Product Designer

📍 Job Overview

Job Title: Product Designer

Company: Flex

Location: United States

Job Type: FULL_TIME

Category: Product Design / GTM Operations Enablement

Date Posted: May 1, 2026

Experience Level: Mid-Level (3+ years)

Remote Status: Fully Remote

🚀 Role Summary

• Owns end-to-end product design for the merchant experience, from initial discovery and user research through to final UI and shipping with engineers.

• Drives user research initiatives, including merchant interviews, surveys, and participation in sales/customer calls to inform product direction and strategy.

• Collaborates closely with engineering, founders, and sales teams to define the merchant roadmap, scope features, and ensure rapid, high-quality product delivery.

• Leverages AI tools (e.g., Claude, Cursor, v0) to accelerate prototyping, validation, and iteration cycles, enhancing traditional design workflows.

• Contributes to the evolution and maintenance of the Flex design system, ensuring consistency and scalability across products.

📝 Enhancement Note: While the role is labeled "Product Designer," its focus on the "merchant experience" and collaboration with sales and GTM teams strongly aligns with roles that bridge product design and Go-To-Market (GTM) operations enablement. The emphasis on understanding merchant needs and translating them into intuitive product features directly supports sales effectiveness and operational efficiency for Flex's brand partners. This role requires a blend of user-centric design principles and a pragmatic understanding of business objectives and operational workflows.

📈 Primary Responsibilities

• Lead the full product design lifecycle for Flex's merchant-facing platform, including user research, ideation, wireframing, prototyping, and UI design.

• Conduct qualitative and quantitative user research to deeply understand merchant pain points, workflows, and business objectives within the HSA/FSA payment space.

• Translate user insights and business requirements into intuitive and effective user flows, wireframes, mockups, and high-fidelity prototypes using Figma.

• Partner with engineering teams to scope features, define technical requirements, and ensure seamless implementation of designs, maintaining design integrity throughout the development process.

• Actively utilize and experiment with AI-powered design tools to enhance productivity, explore innovative solutions, and deliver prototypes and validated concepts rapidly.

• Collaborate with cross-functional teams including sales, customer success, and marketing to gather feedback, align on product strategy, and ensure a cohesive merchant experience.

• Contribute to the development and ongoing refinement of the Flex design system, ensuring a consistent and scalable visual language and component library.

• Participate in cross-company initiatives, including occasional marketing asset creation or website adjustments, demonstrating a flexible and proactive approach to supporting business needs.

• Foster a culture of continuous learning, problem-solving, and operational excellence within the design and product teams.

📝 Enhancement Note: The responsibilities highlight a strong emphasis on user research and direct collaboration with users (merchants) and internal stakeholders (sales, founders), which are critical for effective GTM operations enablement. The requirement to use AI tools suggests a focus on efficiency and innovation in design processes, a key aspect of modern operations.

🎓 Skills & Qualifications

Education: Bachelor's degree in Design, Human-Computer Interaction, Computer Science, or a related field; or equivalent practical experience.

Experience: 3+ years of professional experience in product design, with a significant portion ideally gained at a high-growth startup or within a fast-paced product development environment.

Required Skills:

• Proven expertise in end-to-end product design, encompassing user research, problem definition, user flow design, wireframing, prototyping, and visual UI design.

• Mastery of Figma as the primary design tool for creating user flows, wireframes, mockups, and interactive prototypes.

• Strong command of user research methodologies, including conducting merchant interviews, surveys, user testing, and synthesizing findings into actionable product insights.

• Demonstrated ability to collaborate effectively with engineering teams, product managers, and business stakeholders, fostering strong cross-functional relationships.

• Proficiency in leveraging AI tools within the design workflow for prototyping, exploration, and accelerating design processes.

• Excellent written and verbal communication skills, with the ability to articulate design decisions, user insights, and strategic recommendations clearly.

• A user-first design philosophy, prioritizing deep understanding of user needs and problem-solving before focusing on visual aesthetics.

• Resourcefulness, curiosity, low ego, and a willingness to take initiative and wear multiple hats in an early-stage company environment.

Preferred Skills:

• Experience designing B2B-facing products, particularly within the payments, fintech, or e-commerce checkout spaces.

• Experience in building, maintaining, or contributing to a comprehensive design system.

• Familiarity with or experience in using AI tools to generate code or functional prototypes (e.g., Cursor, v0).

• Background or understanding of the healthcare industry, specifically HSA/FSA regulations, or e-commerce payment processing.

📝 Enhancement Note: The "Who You Are" section clearly outlines a blend of core design skills and operational attributes. The emphasis on "low ego, resourceful, curious, and excited to wear multiple hats" is particularly relevant for operations-minded candidates who understand the need for flexibility and broad contribution in a startup environment. The "nice to have" section points towards specific domain knowledge that would be highly valuable for driving operational efficiency in the fintech/healthcare payment space.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A comprehensive portfolio showcasing end-to-end product design projects, demonstrating your process from problem discovery through to final solution.

• Projects should highlight your ability to conduct user research, define user flows, and create intuitive UI designs, with a strong emphasis on the "middle ground" of experience design.

• Include case studies that detail the user problems you addressed, your design rationale, the tools used (especially Figma and AI tools), and the impact of your solutions.

• Showcase your ability to collaborate with engineers and stakeholders, illustrating how you've incorporated feedback and navigated technical constraints.

Process Documentation:

• Within portfolio case studies, clearly articulate your design process:
  • Discovery & Research: Detail how you identified user needs and business requirements.
  • Ideation & Design: Explain your approach to generating solutions, sketching, wireframing, and prototyping.
  • Iteration & Validation: Show how you tested designs, incorporated feedback, and iterated to improve the user experience.
  • Implementation & Handoff: Describe your collaboration with engineering for successful product launch.
  • Impact Measurement: Where possible, quantify the outcomes of your design work (e.g., conversion rates, user satisfaction, operational efficiency gains).

📝 Enhancement Note: For a role focused on merchant experience and GTM enablement, the portfolio should emphasize how design directly impacts business outcomes and operational workflows for Flex's clients. Demonstrating an understanding of the payment process, merchant challenges, and how design solves these is key.

💵 Compensation & Benefits

Salary Range: $165,000 - $250,000 USD per year

Benefits:

• Competitive compensation package.

• Equity in a fast-growing startup.

• Flexible, remote-friendly work environment, enabling work from anywhere within the United States.

• Mission-driven work focused on making healthcare spending effortless.

• Opportunity to make an early-stage impact and shape company growth.

• Collaborative, high-trust, and transparent company culture.

Working Hours: Standard full-time hours, with flexibility inherent in a remote, startup environment. Expectation of approximately 40 hours per week, with adaptability for project needs and rapid iteration cycles.

📝 Enhancement Note: The provided salary range is typical for mid-level Product Designers in the US, especially in fully remote roles at well-funded startups. The benefits package emphasizes flexibility and impact, common draws for talent in the tech industry. The explicit inclusion of equity and a remote-friendly environment aligns with market expectations for such roles.

🎯 Team & Company Context

🏢 Company Culture

Industry: Fintech / Healthtech / E-commerce Payments

Company Size: Small to Medium-sized (estimated 16-50 employees based on engineering team size and funding stage). This size indicates a dynamic, hands-on environment where individual contributions have significant visibility and impact. For operations professionals, this means opportunities to influence processes directly and work across functional areas.

Founded: Founded to address the challenge of HSA/FSA payment acceptance for online health and wellness brands. The company is backed by prominent venture capital firms like First Round, Core VC, and Rethink Capital, indicating strong growth potential and a data-driven approach to business development.

Team Structure:

• The core product and engineering team consists of approximately 16 individuals, fostering close collaboration and agility.

• The Product Designer will embed with the "merchant team," suggesting a specialized focus within the product organization.

Methodology:

• Data-Driven Product Development: Emphasis on user research, merchant feedback, and product analytics to inform decisions.

• Agile & Iterative Design: Commitment to shipping quickly and iterating based on learnings, a hallmark of fast-moving startups.

• AI Integration: Proactive adoption of AI tools to enhance design workflows and accelerate innovation.

• Operational Excellence: A stated value and expectation for all team members to contribute to efficient and effective processes.

Company Website: https://withflex.com

📝 Enhancement Note: The company's focus on HSA/FSA payments positions it in a niche but rapidly growing market. The culture described is typical of early-stage, venture-backed startups: high energy, collaborative, and focused on rapid growth and innovation. The operations implications are significant: a need for clear processes, efficient workflows, and adaptable team members.

📈 Career & Growth Analysis

Operations Career Level: Mid-Level Product Designer with potential for growth into a Senior Product Designer or Design Lead role. The role is positioned as owning the merchant experience initially, with the expectation to grow into a generalist designer across the broader Flex product surface. This trajectory offers broad exposure to different product areas.

Reporting Structure: Likely reports to a Head of Product, Head of Design, or a Founder, depending on the current organizational structure. The close collaboration with engineers and founders suggests a flat hierarchy.

Operations Impact: The Product Designer's work directly impacts the merchant experience, which is crucial for sales enablement and customer retention. By making it easier for merchants to accept HSA/FSA payments, the designer contributes directly to revenue generation and operational efficiency for Flex's clients, thereby driving Flex's own GTM success.

Growth Opportunities:

• Skill Specialization: Opportunity to deepen expertise in B2B product design, fintech payments, and the healthcare payments landscape.

• Design System Leadership: Potential to take a leading role in evolving and scaling the Flex design system.

• Cross-Functional Leadership: Develop skills in collaborating with and influencing sales, marketing, and engineering teams to drive product strategy.

• AI in Design: Become an early adopter and expert in leveraging AI for accelerated design processes, a highly valuable skill in the evolving design landscape.

• Startup Growth: Gaining experience in a high-growth startup environment provides invaluable lessons in scaling products and teams.

📝 Enhancement Note: The growth path emphasizes not just design craft but also strategic contribution to business operations and GTM efforts, making it attractive for individuals looking to build a well-rounded operational skill set alongside their design expertise.

🌐 Work Environment

Office Type: Fully Remote. This offers maximum flexibility for candidates across the United States.

Office Location(s): Remote within the United States. While specific office locations are not mentioned, the company has headquarters in the United States (implied by company_headquarters).

Workspace Context:

• Collaborative Digital Space: Expect a highly collaborative digital environment, utilizing tools like Slack, Figma, and video conferencing for daily interaction.

• Access to Modern Tools: The company explicitly mentions using AI tools like Claude, Cursor, and v0, indicating a commitment to providing cutting-edge technology to designers.

• Direct User & Stakeholder Interaction: Opportunities to engage directly with merchants, sales teams, and founders, fostering a deep understanding of operational challenges and business needs.

Work Schedule: Flexible remote work, with an expectation of approximately 40 hours per week. The startup environment may require occasional flexibility to meet critical deadlines or launch initiatives, but the overall structure is designed to support remote work-life balance.

📝 Enhancement Note: The remote-first nature of this role is a significant draw, offering flexibility while demanding strong self-discipline and communication skills, which are essential for remote operations roles.

📄 Application & Portfolio Review Process

Interview Process:

• Application Submission: Submit resume and portfolio link. Portfolios are mandatory.

• Portfolio Review: Initial assessment will focus on your design process, problem-solving approach, and how you translate user needs into elegant solutions, particularly for B2B/merchant experiences.

• Recruiter Screen: Discussion on experience, motivations, and cultural fit.

• Hiring Manager/Founder Interview: In-depth discussion about your design philosophy, experience with user research, cross-functional collaboration, and your approach to using AI in design.

• Design Challenge/Case Study Presentation: You may be asked to present a case study from your portfolio or tackle a specific design problem relevant to Flex's merchant experience. This will assess your analytical skills, design thinking, and ability to articulate your process and rationale.

• Engineering/Team Collaboration Interview: Conversation with engineers and other team members to assess collaboration style and technical understanding.

• Final Round: Potentially with founders, focusing on strategic alignment, cultural fit, and long-term vision.

Portfolio Review Tips:

• Showcase Your Process: Clearly articulate your thinking, research, and iteration steps for each project. Don't just show final screens.

• Highlight Merchant/B2B Experience: If you have relevant experience with B2B products, payments, or merchant-facing tools, emphasize it.

• Demonstrate AI Tool Usage: Include examples or discuss how you've integrated AI tools into your workflow to achieve better results faster.

• Quantify Impact: Whenever possible, use metrics to demonstrate the success of your designs (e.g., improved conversion rates, reduced support tickets, increased user satisfaction).

• Tell a Story: Structure your case studies as narratives that clearly define the problem, your solution, and the outcome.

• Tailor to Flex: Briefly explain why you're interested in Flex and how your skills align with their mission and product.

Challenge Preparation:

• Understand the Domain: Research HSA/FSA payments, e-commerce checkout flows, and the challenges faced by health and wellness merchants.

• Focus on User Flows: Be prepared to design or discuss user flows for key merchant tasks (e.g., onboarding, managing payments, viewing analytics).

• Consider AI Integration: Think about how AI could enhance the merchant experience or streamline internal operations.

• Articulate Trade-offs: Be ready to discuss design decisions and the trade-offs you considered.

📝 Enhancement Note: The emphasis on portfolio review and potential design challenges underscores the role's practical nature. Candidates should be prepared to demonstrate not only their design skills but also their ability to understand business context and operational workflows, especially for a B2B product.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The core tool for UI design, wireframing, prototyping, and design system management. Proficiency is essential.

• AI Design Tools: Explicitly mentioned are Claude (likely for content generation or research synthesis), Cursor (AI-powered code editor, suggesting potential for designers to work with code or understand implementation details), and v0 (AI-powered design tool for generating React components). Familiarity or willingness to learn these is crucial.

Analytics & Reporting:

• While not explicitly listed, expect to work with product analytics tools (e.g., Amplitude, Mixpanel, Google Analytics) to understand user behavior and measure the impact of design changes.

CRM & Automation:

• As this is a Product Designer role, direct CRM/automation tool usage might be less critical than understanding how the product integrates with or impacts CRM and sales automation processes for merchants.

• Familiarity with how payment processing and checkout flows interact with merchant back-end systems is advantageous.

📝 Enhancement Note: The explicit mention of AI tools is a significant differentiator. Designers are expected to be early adopters and proficient users, indicating a forward-thinking company culture and a focus on leveraging technology for efficiency.

👥 Team Culture & Values

Operations Values:

• Mission-Driven: A strong commitment to making healthcare spending effortless for consumers and brands.

• Customer-Centric: Deep focus on understanding and serving the needs of merchants and end-users.

• Innovation & Agility: Embracing new technologies (like AI) and operating at startup speed to deliver impactful products.

• Collaboration & Transparency: Open communication and a high-trust environment where team members work together towards common goals.

• Ownership & Accountability: Taking responsibility for projects and driving them to completion with high quality.

• Operational Excellence: A shared commitment to building efficient processes and delivering high-quality outcomes.

Collaboration Style:

• Cross-functional Integration: Designers work hand-in-hand with engineers, founders, sales, and customer-facing teams daily.

• Feedback-Oriented: A culture that encourages constructive feedback to improve designs and processes.

• Proactive & Resourceful: Team members are expected to identify needs and contribute solutions across various areas, even outside their core job description.

📝 Enhancement Note: The emphasis on "operational excellence" and "ownership" directly appeals to individuals with a strong operations mindset, even in a design role. This suggests a culture where efficiency and impact are highly valued.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating Ambiguity: As an early-stage company, processes and priorities may evolve rapidly. The designer must be comfortable with ambiguity and adaptable to change.

• Balancing User Needs with Business Goals: Designing for merchants requires understanding their operational constraints and revenue drivers, alongside end-user needs.

• Rapid Iteration Cycles: The pace of a startup demands quick turnarounds and the ability to iterate designs efficiently, often with incomplete information.

• Domain Complexity: Understanding the nuances of HSA/FSA regulations, payment processing, and e-commerce checkout can be challenging.

Learning & Development Opportunities:

• Mastering AI Design Tools: Becoming an expert in cutting-edge AI tools for design and prototyping.

• Deepening Fintech/Healthtech Expertise: Gaining significant knowledge in a specialized and growing industry.

• Product Strategy Influence: Opportunity to significantly influence the product roadmap and strategic direction for the merchant experience.

• Design System Development: Contributing to and potentially leading the growth of a foundational design system.

• Startup Operations Acumen: Developing a strong understanding of how product design contributes to overall business operations and GTM strategy in a startup.

📝 Enhancement Note: The challenges and growth opportunities are framed to align with an operations professional's perspective, emphasizing analytical problem-solving, process improvement, and strategic business impact.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you used user research to significantly change a product direction. What was your process, and what was the outcome?" (Focus on research methodology, insights, and impact.)

• "How do you approach designing for a B2B audience with complex operational needs, like merchants managing payments?" (Highlight understanding of user workflows, business constraints, and ROI.)

• "Walk us through a project where you collaborated closely with engineers. How did you ensure your design vision was implemented effectively?" (Emphasize communication, problem-solving, and iterative collaboration.)

Company & Culture Questions:

• "Why are you interested in Flex and our mission to simplify HSA/FSA payments?" (Research the company, its impact, and align your values.)

• "How do you handle ambiguity and shifting priorities in a fast-paced startup environment?" (Provide examples of adaptability and proactivity.)

• "Describe your ideal collaboration style with engineers and sales teams." (Focus on open communication, shared goals, and mutual respect.)

Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly outline the problem, your role, the process, the solution, and the results.

• Emphasize Your Process: Detail your research, ideation, iteration, and collaboration steps. Show your thinking.

• Highlight AI Usage: If AI was instrumental, explain how you used it and the specific benefits it brought.

• Quantify Outcomes: Use data and metrics to demonstrate the impact of your design work.

• Be Ready for Deep Dives: Anticipate questions about specific design decisions, trade-offs, and user insights.

• Articulate Merchant Value: Frame your portfolio projects in terms of how they solve problems for merchants and enhance their operational capabilities.

📝 Enhancement Note: The interview preparation advice focuses on how a candidate can showcase not just design skills but also an operations mindset – emphasizing process, efficiency, user impact on business outcomes, and cross-functional collaboration.

📌 Application Steps

To apply for this Product Designer position:

• Submit your resume and a link to your portfolio through the Ashby application portal.

• Portfolio Customization: Curate your portfolio to prominently feature projects that demonstrate your end-to-end design process, user research capabilities, and experience with B2B or merchant-facing products. Explicitly highlight any work involving payment flows, fintech, or operational efficiency improvements.

• Resume Optimization: Tailor your resume to include keywords from the job description such as "Product Design," "User Research," "Figma," "AI Tools," "B2B," "Merchant Experience," and "Cross-functional Collaboration." Quantify your achievements with metrics wherever possible.

• Interview Preparation: Practice articulating your design process, research findings, and decision-making rationale. Prepare to discuss how you leverage AI tools and how your work contributes to business objectives and operational efficiency. Prepare specific examples for behavioral questions.

• Company Research: Thoroughly research Flex, its mission, its target market (health and wellness brands using HSA/FSA), and its competitive landscape. Understand their core product offering and how the merchant experience is central to their success.

⚠️ 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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