Senior Product Designer

📍 Job Overview

Job Title: Senior Product Designer

Company: Pickle

Location: New York, New York, United States

Job Type: Full-time

Category: Product Design

Date Posted: 2025-06-13

Experience Level: 5+ years

Remote Status: Hybrid (4 days in office)

🎨 Role Summary

• Drive end-to-end product design for core marketplace flows including search, discovery, listing, checkout, and post-rental engagement.
• Combine a strong user-centric mindset with analytical skills and refined visual design craft to create beautiful and effective experiences.
• Collaborate closely with Product, Engineering, Growth, and Data teams to ship high-impact features with a focus on measurable results.
• Lead user research efforts, synthesize insights, and translate them into intuitive interaction designs and visual systems.

🖼️ Primary Responsibilities

• Lead discovery and user understanding initiatives, including planning and conducting qualitative research (user interviews, moderated tests).
• Conduct quantitative deep-dives utilizing funnels, heatmaps, and experiment results to inform design decisions.
• Synthesize research insights into actionable artifacts such as journey maps, personas, and identified opportunity areas for product improvement.
• Craft end-to-end product experiences by producing flows, wireframes, high-fidelity mocks, and prototypes for both mobile and web platforms.
• Iterate rapidly on designs based on feedback, balancing the need for speed in a startup environment with attention to design polish and detail.
• Partner with Product and Data teams to define key success metrics, design and implement A/B tests for features, and interpret experimental results.
• Champion a culture of hypothesis-driven experimentation within the design and product teams to continuously optimize user experiences.
• Take ownership of the design system and visual language, evolving the component library to ensure accessibility, responsiveness, and brand consistency across all touchpoints.
• Document design patterns and guidelines to facilitate faster and more consistent collaboration between design and engineering teams.
• Present design work to cross-functional stakeholders, articulating design rationale, trade-offs, and advocating effectively for user needs.
• Collaborate closely with Engineering during the implementation phase to review and test new features from a design perspective, ensuring quality and fidelity.

🎓 Skills & Qualifications

Education: Bachelor's degree in Design, HCI, Computer Science, or a related field is typically expected for a role at this level, though equivalent practical experience and a strong portfolio are often considered just as valuable.

Experience: Minimum of 5 years of professional experience designing consumer-facing digital products. Demonstrated experience in marketplace, e-commerce, social/community, or fashion/luxury environments is highly preferred. A strong portfolio showcasing elegant interaction design, refined visual taste, and measurable results is essential.

Required Skills:

• Proven expertise in end-to-end product design, including user research, interaction design, visual design, and prototyping.
• Strong portfolio demonstrating successful design projects with clear articulation of process, impact, and design solutions.
• Fluency with modern design tools, specifically Figma, for collaborative design, prototyping, and design system management.
• Experience working alongside Growth or Analytics teams, with comfort in using dashboards, SQL, Google Analytics (GA), or similar tools to analyze data and interpret experiments.
• Demonstrated ability to prioritize information effectively, simplify complex user flows, and create clear visual and information hierarchy.
• Deeply ingrained user-centric mindset, coupled with an appreciation for brand identity and effective storytelling through design.
• Excellent written and verbal communication skills, with the ability to clearly frame design problems, articulate rationale, and present work to diverse stakeholders.
• Experience in conducting and synthesizing qualitative user research such as interviews and moderated usability testing.
• Ability to define success metrics for features and collaborate on the design and analysis of A/B tests.

Preferred Skills:

• Familiarity with front-end development frameworks, particularly React/Next.js, and an understanding of technical feasibility and constraints.
• Passion for the fashion tech industry, sustainability initiatives, or peer-to-peer economies.
• Experience contributing to or leading the growth of products from early traction stages to significant scale.
• Experience with design systems and component library management best practices.

🎨 Portfolio & Creative Requirements

Portfolio Essentials:

• Showcase 1-3 key projects that best represent your experience designing consumer-facing digital products, particularly in marketplace, e-commerce, or social contexts.
• Each project should feature compelling case studies that clearly articulate the problem, your design process (including research and iteration), your role, the final solution, and the measurable impact or results achieved.
• Include high-fidelity mockups, interactive prototypes (if applicable), and visual design artifacts that demonstrate refined visual taste and attention to detail.
• If the project involved technical or complex interactions, demonstrate your understanding of feasibility and collaboration with engineering.

Process Documentation:

• Detail your approach to the research and discovery phase, including methodologies used (e.g., user interviews, data analysis) and how insights informed your design direction.
• Illustrate your methods for ideation and iteration, showing sketches, wireframes, alternative design explorations, and how feedback influenced your design decisions.
• Explain your approach to validation and testing, including usability testing, A/B testing methodology, and how you measured the success of your designs.

💵 Compensation & Benefits

Salary Range: Based on industry standards for a Senior Product Designer role in the New York City area, coupled with the company's stage and size (Series A startup likely), the estimated annual salary range is between $130,000 and $170,000 USD. This estimate considers the cost of living in NYC, the required experience level (5+ years), and the specialized skills in marketplace/e-commerce design and data literacy. This range is an estimate and the final offer may vary based on experience, qualifications, and negotiation. Data sources for this estimate include industry salary reports for the NYC area (e.g., Salary.com, Glassdoor, Built In NYC) and typical compensation benchmarks for venture-backed startups at a similar stage.

Benefits:

• Comprehensive Healthcare coverage (Medical, Dental, Vision) to support employee well-being.
• Generous "Take What You Need" paid time off policy, offering flexibility and encouraging work-life balance.
• Meal Pal credits provided to cover the cost of lunch, enhancing convenience for in-office days.
• Stipend offered to assist with setting up a comfortable and productive desk and office environment at home.
• Opportunity to work directly with company founders and the executive team, providing high visibility and influence.
• Access to professional coaching, training, and development resources to support continuous learning and career growth.
• Significant opportunity to grow with the company as it scales, taking on increasing responsibility and leadership.
• Pickle credits for employees, encouraging the team to actively use and engage with the product they are building.
• Participation in fun team events and company parties, fostering a strong team culture.
• Opportunities for company offsites, promoting team bonding and strategic alignment.

Working Hours: Full-time position, typically 40 hours per week. The role requires being in the NYC office Monday through Thursday, indicating a hybrid work model with flexibility on Fridays. Schedule may require adaptability based on project needs and collaboration across time zones if applicable.

🎯Team & Company Context

🏢 Company & Design Culture

Industry: E-commerce / Marketplace / Fashion Tech / Sustainability. Pickle operates within the growing circular economy, specifically focusing on peer-to-peer rentals of clothing and accessories, with plans to expand into other categories. This positions the design team at the intersection of consumer technology, sustainable practices, and the dynamic fashion industry.

Company Size: Approximately 50 employees (based on LinkedIn data). This indicates a relatively small, fast-growing startup environment. For design professionals, this typically means a high degree of ownership, direct impact on the product, and close collaboration across all functions.

Founded: 2021. As a young company, Pickle is likely still establishing and refining its design processes and culture. This presents an opportunity for a senior designer to significantly influence the trajectory and standards of the design team.

Team Structure:

• The design team is likely small, potentially consisting of a few product designers reporting to a Head of Product or a design lead.
• Reporting will be directly to the founders and executive team, indicating a flat hierarchy and direct access to leadership.
• Significant cross-functional collaboration is expected with Product, Engineering, Growth, and Data teams, requiring strong communication and stakeholder management skills.

Methodology:

• Emphasis on data-driven design and hypothesis-driven experimentation, suggesting an iterative design process informed by user behavior and A/B testing results.
• Likely utilizes agile development methodologies, requiring designers to adapt to fast-paced sprints and continuous delivery.
• Focus on user research (qualitative and quantitative) as a foundational element for understanding user needs and informing design strategy.

Company Website: http://shoponpickle.com

📈 Career & Growth Analysis

Design Career Level: Senior Product Designer. This role is for an experienced individual contributor who can operate with a high degree of autonomy, lead complex design initiatives, mentor more junior designers (if applicable), and significantly influence product strategy through design. The responsibilities indicate leadership in research, experimentation, and design systems, aligning with senior-level expectations.

Reporting Structure: Reports directly to the founders and executive team. This is a unique aspect indicating a high level of visibility and the opportunity to directly influence strategic decisions at the highest level of the company. It suggests a flat organizational structure within the design function.

Design Impact: Design has a direct and measurable impact on core business metrics such as conversion rates, user engagement, and potentially user acquisition and retention, given the focus on core marketplace flows. The role requires driving data-informed decisions, ensuring design directly contributes to business growth.

Growth Opportunities:

• Potential for advancement into design leadership roles (e.g., Design Lead, Head of Design) as the company and design team grow, with a timeline dependent on company scaling.
• Opportunities to deepen expertise in specific areas such as marketplace dynamics, growth design, or design systems through challenging projects and continuous learning.
• Mentorship opportunities for future junior designers as the team expands, allowing for development of leadership and coaching skills.

🌐 Work Environment

Studio Type: Hybrid work model with a strong emphasis on in-office collaboration. The requirement to be in the NYC office Monday through Thursday indicates a primary focus on in-person teamwork and a preference for collaborative brainstorming, design sessions, and cross-functional meetings in a physical space.

Office Location(s): New York City, NY. The specific address is not provided in the job description but is located within NYC, requiring candidates to be based locally and commute to the office during the mandated in-office days.

Design Workspace Context:

• The in-office requirement suggests a collaborative workspace designed to facilitate interaction between design, product, and engineering teams.
• Likely provides dedicated desk space, meeting rooms, and potentially creative areas suitable for brainstorming and design reviews.
• The hybrid model offers some flexibility, particularly on Fridays, allowing for focused remote work.

Work Schedule: Full-time, with a mandatory in-office presence from Monday to Thursday. Fridays are likely flexible or remote. This structure is designed to maximize in-person collaboration during the key workdays while offering some flexibility. Typical business hours are expected, though project deadlines may require some flexibility.

📄 Application & Portfolio Review Process

Design Interview Process:

• Initial Application & Portfolio Review: Candidates are required to email their application directly, including specific bullet points on why they are a standout, a link to their portfolio/recent work, and their resume. The portfolio is the first critical screening step, evaluated for relevant experience, visual craft, and process documentation.
• Introductory Call: Likely a screening call with a recruiter or hiring manager to discuss experience, fit, and salary expectations. Be prepared to briefly walk through a key portfolio project.
• Design Portfolio Presentation / Case Study Deep Dive: A dedicated session to present your work in detail, focusing on your process, problem-solving approach, collaboration style, and the impact of your designs. Be ready to discuss 1-3 key projects in depth, explaining the challenges, your decisions, and the outcomes.
• Design Challenge / Whiteboarding Session: May involve a take-home design exercise or a live whiteboarding session to assess problem-solving skills, design thinking, and ability to articulate design rationale under pressure. The challenge will likely relate to marketplace or e-commerce scenarios.
• Cross-Functional Team Interviews: Meetings with members of the Product, Engineering, Growth, and Data teams to assess collaboration skills, communication effectiveness, and ability to work in a data-informed environment.
• Cultural Fit / Leadership Interview: Discussions with founders or executive team members to evaluate cultural alignment, strategic thinking, and potential for leadership and influence within the company.

Portfolio Review Tips:

• Curate your portfolio to specifically highlight projects in marketplace, e-commerce, or consumer-facing digital products that demonstrate measurable results.
• Structure case studies using a clear narrative (Problem, Process, Solution, Impact) and visually showcase your design iterations, research insights, and final designs.
• Clearly articulate your role and contributions within each project, especially in collaborative environments.
• Be prepared to discuss the "why" behind your design decisions and demonstrate your understanding of user needs and business goals.
• Ensure your portfolio is easily accessible and professional, whether it's a dedicated website or a well-organized PDF.

Challenge Preparation:

• Familiarize yourself with common design challenge formats for senior roles, which often involve a realistic product problem related to the company's domain.
• Practice articulating your design process and rationale clearly and concisely, as this is often as important as the final solution.
• Be prepared to ask clarifying questions to define the scope and constraints of the challenge.
• If it's a take-home challenge, manage your time effectively and document your process thoroughly. For whiteboarding, practice sketching and explaining your ideas verbally.
• Consider potential edge cases and different user scenarios in your solution.

ATS Keywords: Product Design, UI/UX Design, User Research, Interaction Design, Visual Design, Design Systems, Figma, Prototyping, Wireframing, User Flows, A/B Testing, Data-Informed Design, Qualitative Research, Quantitative Research, Usability Testing, Marketplaces, E-commerce, Consumer Products, Mobile Design, Web Design, Cross-functional Collaboration, Stakeholder Management, Design Strategy, Information Architecture, Hypothesis Testing, Growth Design, Agile, Sketch, Adobe Creative Suite, InVision, Zeplin, Jira, Confluence, SQL, Google Analytics, React, Next.js, Fashion Tech, Sustainability, Peer-to-Peer, Problem Solving, Communication, Leadership, Mentorship, Storytelling, Accessibility, Responsiveness, Brand Consistency, User-Centered Design.

🛠 Tools & Technology Stack

Primary Design Tools:

• Figma: Required fluency for core design work, including UI design, prototyping, and collaborative design sessions. Expect to utilize its advanced features for design system management and team collaboration.
• Likely use of other standard design tools for specific tasks, though Figma is highlighted as the primary platform.

Collaboration & Handoff:

• Tools for seamless handoff to engineering (e.g., Zeplin, InVision Inspect, or built-in Figma features) are likely used to ensure design specifications are accurately implemented.
• Collaboration platforms (e.g., Slack, Google Workspace) for day-to-day communication and file sharing.
• Project management tools (e.g., Jira, Asana, Trello) are likely used to track design tasks and collaborate with product and engineering on sprints.

Research & Testing:

• Tools for conducting qualitative research (e.g., Zoom, Dovetail for synthesis).
• Platforms for A/B testing and experimentation (likely integrated with the product/growth stack).
• Analytics tools such as Google Analytics (GA) and potentially internal dashboards or SQL for quantitative analysis and understanding user behavior.
• Heatmapping and session recording tools may be used to visualize user interaction patterns.

👥 Team Culture & Values

Design Values:

• User-Centricity: A deep commitment to understanding user needs and designing solutions that address their pain points effectively. This is evident in the emphasis on user research and synthesizing insights.
• Data-Informed Decision Making: Valuing quantitative and qualitative data to inform design choices, measure impact, and drive continuous improvement. This is a core requirement of the role.
• Collaboration & Communication: A strong emphasis on working closely with cross-functional teams (Product, Engineering, Data, Growth) and effectively articulating design rationale and trade-offs.
• Craft & Detail: Appreciation for refined visual design, elegant interaction patterns, and attention to detail in execution, contributing to a high-quality user experience and strong brand identity.

Collaboration Style:

• Highly collaborative and cross-functional, requiring daily interaction with various teams to define problems, iterate on solutions, and ensure successful implementation.
• Likely involves regular design critiques and feedback sessions to ensure design quality and alignment.
• Emphasis on documenting design decisions and patterns, particularly through the design system, to facilitate efficient collaboration and knowledge sharing.

⚡ Challenges & Growth Opportunities

Design Challenges:

• Designing for a two-sided marketplace with potentially conflicting needs and behaviors of renters and listers.
• Balancing rapid iteration and shipping new features quickly with maintaining design quality and consistency in a fast-paced startup environment.
• Utilizing data effectively to inform design decisions while retaining a strong sense of user empathy and intuition.
• Evolving and maintaining a design system as the product scales and new features are introduced.

Learning & Development Opportunities:

• Deepen expertise in marketplace dynamics and growth design strategies through hands-on experience and data analysis.
• Opportunity to contribute significantly to the development and scaling of the company's design system.
• Develop leadership skills through influencing product strategy, mentoring future junior designers, and presenting to executive leadership.
• Stay updated on fashion tech, sustainability trends, and peer-to-peer economy models, gaining specialized domain knowledge.

💡 Interview Preparation

Design Process Questions:

• Be prepared to walk through a complex design problem you've solved, detailing each stage of your process from initial research and problem framing to ideation, iteration, testing, and final delivery. Use examples from your portfolio.
• Discuss your experience with different user research methodologies (qualitative and quantitative) and how you synthesize findings to inform design decisions.
• Explain your approach to collaborating with product managers, engineers, and data analysts throughout the design lifecycle.

Company Culture Questions:

• Research Pickle's mission, values, and recent product developments. Be ready to discuss your interest in the fashion tech, sustainability, or peer-to-peer space and how your passion aligns with Pickle's goals.
• Ask thoughtful questions about the design team structure, collaboration style, and how design influences product strategy at Pickle.
• Be prepared to discuss your experience working in fast-paced, data-driven environments and how you thrive in such settings.

Portfolio Presentation Strategy:

• Select 1-3 projects that best demonstrate your ability to design for complex user flows in a consumer-facing product, ideally in a marketplace or e-commerce context.
• For each case study, clearly articulate the problem you were trying to solve, your design process (including research, iteration, and testing), and the measurable impact of your design solution.
• Visually showcase your work, including user flows, wireframes, high-fidelity mockups, and prototypes.
• Practice presenting your work concisely and confidently, focusing on the story of how you arrived at the solution and the results achieved. Be prepared to answer detailed questions about your design decisions.

📌 Application Steps

To apply for this design position:

• Submit your application by emailing [email protected] with “Senior Product Designer” in the subject line.
• In your email, include 1-3 (maximum) bullet points highlighting why you are a standout applicant for this specific role, referencing your relevant experience and skills.
• Share a link to your online portfolio or attach recent work samples that showcase your product design process, visual craft, and measurable results. Ensure your portfolio is easily accessible and highlights relevant projects.
• Specify which Pickle feature you would be most excited to work on if hired, demonstrating your interest and understanding of the product. Research the Pickle app/website to identify a specific feature.
• Attach your resume as a PDF file, ensuring it is up-to-date and highlights your relevant experience, skills, and accomplishments using keywords from the job description.