Senior Product Designer

📍 Job Overview

Job Title: Senior Product Designer

Company: Cassi Home

Location: New York City, New York, United States

Job Type: FULL_TIME

Category: Product Design / GTM Operations Enablement

Date Posted: 2026-05-06

Experience Level: 5-10 Years

Remote Status: On-site

🚀 Role Summary

• This role is pivotal in transforming complex, real-world operational workflows into intuitive and elegant product experiences.

• The Senior Product Designer will own the end-to-end design of product flows across web, iOS, and Android platforms, catering to multiple user types including property managers, operators, and vendors.

• A key aspect of this position involves integrating AI capabilities into the product in a natural, useful, and differentiated manner to enhance user experience and operational efficiency.

• This is a foundational role, requiring a builder mindset to help define and evolve Cassi's product design language and brand through the product, and to introduce and scale a robust design system.

📝 Enhancement Note: While the job title is "Senior Product Designer," the description heavily emphasizes "transforming complex, real-world operations" and "messy, real-world workflows" into "simple, intuitive systems." This indicates a strong connection to Go-To-Market (GTM) operational enablement, where product design directly supports and streamlines business operations. The focus on "operations," "coordination systems," and "workflow-heavy products" suggests this role will be instrumental in shaping the user experience for Cassi's core operational users, making it relevant to GTM operations professionals who might interact with or rely on such product functionalities.

📈 Primary Responsibilities

• Translate intricate, real-world operational processes and user needs into simple, elegant, and highly intuitive product experiences.

• Design comprehensive, end-to-end user flows across web and mobile platforms (iOS/Android), ensuring seamless user journeys rather than isolated screen designs.

• Develop and maintain user experiences that accommodate multiple user types with distinct permissions and roles within a unified system.

• Collaborate closely and proactively with product management and engineering teams to ensure rapid iteration, quick shipping cycles, and continuous product improvement.

• Define, establish, and evolve Cassi’s product design language, visual identity, and brand consistency as reflected within the product interface.

• Architect, implement, and scale a robust design system that enables faster development cycles without compromising the quality or coherence of the user experience.

• Leverage and integrate AI tools strategically to accelerate and enhance design processes, prototyping, and iteration cycles, ensuring AI features are user-centric and impactful.

• Conduct user research, usability testing, and gather feedback to inform design decisions and drive product evolution based on real-world usage and customer insights.

• Contribute to product strategy by identifying opportunities for design innovation and operational efficiency improvements through product enhancements.

📝 Enhancement Note: The responsibilities highlight a deep involvement in the operational aspects of the business through product design. This Senior Product Designer is expected to "turn messy, real-world workflows" into "simple, intuitive systems," which is a core objective for GTM Operations and Revenue Operations teams aiming to improve efficiency and reduce friction for users. The emphasis on "0→1 product experiences," "complex, multi-step workflows," and "operational tools" further positions this role as critical for enabling and scaling business operations.

🎓 Skills & Qualifications

Education:

• While no specific degree is mandated, a strong portfolio demonstrating a deep understanding of user-centered design principles, system thinking, and product execution is paramount.

Experience:

• Proven experience in designing and shipping 0→1 product experiences that are live and actively used by customers.

• Demonstrated success in owning and simplifying complex, multi-step workflows end-to-end.

• Experience working collaboratively with engineering teams to ship quickly, navigate trade-offs, and iterate on products in production.

• Experience building or scaling a design system to improve development speed and product consistency.

• A track record of making product decisions informed by real user data and usage patterns, not solely by theoretical design best practices.

Required Skills:

• Product Thinking & System Design: Ability to think holistically about user journeys, business objectives, and technical constraints to design cohesive systems, not just isolated interfaces.

• End-to-End Flow Design: Expertise in mapping out and designing complex user flows across multiple platforms and user types.

• Cross-Platform Design (Web & Mobile): Proficiency in designing for both web applications and native iOS/Android mobile experiences, understanding platform-specific nuances and mobile-first principles.

• Design System Development & Implementation: Experience creating, maintaining, and scaling design systems to ensure consistency, efficiency, and quality.

• AI-Native Curiosity & Integration: Active use of AI tools (e.g., Claude Code, Midjourney) for design acceleration, prototyping, and exploring new interaction paradigms; understanding how AI can enhance design and development workflows.

• Builder Mindset & High Agency: Proactive, self-directed individual comfortable with ambiguity, taking initiative, and driving projects from conception to completion.

• Collaboration with Engineering: Strong ability to partner effectively with engineering teams, understanding technical feasibility and making informed trade-offs.

Preferred Skills:

• Experience designing workflow-heavy products, operational tools, marketplaces, or coordination systems.

• Comfort with prototyping tools and a willingness to work closely with code to understand technical implementation.

• Familiarity with user research methodologies and the ability to translate findings into actionable design improvements.

• Experience in defining and evolving a company's product design language and brand identity.

📝 Enhancement Note: The emphasis on "Product thinking > pure design," "systems, not just screens," and "outcomes, not just polish" strongly suggests that candidates familiar with operations metrics, ROI, and efficiency gains will be highly valued. The requirement to "use AI tools to speed up iteration, not replace thinking" indicates a need for an understanding of how AI can augment operational processes.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstration of 0→1 Product Development: Showcase at least one significant project where you took a product or feature from initial concept to successful launch, illustrating problem definition, ideation, execution, and iteration.

• Complex Workflow Simplification Case Studies: Present detailed case studies of how you transformed intricate, multi-step operational workflows into simplified, intuitive user experiences, clearly outlining the problem, your design process, and the impact achieved.

• Cross-Platform Design Examples: Include examples of your work that span both web and mobile (iOS/Android) platforms, demonstrating your ability to design consistent yet platform-appropriate experiences.

• Design System Contributions: If applicable, detail your involvement in building, scaling, or significantly contributing to a design system, highlighting its impact on development speed and product consistency.

• AI Tool Integration Examples: Showcase instances where you leveraged AI tools in your design process, explaining how they accelerated your work, improved outcomes, or shaped the final product.

Process Documentation:

• Workflow Mapping & Optimization: Evidence of your ability to map existing complex operational workflows, identify pain points, and redesign them for improved efficiency and user satisfaction.

• User Journey & Flow Design: Documentation illustrating your process for designing end-to-end user journeys, including wireframes, user flows, and prototypes that clearly articulate the user experience.

• Design System Architecture & Components: Examples of how you structured and documented a design system, including component libraries, style guides, and usage guidelines.

• Iterative Design & Feedback Loops: Demonstrate your process for incorporating user feedback and production data into iterative design improvements, showcasing how you manage feedback and prioritize changes.

📝 Enhancement Note: Given the operational focus of this role, portfolios should emphasize quantifiable results and process improvements. Candidates should be prepared to discuss how their designs directly impacted operational efficiency, reduced task completion times, or improved user adoption for specific operational tasks.

💵 Compensation & Benefits

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

Benefits:

• Equity: Stock options in an early-stage business, representing a stake in the company's growth.

• Full Benefits Package: Comprehensive health, dental, and vision insurance; retirement savings plans (e.g., 401k); paid time off (PTO); and other standard benefits.

• Professional Development: Opportunities for continuous learning, skill enhancement, and exposure to cutting-edge AI tools in design.

Working Hours: 40 hours per week (standard full-time).

📝 Enhancement Note: The salary range provided is typical for a Senior Product Designer role in New York City, particularly for a well-funded early-stage startup with a strong vision. The equity component is a significant draw for candidates looking to join a company at this stage. The "Full Benefits Package" is standard for established companies and startups that are well-capitalized.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology (Software as a Service - SaaS) focusing on asset management and operational coordination for physical world assets, starting with property management.

Company Size: Early-stage startup (implied by "first full-time Senior Product Designer," "closed our Series A in six days," and "first 15 employees"). This implies a small, agile team with high individual impact.

Founded: Cassi was founded recently, indicated by the "early-stage business" and "first 15 employees" context.

Team Structure:

• Small, Integrated Teams: Expect a flat hierarchy where Product, Engineering, and Design work in very close collaboration.

• High Ownership: Individuals are expected to take significant ownership of their areas, contributing beyond traditional role boundaries.

• Cross-Functional Collaboration: Deep partnerships between design, product management, and engineering are fundamental to the company's rapid iteration and shipping model.

Methodology:

• Agile & Iterative Development: Emphasis on shipping quickly, learning from real usage, and continuous iteration based on feedback.

• Data-Informed Design: Decisions are expected to be informed by real usage data and customer insights, moving beyond purely aesthetic considerations.

• AI-Augmented Workflows: Strategic integration of AI tools to enhance design, development, and operational processes.

Company Website: http://cassihome.com/

📝 Enhancement Note: The culture is characterized by speed, ownership, and a strong emphasis on building foundational elements (0→1). The "investors, customers, and the team are all in" suggests a high-conviction, motivated workforce.

📈 Career & Growth Analysis

Operations Career Level: This role is a Senior individual contributor position, acting as the foundational product design expert within the company. It offers significant opportunity to shape the product's direction and establish design best practices from the ground up.

Reporting Structure: Likely reports directly to a Head of Product, CTO, or CEO, given the early stage and the role's foundational nature.

Operations Impact: The Senior Product Designer will have a direct and profound impact on the operational efficiency and user experience of Cassi's core customers (property managers, operators, vendors). By simplifying complex workflows, the role directly contributes to the company's ability to scale its services and onboard new clients effectively, which is critical for GTM success. The design of AI-powered features will also be a key differentiator and driver of operational value.

Growth Opportunities:

• Leadership in Design: As the first design hire, there is a clear path to building and leading a design team as the company scales.

• Product Strategy Influence: Deep involvement in product strategy and roadmap development, influencing the direction of the company's core offerings.

• Technical Skill Expansion: Opportunity to deepen expertise in AI-driven design, system architecture, and potentially work closer to code.

• Industry Expertise: Gaining specialized knowledge in operational technology, property management, and the application of AI in enterprise workflows.

📝 Enhancement Note: This role is ideal for someone who wants to build, not just maintain. The growth trajectory is tied to the company's success, offering significant upside in terms of leadership and strategic influence within the operations and product domains.

🌐 Work Environment

Office Type: In-office, located in Manhattan, New York City. This suggests a collaborative, hands-on environment conducive to rapid prototyping and team interaction.

Office Location(s): New York, NY (Manhattan) — in office.

Workspace Context:

• Collaborative Hub: The office environment is designed to foster close collaboration between product designers, engineers, and product managers, facilitating quick feedback loops and design reviews.

• Tools & Technology: Access to modern design tools (Figma likely), AI-powered design assistants, and potentially development environments for close collaboration with engineers.

• Team Interaction: Frequent informal and formal interactions with the core product and engineering teams, encouraging a shared understanding of user needs and technical constraints.

Work Schedule: Standard 40-hour work week, with the expectation of flexibility inherent in a fast-paced startup environment. The "in-office" requirement underscores the importance of in-person collaboration for rapid iteration and team cohesion.

📝 Enhancement Note: The in-office requirement in Manhattan signifies a commitment to a strong team culture and the benefits of co-located collaboration, which is often crucial for early-stage product development and operational alignment.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Review of resume and portfolio to assess foundational skills, experience, and alignment with the role's requirements.

• Portfolio Presentation & Design Challenge: A deep dive into the candidate's portfolio, focusing on 0→1 projects, workflow simplification, and cross-platform design. This may include a take-home design challenge or an in-session problem-solving exercise focused on a real-world operational scenario.

• Product & Engineering Collaboration: Interviews with product managers and engineers to evaluate collaboration style, communication, and understanding of technical trade-offs.

• Founder/Leadership Interview: A final discussion with company leadership to assess cultural fit, strategic thinking, and long-term vision alignment.

Portfolio Review Tips:

• Highlight 0→1 Impact: Clearly articulate the problem space, your role, the solutions you designed, and the impact (metrics, user feedback) for projects where you built from scratch.

• Showcase Workflow Transformation: For workflow-heavy projects, use diagrams or storytelling to demonstrate how you simplified complexity and improved operational efficiency. Quantify improvements where possible (e.g., reduced task time, increased completion rates).

• Explain Your Process, Not Just the Pixels: Discuss your design decisions, the trade-offs you made, how you incorporated feedback, and how you collaborated with engineering.

• Demonstrate AI Integration: If you've used AI in your design process, explain how it helped you iterate faster, explore more options, or achieve better outcomes.

• Tailor to Cassi's Mission: Show an understanding of Cassi's business – coordinating physical asset management – and how your design skills can directly address their operational challenges.

Challenge Preparation:

• Understand Operational Workflows: Familiarize yourself with common operational tasks in property management, vendor coordination, and asset maintenance.

• Think in Systems: Be prepared to design solutions that consider multiple user types, permissions, and interconnected processes.

• Embrace Ambiguity: Practice problem-solving with incomplete information and focus on defining the core problem before jumping to solutions.

• AI Tool Proficiency: Be ready to discuss how you would leverage AI in the context of the challenge to accelerate your design process or enhance the user experience.

📝 Enhancement Note: The emphasis on "0→1," "complex, real-world operations," and "AI-native curiosity" suggests that candidates who can demonstrate a proactive, problem-solving approach and a clear understanding of how design impacts operational efficiency will stand out.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma is the industry standard for collaborative design and prototyping and is highly likely to be the primary tool.

• Design System Management: Tools or processes for managing and scaling design system components and documentation.

• AI Design Assistants: Tools such as Claude Code, Midjourney, or similar AI platforms for accelerating ideation, asset generation, and code snippets.

Analytics & Reporting:

CRM & Automation:

• The designer will need to understand how their product interfaces with or supports operational workflows that might be managed through CRM or other operational software, even if they don't directly use them.

📝 Enhancement Note: The explicit mention of "AI tools like Claude Code" points to a forward-thinking approach to design and development, where AI is seen as a productivity multiplier. Candidates should be comfortable discussing their experience with such tools.

👥 Team Culture & Values

Operations Values:

• Builder Mentality: A drive to create, innovate, and bring new solutions to life from the ground up.

• Product Thinking & Outcomes: Prioritizing the impact and effectiveness of the product over mere aesthetic polish, focusing on delivering tangible results.

• Execution & Speed: A commitment to moving fast, making decisions, and continuously iterating to deliver value rapidly.

• High Agency & Ownership: Taking initiative, driving projects forward, and feeling responsible for the success of their work.

• AI Integration: An openness and curiosity towards leveraging AI to enhance processes and product capabilities.

Collaboration Style:

• Tightly Coupled Product & Engineering: Design is not a silo; it's an integral part of the product development process, working hand-in-hand with engineers.

• Iterative & Feedback-Driven: A culture that encourages continuous feedback, learning from production usage, and adapting designs based on real-world data.

• Shared Ownership of Success: The team works collectively towards shared goals, with a focus on delivering exceptional user experiences and operational value.

📝 Enhancement Note: The emphasis on "Builder mindset" and "high agency" highlights a culture that values proactivity and a hands-on approach, which is paramount in an early-stage startup environment focused on rapid growth and product development.

⚡ Challenges & Growth Opportunities

Challenges:

• Defining 0→1 Experiences: Establishing foundational design patterns and user flows for a new product category in a complex operational domain.

• Balancing Speed & Quality: Iterating rapidly while ensuring the design system and overall product quality remain high.

• Integrating AI Seamlessly: Designing AI features that feel natural, useful, and truly differentiate the product, avoiding generic or superficial implementations.

• Designing for Multiple User Types: Catering to the distinct needs and workflows of property managers, operators, and vendors within a single, cohesive system.

• Operating in Ambiguity: Navigating a startup environment where requirements may evolve quickly and direction may not always be explicit.

Learning & Development Opportunities:

• Leadership Development: Opportunity to build and lead a design team as Cassi scales.

• Strategic Product Influence: Direct involvement in shaping product strategy and roadmap for a rapidly growing company.

• AI in Design Specialization: Deepening expertise in leveraging AI tools for design, prototyping, and user experience enhancement.

• Industry Domain Expertise: Gaining in-depth knowledge of operational technology, property management, and the challenges of coordinating physical assets.

• Foundational Design System Building: Hands-on experience in creating and scaling a design system from its inception.

📝 Enhancement Note: This role presents a unique opportunity to tackle foundational design challenges in a high-growth environment, with significant potential for leadership and impact.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you designed a 0→1 product or feature. What was the problem, your process, and the outcome?" (Focus on problem framing, user research, and quantifiable impact.)

• "How would you approach designing a system for coordinating field technicians and managing asset maintenance schedules for property managers?" (Focus on system thinking, user segmentation, and workflow simplification.)

• "How do you balance the need for rapid iteration with maintaining design quality and consistency, especially when building a design system from scratch?" (Focus on process, tools, and decision-making.)

Company & Culture Questions:

• "What interests you about Cassi's mission to coordinate physical asset management?" (Research Cassi's market and value proposition.)

• "How do you approach collaboration with product managers and engineers in a fast-paced startup environment?" (Highlight your experience with cross-functional teams and iterative development.)

Portfolio Presentation Strategy:

• Structure for Impact: Organize your portfolio around key projects, clearly stating the problem, your role, your process, and the measurable impact. Use a consistent narrative for each case study.

• Show, Don't Just Tell: Use visuals (wireframes, mockups, prototypes, user flows) effectively to illustrate your solutions. For workflow simplification, use diagrams or before/after comparisons.

• Quantify Results: Whenever possible, present metrics that demonstrate the value of your design work (e.g., increased conversion rates, reduced task completion time, improved user satisfaction scores).

• Explain Your "Why": Be ready to articulate the rationale behind your design decisions, the user needs you addressed, and the trade-offs you made.

• Demonstrate AI Integration: If applicable, dedicate a section or specific examples to how you've leveraged AI tools to enhance your design process or product outcomes.

📝 Enhancement Note: The interview process will likely assess not only design skills but also strategic thinking, problem-solving abilities in complex operational contexts, and the capacity to thrive in a fast-paced, entrepreneurial environment.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the provided link on Ashby.

• Customize Your Resume: Tailor your resume to highlight experience in 0→1 product development, complex workflow simplification, cross-platform design, and AI tool utilization. Use keywords from the job description.

• Curate Your Portfolio: Select 2-3 of your strongest projects that best demonstrate your ability to solve complex operational problems, design end-to-end flows, and work with AI. Ensure each project clearly outlines the problem, your process, and quantifiable results.

• Prepare Your Narrative: Be ready to walk through your portfolio projects, explaining your design decisions, collaboration with engineering, and the impact of your work. Practice articulating how you would approach Cassi's specific challenges.

• Research Cassi: Understand their business model, target users (property managers, operators, vendors), and the operational challenges they aim to solve. This will help you tailor your responses and demonstrate genuine interest.

⚠️ 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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