Staff Product Designer: Revolutionize Healthcare & Retail UX

📍 Job Overview

Job Title: Staff Product Designer: Revolutionize Healthcare & Retail UX

Company: Ontrac Solutions

Location: Chicago, Illinois, United States

Job Type: CONTRACTOR

Category: Product Design / UX/UI

Date Posted: November 23, 2025

Experience Level: 8+ Years (3+ in Lead/Principal Role)

Remote Status: Fully Remote (US-Based)

🚀 Role Summary

• Lead the strategic design and execution of a transformative, healthcare-first user experience across multiple platforms (iOS, Android, Web), integrating retail and pharmacy functionalities.

• Architect and optimize complex, multi-step user flows for critical healthcare services like prescription management and telehealth, alongside integrated retail purchases.

• Drive a data-informed design approach, leveraging user research, behavioral analytics, and A/B testing to enhance user engagement and conversion rates for healthcare consumers.

• Develop and maintain a robust design system, ensuring consistency and scalability for native (Swift, Kotlin) and hybrid (React Native, Flutter) applications, with a strong emphasis on HIPAA compliance and data security.

• Serve as a design thought leader, advocating for accessibility (WCAG standards) and inclusive design, while mentoring other designers to foster a culture of innovation and excellence.

📝 Enhancement Note: This role is positioned as a "Staff Product Designer," indicating a senior-level position with significant strategic influence and ownership. The emphasis on transforming a retail-first company into a healthcare platform suggests a need for strong change management, cross-functional leadership, and a deep understanding of user journeys in complex, regulated environments. The contractor employment type, coupled with a remote-first setting for US-based candidates, points to a project-driven engagement focused on achieving specific transformation milestones.

📈 Primary Responsibilities

• Spearhead the end-to-end design strategy and execution for a new, healthcare-centric digital experience, ensuring a cohesive and intuitive user journey across iOS, Android, and web platforms.

• Design and meticulously optimize intricate user flows encompassing prescription management, virtual telehealth appointments, seamless retail product purchasing, and insurance-integrated transactions.

• Develop an innovative integrated checkout model that allows users to combine pharmacy, healthcare services, and retail items into a single, unified transaction, thereby streamlining the user’s path to purchase.

• Employ a data-driven design methodology, utilizing user research, behavioral analytics, and A/B testing to continuously improve UX for conversions, engagement, and frictionless digital interactions for healthcare consumers.

• Establish and maintain a comprehensive, best-in-class design system to ensure visual and interactive consistency across native (Swift, Kotlin) and hybrid (React Native, Flutter) applications, while collaborating closely with product and engineering teams on HIPAA-compliant, secure, and scalable solutions.

• Champion accessibility standards (WCAG) and inclusive design principles throughout the design process, and provide mentorship and guidance to mid-to-senior level designers to cultivate a high-performing design team.

📝 Enhancement Note: The core responsibilities highlight a blend of strategic leadership and hands-on design execution. The emphasis on an "integrated cart model" and "single transaction" for diverse product types (pharmacy, healthcare services, retail) is a critical and complex design challenge, requiring sophisticated user flow architecture and a deep understanding of commerce principles within a regulated industry. The requirement to develop and maintain a design system for both native and hybrid environments underscores the need for robust system thinking and cross-platform expertise.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong foundation in design principles, user experience, and human-computer interaction is expected, typically demonstrated through a Bachelor's degree in Design, HCI, Computer Science, or a related field, or equivalent practical experience.

Experience: A minimum of 8 years of progressive experience in product design, UX/UI design, or digital health, with at least 3 of those years spent in a principal or lead designer capacity, specifically driving significant product transformations.

Required Skills:

• Proven ability to lead comprehensive design strategy and execution for complex, multi-platform digital products, with a demonstrated track record in product transformation initiatives.

• Expertise in designing intricate, multi-step user flows for challenging domains such as healthcare e-commerce, prescription fulfillment, and multi-category shopping experiences.

• Deep understanding of native mobile design principles, including Apple's Human Interface Guidelines (HIG) for iOS and Google's Material Design for Android.

• Proficiency with industry-standard design and prototyping tools, such as Figma, Sketch, Framer, Principle, or Adobe XD, for creating high-fidelity mockups and interactive prototypes.

• Strong communication, presentation, and storytelling skills, with the ability to articulate design strategies effectively to executive leadership and diverse cross-functional teams.

• Experience working within Agile development methodologies, fostering close collaboration with product managers and engineering teams to deliver iterative, data-driven product enhancements.

Preferred Skills:

• Direct experience in health tech, telemedicine platforms, dedicated pharmacy applications, or integrations with wearable health devices.

• Working knowledge of HIPAA regulations and best practices for designing secure, privacy-conscious healthcare solutions.

• Experience with AI-driven personalization techniques for health recommendations, wellness tracking, or tailored user experiences.

• Expertise in optimizing complex shopping cart functionalities, particularly within regulated industries like healthcare, insurance, or pharmacy.

• Demonstrated skill in motion and interaction design to create highly engaging and dynamic user interfaces.

• Familiarity with React Native or Flutter development environments.

📝 Enhancement Note: The experience requirement emphasizes not just years, but the impact of driving "product transformation" and a minimum of 3 years in a lead/principal role. This suggests a need for a candidate who can operate with a high degree of autonomy and strategic vision. The preferred qualifications highlight a desire for specialized domain knowledge in health tech, which will be crucial for navigating the complexities of the healthcare industry.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A robust portfolio is mandatory, showcasing a minimum of 8 years of product design work with a clear emphasis on healthcare, retail, or e-commerce projects.

• Case studies must demonstrate a deep understanding of user-centered design methodologies and a proven ability to translate complex user needs into intuitive and effective digital solutions.

• Projects should highlight experience in designing and optimizing complex, multi-step user flows, particularly those involving transactions, management of sensitive data, or integration of diverse product categories.

• Evidence of designing for scalability and usability in high-traffic or high-stakes environments is critical, with clear articulation of design decisions and their impact.

Process Documentation:

• Demonstrate a clear understanding of user research methodologies, including qualitative and quantitative data collection, synthesis, and application to inform design decisions.

• Provide examples of how behavioral analytics and A/B testing were used to iterate on designs, optimize user engagement, and improve conversion rates.

• Illustrate experience in collaborating with engineering teams to ensure the successful implementation of designs, with an understanding of technical constraints and capabilities in native (Swift, Kotlin) and hybrid (React Native, Flutter) development.

• Showcase a commitment to accessibility (WCAG standards) and inclusive design, with examples of how these principles were integrated into the design process and deliverables.

📝 Enhancement Note: For a Staff Product Designer role, the portfolio is paramount. It needs to go beyond just visual mockups to demonstrate strategic thinking, process rigor, and measurable impact. Emphasis should be placed on case studies that detail the "why" behind design decisions, the challenges overcome, and the quantifiable outcomes achieved, especially within complex domains like healthcare and integrated commerce.

💵 Compensation & Benefits

Salary Range: As a contractor position with an hourly rate, the estimated range is $70 - $90 per hour. This translates to an annual equivalent of approximately $145,600 - $187,200 for a standard 40-hour work week, before taxes and benefits.

Benefits:

• As a contractor, standard employee benefits such as health insurance, paid time off, and retirement plans are typically not provided by the hiring company.

• Candidates are encouraged to factor in the cost of obtaining their own health insurance, retirement savings (e.g., SEP IRA), and managing their own taxes.

• The role offers significant autonomy and flexibility, typical of contract positions.

Working Hours:

• The role is expected to require approximately 40 hours per week.

• Flexibility in daily scheduling is common for remote contractor roles, allowing for adaptation around personal needs, provided project milestones and team collaboration requirements are met.

📝 Enhancement Note: The salary range provided ($70-$90/hour) is based on industry benchmarks for Staff/Principal Product Designers in major US tech hubs like Chicago, considering the remote nature of the role. This range reflects a senior level of expertise and the demand for specialized skills in healthcare UX and product transformation. The absence of traditional benefits is typical for contractor roles, and candidates should factor this into their overall compensation expectations.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology Consulting, Healthcare Technology, Retail Technology, Digital Transformation. Ontrac Solutions operates within the technology consulting sector, partnering with clients to implement cutting-edge digital solutions. This specific project places a strong emphasis on the healthcare and retail industries, aiming to bridge the gap between traditional retail and modern digital healthcare services.

Company Size: Ontrac Solutions is a technology consulting firm, likely mid-sized, focused on specialized client projects. The client they are partnering with is described as a "dominant force in retail and healthcare," indicating a very large, well-established enterprise.

Founded: Ontrac Solutions' founding date is not specified, but its focus on "cutting-edge solutions" and "business transformation" suggests a modern, forward-thinking approach to technology consulting. The client company, being a "dominant force," has likely been established for a significant period, building a strong market presence before this digital transformation initiative.

Team Structure:

• The immediate team will likely consist of the Staff Product Designer, reporting to a Product Lead or Director within the client organization or Ontrac Solutions.

• Collaboration will be extensive with client-side Product Managers, Engineering Leads (iOS, Android, Web, potentially React Native/Flutter), Researchers, and potentially Marketing or Business stakeholders.

Methodology:

• The project will heavily rely on Agile development methodologies, emphasizing iterative design, rapid prototyping, and continuous feedback loops.

• Data-informed decision-making is a core tenet, with significant use of user research, A/B testing, and behavioral analytics to guide design iterations and product strategy.

• Cross-functional collaboration between design, product, and engineering is essential for successful integration of complex features and compliance requirements.

Company Website: https://ontrac-solutions-llc.breezy.hr (Company Careers Portal)

📝 Enhancement Note: The context highlights a dual-layered environment: Ontrac Solutions as the hiring entity (consulting firm) and a large, established client as the end-user of the design transformation. The Staff Product Designer will need to navigate the dynamics of both organizations, with a primary focus on delivering value to the client's end-users. The "dominant force" client suggests a company with existing infrastructure and processes, making the transformation a significant undertaking.

📈 Career & Growth Analysis

Operations Career Level: Staff Product Designer represents a senior individual contributor role, often considered a principal-level or expert-level position. This role is beyond a typical Senior Designer, implying a significant degree of autonomy, strategic influence, and the expectation to lead complex initiatives and mentor others. The focus is on driving architectural-level design decisions and shaping the future of the product experience.

Reporting Structure: The Staff Product Designer will likely report into a Director of Product, Head of Design, or a senior Product Manager within the client organization or Ontrac Solutions' project leadership team. They will collaborate closely with Product Managers, Engineering Leads, and potentially other senior stakeholders across business units.

Operations Impact: The impact of this role is substantial, directly influencing the user experience for millions of customers accessing healthcare services and retail products. Success will be measured by improvements in user engagement, conversion rates for healthcare services and retail purchases, customer satisfaction, and adherence to critical healthcare compliance standards. The role is pivotal in transforming a retail-focused entity into a comprehensive digital healthcare platform.

Growth Opportunities:

• Leadership Expansion: Potential to transition into a formal leadership role (e.g., Design Manager, Director of Design) if the project extends or if opportunities arise within the client or Ontrac Solutions.

• Domain Specialization: Deepen expertise in health tech, digital pharmacy, and integrated commerce, becoming a recognized expert in these complex and growing fields.

• Strategic Influence: Continue to shape product strategy and roadmaps at a high level, influencing business outcomes through design innovation.

• Broader Project Scope: Opportunity to lead design efforts on other large-scale digital transformation projects across Ontrac Solutions' client portfolio.

📝 Enhancement Note: As a Staff-level designer, the growth path is less about climbing a ladder and more about deepening expertise, increasing strategic impact, and potentially taking on more complex or broader leadership responsibilities. The contractor nature means growth is tied to project success and potential for contract extension or future engagements.

🌐 Work Environment

Office Type: This is a remote-first position for US-based contractors. While there might not be a physical office requirement for the contractor, the client company is a "dominant force in retail and healthcare," suggesting they likely have significant corporate offices. The work will be conducted remotely using digital collaboration tools.

Office Location(s): The primary location specified is Chicago, Illinois, but the "TELECOMMUTE" and "US" location requirements indicate that the role is open to remote candidates across the United States. The client company, being a major player, likely has headquarters or major operational centers in the US, potentially including Chicago.

Workspace Context:

• The work environment will be fully digital, requiring a reliable internet connection and a dedicated home office setup.

• Collaboration will occur through virtual meeting platforms (e.g., Zoom, Google Meet), project management tools (e.g., Asana, Jira), and design collaboration tools (e.g., Figma, Miro).

• The role demands a high degree of self-discipline, time management, and proactive communication to maintain strong working relationships and project momentum in a remote setting.

Work Schedule:

• The standard expectation is a 40-hour work week.

• While remote roles often offer flexibility in daily hours, core collaboration times will likely be established to align with the client's product and engineering teams, necessitating availability during typical business hours in the relevant US time zones.

📝 Enhancement Note: The remote nature of this contractor role emphasizes the need for self-management and strong digital communication skills. Candidates should be comfortable working asynchronously and proactively engaging with team members across different locations and time zones. The "US-based" requirement suggests potential limitations on international remote work due to compliance or tax reasons.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio by Ontrac Solutions or the client's recruiting team to assess basic qualifications and alignment with the role's core requirements.

• Hiring Manager/Lead Interview: A discussion with the hiring manager (likely a Director of Product or Design Lead) to delve deeper into your experience, design philosophy, leadership capabilities, and strategic thinking. Expect questions about past product transformations and complex UX challenges.

• Design Challenge/Portfolio Deep Dive: This may involve presenting a specific case study from your portfolio in detail, explaining your process, rationale, and impact, or a take-home design exercise focused on a relevant problem (e.g., optimizing a healthcare checkout flow). This is where your process documentation and problem-solving skills will be scrutinized.

• Cross-functional Team Interviews: Interviews with Product Managers, Engineering Leads, and potentially other stakeholders to assess collaboration style, communication skills, and ability to integrate with development teams.

• Executive Interview (Potential): For a Staff-level role, a final interview with a senior executive (e.g., VP of Product, Chief Product Officer) may occur to evaluate strategic alignment and overall fit.

Portfolio Review Tips:

• Curate Strategically: Select 3-4 of your most impactful projects that best showcase your experience in healthcare, retail, e-commerce, complex user flows, and product transformation.

• Tell a Story: For each project, clearly articulate the problem statement, your role and responsibilities, the design process you followed (research, ideation, prototyping, testing), key decisions and rationale, challenges faced, and most importantly, the measurable outcomes and impact.

• Highlight Process Rigor: Emphasize your data-informed approach, how you leveraged user research, analytics, and A/B testing. Detail how you approached accessibility and inclusive design.

• Showcase System Thinking: If you have experience with design systems, clearly illustrate your contributions and how you ensured consistency across platforms.

• Prepare for Questions: Be ready to discuss trade-offs, how you handled stakeholder feedback, and what you would do differently.

Challenge Preparation:

• Understand the Domain: Research current trends and challenges in digital healthcare, pharmacy, and integrated retail commerce. Familiarize yourself with HIPAA considerations.

• Focus on Problem-Solving: If a design challenge is given, break down the problem systematically. Define the user, identify key pain points, and propose solutions with clear justifications.

• Prioritize and Justify: In a timed challenge, focus on delivering a well-reasoned solution rather than a polished UI. Clearly articulate your priorities and the trade-offs you're making.

• Practice Presentation: Rehearse presenting your portfolio case studies and any challenge solutions concisely and engagingly, anticipating questions about your process and impact.

📝 Enhancement Note: The interview process for a Staff Product Designer role is rigorous. The portfolio review is not just about aesthetics but about demonstrating strategic thinking, process mastery, and measurable impact. The emphasis on healthcare and integrated commerce means candidates should be prepared to discuss domain-specific challenges and solutions.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly probable as industry standard), Sketch, Framer, Principle, Adobe XD.

• Collaboration: Miro, Mural (for whiteboarding and ideation), Slack, Microsoft Teams (for communication).

• Project Management: Jira, Asana, Trello (for tracking design tasks and sprints).

Analytics & Reporting:

• Web & Mobile Analytics: Google Analytics, Adobe Analytics, Amplitude, Mixpanel (for tracking user behavior, conversions, and feature adoption).

• A/B Testing: Optimizely, VWO (Visual Website Optimizer), Google Optimize (for experimental design and performance testing).

CRM & Automation:

• While less direct for a designer, understanding how CRM data (e.g., Salesforce) or marketing automation platforms inform user segmentation and personalization can be beneficial.

Development Environment Familiarity:

• Native Mobile: Awareness of Swift (iOS) and Kotlin (Android) development environments and principles.

• Cross-Platform: Understanding of React Native or Flutter frameworks and their design implications.

📝 Enhancement Note: Proficiency in Figma is almost a prerequisite for modern design roles, especially at the Staff level. The emphasis on data-informed design means familiarity with analytics and A/B testing tools is crucial. Understanding the development environments (native and cross-platform) will enable better collaboration with engineering teams.

👥 Team Culture & Values

Operations Values:

• User-Centricity: A primary focus on understanding and serving the needs of healthcare consumers, ensuring accessibility, usability, and positive experiences.

• Data-Driven Decision Making: Reliance on research, analytics, and experimentation to validate design hypotheses and measure impact, fostering a culture of continuous improvement.

• Collaboration & Transparency: Open communication and strong partnerships with product management, engineering, and business stakeholders to achieve shared goals.

• Innovation & Excellence: A drive to push boundaries in digital healthcare and retail, seeking novel solutions and maintaining high standards of design quality and execution.

• Integrity & Compliance: A deep respect for data privacy and regulatory requirements (HIPAA), ensuring all designs uphold security and ethical standards.

Collaboration Style:

• Cross-Functional Partnership: The role requires seamless integration with Product Managers to define requirements and roadmaps, and with Engineers to ensure feasible and high-quality implementation.

• Mentorship & Knowledge Sharing: A willingness to mentor junior designers, share best practices, and foster a collaborative design community within the project.

• Feedback-Oriented: An open and constructive approach to receiving and giving feedback, essential for iterative design and team growth.

• Agile Cadence: Working within agile sprints, participating in daily stand-ups, sprint planning, and retrospectives to maintain project velocity and alignment.

📝 Enhancement Note: The company culture, as inferred from the job description, values innovation, user impact, and rigorous execution within a regulated industry. The emphasis on a "healthcare-first" approach and "HIPAA compliance" indicates a strong ethical and responsibility-driven ethos.

⚡ Challenges & Growth Opportunities

Challenges:

• Transforming a Retail-First Mindset: Shifting a deeply ingrained retail-centric approach to a healthcare-first perspective requires significant strategic influence and careful user experience design that acknowledges the distinct needs and sensitivities of healthcare consumers.

• Integrating Complex Workflows: Designing a unified checkout for pharmacy, healthcare services, and retail products, while adhering to strict regulatory requirements (HIPAA, insurance), presents a significant architectural and user flow challenge.

• Balancing Innovation with Compliance: Introducing cutting-edge features and AI-driven personalization while maintaining robust security, data privacy, and compliance with healthcare regulations is a delicate balancing act.

• Cross-Platform Consistency: Ensuring a seamless and consistent user experience across native iOS/Android and hybrid (React Native/Flutter) applications requires meticulous design system management and platform-specific considerations.

Learning & Development Opportunities:

• Deep Health Tech Expertise: Gain invaluable experience in the rapidly evolving health tech and digital pharmacy sectors, a high-demand area.

• Complex System Design: Master the design of intricate, multi-faceted systems that integrate commerce, services, and regulated data.

• Leadership & Mentorship: Develop leadership and mentorship skills by guiding other designers and influencing strategic product decisions.

• Exposure to Advanced Technologies: Potential to work with AI-driven personalization and advanced analytics tools.

• Client Impact: Directly contribute to improving healthcare access and wellness for a vast user base, offering significant professional satisfaction.

📝 Enhancement Note: The challenges listed are inherent to the nature of the project—a significant digital transformation in a regulated industry. The growth opportunities are substantial, offering a chance to specialize in a critical and growing sector while honing leadership and strategic design skills.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you led a significant product transformation. What were the biggest challenges, and how did you overcome them?" (Focus on your strategic approach, ability to influence, and change management skills.)

• "How would you approach designing an integrated checkout experience for pharmacy, healthcare services, and retail products, considering HIPAA compliance?" (Demonstrate your understanding of user flows, data security, and regulatory constraints.)

• "Explain your process for developing or evolving a design system for cross-platform applications (native and hybrid). What are the key considerations?" (Showcase your system thinking and understanding of technical implications.)

Company & Culture Questions:

• "What interests you most about this specific project transforming a retail company into a healthcare platform?" (Show your understanding of the client's mission and your enthusiasm for the challenge.)

• "How do you advocate for accessibility (WCAG) and inclusive design principles in your work?" (Demonstrate your commitment to ethical design and broad user reach.)

• "Describe your experience mentoring junior designers or leading design initiatives within a team." (Assess your leadership potential and collaborative spirit.)

Portfolio Presentation Strategy:

• Structure is Key: For each case study, follow a clear narrative: Problem -> Your Role -> Process -> Solution -> Impact (Metrics).

• Quantify Impact: Wherever possible, use data and metrics to demonstrate the success of your designs (e.g., increased conversion rates, reduced task completion time, improved user satisfaction scores).

• Explain Your 'Why': Be prepared to articulate the rationale behind every significant design decision you made. Why this approach? Why this solution?

• Showcase Collaboration: Mention how you worked with product managers, engineers, and other stakeholders.

• Be Ready for Deep Dives: Anticipate questions about your process, alternative solutions you considered, and how you handled trade-offs or conflicting feedback.

📝 Enhancement Note: Interviewers will be looking for strategic thinking, a deep understanding of the design process, proven ability to drive complex projects, and strong collaboration skills, especially within the context of regulated industries like healthcare. Your portfolio presentation is your primary tool to demonstrate these capabilities.

📌 Application Steps

To apply for this operations position:

• Submit your application through the provided Breezy HR link.

• Curate your portfolio: Select 3-4 of your most relevant and impactful projects, focusing on healthcare, retail, e-commerce, complex user flows, and product transformation. Ensure each case study clearly outlines the problem, your process, your role, the solution, and quantifiable outcomes.

• Tailor your resume: Highlight your 8+ years of experience, specifically mentioning the 3+ years in a lead or principal designer role. Emphasize keywords related to UX/UI, product design, healthcare tech, retail UX, design systems, accessibility, and Agile methodologies.

• Prepare your presentation: Practice walking through your portfolio case studies, articulating your design rationale, problem-solving approach, and the impact of your work. Be ready to discuss your experience with data-informed design and cross-functional collaboration.

• Research the client's industry: Familiarize yourself with current trends and challenges in digital healthcare, pharmacy, and integrated retail commerce. Understand the importance of HIPAA compliance and user experience in this sector.

⚠️ 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.