Staff Product Designer, B2B

📍 Job Overview

Job Title: Staff Product Designer, B2B

Company: Flex

Location: New York, NY; Salt Lake City, UT; San Francisco, CA

Job Type: Full-Time

Category: Product Design (B2B FinTech/PropTech)

Date Posted: 2026-08-21

Experience Level: Staff (10+ years)

Remote Status: Hybrid

🚀 Role Summary

• Lead the B2B product design strategy and vision for the Property Hub team, focusing on property manager and on-site team user needs.

• Drive end-to-end execution of design solutions for complex operational workflows, ensuring seamless integration with existing systems.

• Set high standards for design quality, user experience, and innovation across multiple teams and product areas.

• Collaborate closely with Product Management, Engineering, Data Analytics, Partnerships, and Operations to align on strategic initiatives and deliver impactful features.

• Leverage AI tools and methodologies to enhance productivity, increase design efficiency, and drive product development innovation.

📝 Enhancement Note: This role is a senior individual contributor position with significant influence, requiring a strategic mindset to shape a critical B2B vertical within a FinTech company. The focus on "Property Hub" indicates a specialized area within Flex, likely dealing with the operational aspects of rent collection and property management systems. The emphasis on AI integration suggests a forward-thinking approach to design and development processes.

📈 Primary Responsibilities

• Shape and drive the vision for Flex's B2B product offerings within the Property Hub, owning the strategy and end-to-end design execution.

• Lead design exploration and develop innovative solutions for critical projects, setting a high bar for quality and user experience.

• Design intuitive and precise workflows for property managers and on-site teams, addressing complex financial and resident relationship aspects, including error handling and recovery states.

• Conduct firsthand user research by engaging with leasing offices and property teams to understand their existing systems and workarounds before proposing new solutions.

• Collaborate with Product Management to define product direction, align multiple engineering teams around a cohesive vision, and raise the overall quality bar.

• Partner with PM, analytics, operations, and engineering to structure experiments, define hypotheses, and define success metrics for new features and pilots.

• Build prototypes and artifacts to articulate the future state of product areas, aligning stakeholders and leadership on strategic opportunities.

• Support company strategy with qualitative research, data analysis, industry trends, and expert design insights.

• Establish and evolve the Design System, "Ultraviolet," including foundational patterns and visual language, ensuring consistency across all product teams.

• Define and evolve standards for AI integration across the product development lifecycle, from research to prototyping, and collaborate with engineering on design-to-code quality.

• Establish design-thinking methods and toolkits that can be adopted by other teams, promoting a customer-centered approach organization-wide.

• Play a key role in developing new ways of working through design operations, rituals, toolkits, or AI-assisted workflows.

📝 Enhancement Note: The responsibilities highlight a blend of strategic leadership and hands-on design execution. The emphasis on understanding user workflows in detail, particularly in financial and operational contexts, is crucial for success in this role. The expectation to evolve the Design System and integrate AI suggests a focus on scalability and future-proofing the design practice.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio demonstrating equivalent knowledge and experience in product design is expected.

Experience: 10+ years of experience designing and shipping products, with a significant portion focused on business-facing or professional tools and complex web applications.

Required Skills:

• Deep expertise in designing and shipping complex web applications, including dense data views, reporting dashboards, and multi-step operational workflows.

• Proven ability to design for multi-user, multi-role environments where configurators and users may differ.

• Fluency in experimentation and quantitative reasoning, including designing for tests, reading funnel and cohort data, and iterating based on evidence.

• Strength in designing for critical "unglamorous" states such as errors, edge cases, pending actions, and recovery scenarios.

• Comfort with technical and regulatory constraints, treating them as design material rather than obstacles.

• Demonstrated aptitude for raising the quality bar for peers through mentorship, critiques, standards, or system development.

• Track record of designing simple, intuitive products powered by complex underlying systems.

• Proficiency in documenting and explaining design processes, rationale, best practices, research findings, and data-driven decisions.

• Demonstrated ability to drive execution and ensure team success through proactive problem-solving.

• Expert-level proficiency in Figma and experience using AI tools for sketching and prototyping.

• Comfort with ambiguity and a strong self-starter motivation.

• Passion for improving financial well-being for everyday people.

• A robust portfolio showcasing contributions to shipped solutions. Preferred Skills:

• Experience in FinTech or other regulated environments, particularly designing money movement flows and disclosures with legal and compliance partners.

• Experience in PropTech, or designing for property management, accounting, or other back-office systems.

• Experience designing embedded or white-labeled experiences integrated within third-party products.

• Experience establishing new ways of working (e.g., design operations, rituals, toolkits, AI-assisted workflows) that have been adopted by teams.

📝 Enhancement Note: The experience requirement of 10+ years signals a senior-level position, emphasizing leadership and strategic impact. The specific mention of "dense data views, reporting, and multi-step operational workflows" directly points to the need for expertise in B2B SaaS product design. The inclusion of AI as a partner in the design process is a key differentiator.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase end-to-end design ownership for complex B2B applications or professional tools, highlighting the problem, your process, and the shipped solution.

• Include case studies that demonstrate your ability to design for multi-user workflows and handle intricate operational processes.

• Detail your approach to data analysis, experimentation, and how quantitative reasoning informed your design decisions and iterations.

• Present examples of how you've addressed edge cases, error states, and complex system integrations within your designs.

• Demonstrate your experience in evolving or contributing to design systems, including pattern development and visual language standardization. Process Documentation:

• For each project in your portfolio, clearly articulate your design thinking process, from initial research and problem definition through to solutioning, testing, and implementation.

• Provide evidence of how you collaborated with cross-functional teams (Product, Engineering, Data, Operations) and incorporated their feedback into your design.

• Detail your methods for user research, user testing, and how you synthesized findings to drive product improvements.

• Illustrate your ability to document design decisions, rationale, and outcomes, especially for complex operational workflows and systems.

📝 Enhancement Note: For a Staff Product Designer role, the portfolio must go beyond visual mockups. It needs to demonstrate strategic thinking, a deep understanding of B2B user needs, complex problem-solving capabilities, and the ability to influence product direction. Case studies should explicitly address how designs solved business problems and improved operational efficiency.

💵 Compensation & Benefits

Salary Range:

• Tier 1 (NYC/Bay Area): $200,000 - $250,000 USD per year

• Tier 3 (Salt Lake City): $170,000 - $212,000 USD per year

📝 Enhancement Note: Flex employs a market-based approach with geographic pay differentials. The provided ranges are for Tier 1 (high cost of labor) and Tier 3 (lower cost of labor) markets. Candidates in other locations will have their compensation adjusted accordingly. This is a significant salary range reflecting the senior nature of the Staff Designer role and the FinTech industry.

Benefits:

• Competitive medical, dental, and vision insurance plans.

• Company equity, offering ownership stake in Flex.

• 401(k) plan with a company match, supporting retirement savings.

• Unlimited paid time off (PTO) policy.

• 13 company-paid holidays annually.

• Parental leave benefits.

• Free Flex subscription for employees.

• For non-U.S. employees, competitive compensation, company equity, and Unlimited PTO are offered.

Working Hours: While not explicitly stated as a fixed number of hours per week, the context of a full-time role and the mention of "40 hours" in the input data suggest a standard full-time work expectation, likely around 40 hours per week. Hybrid roles may imply flexibility in daily scheduling but require on-site presence.

🎯 Team & Company Context

🏢 Company Culture

Industry: FinTech (Financial Technology), with a strong presence in PropTech (Property Technology). Flex is modernizing rent payments and financial management for renters and property managers.

Company Size: Growth-stage, indicating a company that has moved beyond startup phase and is scaling operations and revenue, likely with a few hundred employees.

Founded: Founded in 2019 (implied by "deliberately keeping a stealth profile as we built up unprecedented investor support and an enthusiastic user base" and the current year being 2026), suggesting a relatively young but rapidly maturing company with a strong product-market fit.

Team Structure:

• The role is within the "Property Hub" team, focusing on B2B product design.

• This is an individual contributor role with a "large sphere of influence," meaning impact is achieved through design artifacts, setting standards, and mentoring, rather than direct management.

• Designers will work closely with Product Managers, Engineers, Data Analysts, Partnerships, and Operations teams, indicating a highly cross-functional and collaborative environment.

• The team operates in a "highly measured, highly cross-functional environment" where roles can be fluid and roadmaps ambiguous, requiring adaptability and initiative. Methodology:

• Data-driven decision-making is emphasized, with designers expected to be "curious about the numbers," comfortable with "experimentation and quantitative reasoning," and willing to change their minds based on evidence.

• A strong focus on user-centered design, with direct access to customers ("people who use what you make") and a mandate to "learn our partners’ world firsthand."

• Emphasis on setting and evolving standards, including for the Design System and the integration of AI in product development.

• Collaborative approach to problem-solving, with designers expected to "bridge true customer needs with creative solutions."

Company Website: flex.com

📝 Enhancement Note: The company culture appears to be fast-paced, data-informed, and collaborative, typical of a growth-stage FinTech company. The emphasis on individual contributor impact and setting standards is key for a Staff-level role. The blend of FinTech and PropTech suggests a unique market position.

📈 Career & Growth Analysis

Operations Career Level: Staff Product Designer. This is a senior individual contributor role, recognized for deep expertise, strategic thinking, and significant influence across product areas and teams. It's a position that leads through influence, setting standards, and mentoring others, rather than through direct reports.

Reporting Structure: The role is an individual contributor and does not have direct reports. The designer will report to a design leadership figure (e.g., Head of Design, Design Manager) and will work closely with Product Management counterparts. The "sphere of influence" is broad, impacting multiple engineering teams and product verticals.

Operations Impact: This role has a direct impact on Flex's B2B revenue and growth by designing critical tools for property managers. By improving the rent payment experience and reconciliation processes for property partners, the designer contributes to customer retention, acquisition, and the overall efficiency of Flex's B2B operations. The design of these tools directly affects the financial operations of property management companies, making it a high-stakes, high-impact area.

Growth Opportunities:

• Specialization & Leadership: Deepen expertise in B2B FinTech/PropTech design, potentially becoming a recognized authority within the company and industry. Opportunities exist to lead design initiatives for new product areas or strategic company-wide efforts.

• Design System Evolution: Play a pivotal role in shaping and expanding Flex's Design System, influencing design consistency and efficiency across the organization.

• Mentorship & Influence: Elevate the design practice by mentoring junior designers, establishing best practices, and driving adoption of new methodologies (e.g., AI-assisted design, advanced design thinking).

• Strategic Contribution: Influence product strategy and roadmap prioritization through robust research, data analysis, and compelling design proposals.

• Cross-Functional Acumen: Develop strong partnerships and understanding across Product, Engineering, Data, and Operations, which can lead to broader product leadership roles.

📝 Enhancement Note: The "Staff" title signifies a high level of individual contribution and strategic influence. Growth here is less about management and more about deepening expertise, driving significant product initiatives, and elevating the overall design function within the company.

🌐 Work Environment

Office Type: Hybrid. Roles in New York, San Francisco, and Salt Lake City require 2-3 days per week in the office. This indicates a blend of focused individual work and collaborative team interaction.

Office Location(s):

• New York City (HQ)

• Salt Lake City, UT

• San Francisco, CA

Candidates outside these areas may be eligible for relocation assistance.

Workspace Context:

• Collaborative Environment: The hybrid model necessitates in-office days for team collaboration, design critiques, and cross-functional alignment sessions.

• Operations Tools & Technology: Access to industry-standard design tools (Figma, AI tools) and company-specific platforms will be available. The role requires leveraging these tools to their fullest extent for efficient workflow and prototyping.

• Team Interaction: Opportunities to engage directly with product managers, engineers, data analysts, operations teams, and importantly, end-users (property managers) will be frequent, fostering a deep understanding of business needs and user pain points.

Work Schedule: A standard full-time schedule is expected (around 40 hours/week), with flexibility inherent in a hybrid model. The focus is on delivering results and collaborating effectively, with the hybrid setup allowing for dedicated time for deep work and in-person team engagement.

📝 Enhancement Note: The hybrid requirement suggests a company that values both focused individual contribution and the synergy of in-person collaboration, particularly important for complex problem-solving in design.

📄 Application & Portfolio Review Process

Interview Process:

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

• Design Challenge/Case Study: Candidates will likely be asked to present a deep dive into a past project, demonstrating their process, problem-solving approach, and impact. This may involve a take-home assignment or a presentation of existing portfolio work.

• Cross-Functional Interviews: Conversations with Product Management, Engineering, and potentially Data Analytics or Operations leads to assess collaboration style, technical understanding, and strategic thinking.

• Design Team Interview: A session with other designers to evaluate design craft, system thinking, and potential to contribute to the design culture and standards.

• Leadership Interview: Final discussion with senior leadership to assess overall fit, strategic alignment, and vision for the role.

Portfolio Review Tips:

• B2B Focus: Clearly showcase projects related to business-facing tools, operational workflows, or complex data-driven applications. Highlight how your design solved business problems and improved efficiency for users.

• Process & Rationale: For each case study, detail your end-to-end design process. Explain why you made certain decisions, referencing user research, data, constraints, and business goals.

• Quantifiable Impact: Wherever possible, present metrics demonstrating the impact of your designs (e.g., increased user efficiency, reduced error rates, improved conversion, adoption rates).

• Handling Complexity: Showcase your ability to design for intricate systems, edge cases, and multi-user environments. Explicitly address how you managed technical and regulatory constraints.

• AI Integration: If applicable, highlight projects where you leveraged AI to enhance your design process or the user experience, explaining the tools and outcomes.

• Design System Contribution: If you have experience with design systems, demonstrate your contributions, whether it's building new components, evolving patterns, or advocating for their use.

Challenge Preparation:

• Deep Dive: Be prepared to discuss your portfolio projects in granular detail, focusing on challenges, trade-offs, and lessons learned.

• Strategic Thinking: Anticipate questions about how you would approach designing for a new B2B feature or improving an existing workflow, considering user needs, business goals, and technical feasibility.

• Collaboration & Communication: Practice articulating your design rationale clearly and concisely, and be ready to discuss how you collaborate with non-design stakeholders.

• Data & Experimentation: Be ready to discuss how you use data and experimentation to inform your design decisions and measure success.

📝 Enhancement Note: The interview process for a Staff Designer is rigorous, focusing on strategic impact, deep problem-solving, and collaborative leadership. A well-curated portfolio that clearly articulates process, rationale, and impact is paramount.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Expert-level proficiency is required for UI design, prototyping, and collaboration.

• AI Tools: Experience using AI for sketching, prototyping, research assistance, and potentially design system generation.

• Prototyping Tools: Beyond Figma, familiarity with other advanced prototyping tools may be beneficial for complex interactions.

Analytics & Reporting:

• Data Analysis Tools: Comfort with tools like Amplitude, Mixpanel, or internal BI platforms to analyze user behavior, funnel data, and cohort performance.

• Data Visualization Tools: Ability to interpret and potentially contribute to dashboards (e.g., Tableau, Looker) to understand product performance and user trends.

CRM & Automation:

• While not directly designing CRM systems, understanding how B2B products integrate with or complement CRM functionalities (e.g., Salesforce) is advantageous.

• Familiarity with workflow automation concepts and how design can support or enable them.

📝 Enhancement Note: The emphasis on Figma and AI tools highlights modern design practices. The requirement to work with data analytics tools is crucial for a data-informed design approach in a B2B context.

👥 Team Culture & Values

Operations Values:

• Customer Centricity: A deep commitment to understanding and solving the real-world problems of property managers and on-site teams.

• Data-Driven Decision Making: Valuing evidence, experimentation, and quantitative reasoning to guide design choices and product direction.

• Excellence & Quality: Setting a high bar for design craft, user experience, and the robustness of solutions, especially in critical financial workflows.

• Collaboration & Influence: Working effectively across teams, sharing knowledge, and influencing stakeholders to achieve shared goals.

• Adaptability & Learning: Embracing ambiguity, a fast-paced environment, and a continuous learning mindset, especially with evolving technologies like AI.

• Impact & Ownership: Taking ownership of critical product areas and driving initiatives that lead to measurable business and user outcomes.

Collaboration Style:

• Cross-Functional Integration: Seamless collaboration with Product Management, Engineering, Data, and Operations to ensure holistic product development.

• Constructive Critique: An environment where design critiques are valued for elevating work, fostering learning, and ensuring high quality.

• Knowledge Sharing: A culture that encourages sharing best practices, toolkits, and insights to uplift the entire design team and organization.

• Experimentation Culture: A willingness to test hypotheses, learn from outcomes, and iterate rapidly based on user feedback and data.

📝 Enhancement Note: The values emphasize a results-oriented, collaborative, and user-focused approach, common in successful growth-stage tech companies. The specific mention of "AI as a partner" and "data-driven" is particularly relevant to this role.

⚡ Challenges & Growth Opportunities

Challenges:

• Complexity of B2B Workflows: Designing for the intricate, often highly regulated, operational workflows of property management requires deep domain understanding and meticulous attention to detail.

• Balancing User Needs with Technical/Regulatory Constraints: Effectively integrating complex system requirements, financial regulations, and legal compliance into intuitive user experiences.

• Driving Alignment Across Multiple Teams: As a senior IC, influencing and aligning disparate teams around a cohesive B2B product vision and design standards.

• Evolving Design Practice: Staying at the forefront of design innovation, particularly in integrating AI effectively and evolving the Design System to meet future needs.

• Ambiguity and Rapid Growth: Navigating an ambiguous roadmap and a fast-paced growth environment requires resilience, adaptability, and proactive problem-solving.

Learning & Development Opportunities:

• FinTech/PropTech Domain Expertise: Deepen understanding of financial technology, property management operations, and regulated product design.

• AI in Design: Gain hands-on experience and leadership in leveraging AI tools and methodologies to transform the product development lifecycle.

• Design System Leadership: Contribute significantly to the evolution and adoption of a growing Design System, impacting product consistency and developer efficiency.

• Strategic Product Influence: Develop skills in product strategy, roadmap prioritization, and cross-functional leadership through direct involvement in key initiatives.

• Mentorship & Coaching: Hone leadership and communication skills by mentoring other designers and championing design excellence across the company.

📝 Enhancement Note: The challenges are typical for senior roles in complex B2B environments, offering significant opportunities for professional development and impact.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you led the design vision for a complex B2B product area. What was your process for aligning multiple teams, and what was the ultimate outcome?" (Focus on your strategic thinking, influence, and ability to weave together disparate visions.)

• "How do you approach designing for operational workflows that involve complex financial transactions, error states, and regulatory constraints? Provide a specific example." (Highlight your understanding of financial/operational design and attention to detail.)

• "Tell us about a project where you leveraged AI in your design process. What tools did you use, what was the impact on your productivity or the product, and what were the challenges?" (Demonstrate your forward-thinking approach and practical application of AI.) Company & Culture Questions:

• "Based on what you know about Flex, what do you see as the biggest design opportunities and challenges for our B2B Property Hub?" (Showcase your research and strategic understanding of the company and its market.)

• "How do you typically collaborate with Product Managers, Engineers, and Data Analysts? Describe a situation where you had to influence a technical or product decision." (Assess your cross-functional collaboration and influence skills.)

• "How do you measure the success of your designs, especially in a B2B context where direct user feedback might be less frequent than in B2C?" (Focus on your data analysis, experimentation, and quantitative reasoning skills.) Portfolio Presentation Strategy:

• Structure: Organize your portfolio around 2-3 key B2B projects that showcase your end-to-end process, strategic thinking, and problem-solving.

• Narrative: For each project, tell a compelling story: the problem, your role, the constraints, your process (research, ideation, iteration), the solutions, and the measurable impact.

• Focus on "Why": Clearly explain the rationale behind your design decisions, referencing data, user insights, and business objectives.

• Demonstrate Complexity: Highlight how you handled complex requirements, edge cases, and technical limitations.

• Quantify Impact: Use metrics whenever possible to demonstrate the value your designs brought to the business and users.

• Be Ready for Deep Dives: Prepare to answer detailed questions about any aspect of your work, from initial research to final implementation.

📝 Enhancement Note: Interview questions will probe for strategic thinking, deep B2B design experience, quantitative reasoning, and the ability to influence. A well-prepared portfolio presentation is crucial for demonstrating these capabilities.

📌 Application Steps

To apply for this Staff Product Designer position:

• Submit your application through the provided link on Greenhouse.

• Curate Your Portfolio for B2B Impact: Select 2-3 of your strongest B2B product design case studies that best represent your experience with complex operational workflows, data-dense interfaces, and multi-user environments. Ensure each case study clearly articulates the problem, your process, your specific contributions, and measurable outcomes.

• Optimize Your Resume for Operations & Design Keywords: Tailor your resume to highlight keywords such as "B2B Product Design," "FinTech," "PropTech," "Design Systems," "Interaction Design," "Data Analysis," "Prototyping," "Figma," "AI-assisted Design," and "Cross-functional Collaboration." Quantify achievements wherever possible.

• Prepare Your Portfolio Presentation: Rehearse a concise and compelling presentation of your selected case studies. Focus on telling a clear story, explaining your rationale, and demonstrating how your design decisions led to positive business and user outcomes. Be ready to discuss your process for handling complexity, constraints, and ambiguity.

• Research Flex and the FinTech/PropTech Landscape: Understand Flex's mission, its product offerings, and its position in the market. Familiarize yourself with common challenges and opportunities in FinTech and PropTech, particularly concerning B2B solutions and operational efficiency.

⚠️ 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.