Senior UX Designer (External Facing)

📍 Job Overview

Job Title: Senior UX Designer (External Facing)

Company: Ryan Specialty

Location: Chicago, Illinois, United States

Job Type: Full-Time

Category: Digital Solutions / Product Design Operations

Date Posted: April 27, 2026

Experience Level: Mid-Senior Level (5-10 years)

Remote Status: Hybrid (3 days in office, 2 days remote)

🚀 Role Summary

• Lead the end-to-end design process for RT Specialty's digital product ecosystem, impacting both internal workflows and external client-facing platforms, with a strong emphasis on user-centered design principles and agile development methodologies.

• Develop and execute pixel-perfect, development-ready deliverables for responsive web touchpoints, translating user needs and business requirements into intuitive and effective user experiences.

• Act as a key design contributor within cross-functional teams, collaborating closely with Product Owners, Engineers, Marketing, and Business stakeholders to ensure seamless integration of user experience best practices and drive measurable improvements in customer satisfaction and business outcomes.

• Champion the adoption and optimization of a design system, ensuring consistency, scalability, and efficiency across all digital touchpoints within the organization's rapidly evolving product suite.

📝 Enhancement Note: This role is positioned within a "Digital Solutions" group, indicating a focus on operational efficiency and digital transformation within the insurance sector. The "External Facing" designation suggests a direct impact on client acquisition, retention, and overall customer journey optimization, rather than purely internal tools. The requirement for "full-stack" UX skills (UI + UX/IA + UX research) implies a need for a highly versatile designer capable of handling the entire design lifecycle independently.

📈 Primary Responsibilities

• Drive the design strategy and execution for specific product areas, such as internal policy management tools or external quoting platforms, ensuring alignment with user needs, business objectives, and technical feasibility.

• Conduct user research, analyze data, and interpret user testing insights to inform design decisions, validate concepts, and advocate for user-centric solutions.

• Create comprehensive design documentation, including wireframes, storyboards, process flows, sitemaps, and high-fidelity prototypes, to effectively communicate design direction and ensure clarity for development teams.

• Collaborate with product management and engineering teams to understand product requirements, refine the visual and interactive experience, and deliver designs that are both innovative and technically achievable within agile development cycles.

• Propose, document, optimize, and implement design system components to maintain consistency, improve scalability, and accelerate the design and development process across the digital product portfolio.

• Proactively identify and address UX problems within existing digital experiences, cataloging issues and proposing solutions that enhance user satisfaction and operational efficiency.

• Present design concepts and recommendations to senior leadership and external partners, using data, research, and compelling narratives to justify design choices and demonstrate potential user and business impact.

• Stay abreast of evolving design industry trends, competitive landscape within the insurance sector, and UX best practices to continuously elevate the quality of digital experiences.

📝 Enhancement Note: The responsibilities emphasize a blend of strategic leadership and hands-on execution. The requirement to "juggle several projects" and "make decisions that balance quality, time, and resources" highlights the need for strong project management and prioritization skills, critical for senior-level operations and product design roles. The explicit mention of "Jobs-to-be-Done (JTBD)" indicates a methodological approach to understanding user motivations and designing solutions that directly address core user needs.

🎓 Skills & Qualifications

Education:

Experience:

• Minimum of 6 years of progressive experience in UX/Product Design, with a proven track record of successfully delivering final developed digital products.

• Demonstrated experience designing for complex, regulated domains such as insurance, e-commerce, or other enterprise-level software projects within an agile development environment.

Required Skills:

• UX/Product Design: Comprehensive understanding of the full design lifecycle from research and ideation to final execution and iteration.

• UI Design: Strong proficiency in creating visually appealing, user-friendly interfaces with a keen eye for detail, typography, color theory, and layout.

• Information Architecture (IA): Ability to structure and organize content effectively to support user navigation and task completion.

• UX Research: Experience in planning, conducting, and interpreting user research methodologies (e.g., user interviews, usability testing, surveys) to gather actionable insights.

• Prototyping & Wireframing: Skill in creating low-fidelity wireframes and high-fidelity interactive prototypes to communicate design concepts and test user flows.

• Design Systems: Experience contributing to or leveraging established design systems to ensure consistency and efficiency.

• Agile Methodologies: Familiarity and experience working within agile development frameworks (Scrum, Kanban).

• Responsive Web Design: Expertise in designing for various screen sizes and devices, ensuring a seamless user experience across desktop, tablet, and mobile.

• Communication & Presentation: Exceptional verbal and written communication skills, with the ability to articulate design rationale, present complex ideas clearly, and tailor messages to diverse audiences.

• Time Management & Prioritization: Proven ability to manage multiple projects simultaneously, prioritize tasks effectively, and meet deadlines in a fast-paced environment.

Preferred Skills:

• Figma Proficiency: Advanced skills in Figma for design, prototyping, and collaboration.

• Design System Development: Experience in building, maintaining, and scaling design systems from the ground up.

• Insurance Industry Expertise: Deep understanding of insurance products, workflows, and customer journeys.

• Service Design: Familiarity with service design principles and methodologies for mapping and improving end-to-end customer experiences.

• Interaction Design: Expertise in designing intricate micro-interactions and dynamic user interfaces.

📝 Enhancement Note: The explicit requirement for "6+ years of experience with UX/Product Design, including the final development and execution process" and "Portfolios should highlight challenges you faced, how you collaborated with others, what you learned, and the user/business impact of your work" indicates a strong emphasis on practical, impact-driven design experience. The insurance industry experience requirement is critical and should be prominently featured in candidate applications.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrate End-to-End Design Process: Showcase a minimum of 2-3 comprehensive case studies that illustrate your entire design process, from initial problem identification and user research to ideation, prototyping, user testing, and final implementation.

• Highlight Collaboration & Problem-Solving: Clearly articulate the challenges faced, the collaborative efforts with cross-functional teams (engineers, product managers, business stakeholders), and the specific strategies employed to overcome obstacles.

• Quantify User & Business Impact: Present measurable outcomes and the impact of your design solutions on user satisfaction, key business metrics (e.g., conversion rates, task completion times, customer retention), and operational efficiency.

• Showcase Technical Proficiency: Include examples of your ability to create pixel-perfect, development-ready deliverables, demonstrating an understanding of technical constraints and best practices for handoff.

Process Documentation:

• Workflow Design & Optimization: Provide examples of how you have mapped, analyzed, and optimized complex user workflows to improve efficiency and user experience, particularly within enterprise or regulated environments.

• System Implementation & User Adoption: Illustrate experience in integrating new design solutions or systems, detailing strategies for user adoption and change management.

• Metrics & Performance Analysis: Demonstrate how you use data, analytics, and user feedback to measure the performance of designs, identify areas for improvement, and iterate on solutions.

📝 Enhancement Note: The emphasis on a portfolio that highlights "challenges," "collaboration," "learning," and "impact" is crucial. Candidates should structure their portfolio around storytelling that clearly links their design decisions to tangible business and user outcomes, especially within complex domains like insurance. This suggests a focus on demonstrating strategic thinking and problem-solving capabilities beyond just visual design execution.

💵 Compensation & Benefits

Salary Range:

• $104,000 - $130,000 annually.

Benefits:

• Comprehensive Health & Well-being: Includes paid parental leave, mental health services, and other benefits designed to support physical, financial, and emotional well-being.

• Time Off: Generous paid time off, including company holidays, vacation days, and sick/personal days.

• Performance-Based Incentives: Eligible for bonuses for full-time roles, reflecting performance and company success.

• Total Rewards Program: Access to Ryan Specialty's extensive Total Rewards information available on their dedicated website.

Working Hours:

• Standard full-time hours, estimated at 40 hours per week, with a hybrid arrangement requiring 3 days in the office and 2 days remote.

📝 Enhancement Note: The salary range provided is competitive for a Senior UX Designer role in a major metropolitan area like Chicago, especially considering the specialized industry requirement. The mention of "Total Rewards" and the specific benefits like paid parental leave and mental health services indicate a company that values employee well-being and offers a competitive benefits package beyond standard offerings, which is attractive to experienced professionals.

🎯 Team & Company Context

🏢 Company Culture

Industry: Specialty Insurance Distribution (Wholesale Brokerage), a division of Ryan Specialty. The company operates as a leading provider of specialized insurance products and services, focusing on complex risks and offering creative solutions to retail brokerage firms.

Company Size: Ryan Specialty is a significant player in the insurance market. While specific employee numbers for the Digital Solutions group aren't detailed, the parent company's overall size suggests a robust organization with established processes and a commitment to digital innovation.

Founded: RT Specialty is a division of Ryan Specialty, which was founded to address the evolving needs in the specialty insurance market. This implies a culture that is dynamic, responsive to market changes, and focused on delivering superior execution.

Team Structure:

• Digital Solutions Group: This role is part of the Digital Solutions group, indicating a dedicated effort towards leveraging technology and design to enhance business operations and client engagement.

• Cross-Functional Collaboration: The Senior UX Designer will work closely with Product Owners, Engineers, Marketing, and Business partners, suggesting a collaborative and integrated team environment where diverse perspectives are valued.

• Reporting: While not explicitly stated, senior roles in such teams typically report to a Design Lead, Head of Product, or Director of Digital Solutions, indicating a clear hierarchy with opportunities for mentorship and guidance.

Methodology:

• User-Centered Design: A core methodology, emphasizing understanding user needs through research and data to drive design decisions.

• Agile Development: Projects are executed within an agile environment, requiring flexibility, iterative development, and continuous feedback loops.

• Data-Driven Decisions: Design recommendations are expected to be justified by available data, research findings, and user testing insights.

Company Website: https://www.ryanspecialty.com/

📝 Enhancement Note: The company's positioning as a "leader in the industry" through "superior execution" suggests a high-performance culture. The focus on "digital transformation" within a traditional industry like insurance implies a forward-thinking approach and an environment ripe for innovation, making it an attractive prospect for operations and design professionals looking to make a significant impact.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior UX Designer role, indicating a mid-to-senior level position. It requires significant experience and the ability to lead design efforts independently for product areas, mentor junior designers (potentially), and influence product strategy through design.

Reporting Structure: The role likely reports into a Design Lead or Head of Digital Solutions, working within a cross-functional product team. This structure allows for direct collaboration with business and engineering leaders, providing visibility into strategic decision-making.

Operations Impact: The Senior UX Designer will have a direct impact on the efficiency and effectiveness of both internal operational workflows and external client-facing platforms. By improving user experiences, this role contributes to increased customer satisfaction, reduced operational friction, higher user adoption rates, and ultimately, enhanced business outcomes and revenue generation for RT Specialty.

Growth Opportunities:

• Leadership Development: Potential to grow into a Lead UX Designer or Design Manager role, overseeing a team and shaping the overall design strategy.

• Specialization: Opportunity to deepen expertise in specific areas of UX, such as advanced user research, design systems, or interaction design within the complex insurance domain.

• Cross-Functional Advancement: Potential to move into Product Management or other strategic roles within the Digital Solutions group, leveraging a deep understanding of user needs and business processes.

• Industry Expertise: Develop profound knowledge of the specialty insurance industry, making them a valuable asset for future roles within the company or the broader insurance technology sector.

📝 Enhancement Note: The "full-stack" nature of the role and the seniority level suggest that this is a key position for driving digital product evolution. Growth opportunities are likely tied to demonstrating leadership, strategic thinking, and significant impact on critical business objectives within the insurance sector.

🌐 Work Environment

Office Type: Hybrid work model, requiring 3 days per week in the office and 2 days remote. This suggests a blend of in-person collaboration and remote flexibility.

Office Location(s): Chicago, IL (Wacker Drive) or Buffalo, NY. Candidates can choose their preferred location.

Workspace Context:

• Collaborative Spaces: The office environment likely includes collaborative spaces designed for team meetings, brainstorming sessions, and cross-functional work, facilitating interaction with engineers, product managers, and business partners.

• Technology & Tools: Access to industry-standard design software (Figma) and other relevant technologies crucial for UX and UI design, prototyping, and research.

• Team Interaction: Opportunities for regular in-person interaction with design colleagues and stakeholders, fostering strong working relationships and knowledge sharing.

Work Schedule: The role operates on a standard full-time schedule (approximately 40 hours per week). The hybrid arrangement offers flexibility, allowing professionals to balance in-office collaboration with remote work.

📝 Enhancement Note: The hybrid model is a common and often preferred arrangement for design professionals, offering a balance between face-to-face collaboration essential for design sprints and remote work for focused execution and personal well-being. The choice between Chicago and Buffalo provides geographical flexibility.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter or hiring manager will likely conduct an initial phone screen to assess basic qualifications, experience, and cultural fit.

• Portfolio Review & Presentation: Candidates will be asked to present their portfolio, detailing 2-3 key projects. This is a critical stage where your ability to articulate your process, challenges, collaborations, and impact will be evaluated. Be prepared to discuss the "why" behind your design decisions.

• Hiring Manager/Team Interview: An interview with the hiring manager and potentially other senior members of the Digital Solutions team. This will delve deeper into your experience, problem-solving skills, and understanding of UX/UI principles in complex domains.

• Design Challenge/Case Study: A potential take-home assignment or a live design exercise focused on a specific problem relevant to the insurance industry or the company's digital products. This assesses your practical design skills and approach to problem-solving.

• Cross-Functional Stakeholder Interviews: Interviews with key collaborators such as Product Owners, Engineers, or Marketing leads to assess communication, collaboration style, and ability to work effectively in a cross-functional team.

Portfolio Review Tips:

• Focus on Impact: Clearly articulate the user and business impact of each project. Use metrics and data whenever possible to quantify success.

• Tell a Story: Structure your case studies as narratives, highlighting the problem, your approach, the constraints, your contributions, and the lessons learned.

• Show, Don't Just Tell: Use visuals (screenshots, prototypes, user flows) to illustrate your design process and final outcomes.

• Tailor to the Role: Emphasize projects that demonstrate experience in complex domains, agile environments, and ideally, the insurance industry. Highlight your "full-stack" capabilities.

• Be Ready for Questions: Anticipate questions about your design choices, how you handle feedback, and how you collaborate with technical teams.

Challenge Preparation:

• Understand the Domain: Research the specialty insurance industry, common user needs, and typical digital product functionalities.

• Practice Design Thinking: Be prepared to apply a structured problem-solving approach, starting with defining the problem, empathizing with users, ideating solutions, prototyping, and testing.

• Focus on Constraints: Acknowledge and incorporate potential technical and business constraints into your design solutions.

• Communicate Clearly: Practice articulating your thought process and design rationale concisely and persuasively.

📝 Enhancement Note: The emphasis on portfolio presentation and a potential design challenge indicates that Ryan Specialty values practical application and the ability to articulate design thinking. Candidates should prepare to demonstrate not just proficiency in design tools but also strategic thinking, user empathy, and a results-oriented approach.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Explicitly mentioned as the primary tool for UX/UI design, prototyping, and collaboration. Proficiency is expected, or a strong ability to learn quickly.

• Prototyping Tools: Experience with various prototyping tools beyond Figma for creating interactive mockups and user flow demonstrations.

• Wireframing Tools: Familiarity with tools used for low-fidelity design concepts and information architecture mapping.

Analytics & Reporting:

• User Analytics Platforms: Experience with tools like Google Analytics, Adobe Analytics, or similar platforms to track user behavior, measure engagement, and inform design decisions.

• Data Visualization Tools: Familiarity with tools that help in presenting user data and design impact effectively.

CRM & Automation:

• While not explicitly mentioned for the UX role, a general understanding of how CRM systems (like Salesforce) and automation platforms integrate with user-facing applications could be beneficial for understanding the broader business context.

📝 Enhancement Note: Figma is a critical tool for this role. Candidates should be prepared to showcase their Figma skills and potentially discuss their experience with other design software they've used in the past. Understanding how design integrates with analytics and broader business systems is a plus.

👥 Team Culture & Values

Operations Values:

• User-Centricity: A strong commitment to understanding and prioritizing user needs in all design and development efforts.

• Collaboration: Emphasis on working effectively in cross-functional teams, fostering open communication and shared ownership.

• Impact-Driven: Focus on delivering tangible results that improve customer satisfaction, enhance operational efficiency, and contribute to business growth.

• Continuous Improvement: A culture that encourages learning, iteration, and proactive problem-solving to refine processes and product experiences.

• Innovation: Embracing new ideas and technologies to drive digital transformation within the insurance sector.

Collaboration Style:

• Cross-Functional Integration: A collaborative approach that involves close partnerships with Product Management, Engineering, Marketing, and Business stakeholders to ensure holistic product development.

• Feedback Exchange: An open environment for constructive feedback and iterative design reviews, promoting continuous learning and refinement.

• Knowledge Sharing: Encouraging the sharing of best practices, design patterns, and insights across the team and wider organization to foster collective growth and maintain design consistency.

📝 Enhancement Note: The company's emphasis on "superior execution" and "creative solutions" suggests a culture that values high performance, problem-solving, and a proactive approach to business challenges. The hybrid work model likely supports a balance between focused individual work and collaborative team efforts.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating Complex Domain: Designing for the intricacies of the specialty insurance industry requires a deep understanding of complex products, regulations, and user workflows.

• Balancing Stakeholder Needs: Effectively managing competing priorities and requirements from various business units, product owners, and end-users.

• Driving Design System Adoption: Championing and implementing a design system across diverse product areas can be challenging, requiring strong advocacy and change management skills.

• Agile Iteration Speed: Maintaining high design quality and user focus while adhering to rapid agile development cycles and tight deadlines.

• Measuring Impact: Quantifying the exact impact of design changes on user behavior and business outcomes in a complex financial services environment.

Learning & Development Opportunities:

• Deep Dive into Insurance: Gain specialized knowledge of the specialty insurance market, becoming an expert in user needs and industry-specific digital solutions.

• Design System Leadership: Opportunity to play a significant role in the development and ongoing evolution of a critical design system.

• Cross-Functional Skill Development: Enhance collaboration and communication skills by working closely with engineering, product, and business teams.

• Strategic Influence: Contribute to the strategic direction of digital products and the company's digital transformation initiatives.

• Industry Conferences & Training: Potential for participation in relevant UX, design, and insurance industry conferences and specialized training programs.

📝 Enhancement Note: The role presents a significant opportunity to gain deep expertise in a specialized industry while honing "full-stack" UX skills. Overcoming the challenges will directly contribute to professional growth and impact.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you led the design for a complex product area. What were the biggest challenges, how did you approach them, and what was the outcome?" (Focus on your leadership, problem-solving, and impact.)

• "How do you balance user needs with business requirements and technical constraints in an agile environment?" (Prepare to discuss your process for trade-offs and prioritization.)

• "Walk us through a project where you had to advocate for a specific design decision based on user research or data. How did you present your case and to whom?" (Highlight your communication, research, and persuasion skills.)

Company & Culture Questions:

• "What interests you about Ryan Specialty and the insurance industry?" (Research the company's mission, values, and recent news.)

• "How do you contribute to a collaborative team environment, especially in a hybrid setting?" (Discuss your communication and teamwork strategies.)

• "How do you stay current with UX trends and best practices, and how do you apply them?" (Show your commitment to continuous learning.)

Portfolio Presentation Strategy:

• Structure: Organize your presentation logically: Problem > Research > Solution (Design Process) > Impact > Learnings.

• Focus on "Why": For each design decision, explain the rationale behind it, referencing user needs, business goals, or data.

• Quantify Impact: Use numbers and metrics to prove the value of your work.

• Highlight Collaboration: Explicitly mention who you worked with and how you collaborated.

• Be Concise: Respect the allotted time and focus on the most impactful aspects of your projects.

• Prepare for Deep Dives: Be ready to answer detailed questions about any aspect of your projects.

📝 Enhancement Note: Candidates should prepare to showcase not only their design skills but also their strategic thinking, communication prowess, and ability to drive impact within a complex business context. The portfolio presentation is a key opportunity to demonstrate these capabilities.

📌 Application Steps

To apply for this Senior UX Designer position:

• Submit your application through the provided Workday application link.

• Tailor Your Resume: Customize your resume to highlight your 6+ years of UX/Product Design experience, emphasizing projects within complex domains and any insurance industry experience. Use keywords from the job description such as "UX Design," "UI Design," "Figma," "Agile," "Product Design," and "Insurance."

• Curate Your Portfolio: Select 2-3 of your strongest case studies that best demonstrate your end-to-end design process, collaboration skills, and measurable impact. Ensure each case study clearly outlines the problem, your role, your process, and the user/business outcomes.

• Prepare Your Presentation: Practice presenting your portfolio, focusing on storytelling, articulating your design rationale, and quantifying the impact of your work. Be ready to answer in-depth questions about your projects and design philosophy.

• Research Ryan Specialty: Understand the company's position in the specialty insurance market, its mission, and its commitment to digital solutions. This will help you tailor your responses and demonstrate genuine interest.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions to provide a comprehensive overview. All details, including specific responsibilities, qualifications, and application requirements, should be verified directly with Ryan Specialty through their official application portal or by contacting their HR department.