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: User Experience (UX) Design / Product Design

Date Posted: 2026-06-01

Experience Level: 6+ Years

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

🚀 Role Summary

• Lead end-to-end user experience (UX) and user interface (UI) design for critical digital products, including client-facing platforms and internal workflow tools, within the Digital Solutions group.

• Drive the creation of high-fidelity, development-ready designs and prototypes for responsive web touchpoints, balancing user needs, business objectives, and technical constraints.

• Collaborate extensively with cross-functional teams, including Product Owners, Engineers, Marketing, and Business stakeholders, to deliver exceptional user experiences that enhance customer satisfaction and achieve business outcomes.

• Contribute to the development and optimization of a comprehensive design system, ensuring consistency and scalability across digital products.

📝 Enhancement Note: While the title is "Senior UX Designer," the role explicitly requires "full-stack" UX/UI/IA/Research skills with a strong emphasis on UI. This signals a hands-on, execution-focused position rather than purely strategic or managerial. The target audience for this enhanced description should be experienced designers capable of delivering pixel-perfect designs and understanding technical feasibility.

📈 Primary Responsibilities

• Champion a user-centered design approach, translating user needs, jobs-to-be-done (JTBD), and business requirements into intuitive and effective digital experiences.

• Partner with Product Managers and Engineers to deeply understand product vision, requirements, and technical limitations, iteratively refining designs to achieve optimal visual and interactive quality.

• Generate a range of design concepts and high-fidelity prototypes, demonstrating the ability to pivot quickly based on feedback, research, and project needs.

• Present compelling design rationale and concepts to leadership and external partners, utilizing data, user research insights, and business metrics to support recommendations and drive decision-making.

• Conduct or collaborate with UX Researchers to plan, execute, and interpret user testing, gathering actionable insights to inform design iterations and improvements.

• Proactively identify, analyze, and resolve UX problems within existing digital products to enhance usability and user satisfaction.

• Develop clear and comprehensive design documentation, including wireframes, storyboards, process flows, sitemaps, and polished final designs, to guide development teams and stakeholders.

• Contribute to the maintenance, optimization, and implementation of the company's design system, ensuring adherence to standards and promoting reusability.

• Facilitate design reviews and discussions within the UX team to ensure consistency, share knowledge, and inform updates across adjacent products and features.

• Maintain current knowledge of design trends, competitive landscapes (particularly within the insurance industry), and emerging UX best practices to inspire innovation.

📝 Enhancement Note: The responsibilities highlight a blend of individual contribution and collaborative influence. The emphasis on "jobs-to-be-done (JTBD)" and "user needs" points to a need for designers who can think strategically about user problems, not just aesthetics. The requirement to "gather, catalog, and address UX problems" indicates a proactive approach to continuous improvement of existing products.

🎓 Skills & Qualifications

Education:

Experience:

• 6+ years of progressive experience in UX/Product Design, with a proven track record in the final development and execution phases of digital product creation.

Required Skills:

• "Full-Stack" UX/UI Design: Comprehensive expertise across information architecture (IA), interaction design (IxD), user research, and visual/UI design.

• Prototyping & Wireframing: Proficiency in creating detailed wireframes, interactive prototypes, and high-fidelity mockups to communicate design intent.

• User-Centered Design (UCD): A strong understanding and practical application of UCD principles, research methodologies, and empathy-driven problem-solving.

• Responsive Web Design: Experience designing intuitive and effective user experiences for various screen sizes and devices.

• Agile Methodologies: Familiarity and experience working within Agile/Scrum development frameworks.

• Communication & Presentation: Exceptional ability to articulate design decisions, present concepts effectively to diverse audiences (technical and non-technical), and foster collaboration.

• Time Management & Prioritization: Proven ability to manage multiple projects simultaneously, prioritize tasks, and meet deadlines in a fast-paced environment, operating with a high degree of autonomy.

• Detail Orientation & Big Picture Thinking: Capacity to maintain meticulous attention to detail while understanding and contributing to the overall strategic vision.

• Insurance Industry Knowledge: Specific experience or a strong understanding of the insurance industry is a strict requirement.

Preferred Skills:

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

• Design Systems: Experience in creating, contributing to, or implementing design systems.

• User Research: Hands-on experience conducting user interviews, usability testing, and synthesizing research findings.

• Technical Understanding: Familiarity with front-end development processes and technologies (e.g., JavaScript, presentation layer coding) to facilitate effective collaboration with engineers.

📝 Enhancement Note: The explicit mention of "full-stack skills" and the mandatory "insurance industry experience" are critical differentiators. Candidates must showcase a breadth of skills and domain expertise. The "6+ years" combined with the "Senior" title suggests a need for demonstrated leadership in design thinking and execution, not just task completion.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Case Studies: Showcase 3-5 robust case studies detailing challenging UX/UI projects. Each case study should clearly outline:

  • The specific user or business problem addressed.
  • Your role and responsibilities within the project.
  • The design process undertaken (research, ideation, iteration, testing).
  • Key collaboration efforts with cross-functional teams (Engineers, Product Managers, Stakeholders).
  • The user and business impact/outcomes of your design solutions, supported by data or metrics where possible.
  • What you learned from the experience and how it influenced future work.

• Process Documentation: Demonstrate a clear understanding of design documentation standards by including examples of wireframes, user flows, sitemaps, and high-fidelity mockups within your case studies.

• System Implementation: If applicable, include examples of contributions to or utilization of design systems, showcasing an understanding of consistency, scalability, and component-based design.

• ROI Demonstration: Highlight projects where your design efforts directly contributed to measurable business outcomes such as increased conversion rates, improved user satisfaction scores, reduced support tickets, or enhanced operational efficiency.

Process Documentation:

• Workflow Design: Provide examples of how you've mapped out and optimized user workflows for complex processes, demonstrating an ability to simplify intricate tasks.

• Implementation Methods: Illustrate your approach to preparing design specifications and collaborating with development teams to ensure accurate implementation of designs.

• Measurement & Analysis: Showcase how you've used data, analytics, and user feedback to measure the success of design initiatives and inform iterative improvements.

📝 Enhancement Note: The portfolio requirements are heavily focused on demonstrating tangible impact and a well-defined process. Candidates must be prepared to articulate not just what they designed, but why, how, and what the result was. The emphasis on "user and business impact" and "ROI" is crucial for a senior-level role in a commercial organization.

💵 Compensation & Benefits

Salary Range: $104,000 - $130,000 annually

Benefits:

• Comprehensive Health & Wellness:

  • Paid parental leave.
  • Mental health services.

• Time Off:

  • Generous Paid Time Off (PTO) policy.
  • Company holidays.
  • Dedicated vacation days.
  • Sick days.
  • Personal days.

• Performance & Financial:

  • Eligibility for annual bonuses.

• Total Rewards: Access to Ryan Specialty's comprehensive Total Rewards program, detailed at https://benefits.ryansg.com/.

Working Hours: Standard 40-hour work week, with flexibility expected given the hybrid nature and fast-paced environment.

📝 Enhancement Note: The provided salary range is specific and competitive for a Senior UX Designer role in a major metropolitan area like Chicago. The benefits package is robust, with particular emphasis on parental leave and mental health support, aligning with modern employee expectations. The "Total Rewards" mention suggests a structured approach to compensation and benefits beyond the base salary.

🎯 Team & Company Context

🏢 Company Culture

Industry: Specialty Insurance Distribution. Ryan Specialty (RT Specialty) operates as a leading wholesale distributor of specialty insurance products and services, serving retail brokerage firms with complex risk needs across various lines of business.

Company Size: Large enterprise (likely 1,000+ employees based on LinkedIn data for Ryan Specialty, though specific division size may vary). This scale implies established processes, potential for cross-departmental collaboration, and opportunities for impact within a structured organization.

Founded: Ryan Specialty was founded in 2010. This indicates a relatively modern company with established practices but still agile enough to embrace digital transformation.

Team Structure:

• Digital Solutions Group: The UX Designer will be part of the Digital Solutions group, suggesting a dedicated focus on technology and digital product development.

• Cross-Discipline Teams: The role involves partnering with cross-discipline teams, including Product Owners, Engineers, Marketing, and Business Partners, indicating a collaborative, product-centric team environment.

• Reporting: The role likely reports into a UX Design Lead or Manager within the Digital Solutions group, with potential dotted-line reporting or close collaboration with Product Management leadership.

Methodology:

• Agile Environment: The team operates within an Agile framework, emphasizing iterative development, rapid feedback loops, and cross-functional team synergy.

• User-Centric Approach: Design decisions are driven by user needs, jobs-to-be-done, and data-driven insights, ensuring products are both user-friendly and business-effective.

• Data-Informed Design: Research, analytics, and user testing are integral to the design process, informing iterations and validating design solutions.

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

📝 Enhancement Note: The company operates in a specialized B2B financial services sector (specialty insurance), which often means complex user journeys and a need for clear, efficient digital tools. The "Digital Solutions Group" implies a strategic investment in technology to improve both internal operations and external client services. The hybrid model indicates a trust-based culture that values work-life balance.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior-level individual contributor role. It demands a high degree of autonomy, strategic thinking, and the ability to lead design efforts for specific product areas. The focus is on execution excellence and influencing product direction through design expertise.

Reporting Structure: The Senior UX Designer will typically report to a Design Manager or Director within the Digital Solutions team. They will work closely with Product Managers, Engineering Leads, and business stakeholders on a day-to-day basis, forming project-specific "squads" or feature teams.

Operations Impact: The Senior UX Designer's work directly impacts operational efficiency and revenue generation by:

• Improving the usability and effectiveness of internal tools, leading to faster policy management, claims processing, and sales cycles.

• Enhancing client-facing platforms, driving customer acquisition, retention, and satisfaction.

• Ensuring digital products are intuitive and reduce errors, thereby minimizing operational costs and rework.

Growth Opportunities:

• Specialization: Deepen expertise in UX strategy, user research, interaction design, or design systems within the insurance domain.

• Leadership: Transition into a Lead UX Designer role, mentoring junior designers, or a UX Manager role, overseeing a team and strategic design initiatives.

• Product Strategy: Influence product roadmaps and long-term strategy through deep understanding of user needs and market trends.

• Cross-Functional Mobility: Opportunities to move into Product Management or other roles within the Digital Solutions group or broader Ryan Specialty organization.

📝 Enhancement Note: The "Senior" title coupled with the "full-stack" requirement suggests this role is for a designer who can operate independently and lead projects from conception to delivery. The growth path clearly indicates opportunities for both individual technical advancement and potential leadership roles within the digital product development function. The emphasis on "operations impact" is key for candidates looking to see how their design work contributes to business success.

🌐 Work Environment

Office Type: Hybrid work model, with 3 days per week expected in the Chicago, IL office and 2 days remote. This suggests a modern office environment designed for collaboration, with amenities to support in-person teamwork and ideation.

Office Location(s): Chicago, IL (Wacker Drive specified) and Buffalo, NY. Candidates can choose their primary office location. The Chicago location is in a major business district, likely offering good accessibility.

Workspace Context:

• Collaborative Spaces: The office environment is expected to facilitate cross-functional collaboration, team meetings, design critiques, and brainstorming sessions.

• Technology Access: Employees will have access to necessary design tools (Figma is preferred) and company systems to perform their duties effectively, whether in-office or remote.

• Team Interaction: Opportunities for regular interaction with fellow designers, product managers, engineers, and business stakeholders, fostering a dynamic and engaged work environment.

Work Schedule: A standard 40-hour work week is expected, with the flexibility of the hybrid model allowing for a balance between in-office collaboration and remote focus time. The fast-paced environment may necessitate occasional adjustments to meet project deadlines.

📝 Enhancement Note: The hybrid model is a significant aspect of the work environment, offering flexibility while maintaining in-person collaboration. The mention of Chicago and Buffalo locations provides options for candidates. The environment is likely geared towards tech and product development teams, fostering innovation and teamwork.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A brief call with a recruiter to assess basic qualifications, interest, and cultural fit.

• Portfolio Review & Skills Assessment: A presentation of your portfolio to the hiring manager and potentially other senior designers/product managers. This is the critical stage to showcase your "full-stack" capabilities, process, and impact. Expect to walk through 1-2 key case studies in detail.

• Design Challenge (Potential): You may be given a small design exercise or a take-home challenge to assess your problem-solving skills, design thinking, and ability to work within constraints.

• Cross-Functional Interviews: Interviews with Product Owners, Engineering Leads, and potentially business stakeholders to evaluate collaboration skills, communication effectiveness, and understanding of business needs.

• Final Interview: A discussion with senior leadership (e.g., Director of Digital Solutions) to confirm strategic alignment, leadership potential, and overall fit.

Portfolio Review Tips:

• Tailor Your Presentation: Select case studies that best demonstrate your "full-stack" skills (UX strategy, research, UI design, prototyping) and experience in complex domains like insurance.

• Focus on Impact: Clearly articulate the user and business outcomes of your work. Quantify success whenever possible using metrics.

• Explain Your Process: Detail your thought process, decision-making, and how you overcame challenges. Emphasize collaboration and stakeholder management.

• Prepare for "Why": Be ready to explain why you made specific design choices, supported by research or data.

• Showcase Figma: If you have strong Figma skills, highlight them. If not, be prepared to articulate your ability to quickly learn and master new tools like Figma.

Challenge Preparation:

• Understand the Domain: Research Ryan Specialty, RT Specialty, and the specialty insurance industry. Understand common user needs and pain points for brokers and clients.

• Practice Design Thinking: Be prepared to articulate your approach to problem-solving, ideation, and iteration.

• Communicate Clearly: Practice explaining your design decisions concisely and persuasively, anticipating questions from technical and non-technical audiences.

📝 Enhancement Note: The emphasis on a portfolio review and potential design challenge indicates that practical design skills and process demonstration are paramount. Candidates should prepare to deeply discuss their work and rationale, showcasing both strategic thinking and execution prowess. The mention of "insurance industry experience" as a requirement suggests interviewers will probe this area specifically.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Explicitly mentioned as the preferred tool for UX/UI design, prototyping, and collaboration. Proficiency is highly desired.

• Prototyping Tools: While Figma is preferred, familiarity with other prototyping tools is beneficial.

• Wireframing Tools: Experience with tools for creating low-fidelity wireframes and user flows.

Analytics & Reporting:

• Familiarity with analytics platforms (e.g., Google Analytics, Adobe Analytics) to understand user behavior and measure design impact is helpful, though not explicitly required.

CRM & Automation:

• While not a direct CRM role, understanding how UX design integrates with CRM systems (like Salesforce, if used internally) and automation platforms to create seamless user journeys is advantageous. Experience designing for internal workflow tools that might interact with such systems is relevant.

📝 Enhancement Note: Figma is the cornerstone of the toolset. Candidates should highlight their proficiency and experience with it. While direct experience with analytics or CRM tools isn't mandatory for the UX designer, an understanding of how their designs fit into the broader MarTech/SalesTech stack and impact data collection or workflow automation will be a strong plus.

👥 Team Culture & Values

Operations Values:

• Execution Excellence: A strong focus on delivering high-quality, pixel-perfect designs that are development-ready and meet business objectives.

• User-Centricity: A commitment to understanding and advocating for the user throughout the design and development process.

• Collaboration: Valuing teamwork and open communication with cross-functional partners to achieve shared goals.

• Continuous Improvement: An ongoing drive to identify and address UX issues, optimize existing experiences, and stay current with industry best practices.

• Data-Driven Decisions: Utilizing research, analytics, and user feedback to inform design choices and measure impact.

Collaboration Style:

• Cross-Functional Integration: Designers are expected to work seamlessly with Product Managers, Engineers, and Business Stakeholders, acting as a bridge between user needs and technical feasibility.

• Open Feedback Culture: Encouraging constructive feedback during design reviews and critiques to elevate the quality of work.

• Knowledge Sharing: Promoting the sharing of insights, best practices, and learnings within the design team and broader organization.

📝 Enhancement Note: The culture appears to blend a results-oriented approach (execution, impact) with a collaborative and user-focused mindset. The emphasis on "alignment with Ryan Specialty culture" suggests candidates should research the company's stated values and be prepared to demonstrate how they embody them.

⚡ Challenges & Growth Opportunities

Challenges:

• Complex Domain: Navigating the intricacies of the specialty insurance industry and translating complex business logic into user-friendly interfaces.

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

• Technical Constraints: Working within existing technical architectures and development cycles while pushing for innovative user experiences.

• Design System Evolution: Contributing to and maintaining a design system in a growing organization requires discipline and strategic thinking.

• Hybrid Work Model: Adapting to a hybrid environment, ensuring effective communication and collaboration across in-office and remote team members.

Learning & Development Opportunities:

• Industry Expertise: Gaining deep knowledge of the specialty insurance sector, a valuable niche in the B2B market.

• Advanced Design Skills: Opportunities to hone "full-stack" design capabilities, particularly in Figma and potentially user research.

• Cross-Functional Exposure: Learning about product management, engineering processes, and various business functions within an insurance distribution company.

• Design System Contribution: Developing expertise in creating and managing scalable design systems.

• Career Advancement: Clear pathways to Lead Designer or management roles, or specialization in strategic UX areas.

📝 Enhancement Note: The challenges are typical for senior roles in established, complex industries. The growth opportunities are substantial, offering both skill development and career progression within a specialized field. Candidates should view these challenges as opportunities to demonstrate their problem-solving skills and adaptability.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you led the design for a complex product area. What was your process, and what was the outcome?" (Focus on your full-stack approach, leadership, and impact.)

• "How do you balance user needs with business objectives and technical constraints? Provide an example." (Highlight your ability to make trade-offs and find optimal solutions.)

• "Walk us through a challenging UX problem you solved for the insurance industry (or a similar complex domain). What data or research informed your decisions?" (Demonstrate domain understanding and data-driven design.)

Company & Culture Questions:

• "Why are you interested in Ryan Specialty and the specialty insurance industry?" (Show research and genuine interest in the domain.)

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

Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly define the problem, your role, your process, your solutions, and the impact. Use visual aids effectively.

• Highlight Figma: Be prepared to discuss your specific workflows and techniques within Figma.

• Quantify Impact: Use numbers and data to demonstrate the success of your designs (e.g., "increased conversion by X%", "reduced user errors by Y%").

• Show, Don't Just Tell: Use visuals of your wireframes, prototypes, and final designs to illustrate your points.

• Be Ready for Deep Dives: Anticipate detailed questions about your design decisions, research methodologies, and collaboration processes.

📝 Enhancement Note: Interview preparation should strongly emphasize showcasing "full-stack" capabilities, domain-specific experience (insurance), and the ability to articulate impact. Candidates must be ready to defend their design choices with data and a clear understanding of business goals.

📌 Application Steps

To apply for this Senior UX Designer position:

• Submit your application through the provided Workday link.

• Portfolio Customization: Curate your online portfolio to prominently feature 2-3 detailed case studies that best align with the requirements: "full-stack" UX/UI skills, experience in complex domains (especially insurance), and demonstrable user/business impact. Ensure your process, collaboration, and outcomes are clearly articulated.

• Resume Optimization: Tailor your resume to highlight keywords from the job description, such as "UX Design," "UI Design," "Information Architecture," "UX Research," "Figma," "Insurance Industry," "Agile," "Responsive Web Design," and "User-Centered Design." Quantify achievements where possible.

• Interview Preparation: Practice presenting your portfolio, focusing on clear communication of your design process, rationale, and the impact of your work. Prepare answers for common UX/UI strategy and behavioral questions. Research Ryan Specialty and the specialty insurance market.

• Company Research: Gain an understanding of Ryan Specialty's business model, its position in the insurance market, and its digital initiatives. This will help you tailor your responses and demonstrate genuine interest during interviews.

⚠️ 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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