AI Security: Gain specialized knowledge in a cutting-edge and critical field, becoming an expert in designing for AI safety and security.

• Design System Development: Contribute significantly to building and evolving a design system, which is a valuable skill for any designer aiming for senior or lead roles.

• Cross-Functional Expertise: Develop a strong understanding of product management, engineering workflows, and GTM strategies within a tech startup context.

• Leadership Potential: As the company scales, there will be opportunities to take on leadership roles, mentor junior team members, and influence the strategic direction of design at Gray Swan AI.

📝 Enhancement Note: The challenges presented are inherent to working with advanced technology in a startup environment. They offer significant opportunities for professional growth, allowing a designer to develop specialized expertise, hone their problem-solving skills, and build a strong foundation for future career advancement.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to translate a highly technical or complex process into a simple and intuitive user experience. What was your process, and what was the outcome?" (Focus on problem definition, user research, design iterations, and quantifiable results.)

• "How do you approach balancing the needs of technical users with creating engaging and 'playful' design elements? Can you provide an example?" (Highlight your understanding of user segmentation and your ability to adapt design principles.)

Company & Culture Questions:

• "What interests you about Gray Swan AI's mission to protect against AI security threats?" (Show genuine interest in the company's purpose and its impact.)

• "How do you see your design philosophy aligning with our emphasis on high ownership and fast-paced execution in a startup environment?" (Articulate your proactive approach and ability to thrive in dynamic settings.)

Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly outline the problem, your role and responsibilities, your design process (research, ideation, prototyping, testing), key decisions made, challenges overcome, and the final outcome/impact.

• Quantify Achievements: Use data and metrics to demonstrate the success of your designs. For Gray Swan AI, focus on how your designs improved user understanding, efficiency, or trust in complex systems.

• Highlight Relevant Experience: Emphasize projects that showcase experience with complex technical workflows, gamified elements, or innovative UI/UX. If you have AI safety or ethical design experience, make it a focal point.

• Be Prepared for Deep Dives: Expect detailed questions about your process, your rationale for specific design choices, and how you handled trade-offs. Be ready to discuss your collaboration with engineers and product managers.

• Showcase Design System Contributions: If you have experience building or maintaining design systems, be ready to discuss its structure, components, and how it facilitated efficient design and development.

📝 Enhancement Note: The interview process is designed to assess not only your design skills but also your strategic thinking, problem-solving abilities, and cultural fit. Be prepared to articulate your process thoroughly and demonstrate how you can contribute to a mission-driven, high-ownership startup environment.

📌 Application Steps

To apply for this Product Designer position:

• Submit your application through the provided Ashby link.

• Tailor Your Resume: Ensure your resume clearly highlights 4+ years of relevant product UI/UX design experience, emphasizing accomplishments in translating complex technical workflows into intuitive user experiences. Use keywords from the job description such as "Product Design," "UI/UX," "Design System," "Prototyping," and "User-Centered Design."

• Curate Your Portfolio: Select 2-3 of your strongest case studies that best showcase your end-to-end design process, problem-solving skills, and experience with relevant project types (e.g., complex workflows, gamified elements, tooling). Ensure each case study clearly articulates the problem, your role, your process, your solutions, and the impact of your work.

• Prepare Your Portfolio Presentation: Practice walking through your selected case studies, focusing on telling a compelling story about your design journey and decision-making process. Be ready to discuss how you would apply your skills to Gray Swan AI's Arena product.

• Research Gray Swan AI: Familiarize yourself with the company's mission, products, and values. Understand the importance of AI security and safety. This will help you tailor your responses and demonstrate genuine interest during interviews.

⚠️ 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.