Founding Product Designer

📍 Job Overview

Job Title: Founding Product Designer

Company: True Talent Solutions Partners

Location: New York, New York, United States

Job Type: Full-Time

Category: Product Design / Operations Technology

Date Posted: 2026-11-04

Experience Level: 5-10 Years

Remote Status: On-site

🚀 Role Summary

• Spearhead the end-to-end user experience design for an early-stage AI company focused on revolutionizing insurance claims operations.

• Drive product strategy and user-centric design by leveraging product analytics, heatmaps, user research, and direct observation to inform design decisions.

• Collaborate intimately with product management and engineering teams to translate complex insurance workflows into intuitive, effective, and technically feasible software solutions.

• Design innovative interactions for AI agents, ensuring clarity in their actions, data sources, reasoning, and uncertainty levels, while enabling user review and intervention.

• Evolve the product's interface from an initial concept to a robust, enterprise-ready experience as the user base and organizational adoption grow within the insurance sector.

• Establish foundational design principles and a scalable design system, incorporating AI tools for prototyping and rigorously evaluating design impact on user effort reduction.

📝 Enhancement Note: This role is positioned as a "Founding Product Designer," indicating a high degree of autonomy and impact. The focus on "AI company building software to streamline insurance claims operations" strongly suggests a need for expertise in operational software, complex workflow simplification, and potentially human-in-the-loop AI interactions, which are critical for revenue operations and GTM efficiency in specialized industries. The "On-site, five days per week" requirement in New York City implies a collaborative, in-person environment essential for rapid iteration in an early-stage startup.

📈 Primary Responsibilities

• End-to-End User Experience Ownership: Take full ownership of the user experience across all customer-facing product surfaces, including claims workspaces, analytical dashboards, and other core application modules.

• Data-Informed Design & Research: Conduct comprehensive user research, including analyzing product analytics, heat maps, conducting discovery calls, and direct user observation, to identify pain points and opportunities for improvement.

• Cross-Functional Design Partnership: Collaborate closely with product managers and engineers to translate complex customer problems and business requirements into detailed workflows, wireframes, mockups, and high-fidelity prototypes.

• AI Interaction Design: Design intuitive and transparent interfaces for AI agents, focusing on clearly communicating AI actions, data provenance, reasoning processes, and confidence levels to enable effective human oversight and intervention.

• Enterprise-Readiness Evolution: Guide the product's design evolution from an initial Minimum Viable Product (MVP) to a sophisticated, enterprise-grade solution capable of meeting the stringent demands of larger insurance organizations.

• Design System & Principle Establishment: Develop and implement core design principles, style guides, and a comprehensive design system to ensure consistency, scalability, and efficiency across the product.

• Prototyping & Iteration with AI Tools: Utilize AI-powered prototyping tools (e.g., Claude, Lovable) to rapidly iterate on design concepts and explore innovative interaction patterns.

• Impact Measurement & Optimization: Define and track key design metrics, such as user effort reduction, task completion rates, and adoption, to evaluate the effectiveness of design changes and drive continuous improvement.

📝 Enhancement Note: The responsibilities highlight a deep dive into "claims operations," which is a critical component of the insurance industry's revenue cycle and operational efficiency. The emphasis on "complex workflows," "AI agents," and "enterprise-ready experience" indicates a need for a designer who understands operational software and can simplify intricate processes for specialized users. This role directly impacts the efficiency and effectiveness of downstream revenue-generating activities by streamlining the claims process.

🎓 Skills & Qualifications

Education:

• Bachelor's or Master's degree in Design, Human-Computer Interaction (HCI), Computer Science, or a related field, or equivalent practical experience. Experience:

• 5-8 years of progressive product design experience, with a significant portion in early-stage startup environments, ideally as a founding designer or the first dedicated design hire.

• Proven track record of successfully launching and iterating on complex software products. Required Skills:

• End-to-End Product Design: Demonstrated ability to manage the entire design lifecycle from conceptualization to implementation and iteration.

• UX Research & Data Analysis: Proficient in user research methodologies (interviews, surveys, usability testing) and skilled in analyzing product analytics, behavioral data, and heat maps to drive design decisions.

• Workflow Simplification: Expertise in dissecting and simplifying complex operational workflows into intuitive user interfaces.

• Technical Software Design: Experience designing dense, technical applications regularly used by operational teams (e.g., finance, logistics, insurance, compliance).

• Prototyping Proficiency: Advanced skills in creating interactive prototypes using tools like Figma, Sketch, Adobe XD, and specifically experience with AI prototyping tools (e.g., Claude, Lovable).

• Design System Development: Experience creating, implementing, and maintaining design systems for consistency and scalability.

• Cross-Functional Collaboration: Ability to effectively partner with product managers, engineers, and other stakeholders.

• AI Interaction Design: Understanding of how to design effective human-AI interactions, particularly for human-in-the-loop systems.

• U.S. Work Authorization: Must possess the legal right to work in the United States.

Preferred Skills:

• Insurance/Claims Domain Expertise: Prior experience designing software for the insurance, claims processing, healthcare, or other highly regulated industries.

• Human-in-the-Loop AI Design: Specific experience designing systems where humans and AI collaborate closely.

• Enterprise Software Design: Experience scaling product design for large enterprise clients with complex needs.

• AI Agent Design: Familiarity with designing interfaces for generative AI or specialized AI agents.

📝 Enhancement Note: The requirement for "dense, technical software used regularly by operational teams" is a strong indicator that candidates with experience in FinTech, InsurTech, or other B2B SaaS platforms focused on operational efficiency will be highly valued. The emphasis on "data-informed approach" and "behavioral analytics" aligns with the data-centric nature of Revenue Operations and Sales Operations roles.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Comprehensive Case Studies: Showcase 3-5 detailed case studies demonstrating end-to-end product design ownership for complex technical software. Each case study should clearly articulate the problem, your role, the design process, key decisions, challenges faced, and measurable outcomes.

• Workflow Optimization Examples: Include projects that specifically highlight your ability to simplify and improve complex operational workflows, demonstrating a deep understanding of user processes and efficiency gains.

• Data-Driven Design Evidence: Provide examples where user research, product analytics, or behavioral data directly influenced your design decisions and led to demonstrable improvements.

• AI Interaction Design Showcase: If available, include examples of designing interfaces for AI-driven features or human-in-the-loop systems, showcasing your approach to clarity, trust, and user control.

• Design System Contributions: Showcase contributions to or creation of design systems, illustrating your understanding of consistency, scalability, and collaboration.

Process Documentation:

• User Journey Mapping: Demonstrate proficiency in mapping complex user journeys within operational contexts.

• Information Architecture Design: Illustrate your ability to structure complex information logically and intuitively for technical users.

• Interaction Design Specifications: Provide examples of detailed interaction design specifications that effectively communicate intended user flows and behaviors to engineering teams.

• Usability Testing & Iteration Reports: Document your process for conducting usability tests and how feedback was integrated into design iterations.

📝 Enhancement Note: For a founding designer role, the portfolio is paramount. It needs to demonstrate not just aesthetic skill but a strategic, problem-solving mindset applied to operational challenges. The ability to articulate the "why" behind design choices, supported by data and a clear understanding of user workflows, will be critical. The focus on "AI agents" and "enterprise-ready" suggests a need to showcase how designs scale and integrate complex technologies.

💵 Compensation & Benefits

Salary Range:

• Base Salary: $170,000 - $220,000 USD annually.

• Equity: As a founding team member, significant equity participation is expected to be part of the total compensation package, though specific details will be discussed during the interview process.

Benefits:

• Comprehensive Health Insurance: Medical, dental, and vision insurance plans.

• Generous Paid Time Off (PTO): Including vacation days, sick leave, and company holidays.

• 401(k) Retirement Plan: With potential company matching contributions.

• Professional Development Stipend: For conferences, courses, and learning resources relevant to design and AI.

• Equity Options: Significant stock options in an early-stage startup.

• Relocation Assistance: Available for candidates relocating to New York City (details to be discussed).

Working Hours:

• Standard U.S. business hours (approximately 40 hours per week), with flexibility expected due to the startup environment and the need for rapid iteration. Occasional evening or weekend work may be required during critical project phases.

📝 Enhancement Note: The salary range provided is competitive for a senior/founding product designer role in New York City. The inclusion of equity is standard for founding team members in early-stage startups and represents a significant portion of the total compensation. The benefits package is typical for a tech startup, with a focus on health and professional growth. The mention of "visa transfers may be supported" but "new visa sponsorship is not available" is crucial for international candidates.

🎯 Team & Company Context

🏢 Company Culture

Industry: Artificial Intelligence (AI) / InsurTech / Software as a Service (SaaS)

Company Size: Early-Stage Startup (likely fewer than 50 employees)

Founded: Recently founded (specific year not provided, but implied by "early-stage AI company" and "founding product designer" title).

Team Structure:

• Lean & Agile: Expect a small, highly collaborative, and fast-paced team environment.

• Cross-Functional Pods: Likely organized into small, agile teams comprising product, engineering, and design, working on specific product areas.

• Direct Access to Leadership: As a founding member, you will have direct interaction with the founders and executive team.

• Flat Hierarchy: Emphasis on open communication and shared ownership across all team members.

Methodology:

• Agile Development: Iterative development cycles, focusing on rapid prototyping and feedback loops.

• Data-Driven Decision Making: Strong emphasis on using data from user research, product analytics, and AI model performance to guide product development.

• User-Centric Design: Core philosophy of deeply understanding user needs and translating them into effective solutions.

• AI Integration Focus: Continuous exploration and integration of AI capabilities to enhance operational efficiency and user experience.

Company Website: https://truetalentsolutionspartners.com

📝 Enhancement Note: The company is positioned at the intersection of AI and InsurTech, aiming to solve real-world operational challenges in a traditionally complex industry. The "founding designer" role implies a culture that values initiative, ownership, and the ability to build foundational elements from scratch. Expect a high-energy environment with a strong focus on innovation and problem-solving.

📈 Career & Growth Analysis

Operations Career Level: Founding / Principal Product Designer

Reporting Structure: Directly to the Head of Product or CEO/CTO in the initial stages. As the company grows, this may evolve to reporting into a VP of Product or Design Lead.

Operations Impact: This role has a direct and profound impact on the company's ability to acquire and retain customers by defining the core user experience of a product designed to solve critical operational inefficiencies in the insurance claims process. Success in this role directly contributes to revenue generation by enabling smoother, faster, and more accurate claims handling, which is key to insurer profitability.

Growth Opportunities:

• Leadership Track: Opportunity to build and lead a design team as the company scales, defining its design culture and processes.

• Strategic Influence: Significant input into product strategy, roadmap prioritization, and the overall direction of the company.

• Deep Domain Expertise: Develop specialized knowledge in AI applications within the insurance and claims operations sectors.

• Skill Expansion: Gain experience in designing for AI agents, human-in-the-loop systems, and enterprise-level SaaS products.

• Founding Team Member Status: Benefit from the experience of building a company from the ground up, with potential for significant financial upside through equity.

📝 Enhancement Note: As the first design hire, this role offers unparalleled opportunities for growth and impact. The candidate will not only shape the product but also the future design function of the company. This is a high-risk, high-reward opportunity typical of early-stage startups, appealing to individuals who thrive on building and defining new functions.

🌐 Work Environment

Office Type: Dedicated office space in New York City, requiring full-time on-site presence.

Office Location(s): New York, New York. Specific neighborhood details are not provided but assume a professional business district location.

Workspace Context:

• Collaborative Hub: The on-site requirement suggests a focus on in-person collaboration, brainstorming, and rapid iteration. Expect a dynamic environment where spontaneous discussions and whiteboarding sessions are common.

• Startup Amenities: Likely to include modern office infrastructure, collaboration spaces, and access to necessary design and development tools.

• Integrated Teams: Close proximity and regular interaction with product managers, engineers, and leadership to foster a cohesive product development culture.

• Focus on Innovation: The environment will likely encourage experimentation and the exploration of cutting-edge AI technologies.

Work Schedule:

• The role is based on a standard 40-hour work week, but the nature of a startup, especially an early-stage one, implies a need for flexibility and dedication. Expect periods of intense work around key milestones, product launches, or critical problem-solving.

📝 Enhancement Note: The mandatory on-site presence signifies a company culture that values face-to-face interaction, rapid communication, and a shared physical space for team cohesion and accelerated development, which is often crucial for early-stage startups.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Review of resume and portfolio by a recruiter or hiring manager to assess basic qualifications and alignment with the role.

• Portfolio Presentation & Design Exercise: A significant portion of the interview process will involve presenting your portfolio, walking through key case studies, and potentially completing a take-home design challenge or an in-person design exercise focused on a relevant problem.

• Cross-Functional Interviews: Interviews with Product Management and Engineering leads to assess collaboration skills, technical understanding, and ability to translate complex requirements.

• Founder/CEO Interview: A final interview with the company's founder(s) to evaluate cultural fit, strategic thinking, and long-term vision alignment.

• Reference Checks: Standard background and professional reference checks.

Portfolio Review Tips:

• Tell a Story: For each case study, clearly articulate the narrative: the problem, your specific role and contributions, the design process, key decisions, trade-offs, and the impact of your work.

• Focus on Process & Rationale: Emphasize how you arrived at your solutions. Explain your research methods, design rationale, and how data informed your choices.

• Highlight Operational Complexity: Showcase projects that involved simplifying complex technical or operational workflows. Explain the intricacies and how your design addressed them.

• Demonstrate AI Design Thinking: If you have relevant experience, clearly explain your approach to designing for AI, user trust, and human-in-the-loop systems.

• Quantify Impact: Whenever possible, use metrics to demonstrate the success of your designs (e.g., reduction in task time, increase in conversion rates, improved user satisfaction scores).

• Tailor to the Role: Emphasize aspects of your work that align with InsurTech, AI, and complex B2B SaaS environments.

Challenge Preparation:

• Understand the Domain: Research the insurance claims process, common pain points, and the role of AI in this sector.

• Embrace Ambiguity: As a founding designer, you'll need to be comfortable working with incomplete information and defining solutions from scratch.

• Think Strategically: Be prepared to discuss not just design execution but also product strategy, user acquisition, and long-term product vision.

• Practice Articulation: Be ready to clearly and concisely explain your design process, decisions, and the impact of your work to both technical and non-technical audiences.

📝 Enhancement Note: The interview process for a founding role is rigorous, aiming to assess not only design skills but also strategic thinking, adaptability, and the ability to thrive in a high-growth startup environment. A strong portfolio that showcases experience with complex operational software and AI interactions will be key to advancing.

🛠 Tools & Technology Stack

Primary Design Tools:

• Wireframing & Prototyping: Figma (highly probable), Sketch, Adobe XD.

• User Research & Analytics: Mixpanel, Amplitude, Hotjar, Google Analytics, UserTesting.com.

• Collaboration & Project Management: Jira, Asana, Trello, Slack.

• Design System Tools: Storybook, Zeroheight, or internal documentation platforms.

AI Prototyping Tools:

• Claude: For testing AI agent interactions, content generation, and conversational interfaces.

• Lovable: Likely refers to tools for low-code/no-code AI prototyping or specific AI assistant development platforms.

• Other AI/ML Platforms: Familiarity with concepts from platforms like OpenAI (GPT models), Google AI, or Hugging Face could be beneficial.

Other Relevant Technologies:

• CRM Systems: Salesforce, HubSpot (understanding how design impacts CRM data and workflows).

• Data Visualization Tools: Tableau, Power BI (for understanding how design supports data reporting).

📝 Enhancement Note: Proficiency in Figma is almost a given for modern product designers. The specific mention of AI prototyping tools like Claude and Lovable indicates a forward-thinking approach and a requirement for candidates to experiment with these technologies. Understanding how design integrates with data analytics and CRM systems is crucial for roles impacting operational efficiency.

👥 Team Culture & Values

Operations Values:

• User Obsession: A deep commitment to understanding and solving user problems, particularly for operational professionals in the insurance industry.

• Data-Driven Innovation: Leveraging data and AI to drive product development and operational efficiency.

• Bias for Action: A culture that encourages rapid iteration, experimentation, and execution.

• Ownership & Accountability: Each team member is expected to take ownership of their work and drive it to completion.

• Transparency & Collaboration: Open communication and a collaborative spirit across all functions.

Collaboration Style:

• Integrated Teams: Design is not a silo; it's an integral part of product and engineering teams.

• Iterative Feedback Loops: Regular design critiques, user feedback sessions, and cross-functional reviews.

• Shared Vision: All team members are aligned around the company's mission to transform insurance claims operations.

• Constructive Dialogue: Openness to diverse perspectives and constructive debate to arrive at the best solutions.

📝 Enhancement Note: The company's values likely revolve around innovation, user focus, and execution, which are critical for a successful startup in the AI and InsurTech space. The collaborative style emphasizes cross-functional synergy, essential for translating complex operational needs into functional software.

⚡ Challenges & Growth Opportunities

Challenges:

• Complexity of Insurance Workflows: Navigating and simplifying highly intricate, regulated, and often legacy-driven insurance claims processes.

• Designing for AI Transparency: Creating user interfaces that clearly explain AI actions, reasoning, and limitations to build trust and enable effective human oversight.

• Balancing Startup Pace with Enterprise Needs: Evolving an early-stage product to meet the rigorous demands of enterprise clients while maintaining agility.

• Establishing Design Foundations: Building a design system, processes, and culture from the ground up with limited resources.

• Rapid Technological Evolution: Keeping pace with advancements in AI and integrating them effectively into the product.

Learning & Development Opportunities:

• AI in Operations Specialization: Deepen expertise in applying AI to solve specific operational challenges in regulated industries.

• Leadership Development: Opportunity to grow into a design leadership role and build a team.

• Product Strategy Contribution: Influence the strategic direction of a nascent product in a high-potential market.

• Cross-Functional Skill Building: Gain exposure to product management, engineering, and business strategy in a startup context.

• Industry Trend Immersion: Stay at the forefront of AI and InsurTech developments through hands-on experience.

📝 Enhancement Note: The challenges are inherent to building a new product in a complex domain with cutting-edge technology. The growth opportunities are substantial, offering a chance to shape a product, a team, and a career trajectory significantly.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to simplify a highly complex technical or operational workflow for users. What was your process, and what was the outcome?" (Focus on your structured approach, user research, and measurable impact).

• "How would you approach designing an AI agent that needs to explain its reasoning and potential uncertainty to insurance claims adjusters?" (Emphasize clarity, trust-building, and human-in-the-loop design principles).

• "What are the key considerations when evolving an early-stage product design into an enterprise-ready solution?" (Discuss scalability, security, compliance, and integration needs). Company & Culture Questions:

• "What interests you most about AI's role in the insurance industry, specifically claims operations?" (Showcase your research and genuine interest in the domain).

• "How do you contribute to a collaborative design and product development culture in a fast-paced startup environment?" (Highlight your teamwork, communication, and adaptability).

• "How do you measure the success of your design work, particularly in terms of operational efficiency and user effort reduction?" (Be ready to discuss metrics and ROI). Portfolio Presentation Strategy:

• Prioritize Relevance: Select case studies that best demonstrate your experience with complex workflows, technical software, and ideally, AI or regulated industries.

• Structure for Clarity: Use a consistent structure for each case study: Problem -> Your Role -> Process -> Solution -> Impact.

• Highlight Your Process: Walk through your design thinking, research methods, and decision-making rationale. Explain why you made certain choices.

• Quantify Results: Whenever possible, provide data or metrics to support the impact of your designs.

• Be Prepared for Deep Dives: Expect detailed questions about your contributions, challenges, and trade-offs.

📝 Enhancement Note: Interview preparation should focus on demonstrating a deep understanding of user-centric design, strong analytical and problem-solving skills, and the ability to thrive in an ambiguous, fast-paced startup environment. Highlighting experience with complex operational software and AI interactions will be critical.

📌 Application Steps

To apply for this Founding Product Designer position:

• Submit your application through the provided Ashby link.

• Portfolio Customization: Ensure your portfolio is readily accessible and prominently features case studies relevant to complex operational workflows, technical software design, and ideally, AI or regulated industries. Prioritize depth over breadth.

• Resume Optimization: Tailor your resume to highlight experience with early-stage startups, end-to-end product design ownership, user research, data-informed decision-making, and any experience with AI or InsurTech. Quantify achievements where possible.

• Prepare Your Narrative: Be ready to articulate your design process, rationale, and the impact of your work clearly and concisely, especially for your portfolio walkthrough. Practice explaining complex concepts to both technical and non-technical audiences.

• Company Research: Gain a solid understanding of the insurance claims process, common operational challenges, and the potential of AI in this sector. Research the company's mission and founders to articulate your alignment.

⚠️ 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.