Sr. Product Designer

📍 Job Overview

Job Title: Sr. Product Designer

Company: Cloaked

Location: New York City, New York, United States

Job Type: FULL_TIME

Category: Product Design / UX/UI

Date Posted: 2026-05-07

Experience Level: 5-10 years

Remote Status: Hybrid

🚀 Role Summary

• Lead end-to-end product design for Cloaked's mobile and web platforms, encompassing user research, strategy, and high-fidelity UI delivery.

• Develop, evolve, and maintain a robust, cross-platform design system to ensure visual and interaction consistency.

• Define and refine scalable user flows, interaction models, and design frameworks that enhance user experience and product cohesion.

• Craft aesthetically compelling and highly usable interfaces that prioritize accessibility, visual impact, and user-centricity.

• Actively integrate and leverage AI tools as a core component of the design workflow for accelerated iteration and innovation.

📝 Enhancement Note: This role, while titled "Sr. Product Designer," carries significant leadership responsibilities, indicated by terms like "Lead and design" and "elevate both the product and the design culture." The emphasis on building and maintaining a design system and collaborating closely with Product and Engineering suggests a strategic, foundational role within the design team, aligning with senior-level expectations for driving design standards and impact.

📈 Primary Responsibilities

• Spearhead the complete product design lifecycle for both mobile and web applications, from initial user research and strategic planning through to the delivery of polished user interfaces.

• Construct, enhance, and manage Cloaked's comprehensive design system, ensuring seamless visual and interactive consistency across all product touchpoints and platforms.

• Define and meticulously refine user flows, interaction models, and scalable design frameworks to promote clarity, cohesion, and intuitive navigation.

• Produce elegant and sophisticated user interfaces that effectively balance user needs, accessibility standards, and striking visual appeal.

• Foster close, collaborative partnerships with Product Management and Engineering teams to ensure alignment between user requirements, technical feasibility, and strategic business objectives.

• Utilize user insights, product analytics, and rigorous usability testing to drive rapid iteration cycles and inform data-driven design decisions.

• Serve as a vocal advocate for design excellence and consistency throughout the entire organization, influencing product development and cross-functional team understanding.

• Proactively utilize advanced AI design tools to streamline the design process, generate interface concepts, iterate on code-based designs, and push the boundaries of creative output.

📝 Enhancement Note: The responsibilities highlight a blend of strategic and tactical execution. The emphasis on "end-to-end design," "design system," and "AI tools" indicates a senior role focused on establishing and scaling design practices within a growing startup. Collaboration with Product and Engineering is crucial, suggesting a need for strong communication and problem-solving skills in a cross-functional environment.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio demonstrating equivalent practical experience and a deep understanding of design principles is expected.

Experience: Minimum of 6+ years of professional experience in product design, with a proven track record of leading design initiatives and delivering high-quality user experiences.

Required Skills:

• Design System Expertise: Demonstrated experience in building, evolving, or significantly contributing to cross-platform design systems that ensure scalability and consistency.

• UI Craftsmanship: Exceptional visual design skills, including a keen eye for visual hierarchy, typography, motion design principles, and layout composition.

• End-to-End Product Design: Proven ability to manage the full design process, from foundational user research and UX strategy to detailed UI execution and final delivery.

• Systems Thinking: Strong capacity to analyze complex problems and translate them into cohesive, modular, and user-friendly design solutions.

• Proficiency in Design Tools: Expert-level command of Figma and Adobe Creative Suite, along with familiarity and practical experience with rapid prototyping tools.

• Communication Skills: Excellent verbal and written communication abilities, with the capacity to articulate design decisions clearly and persuasively to both technical and non-technical stakeholders.

• Organizational Skills: Highly organized and reliable, with a proven ability to manage multiple projects, prioritize tasks effectively, and deliver consistent, high-quality work.

Preferred Skills:

• Multi-Platform Design Experience: Prior experience designing specifically for mobile platforms (iOS/Android) or complex multi-platform ecosystems.

• Startup/Scaling Environment Experience: Prior work experience within fast-scaling startup environments, understanding the unique challenges and pace.

• Agency or Consulting Background: Experience gained from agency or consulting roles, working on a diverse range of product challenges and client needs.

📝 Enhancement Note: The requirements emphasize a senior-level designer capable of both strategic system building and detailed execution. The explicit mention of AI tools suggests a forward-thinking candidate who embraces new technologies in their workflow. The "Nice to Have" section points towards candidates who can hit the ground running in a startup environment and adapt to diverse project needs.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Design System Case Study: Showcase a significant contribution to building or evolving a design system, detailing its components, governance, and impact on product consistency and development efficiency.

• End-to-End Product Design Example: Present a detailed case study of a product or feature designed from concept through launch, highlighting your role in research, strategy, UX flows, UI design, and iteration based on feedback.

• Scalable Frameworks & Flows: Demonstrate examples of user flows, interaction models, or design frameworks that were designed for scalability and adaptability across different product areas or platforms.

• UI Craftsmanship Showcase: Include high-fidelity mockups and interactive prototypes that exhibit exceptional visual design skills, attention to detail, and a strong understanding of usability and accessibility principles.

• AI Tool Integration: If possible, include a case study or example showcasing how AI tools were integrated into your design workflow to achieve specific outcomes (e.g., faster iteration, novel solutions, enhanced efficiency).

Process Documentation:

• User Research & Strategy: Document your approach to user research, including methodologies used, insights gathered, and how these insights informed your product strategy and design decisions.

• Design System Development & Maintenance: Outline your process for developing, documenting, and maintaining a design system, including collaboration with engineering and product teams.

• Iterative Design & Testing: Detail your process for iterative design, including how you incorporate feedback from usability testing, A/B testing, and analytics to refine user experiences.

• Cross-Functional Collaboration: Provide examples of your process for collaborating effectively with Product Managers and Engineers, ensuring design alignment and successful implementation.

📝 Enhancement Note: Given the Sr. level and emphasis on design systems and AI tools, a portfolio demonstrating strategic thinking, system-level impact, and modern workflow integration is critical. Candidates should be prepared to articulate their process and the impact of their work, particularly how they drive consistency and efficiency through design.

💵 Compensation & Benefits

Salary Range: $175,000 - $215,000 USD per year. This range reflects the senior nature of the role, the high cost of living in New York City, and the company's commitment to offering competitive compensation based on market data.

Benefits:

• Competitive Compensation Package: Includes a combination of salary, performance-based bonus, and equity, reflecting above-market rates.

• Comprehensive Health Coverage: Top-tier Health, Dental, and Vision insurance plans.

• Retirement Savings: 401K plan to support long-term financial planning.

• Flexible Work Environment: Hybrid work model with flexible arrangements and remote work options as needed.

• Home Office Support: Home office stipend and a new company laptop, along with other necessary tech equipment.

• Generous PTO: Competitive Paid Time Off policy, with a minimum recommended quarterly usage to prevent burnout.

• Wellness Stipend: Monthly stipend for physical, mental, or emotional well-being activities (e.g., gym memberships, meditation apps, personal training).

• Meal Stipend: Monthly meal stipend to support busy schedules.

• Professional Development: Unlimited professional development fund for continuous learning, conferences, and industry events.

Working Hours: While the standard is approximately 40 hours per week, the company emphasizes flexible work arrangements, allowing for adaptable schedules to accommodate personal needs and project demands, while ensuring consistent output and collaboration.

📝 Enhancement Note: The salary range is explicitly provided and aligns with senior product design roles in major tech hubs like NYC. The benefits package is robust, with a strong emphasis on employee well-being, professional growth, and flexibility, which are attractive to experienced professionals. The "above market rate pay and equity" statement suggests a competitive offering for a Series B startup.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology / Software (Privacy Tech). Cloaked operates within the burgeoning privacy tech sector, aiming to empower users with greater control over their personal data online. This sector is characterized by rapid innovation, a strong mission-driven ethos, and a focus on user empowerment.

Company Size: Series B startup. As a Series B funded company, Cloaked is likely past the initial startup phase, possessing established product-market fit and a growing team focused on scaling operations, product development, and market reach. This size typically means a dynamic, fast-paced environment with opportunities for significant impact.

Founded: The company was founded with a vision to rebuild consumer trust in data usage by prioritizing individual privacy and opt-in mechanisms. This mission is central to its identity and product development.

Team Structure:

• Operations: A hybrid model is in place for the NYC-based team, indicating a blend of in-office collaboration and remote flexibility.

• Cross-functional Collaboration: Close collaboration is expected between Product Design, Product Management, and Engineering, forming a core product development triad.

• Design Culture: The role aims to "elevate both the product and the design culture," suggesting an environment where design is valued, integrated early, and influential in decision-making.

Methodology:

• User-Centric Design: The product vision is centered on serving user needs, with privacy and opt-in at its core. Design decisions are expected to be informed by user insights, analytics, and usability testing.

• AI-Augmented Workflow: A key aspect of the design process involves actively using AI tools for interface generation, iteration, and accelerating workflow.

• Systematic Approach: Emphasis on building and maintaining design systems and scalable frameworks points to a structured approach to product development and design consistency.

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

📝 Enhancement Note: Cloaked is positioned as a mission-driven privacy startup. The Series B funding stage implies a growth-oriented environment where design plays a critical role in shaping the product and user experience. The hybrid model and emphasis on design culture suggest a balance between collaboration and individual work, with a strong focus on modern design practices.

📈 Career & Growth Analysis

Operations Career Level: This role is classified as "Sr. Product Designer," indicating a mid-to-senior level position. It requires significant autonomy, strategic input, and the ability to lead design initiatives end-to-end. The scope includes shaping product direction, influencing design culture, and mentoring junior team members (though not explicitly stated, it's common at this level).

Reporting Structure: While not explicitly detailed, a Sr. Product Designer typically reports to a Head of Design, Design Manager, or potentially a senior Product leader in a smaller organization. Close collaboration with Product Managers and Engineering Leads is a given.

Operations Impact: The Sr. Product Designer will have a direct and significant impact on the company's core product, influencing user acquisition, engagement, and retention through intuitive and privacy-focused design. Their work in building the design system will create downstream efficiencies for the entire product and engineering organization, directly contributing to faster iteration cycles and improved product quality. The emphasis on AI tool integration also positions this role at the forefront of design innovation, potentially setting new benchmarks for productivity and creative output within the company.

Growth Opportunities:

• Design Leadership: Potential to grow into a Design Lead or Manager role as the design team expands, taking on more strategic oversight and people management responsibilities.

• Specialization: Opportunity to deepen expertise in privacy tech, AI-driven design, or complex system design, becoming a subject matter expert.

• Cross-Functional Influence: Develop stronger strategic partnerships across Product and Engineering, influencing broader product strategy and company direction.

• Mentorship: Actively mentor and guide junior designers, contributing to the growth of the design team and fostering a strong design culture.

• Impactful Product Contribution: Contribute to a product with a strong social mission, directly impacting user privacy and trust in the digital space.

📝 Enhancement Note: The "Sr." title and emphasis on leading design culture, systems thinking, and AI integration suggest a role with substantial growth potential beyond individual contribution. It's a position for someone looking to make a significant mark on a product and its underlying design framework.

🌐 Work Environment

Office Type: The company operates with a hybrid model for its NYC-based team. This suggests a physical office space designed for collaboration, team meetings, and focused work, complemented by the flexibility of remote work. The mention of a "fully built out kitchen packed with drinks and snacks" indicates an effort to create a comfortable and well-equipped in-office experience.

Office Location(s): New York City, New York. This location offers access to a vibrant tech ecosystem, talent pool, and networking opportunities. Specific office details regarding accessibility or amenities beyond the kitchen are not provided but can be inferred to be standard for a modern tech office.

Workspace Context:

• Collaborative Focus: The hybrid model likely means the office is optimized for team interaction, brainstorming sessions, and collaborative design sprints when team members are present.

• Technology & Tools: Employees receive a new company laptop and other necessary tech, ensuring they have the tools required for design work, including advanced AI capabilities. The office environment will likely support these tools with robust infrastructure.

• Team Interaction: Regular team outings and socials are organized, fostering a strong sense of community and camaraderie beyond daily work tasks. This indicates a culture that values connection and team building.

Work Schedule: While a standard 40-hour work week is implied, the company emphasizes "flexible work arrangements" and "ability to work remotely as needed." This suggests a results-oriented environment where work-life balance is supported, allowing designers to manage their schedules effectively while meeting project deadlines and collaborative needs.

📝 Enhancement Note: The hybrid model in NYC, coupled with perks like a well-stocked kitchen and team events, points to a company that invests in creating a positive and productive work environment. The emphasis on flexibility is a key element for modern tech professionals.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio to assess qualifications and experience alignment.

• Portfolio Presentation & Discussion: A dedicated session where you present your work, focusing on key case studies that highlight your design systems, end-to-end design process, and use of AI tools. Be prepared to discuss your strategic thinking, problem-solving approach, and the impact of your contributions.

• Cross-functional Interviews: Meetings with Product Managers and Engineers to evaluate collaboration style, communication skills, and technical understanding. Expect discussions on how you translate user needs into technical requirements and vice-versa.

• Design Culture/Leadership Interview: A conversation potentially with a senior leader to assess your vision for design, ability to champion design excellence, and cultural fit within the team.

• Final Round: Likely a discussion with a founder or senior executive to finalize alignment on company mission and strategic vision.

Portfolio Review Tips:

• Curate for Impact: Select 3-4 of your strongest projects that best demonstrate your skills in design systems, end-to-end product design, and AI integration. Prioritize projects with clear problem statements, well-defined processes, and measurable outcomes.

• Tell a Story: For each case study, clearly articulate the problem, your role, the process you followed, the challenges you faced, your solutions, and the impact of your work. Use visuals effectively to support your narrative.

• Highlight Design Systems & AI: Ensure your portfolio explicitly showcases your experience with design systems and your proficiency with AI design tools. Detail how you built, maintained, or leveraged these for efficiency and innovation.

• Demonstrate Systems Thinking: Show how you approach complex problems systematically, creating modular, scalable, and cohesive design solutions.

• Be Ready for Q&A: Anticipate deep-dive questions about your design decisions, trade-offs, and how you handle feedback and critique.

Challenge Preparation:

• Design Exercise: You may be given a take-home design challenge or a live design exercise focused on a specific product problem. This will likely assess your ability to apply design thinking, create user flows, and produce high-fidelity mockups under a time constraint.

• Focus on Process: For any challenge, be prepared to explain your thought process, the assumptions you made, and the rationale behind your design choices.

• AI Integration: If applicable, consider how AI tools could be leveraged to accelerate your work on the challenge.

• Presentation Skills: Practice presenting your work concisely and persuasively, focusing on key elements and impact.

📝 Enhancement Note: The interview process emphasizes portfolio demonstration and strategic thinking, especially concerning design systems and AI. Candidates should prepare to not just show their work but explain the why and how, showcasing their ability to lead and impact a growing product and design culture.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The core tool for UI design, prototyping, and collaboration. Mastery is essential for creating high-fidelity interfaces and design system components.

• Adobe Creative Suite: Proficiency in tools like Photoshop and Illustrator for asset creation, image manipulation, and graphic design elements.

• Rapid Prototyping Tools: Familiarity with tools that facilitate quick iteration and user testing of interactive concepts (e.g., ProtoPie, Framer, or advanced Figma prototyping).

Analytics & Reporting:

• User Analytics Platforms: Experience with tools like Google Analytics, Mixpanel, Amplitude, or similar platforms to understand user behavior, track key metrics, and inform design decisions.

• Usability Testing Platforms: Familiarity with tools for conducting remote or in-person usability tests (e.g., UserTesting.com, Lookback).

CRM & Automation:

Emerging Technologies:

• AI Design Tools: Active and proficient use of AI tools integrated into the design workflow. This could include AI-powered ideation tools, code generation tools (e.g., for basic UI code snippets), or AI-assisted design iteration platforms.

📝 Enhancement Note: The technology stack is heavily focused on industry-standard design tools, with a significant emphasis on Figma and the integration of AI tools. This signals a forward-thinking approach to design workflows.

👥 Team Culture & Values

Operations Values:

• User Privacy & Trust: Central to the company's mission. Designers are expected to champion user privacy and build trust through thoughtful design.

• Design Excellence & Craft: A commitment to high-quality visual and interaction design, ensuring polished and intuitive user experiences.

• Innovation & AI Integration: Embracing new technologies, particularly AI, to push creative boundaries and enhance design efficiency.

• Collaboration & Transparency: Working effectively across teams, sharing insights, and fostering an open environment for feedback and idea exchange.

• Efficiency & Scalability: Designing modular systems and frameworks that support rapid development and future growth.

Collaboration Style:

• Cross-functional Partnership: Proactive engagement with Product and Engineering to ensure seamless integration of design into the development pipeline. This involves clear communication, shared understanding of goals, and mutual respect for expertise.

• Iterative Feedback Culture: An environment where feedback is actively sought, given constructively, and used to refine designs. This includes user feedback, peer reviews, and stakeholder input.

• Knowledge Sharing: Encouraging the sharing of best practices, new design techniques, and insights from AI tool usage to elevate the collective skill of the design team.

📝 Enhancement Note: The company values are deeply tied to its mission of privacy and trust, combined with a drive for design quality and innovation. The collaborative style emphasizes integration and continuous improvement, crucial for a fast-paced startup environment.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Privacy with Usability: Designing intuitive interfaces that effectively communicate complex privacy settings and empower users without overwhelming them.

• Scaling Design Systems: Evolving a design system to support rapid feature development and diverse product needs across mobile and web.

• Integrating AI Effectively: Moving beyond surface-level use of AI tools to truly leverage them for significant design innovation and efficiency gains, while maintaining design integrity.

• Fast-Paced Startup Environment: Adapting to rapid changes in product direction, priorities, and team growth while maintaining design quality and consistency.

Learning & Development Opportunities:

• AI in Design Specialization: Become an expert in leveraging AI tools for product design, potentially shaping how the company approaches design workflows in the future.

• Privacy Tech Domain Expertise: Develop deep knowledge of the privacy landscape and how design can address user concerns and regulatory requirements.

• System Design Leadership: Grow expertise in building and scaling complex design systems that support a growing product suite.

• Mentorship and Team Growth: Contribute to building and mentoring a high-performing design team.

• Industry Conferences & Training: Utilize the unlimited professional development fund to attend leading design conferences, workshops, and pursue relevant certifications.

📝 Enhancement Note: The challenges presented are common for senior roles in innovative tech companies, particularly those focused on emerging tech like AI and in a critical sector like privacy. The growth opportunities align with advancing one's career in design leadership, specialization, and contributing to a mission-driven product.

💡 Interview Preparation

Strategy Questions:

• "How would you approach designing a user flow for users to manage their privacy settings, balancing granular control with simplicity?" (Preparation: Think about progressive disclosure, clear affordances, and user education).

• "Describe a time you had to influence stakeholders who had different priorities. How did you align them around a design solution?" (Preparation: Focus on data-driven arguments, empathy, and collaborative problem-solving).

Company & Culture Questions:

• "What excites you about Cloaked's mission to rebuild consumer trust in data usage?" (Preparation: Research the company's mission, values, and the broader privacy tech landscape).

• "How do you see your role in elevating the design culture at Cloaked?" (Preparation: Discuss your philosophy on design advocacy, mentorship, and fostering collaboration).

Portfolio Presentation Strategy:

• Structure Your Narrative: For each project, use a clear framework: Problem -> Your Role -> Process -> Solution -> Impact -> Learnings.

• Show, Don't Just Tell: Use high-fidelity mockups, interactive prototypes, and clear visuals. For design systems, show component libraries and how they're applied.

• Highlight AI Integration: Explicitly call out where and how AI tools were used, and what the benefits were. Be ready to demonstrate this if possible.

• Be Data-Informed: Quantify your impact whenever possible (e.g., "improved conversion by X%", "reduced user errors by Y%").

• Engage and Discuss: Be prepared for deep questions. Treat it as a collaborative discussion rather than a one-way presentation.

📝 Enhancement Note: Interview preparation should focus on demonstrating strategic thinking, leadership potential, and a deep understanding of modern design practices, including AI and design systems, within the context of Cloaked's privacy mission.

📌 Application Steps

To apply for this Sr. Product Designer position:

• Submit your application through the provided link on Ashby.

• Portfolio Customization: Tailor your portfolio to highlight 2-3 key projects that best showcase your experience with design systems, end-to-end product design, and AI tool integration. Focus on demonstrating your strategic thinking and impact.

• Resume Optimization: Ensure your resume clearly articulates your 6+ years of experience, emphasizing achievements in UI/UX, design systems, and collaborative product development. Use keywords relevant to the job description (e.g., Figma, AI Design Tools, Systems Thinking).

• Prepare Your Narrative: Practice presenting your portfolio case studies concisely, focusing on the problem, your process, your solutions, and the measurable impact of your work. Be ready to discuss your approach to collaboration and design leadership.

• Research Cloaked: Thoroughly understand Cloaked's mission, product, and the privacy tech landscape. Prepare thoughtful questions about the company, team, and the challenges of the role.

⚠️ 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.