Senior Product Designer, Benefits

📍 Job Overview

Job Title: Senior Product Designer, Benefits

Company: Justworks

Location: New York, New York, United States

Job Type: Full-time

Category: Product Design / GTM Operations Enablement

Date Posted: July 27, 2026

Experience Level: 5-10 years

Remote Status: Hybrid

🚀 Role Summary

• Lead the design of critical Benefits experiences within a B2B SaaS platform, focusing on enhancing user journeys for admins, members, and their families.

• Drive the end-to-end product design lifecycle, from initial discovery and conceptualization through to final delivery and launch, ensuring elegant and user-centric solutions.

• Apply robust systems thinking to design complex, interconnected workflows, particularly within regulated domains like HR tech, benefits, and insurance.

• Collaborate extensively with cross-functional teams, including Product Management, Engineering, Research, and Data Science, to translate user needs and business objectives into actionable design strategies.

• Contribute to the evolution and maintenance of the company's design system, ensuring consistency and efficiency across the product suite.

📝 Enhancement Note: This role is categorized under Product Design with a strong GTM Operations Enablement component, as the Benefits experience directly impacts customer acquisition, retention, and operational efficiency for businesses using Justworks. The focus on B2B SaaS and regulated industries implies a need for designers adept at balancing complex user needs with strict compliance and business requirements.

📈 Primary Responsibilities

• Spearhead the design strategy and execution for the Benefits product area, ensuring alignment with company-wide GTM objectives and customer success metrics.

• Translate complex user needs and business requirements into intuitive and effective design solutions for benefits administration, enrollment, and management.

• Conduct and leverage user research, data analysis, and usability testing to validate design hypotheses and inform iterative improvements.

• Develop wireframes, prototypes, and high-fidelity mockups to communicate design concepts and user flows to stakeholders and development teams.

• Champion best practices in design, contributing to the growth and refinement of the internal design system to ensure scalability and brand consistency.

• Actively participate in design critiques and provide constructive feedback to peers, fostering a collaborative and high-performing design team environment.

• Mentor and guide less experienced designers, sharing expertise in product design methodologies and domain-specific challenges.

• Own the design process from discovery through delivery, ensuring seamless handoffs and close collaboration with engineering to maintain design integrity post-launch.

📝 Enhancement Note: The responsibilities emphasize a senior-level contribution, requiring ownership of the design process, cross-functional leadership, and a strategic approach to problem-solving within a complex domain like Benefits. The mention of "measurable outcomes" and "business impact" points to an expectation of data-driven design and demonstrable ROI.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio and relevant experience are paramount. A Bachelor's degree in Design, HCI, Computer Science, or a related field is often preferred.

Experience: 5+ years of professional experience in product design, with a significant portion focused on B2B SaaS, HR tech, benefits, insurance, or similarly regulated industries. Demonstrated experience in leading design initiatives from conception to launch.

Required Skills:

• Product Design Leadership: Proven ability to lead complex product design efforts, from discovery through to delivery.

• Systems Thinking: Expertise in designing interconnected user journeys and workflows across multiple product areas, not just isolated features.

• User-Centric Design: Deep understanding of user research methodologies, usability testing, and data analysis to inform design decisions.

• Prototyping & Experimentation: Proficiency in rapid prototyping and validation through experimentation to test design hypotheses.

• Cross-functional Collaboration: Adept at working fluidly with Product Managers, Engineers, Researchers, Marketers, and Data Scientists.

• Design Systems Proficiency: Experience in both leveraging and contributing to design systems, ensuring consistency and efficiency.

• Visual Design & Craft: Strong attention to detail with a refined sense of craft in visual design, typography, and brand expression.

• Figma Fluency: High proficiency in Figma for design, prototyping, and collaboration.

Preferred Skills:

• B2B SaaS & HR Tech Expertise: Direct experience in designing for business software, particularly in the HR technology or payroll space.

• Benefits/Insurance Domain Knowledge: Specific experience designing for benefits, healthcare, insurance, or other heavily regulated industries.

• Complex Workflow Design: Experience with designing for content-heavy and complex operational workflows.

• Mentorship: Experience guiding and supporting junior designers.

📝 Enhancement Note: The emphasis on "5+ years of professional experience" and the requirement for a portfolio demonstrating "leading complex product design efforts" and "measurable outcomes" indicates this is a senior individual contributor role with significant autonomy and strategic influence. The domain-specific requirements (Benefits, HR Tech, regulated industries) are critical for candidates to highlight.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A curated portfolio showcasing at least 3-5 professional (non-speculative) design case studies.

• Each case study must clearly articulate:

  • The specific design problem and business context.
  • Your role and involvement in the process.
  • The discovery and research methodologies employed.
  • Your design process, including ideation, iteration, and prototyping.
  • Collaboration with cross-functional teams (PM, Eng, Research).
  • The final design solution and its rationale.
  • Measurable business impact or user outcomes achieved.

• Demonstration of systems thinking in at least one case study, illustrating how you designed for interconnectedness and scalability.

• Examples of contributions to or utilization of a design system. Process Documentation:

• The portfolio should implicitly or explicitly demonstrate your understanding of end-to-end product development lifecycles, from discovery through launch.

• Evidence of user research, data analysis, and validation techniques used to inform design decisions.

• Examples of how you collaborated with engineering to ensure high-quality implementation.

📝 Enhancement Note: The portfolio is a critical component for this role, serving as direct evidence of the candidate's ability to handle complex design challenges, collaborate effectively, and deliver impactful solutions. The emphasis on "measurable outcomes" and "business impact" means candidates should quantify their achievements wherever possible.

💵 Compensation & Benefits

Salary Range:

• The base wage range for this position based in our New York City Office is targeted at $166,000.00 to $214,000.00 per year.

• Actual compensation will be determined by multiple factors, including skill set, relevant experience level, and specific work location. Salary ranges for positions in other locations may differ based on the local cost of labor. Benefits:

• Health insurance

• Wellness program offerings

• Company retreats

• Additional benefits and perks are detailed in Justworks' Total Reward Philosophy, accessible via their careers page. Working Hours:

• A standard full-time work schedule is implied, with 40 hours per week being a common benchmark. The hybrid work arrangement suggests flexibility within a structured framework.

📝 Enhancement Note: The provided salary range is specific to New York City, which is a high-cost-of-living area. Candidates in other locations should expect adjustments. The mention of "Total Reward Philosophy" suggests a comprehensive benefits package beyond the listed items.

🎯 Team & Company Context

🏢 Company Culture

Industry: HR Technology (HR Tech) / Business Services / SaaS

Company Size: The company size is not explicitly stated, but the mention of "scaling our Benefits experience" and "leaders in the startup community" suggests a growth-stage company, likely mid-to-large, with a significant employee base and customer reach.

Founded: Founded in 2014, Justworks has established itself as a key player in the HR tech space, providing payroll, benefits, HR, and compliance solutions to small and medium-sized businesses.

Team Structure:

• The role is within the Benefits team, which is focused on providing enterprise-level benefits to businesses that might not otherwise have access.

• The design team is cross-functional, working closely with Product Managers, Researchers, Engineers, Marketers, and Data Scientists.

• There is a structure that supports collaboration and potentially mentorship, with senior designers guiding less experienced ones. Methodology:

• Data-driven approach with a focus on continuous iteration and problem-solving.

• Emphasis on user empathy, attention to detail, and delivering practical outcomes.

• Strong commitment to core company values: Camaraderie, Openness, Grit, Integrity, and Simplicity.

• Agile development methodologies are likely employed, given the SaaS environment and focus on iteration.

Company Website: https://www.justworks.com/careers

📝 Enhancement Note: Justworks operates in a competitive HR Tech landscape, where delivering a seamless and compliant user experience for benefits is a significant differentiator. The company culture appears collaborative, values-driven, and focused on growth and impact.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior Product Designer role, indicating a level of expertise and autonomy. It's a key individual contributor position within the product development lifecycle, focusing on strategic design challenges and user experience for a critical product area.

Reporting Structure: The Senior Product Designer will report into a Design leadership role (e.g., Head of Design, Design Manager) and will work collaboratively with Product Managers and Engineering Leads for specific product initiatives.

Operations Impact: The Benefits team's mission directly impacts Justworks' ability to attract and retain customers by providing essential services. The Senior Product Designer's work directly influences the usability, compliance, and perceived value of these benefits, thereby impacting customer acquisition, retention, and overall revenue growth.

Growth Opportunities:

• Skill Advancement: Opportunity to deepen expertise in B2B SaaS product design, complex workflow design, and the HR/Benefits domain.

• Leadership Development: Potential to take on more significant design leadership responsibilities, mentor junior designers, and influence product strategy.

• Design System Contribution: Opportunity to shape and evolve a growing design system, impacting design consistency across the entire product.

• Cross-functional Influence: Elevate influence across product, engineering, and business teams through impactful design solutions.

• Career Progression: Potential pathways to Principal Designer, Design Lead, or management roles within the design organization.

📝 Enhancement Note: This role offers significant growth potential for a product designer looking to specialize in a critical B2B SaaS domain and contribute strategically to a company's core offering. The emphasis on "systems thinking" and "end-to-end lifecycle" suggests a path towards more complex product ownership and strategic design leadership.

🌐 Work Environment

Office Type: Hybrid work environment, indicating a blend of remote and in-office collaboration. The New York City office serves as a central hub for in-person collaboration.

Office Location(s): New York, New York, United States. Specific details on office amenities and accessibility would typically be found on the company's careers page.

Workspace Context:

• Collaborative Environment: The hybrid model encourages collaboration through scheduled in-office days and virtual tools for remote interaction.

• Operations Tools & Technology: Access to industry-standard design tools (Figma), collaboration platforms (Slack, Jira), and potentially internal design system resources.

• Team Interaction: Opportunities for regular interaction with designers, product managers, researchers, and engineers through meetings, critiques, and project work.

Work Schedule: A standard full-time schedule is expected, likely with some flexibility inherent in a hybrid model. The emphasis on "Nimble Learning" and "Results-driven" suggests a focus on outcomes rather than strict time adherence, within professional norms.

📝 Enhancement Note: The hybrid model is a common feature in modern tech companies, balancing flexibility with the benefits of in-person collaboration. For a Senior Product Designer, this environment should foster both independent work and strong team dynamics.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter will likely review applications and portfolios for basic qualifications and cultural fit.

• Portfolio Review & Initial Interview: A hiring manager or senior designer will assess the portfolio for case studies demonstrating relevant skills, process, and impact. This will likely be followed by an interview discussing the portfolio and experience.

• Design Challenge/Exercise: Candidates may be given a take-home design challenge or an in-person/virtual whiteboard exercise focused on problem-solving, systems thinking, and design process within the Benefits domain.

• Cross-functional Interviews: Interviews with Product Managers, Engineers, and potentially researchers to assess collaboration skills and domain understanding.

• Final Interview: A discussion with senior leadership to assess strategic thinking, cultural fit, and overall suitability for the Senior role.

Portfolio Review Tips:

• Quantify Impact: For each case study, clearly articulate the problem, your process, the solution, and the measurable business or user outcomes. Use metrics where possible (e.g., conversion rate improvement, task completion time reduction, user satisfaction scores).

• Show Your Process: Detail your thought process, research methods, ideation stages, and iterations. Demonstrate how you arrived at the final solution, not just the end result.

• Highlight Collaboration: Show examples of how you worked with cross-functional partners, managed feedback, and navigated trade-offs.

• Tailor to the Role: Emphasize projects that align with B2B SaaS, HR Tech, and Benefits/Insurance domains, as well as those showcasing systems thinking.

• Visual Clarity: Ensure your portfolio is well-organized, visually appealing, and easy to navigate.

Challenge Preparation:

• Understand the Domain: Research Justworks, its Benefits offering, and the typical challenges faced by businesses and individuals in managing benefits.

• Focus on Systems: If a challenge is presented, think about the interconnectedness of features and user flows. Consider edge cases and long-term scalability.

• Articulate Your Approach: Be prepared to clearly explain your design decisions, rationale, and process, even if the outcome is not fully realized within the challenge timeframe.

• Time Management: Practice delivering a concise and well-structured presentation within time constraints.

📝 Enhancement Note: The interview process is designed to rigorously evaluate not only design skills but also the candidate's ability to collaborate, think strategically, and deliver quantifiable results within a complex, regulated industry. A strong, well-documented portfolio is essential for advancing.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The primary tool for UI design, prototyping, and collaboration. Candidates must be highly proficient.

• Design Systems: Experience with creating, maintaining, or heavily utilizing established design systems.

• Prototyping Tools: While Figma covers this, familiarity with other prototyping methods or tools might be beneficial.

Analytics & Reporting:

• Data Analysis Tools: While not a primary design tool, understanding how to interpret data from tools like Amplitude, Mixpanel, or internal BI dashboards is crucial for informing design decisions.

• User Research Platforms: Familiarity with tools for conducting user interviews, surveys, and usability testing (e.g., UserTesting.com, Lookback, SurveyMonkey).

CRM & Automation:

• Project Management: Tools like Jira, Asana, or Trello are commonly used for managing product development workflows and tracking progress.

• Collaboration Tools: Slack, Google Workspace, Confluence for communication and documentation.

📝 Enhancement Note: Proficiency in Figma and experience with design systems are non-negotiable requirements. The ability to leverage data for design decisions is also a key expectation for a senior role.

👥 Team Culture & Values

Operations Values:

• Customer Focus: Building strong customer relationships and delivering user-centric solutions that address real needs in the Benefits space.

• Teamwork & Communication: Fostering open communication, active listening, and collaboration across diverse teams to achieve shared goals.

• Nimble Learning: Embracing experimentation, learning from both successes and failures, and adapting quickly to new challenges and insights.

• Results-Driven: Consistently achieving desired outcomes and demonstrating the impact of design work on business objectives.

• Creative Thinking: Identifying new opportunities and innovative solutions by challenging existing practices.

• Systems Thinking: Designing holistically, considering how different parts of the product and user journey connect.

Collaboration Style:

• Open & Receptive: Encouraging sharing of information, understanding different perspectives, and being receptive to feedback.

• Camaraderie: Working together toward common goals, enjoying the process, and supporting colleagues.

• Integrity-Led: Acting with honesty and transparency, following through on commitments.

• Simplicity-Focused: Striving for clarity and ease of use in design solutions.

📝 Enhancement Note: Justworks' core values (Camaraderie, Openness, Grit, Integrity, Simplicity) are deeply embedded in their culture. Candidates should demonstrate how their working style aligns with these principles, particularly in how they collaborate, communicate, and approach problem-solving.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Complexity: Navigating the intricate requirements of benefits administration, compliance, and user choice within a regulated industry.

• Balancing Stakeholder Needs: Effectively integrating needs from various stakeholders (users, business, engineering, legal, compliance) into cohesive design solutions.

• Scalability of Design Systems: Contributing to a design system that supports rapid growth and diverse product needs across the platform.

• Driving Adoption: Ensuring that new features and design improvements are effectively adopted by users and contribute to business goals.

• Hybrid Work Dynamics: Mastering collaboration and communication in a hybrid work environment to maintain team cohesion and productivity.

Learning & Development Opportunities:

• Domain Specialization: Deepen expertise in the HR Tech and Benefits industry, becoming a go-to expert for design within this critical area.

• Strategic Design Influence: Gain exposure to higher-level product strategy and influence decision-making through compelling design advocacy.

• Mentorship & Leadership: Develop mentoring skills and potentially step into leadership roles as the design team grows.

• Industry Trends: Stay abreast of evolving trends in HR tech, benefits, and product design through company-sponsored learning and industry engagement.

📝 Enhancement Note: This role presents a significant opportunity for professional growth by tackling complex design problems in a high-impact domain. The challenges are framed as opportunities for skill development and strategic contribution.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to design for a complex, regulated workflow. What were the key challenges, and how did you ensure compliance while meeting user needs?" (Focus on systems thinking, research, and trade-offs.)

• "Walk us through a product design case study from your portfolio that best demonstrates your ability to drive an initiative from discovery through delivery and its business impact." (Prepare to discuss problem framing, process, collaboration, and quantified outcomes.)

• "How do you approach balancing the needs of different stakeholders (e.g., users, product managers, engineers, legal) when designing a new feature?" (Highlight collaboration, communication, and negotiation skills.) Company & Culture Questions:

• "Based on your understanding of Justworks and the HR Tech landscape, what do you see as the biggest design opportunities for our Benefits product?" (Demonstrate research and strategic thinking.)

• "How do you embody Justworks' core values—Camaraderie, Openness, Grit, Integrity, Simplicity—in your day-to-day work?" (Provide specific examples linking your behaviors to their values.)

• "How do you measure the success of your design work, and what metrics do you typically track?" (Focus on data-driven design and ROI.) Portfolio Presentation Strategy:

• Tell a Story: Frame each case study as a narrative, highlighting the problem, your journey, and the resolution.

• Focus on Process: Don't just show final screens; explain why you made certain decisions, the research that informed them, and the iterations you went through.

• Quantify Everything Possible: Use data and metrics to demonstrate the impact of your work on users and the business.

• Be Prepared for Questions: Anticipate questions about your role, challenges, trade-offs, and alternative approaches.

• Showcase Systems Thinking: Explicitly point out how your designs consider interconnectedness and scalability.

📝 Enhancement Note: Interview preparation should focus on showcasing a blend of design craft, strategic thinking, domain understanding, and strong collaboration skills, all underpinned by a data-driven and user-centric approach aligned with Justworks' values.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the Justworks careers portal via the provided link.

• Portfolio Customization: Curate your portfolio to prominently feature 3-5 case studies that align with B2B SaaS, HR Tech, Benefits, or regulated industries, and that clearly demonstrate systems thinking and end-to-end product lifecycle ownership. Ensure each case study includes problem definition, your process, collaboration, solution, and quantifiable business impact.

• Resume Optimization: Tailor your resume to highlight your 5+ years of relevant experience, specific skills in Figma, design systems, user research, and cross-functional collaboration. Use keywords from the job description and emphasize achievements with metrics where possible.

• Interview Preparation: Practice articulating your design process, presenting your portfolio case studies compellingly, and preparing thoughtful answers to strategy, company culture, and behavioral questions. Be ready to discuss your approach to complex workflows and user needs.

• Company Research: Thoroughly research Justworks, its mission, values, and its Benefits product offering. Understand their market position and the challenges faced by their customers to better tailor your application and interview responses.

⚠️ 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.