Product Designer (UI/UX) - Contract

📍 Job Overview

Job Title: Product Designer (UI/UX) - Contract Company: Smyl Fitness Rx Location: Remote (must overlap 4+ hours with Central Time) Job Type: CONTRACTOR Category: Product Design / UI/UX Date Posted: September 13, 2025 Experience Level: 5-10 Years

🚀 Role Summary

• Lead the establishment of the User Experience (UX) and visual design foundation for a digital health platform focused on older adults.
• Develop a cohesive and scalable user experience, bridging the gap between complex technical systems and end-users.
• Create a unified UX vision that caters to both internal administrative interfaces and client-facing applications, ensuring accessibility and human-centered design principles.
• Collaborate closely with product, engineering, and operations teams to deliver high-impact tools within a fast-paced startup environment.

📝 Enhancement Note: While the initial posting is for a "Product Designer (UI/UX)", the detailed responsibilities and required skills, particularly the emphasis on user flows, prototyping, usability studies, and the need to translate requirements into functional designs, strongly indicate a core focus on User Experience (UX) design, with UI design as a critical component. The role also requires an understanding of technical constraints and collaboration with engineering for frontend theming, which is common in operations-adjacent design roles focused on internal tools or customer-facing platforms that support business processes.

📈 Primary Responsibilities

• Develop and articulate a unified UX vision for both internal administrative interfaces and external customer-facing applications, ensuring a consistent and intuitive user journey.
• Establish a comprehensive visual language, design system, and reusable UI component library to ensure brand consistency and accelerate development cycles.
• Translate complex functional requirements and user needs into clear user flows, wireframes, high-fidelity mockups, and interactive prototypes.
• Conduct rigorous usability studies, A/B tests, and user interviews, particularly with older adult users and internal staff, to gather feedback and iterate on designs.
• Ensure all designs adhere to strict accessibility standards (WCAG/a11y) and consider digital literacy best practices for diverse user populations.
• Collaborate closely with engineering teams to provide detailed design specifications, QA guidance, and assist with frontend theming, particularly within React/TypeScript environments.
• Leverage generative AI platforms (e.g., Replit, Lovable) to rapidly build and test design prototypes, facilitating faster iteration and validation.
• Maintain clear and organized design documentation for seamless handoff and ongoing collaboration with cross-functional teams.

📝 Enhancement Note: The description emphasizes a hands-on approach to design, including rapid prototyping with AI tools and providing technical guidance for frontend implementation. This suggests the role requires not just conceptual design but also a practical understanding of how designs translate into functional code, a common requirement for designers working closely with engineering and product operations in startups. The need to design for both administrative and end-user interfaces highlights a scope that extends beyond typical consumer product design, touching on internal operational efficiency and partner enablement.

🎓 Skills & Qualifications

Education:

• No specific degree is mandated, but a strong portfolio demonstrating end-to-end design ownership and a deep understanding of UX principles is paramount.

Experience:

• Minimum of 5 years of dedicated UI/UX design experience, with a proven track record of successfully launching digital products.
• Demonstrated experience in designing for mobile-first and tablet-friendly interfaces, considering various screen sizes and interaction methods.
• Proven ability to design for data-rich environments and form-heavy interfaces, such as administrative dashboards and complex operational tools.
• Hands-on experience with rapid prototyping tools such as Figma, Replit, or Lovable, with the ability to create testable and interactive mockups.
• Solid understanding and practical application of accessibility standards (WCAG/a11y) and digital literacy considerations for diverse user groups.
• Excellent communication, documentation, and collaboration skills to effectively hand off designs and work with cross-functional teams.

Required Skills:

• Expertise in User Experience (UX) design principles and methodologies.
• Proficiency in User Interface (UI) design, including visual hierarchy, typography, and layout.
• Strong skills in creating detailed user flows, wireframes, and high-fidelity mockups.
• Demonstrated experience in conducting usability studies and A/B testing.
• Deep understanding of accessibility standards (WCAG) and inclusive design practices.
• Proficiency with industry-standard design and prototyping tools (e.g., Figma).
• Ability to work effectively in a remote, fast-paced startup environment.
• Strong analytical skills for interpreting user feedback and data.

Preferred Skills:

• Experience within the U.S. healthcare sector or other regulated domains (e.g., HIPAA).
• Familiarity with designing for older adult populations or individuals with varying digital literacy levels.
• Exposure to frontend development technologies such as React and TypeScript, with the ability to tweak or understand frontend theming.
• Experience with UX testing frameworks or tools (e.g., Cypress, Playwright, Gherkin).
• Familiarity with generative AI platforms for design and prototyping.

📝 Enhancement Note: The requirement for "5+ years of UI/UX design experience, with a portfolio demonstrating end-to-end ownership" and the preference for healthcare/older adult experience suggest a mid-to-senior level designer. The emphasis on data-rich, form-heavy environments and accessibility, coupled with the need to work with engineering on frontend theming, indicates a role that bridges pure design with a practical understanding of implementation and operational usability.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A comprehensive portfolio showcasing end-to-end product design ownership, from initial concept to final implementation.
• Demonstrate a clear process for user research, ideation, wireframing, prototyping, and visual design.
• Include case studies that highlight problem-solving skills, design decisions, and the impact of your work on user experience and business goals.
• Showcase examples of designing for both administrative/internal tools and consumer-facing applications.
• Feature projects that demonstrate expertise in mobile-first and tablet-friendly design, with attention to responsive layouts.
• Highlight specific examples of implementing accessibility standards (WCAG) in your designs.
• Include projects that involved data-rich interfaces or complex data visualization.

Process Documentation:

• Case studies should clearly outline your design process, including methodologies used for user research, requirement gathering, and iteration.
• Demonstrate how you translate business requirements and user needs into actionable design solutions.
• Provide examples of how you conducted usability testing and incorporated feedback to refine designs.
• Showcase your ability to create and maintain design systems or component libraries for consistency and scalability.
• If possible, include examples of design handoffs to engineering teams, detailing the specifications and collaboration process.

📝 Enhancement Note: Given the startup environment and the need for a "design vision" and "foundations," the portfolio should emphasize strategic thinking, system design (design systems), and the ability to establish best practices. The inclusion of AI prototyping tools suggests an openness to innovative workflows that should ideally be reflected in the portfolio's methodology.

💵 Compensation & Benefits

Salary Range:

• As this is a contract role with potential for ongoing part-time work after an initial full-time phase, compensation will likely be structured as an hourly rate or a fixed project fee. Based on the experience level (5+ years), the location requirement (US-based with Central Time overlap), and the specialized skills required (UI/UX, accessibility, healthcare context, prototyping tools), an estimated hourly rate for a contract Product Designer in Chicago, Illinois, would typically range from $55 to $95 USD per hour. This range can fluctuate based on the specific depth of expertise, the duration of the contract, and the negotiation between the candidate and Smyl Fitness Rx.

Benefits:

• This is a contract position, so traditional employee benefits like health insurance, paid time off, and retirement plans are typically not provided.
• Flexibility: The role offers flexibility in work hours, especially in Phase 2, allowing for a good work-life balance.
• Impactful Work: Opportunity to work on a mission-driven product that addresses critical health needs for older adults.
• Startup Environment: Exposure to a fast-paced, innovative startup culture with direct collaboration with core team members.
• Professional Development: Potential to shape the design direction of a growing digital health platform.

Working Hours:

• Phase 1: Full-time engagement, approximately 30–40 hours per week for 1-2 months.
• Phase 2: Ongoing, flexible part-time contract for iteration and upkeep.
• A mandatory overlap of at least 4 hours with the Central Time Zone (CT) is required for effective collaboration.

📝 Enhancement Note: The salary estimate is based on industry benchmarks for contract UI/UX designers in major US tech hubs like Chicago, considering the experience level specified. Benefits are generally limited for contractors, highlighting the importance of the hourly rate and the nature of the work itself.

🎯 Team & Company Context

🏢 Company Culture

Industry: Digital Health / Health Technology / Geriatric Care Company Size: Small Startup (exact employee count not specified, but described as a "small, cross-functional team") Founded: 2021 (implied by context of being a startup addressing current health trends)

Team Structure:

• The team is described as small and cross-functional, indicating close collaboration between product, engineering, and operations.
• Designers will likely report to a Product Lead or Head of Product, working directly with engineers for implementation.
• Collaboration is expected to be direct and iterative, with frequent communication due to the small team size and hybrid work model.

Methodology:

• Emphasis on a human-centered design approach, focusing on the needs of older adults.
• Agile and iterative development process, utilizing rapid prototyping and user feedback loops.
• Data-driven decision-making, informed by usability studies, A/B tests, and analytics.
• Cross-functional collaboration is key, with close integration between design, engineering, and operations.
• Adoption of modern tools and technologies, including generative AI for design and development.

Company Website: smylfitness.com

📝 Enhancement Note: The company's focus on a vulnerable population (older adults) and the health sector suggests a culture that values impact, empathy, and rigorous adherence to standards (like accessibility and potentially HIPAA). The startup nature implies a dynamic, hands-on environment where individuals can have significant influence.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a specialized individual contributor role focused on Product Design, specifically UI/UX. While not a traditional "Operations" role (like Revenue Ops or Sales Ops), it plays a critical supporting function for the operationalization of the product and user experience. The designer is responsible for ensuring the platform is usable, accessible, and scalable, which directly impacts the operational efficiency of Smyl Fitness Rx's service delivery.

Reporting Structure: The Product Designer will likely report to a Product Manager or Head of Product, collaborating directly with software engineers and potentially interacting with operations staff who manage customer onboarding and support.

Operations Impact: The designer's work directly influences user adoption, customer satisfaction, and the efficiency of the platform. A well-designed, accessible, and intuitive platform reduces support overhead, improves user engagement, and can streamline internal operational workflows. By establishing a strong design foundation, the designer enables the company to scale its services effectively and serve its target demographic with high-quality care delivery.

Growth Opportunities:

• Design Leadership: Opportunity to build out and lead the design function as the company grows, potentially establishing a dedicated design team and system.
• Product Strategy Influence: Direct input into the product roadmap and strategic vision, particularly regarding user experience and platform usability.
• Domain Expertise: Deepen understanding and expertise in the digital health sector, specifically in designing for older adults and navigating healthcare-related compliance.
• Skill Expansion: Opportunity to gain exposure to frontend development (React/TypeScript) and AI-driven design tools, enhancing technical skill sets.
• Long-Term Engagement: Potential for transition to a more permanent role or extended contract work based on performance and company needs.

📝 Enhancement Note: While the title is "Product Designer," the context of a startup and the need to establish foundational elements implies significant growth potential for someone who can contribute strategically to the product's evolution and operational readiness. The role interfaces with operational needs by ensuring user-friendliness and efficiency.

🌐 Work Environment

Office Type: Remote Office Location(s): The role is fully remote, with the specific requirement to overlap 4+ hours with the Central Time Zone (CT). This suggests that while the company may have a physical presence or headquarters in Chicago, the team is distributed, and collaboration occurs primarily through digital channels.

Workspace Context:

• Digital Collaboration: Expect to work primarily through video conferencing, instant messaging, and collaborative design tools.
• Cross-Functional Interaction: Frequent interaction with product managers, engineers, and potentially customer success or operations personnel to gather requirements and ensure design alignment.
• Autonomous Work: As a contractor, there will be a high degree of autonomy in managing your workflow and deliverables, supported by clear project goals and feedback loops.
• Tools and Technology: Access to and proficiency with digital collaboration tools, project management software, and advanced design/prototyping platforms will be essential.

Work Schedule:

• Phase 1: Requires a commitment of 30-40 hours per week, structured to accommodate the 4+ hour overlap with Central Time.
• Phase 2: Flexible part-time hours, allowing for adaptation to ongoing project needs and candidate availability.

📝 Enhancement Note: The remote nature, combined with the time zone overlap requirement, suggests a need for strong self-management, proactive communication, and comfort with asynchronous and synchronous digital collaboration.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Likely a brief call to assess basic qualifications, experience, and cultural fit, potentially with a recruiter or hiring manager.
• Portfolio Review & Skills Assessment: A dedicated session to walk through your portfolio, focusing on specific case studies that demonstrate your process, problem-solving abilities, and impact. Expect to discuss your approach to UI/UX, accessibility, and rapid prototyping.
• Technical/Design Challenge: Potentially a small design exercise or case study to evaluate your practical design skills, problem-solving approach, and ability to meet specific requirements under a time constraint. This might involve critiquing an existing interface or designing a solution for a given problem.
• Cross-Functional Interviews: Meetings with members of the product and engineering teams to assess collaboration style and technical understanding.
• Final Interview: Likely with a senior leader (e.g., CEO, Head of Product) to discuss overall vision, cultural alignment, and contract terms.

Portfolio Review Tips:

• Curate Strategically: Select 3-4 strong case studies that best represent your end-to-end product design process and highlight relevant experience (mobile-first, data-rich, accessibility).
• Tell a Story: For each case study, clearly articulate the problem, your role, the design process, key decisions, challenges overcome, and the measurable impact of your solutions.
• Show, Don't Just Tell: Use visuals (wireframes, mockups, prototypes) to illustrate your design thinking. Explain why you made certain design choices.
• Highlight Process: Detail your approach to user research, ideation, prototyping with tools like Replit or Figma, and usability testing.
• Demonstrate Accessibility: Explicitly call out how you incorporated accessibility standards into your designs.
• Address Technical Collaboration: If possible, show how you collaborated with engineers or provided design specifications for implementation.
• Be Ready for Specifics: Prepare to discuss your experience with healthcare, older adults, and data-intensive applications if applicable.

Challenge Preparation:

• Research Smyl Fitness Rx's mission and target audience to understand their context.
• Familiarize yourself with common UI/UX challenges in health tech and for older adult users.
• Practice articulating your design process and rationale concisely.
• Be prepared to discuss how you would approach establishing a design system for a startup.
• Understand the importance of accessibility and how to implement it effectively.

📝 Enhancement Note: The interview process is likely to be thorough, focusing on practical skills and the ability to quickly contribute to establishing design foundations. The portfolio is the most critical element, so tailoring it to the requirements and practicing the presentation is key.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (expected for wireframing, mockups, and design systems), Replit or Lovable (for rapid prototyping with AI).
• Collaboration: Slack, Zoom, Google Workspace (or similar for communication and document sharing).
• Project Management: Tools like Jira, Asana, or Trello may be used by the team.

Analytics & Reporting:

• While the designer isn't typically responsible for data analysis, they will need to interpret data from usability studies, A/B tests, and potentially user analytics to inform design decisions. Familiarity with analytics concepts is beneficial.

CRM & Automation:

• Not directly relevant to the designer's core responsibilities, but understanding how the platform integrates with CRM or automation tools might be helpful for context.

📝 Enhancement Note: Proficiency in Figma is almost a given. The explicit mention of Replit or Lovable for AI-driven prototyping is a unique requirement that candidates should highlight if they have experience or a willingness to learn. Understanding the output requirements for engineering (React/TypeScript) is also important.

👥 Team Culture & Values

Operations Values:

• Mission-Driven: A strong commitment to improving the health and well-being of older adults.
• User-Centric: Prioritizing the needs, accessibility, and experience of the end-users.
• Collaboration: Working effectively in a small, cross-functional team where open communication and teamwork are vital.
• Innovation: Embracing new technologies and methodologies (like AI in design) to solve complex problems.
• Agility & Iteration: A willingness to adapt, learn quickly, and iterate on designs based on feedback and data.
• Impact Focus: Driving tangible improvements in user health outcomes and operational efficiency.

Collaboration Style:

• Close-Knit Team: Expect direct and frequent communication with product and engineering.
• Iterative Design Feedback: Design solutions will likely undergo multiple rounds of review and refinement.
• Shared Ownership: In a startup, team members often share ownership of product success and contribute beyond their strict job descriptions.
• Transparent Communication: Open sharing of progress, challenges, and ideas is crucial for a small team.

📝 Enhancement Note: The company's focus on a sensitive population and a mission to improve health suggests a culture that values empathy, diligence, and a collective drive towards a common goal. The designer's role is to ensure the product is not just functional but also compassionate and effective.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing User Needs: Designing for older adults can present unique challenges related to digital literacy, cognitive abilities, and physical limitations, requiring careful consideration of accessibility and usability.
• Dual Audiences: Creating a unified experience that effectively serves both internal administrative users and external older adult users with distinct needs and workflows.
• Startup Resource Constraints: Working within a startup environment may involve managing resources efficiently and prioritizing tasks effectively.
• Rapid Evolution: The need to adapt quickly to evolving product requirements, user feedback, and technological advancements.
• Frontend Integration: Ensuring designs are feasible and effectively implemented by the engineering team, especially with limited design resources for ongoing QA.

Learning & Development Opportunities:

• Domain Specialization: Gaining deep expertise in health tech, particularly in designing for geriatric populations.
• Design System Development: Opportunity to build and own a design system from the ground up, establishing scalable design practices.
• AI in Design: Hands-on experience with cutting-edge AI tools for rapid prototyping and design exploration.
• Cross-Functional Learning: Exposure to product management and software engineering processes, broadening understanding of the product development lifecycle.
• Impactful Contribution: Directly influencing the user experience and operational success of a product with significant social impact.

📝 Enhancement Note: The challenges are typical for a startup designer, especially one in a specialized field. The growth opportunities are significant, offering a chance to shape a product and gain valuable niche experience.

💡 Interview Preparation

Strategy Questions:

• Vision & Strategy: "How would you approach developing a unified UX vision for a platform serving two distinct user groups (older adults and internal staff)?" Be prepared to discuss your process for understanding user needs, defining core principles, and translating them into a cohesive design strategy.
• Accessibility First: "Describe your process for ensuring designs meet WCAG standards and are inclusive for users with varying digital literacy." Be ready to provide specific examples of how you've implemented accessibility features.
• Prototyping & Iteration: "How would you utilize AI tools like Replit or Lovable to accelerate the design and testing process for a new feature?" Discuss your approach to rapid prototyping and user feedback integration.
• Design Systems: "What are the key components of a design system, and how would you go about establishing one for a growing startup like Smyl Fitness Rx?" Be prepared to discuss scalability, maintenance, and team adoption.
• Healthcare Context: "What specific design considerations are crucial when designing for older adults in a healthcare context?" Highlight your understanding of potential user challenges and how design can mitigate them.

Company & Culture Questions:

• "What excites you about Smyl Fitness Rx's mission to help older adults?" Be genuine and connect your passion to their work.
• "How do you approach collaboration within a small, cross-functional team?" Discuss your communication style and experience working with engineers and product managers.
• "How do you handle feedback on your designs, especially when working in a fast-paced environment?" Emphasize your adaptability and constructive approach.

Portfolio Presentation Strategy:

• Structure: Organize your presentation logically, starting with an overview of your approach, then diving into 2-3 detailed case studies.
• Focus on Process: For each case study, clearly articulate the problem, your role, the research and design process, key decisions, challenges, and outcomes.
• Visuals are Key: Use high-quality visuals of wireframes, mockups, and prototypes. Explain why you made design choices.
• Quantify Impact: If possible, use metrics to demonstrate the success of your designs (e.g., improved conversion rates, reduced errors, increased user satisfaction).
• Prepare for Technical Questions: Be ready to discuss your experience with Figma and any familiarity with React/TypeScript theming.
• Accessibility Emphasis: Clearly highlight your contributions to accessibility in your portfolio pieces.

📝 Enhancement Note: The interview will likely test your ability to think critically about user problems, articulate design rationale, and demonstrate practical skills relevant to a startup environment. Preparing specific examples from your portfolio that align with the job requirements is crucial.

📌 Application Steps

To apply for this Product Designer (UI/UX) contract position:

• Submit your application via the provided link on Workable.
• Portfolio Tailoring: Ensure your resume and cover letter (if applicable) clearly highlight your 5+ years of UI/UX experience, mobile-first design expertise, accessibility knowledge, and experience with prototyping tools.
• Portfolio Preparation: Curate your portfolio to showcase 2-3 strong case studies that demonstrate end-to-end ownership, problem-solving, and impact, with a focus on mobile, data-rich, or accessibility-related projects. Be ready to discuss your design process in detail.
• Company Research: Familiarize yourself with Smyl Fitness Rx's mission, target audience, and the digital health landscape for older adults to articulate your interest and understanding during interviews.
• Time Zone Alignment: Be prepared to confirm your ability to overlap at least 4 hours with the Central Time Zone during work hours.

⚠️ 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.