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 / Digital Product Design

Date Posted: April 27, 2026

Experience Level: 6+ Years

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

🚀 Role Summary

• This Senior UX Designer role focuses on shaping user experiences for both internal workflow tools and external client-facing platforms within the Digital Solutions group, emphasizing a user-centered approach to drive customer satisfaction and business outcomes.

• The position requires a blend of UX/UI design, information architecture, and UX research skills, with a strong emphasis on UI design, to create pixel-perfect, development-ready deliverables for responsive web touchpoints.

• The role involves leading design efforts for specific product areas, collaborating closely with cross-functional teams, and managing multiple projects simultaneously while balancing quality, time, and resources.

• Candidates will be expected to contribute to a design system, conduct user research, and stay abreast of industry best practices in both UX and the insurance sector.

📝 Enhancement Note: While the title is "Senior UX Designer," the description emphasizes "full-stack" skills (UI + UX/IA + UX research) and strong UI skills, indicating a hands-on role requiring comprehensive design capabilities from concept to execution. The "External Facing" aspect suggests a focus on customer-facing applications, which will be a key consideration for portfolio review.

📈 Primary Responsibilities

• Lead user experience design initiatives for assigned product areas (e.g., internal policy management tools, external quoting platforms) in partnership with product managers, engineers, and business stakeholders.

• Identify user needs and business requirements to conceptualize, plan, and execute high-fidelity prototypes and development-ready design deliverables for responsive web interfaces.

• Conduct user research and collaborate with UX researchers to gather, interpret, and apply user testing insights to inform design decisions and problem-solving.

• Develop and present design concepts, wireframes, storyboards, process flows, and high-fidelity mockups to team leadership and external partners, using data and research to support recommendations.

• Contribute to the documentation, optimization, and implementation of a comprehensive design system to ensure consistency and efficiency across digital products.

• Collaborate closely with engineering teams to understand technical constraints and ensure designs are implementable while maintaining a high-quality user experience.

• Proactively identify and address UX problems within existing digital products, cataloging issues and proposing solutions.

• Stay current with evolving UX/UI best practices, design trends, and competitive landscape within the insurance industry.

📝 Enhancement Note: The responsibilities highlight a need for end-to-end design ownership, from user research and conceptualization to detailed UI design and collaboration with development. The emphasis on "jobs-to-be-done (JTBD)" suggests a strategic approach to understanding user motivations and aligning design solutions with those needs.

🎓 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 products.

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

Required Skills:

• User Experience (UX) Design: Deep understanding of UX principles, user-centered design methodologies, and the entire UX lifecycle.

• UI Design: Strong visual design skills, with the ability to create pixel-perfect, aesthetically pleasing, and functional user interfaces.

• Information Architecture (IA): Proficiency in organizing and structuring content and features logically for intuitive navigation and usability.

• UX Research & Testing: Experience planning, conducting, and interpreting user research, usability testing, and gathering user feedback.

• Prototyping & Wireframing: Ability to rapidly create low-fidelity wireframes, interactive prototypes, and high-fidelity mockups.

• Design Tools: Proficiency with current UX/Service Design tools, with Figma being the preferred platform.

• Agile Methodologies: Experience working within agile development frameworks.

• Communication & Presentation: Excellent verbal, written, and visual communication skills; ability to present design concepts and rationale effectively to diverse audiences.

• Time Management & Prioritization: Strong organizational skills to manage multiple projects, prioritize tasks, and meet shifting deadlines in a fast-paced environment.

Preferred Skills:

• Figma Expertise: Advanced proficiency and experience with Figma.

• Design Systems: Experience in creating, maintaining, and implementing design systems.

• Insurance Industry Knowledge: In-depth understanding of insurance products, processes, and customer journeys.

• Service Design: Familiarity with service design principles and methodologies.

• JavaScript & Development Fundamentals: Basic understanding of general development processes, technologies, and frameworks (e.g., JavaScript, presentation layer coding).

📝 Enhancement Note: The requirement for "6+ years of experience" and specific industry knowledge (insurance) are critical filters. The emphasis on a "strong portfolio highlighting challenges faced, collaboration, learnings, and user/business impact" is paramount. Candidates should be prepared to showcase projects that demonstrate their ability to navigate complex domains and deliver measurable results.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Project Case Studies: Showcase 3-5 distinct projects that demonstrate a full UX/UI design process, from initial problem definition and research to final design and impact. Each case study should clearly articulate the challenge, your role, the process followed, collaboration efforts, key decisions made, and the measurable user and business outcomes.

• Problem-Solving Examples: Include examples that highlight your user-centered approach, particularly in complex or regulated domains like insurance. Demonstrate how you applied research, data, and empathy to solve critical user needs.

• UI Design Excellence: Portfolios must include high-fidelity mockups and interactive prototypes that showcase strong visual design skills, attention to detail, and adherence to UI best practices.

• Cross-Functional Collaboration: Evidence of successful collaboration with product managers, engineers, and business stakeholders, illustrating how you translated requirements into effective design solutions.

• Impact & Metrics: Clearly articulate the impact of your designs, ideally supported by quantifiable metrics (e.g., increased conversion rates, reduced task completion times, improved customer satisfaction scores).

Process Documentation:

• Workflow Design: Demonstrate experience in mapping out user flows, task analyses, and information architecture for complex digital products.

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

• Iterative Design: Showcase how you iterated on designs based on user feedback, A/B testing, or other analytical insights.

📝 Enhancement Note: The portfolio is explicitly mentioned as a critical component of the application. Candidates must tailor their portfolio to highlight projects within regulated industries or complex domains, specifically demonstrating their ability to deliver both user-centric and business-aligned solutions within the insurance context. The emphasis on impact and collaboration is key.

💵 Compensation & Benefits

Salary Range:

• $104,000 - $130,000 annually.

Benefits:

• Comprehensive Health & Well-being:

  • Paid time off (PTO)
  • Company holidays
  • Mental health services

• Family Support:

  • Paid parental leave

• Financial Incentives:

  • Bonuses (for full-time roles)

• Total Rewards: Access to Ryan Specialty's Total Rewards program, detailed on their benefits website.

Working Hours:

• Standard full-time workweek, likely around 40 hours. The role operates on a hybrid schedule (3 days in office, 2 days remote), suggesting a need for structured workdays that accommodate both in-person collaboration and remote focus.

📝 Enhancement Note: The salary range is provided, which is a significant advantage for candidates. The benefits package is described as "comprehensive and best-in-class," with specific mentions of parental leave and mental health services, indicating a focus on employee well-being. The hybrid work model requires careful planning for time management and collaboration.

🎯 Team & Company Context

🏢 Company Culture

Industry: Specialty Insurance Distribution. Ryan Specialty is a leading wholesale distributor of specialty insurance products and services, operating within a complex and regulated financial services sector.

Company Size: (Derived from LinkedIn data, not explicitly provided in input, but typically large for a company with multiple divisions like RT Specialty) The company is a significant player in the insurance market, suggesting a structured corporate environment with established processes.

Founded: (Not explicitly provided, but Ryan Specialty Group was founded in 2010) The company has a history of growth and established operations, indicating a mature organizational structure.

Team Structure:

• Digital Solutions Group: The UX Designer will be part of this group, which focuses on digital product development.

• Cross-Discipline Teams: The role involves close collaboration with Product Owners, Engineers, Marketing, and Business Partners, indicating a matrixed or project-based team structure common in digital product development.

• Reporting: Likely reports to a UX Design Lead or Director within the Digital Solutions group.

Methodology:

• User-Centric Design: The company emphasizes building user experiences driven by user needs, jobs-to-be-done (JTBD), and business needs.

• Agile Environment: The description explicitly mentions working within an agile environment, implying iterative development cycles, sprint planning, and cross-functional team collaboration.

• Data-Informed Decisions: Expectation to leverage research, analytics, and user testing insights to inform design decisions.

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

📝 Enhancement Note: Ryan Specialty operates in the specialized insurance sector, which often demands a high degree of professionalism, attention to detail, and adherence to compliance. The "Digital Solutions" group suggests a forward-thinking approach to technology and customer experience within this traditional industry. The emphasis on collaboration indicates a team-oriented, project-driven work environment.

📈 Career & Growth Analysis

Operations Career Level: Senior UX Designer. This level implies significant experience, autonomy, and the ability to lead design initiatives for product areas. It suggests a role that influences strategy and mentors junior designers.

Reporting Structure: Likely reports to a Director or VP of Digital Solutions or UX Design. Collaboration will be extensive with Product Managers, Engineers, and various business units.

Operations Impact: The role directly impacts customer satisfaction, user adoption of digital platforms, and operational efficiency for both internal users and external clients. Successful UX design can lead to increased customer retention, streamlined policy management, and improved business outcomes for Ryan Specialty.

Growth Opportunities:

• Leadership Development: Opportunity to lead design for significant product areas, mentor junior designers, and potentially move into management roles within UX or Digital Solutions.

• Skill Specialization: Deepen expertise in specific areas like design systems, complex domain design, or UX research methodologies.

• Industry Expertise: Develop specialized knowledge and a strong portfolio within the insurance industry, a niche with significant demand for skilled UX professionals.

• Cross-Functional Mobility: Potential to move into Product Management or other strategic roles within Digital Solutions based on demonstrated capabilities.

📝 Enhancement Note: The "Senior" title suggests a path beyond individual contribution, with potential for leadership. The hybrid model and focus on digital transformation within a traditional industry offer unique growth opportunities for designers looking to make a tangible impact.

🌐 Work Environment

Office Type: Hybrid work environment with 3 days in the office and 2 days remote. This suggests a blend of collaborative in-person work and focused individual work.

Office Location(s): Chicago, IL (Wacker Drive) or Buffalo, NY. The specific office in Chicago is likely a modern corporate setting.

Workspace Context:

• Collaborative Spaces: The office environment is expected to facilitate collaboration with cross-functional teams, including designers, engineers, and product managers.

• Technology Access: Access to necessary design tools (Figma) and other company-provided technology.

• Team Interaction: Opportunities for in-person brainstorming, design reviews, and team meetings.

Work Schedule:

• Standard business hours are expected, with flexibility to manage project deadlines. The hybrid model requires discipline in structuring workdays for both in-office collaboration and remote productivity.

📝 Enhancement Note: The hybrid model is a key feature, requiring candidates to be comfortable with both autonomous remote work and in-office collaboration. The specific office location in Chicago suggests a professional, urban work setting.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: HR or Recruiter call to assess basic qualifications, interest, and cultural fit.

• Portfolio Review & Interview: A dedicated session with the hiring manager and potentially other UX/design team members to review the candidate's portfolio. This will focus on specific projects, design process, problem-solving approach, and impact.

• Technical/Skills Interview: May involve a design challenge or a deep dive into specific UX/UI skills, tools, and methodologies.

• Cross-Functional Interviews: Discussions with Product Owners, Engineers, or other stakeholders to assess collaboration skills and understanding of the product development lifecycle.

• Final Interview: Potentially with senior leadership to discuss strategic alignment and overall fit.

Portfolio Review Tips:

• Focus on Impact: Clearly articulate the "why" behind your design decisions and the quantifiable results achieved. For this role, emphasize projects that demonstrate success in complex domains or regulated industries like insurance.

• Showcase Process, Not Just Polish: Detail your thought process, research methods, iterations, and how you overcame challenges. Use wireframes, user flows, and prototypes to illustrate your journey.

• Highlight Collaboration: Provide examples of how you worked with engineers, product managers, and other stakeholders, explaining how you incorporated feedback and managed differing perspectives.

• Tailor to the Role: Select projects that best represent your ability to handle external-facing products, complex domains, and ideally, experience within insurance or similar regulated sectors.

• Be Ready for Figma Discussion: Given Figma is the preferred tool, be prepared to discuss your proficiency and how you leverage its features.

Challenge Preparation:

• Be prepared for a potential design exercise that might involve a hypothetical problem relevant to Ryan Specialty's business (e.g., designing a new feature for a quoting platform, improving a policy management workflow).

• Practice articulating your design decisions concisely and justifying them with user-centered principles and business objectives.

• Understand the insurance industry context, even if you don't have direct experience, to demonstrate an ability to quickly grasp complex domains.

📝 Enhancement Note: The portfolio review is critical. Candidates should prepare to walk through 2-3 key projects in detail, focusing on the "Senior" aspects of their contributions: leadership, strategic thinking, and significant impact. Understanding the insurance industry's nuances will be a strong differentiator.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The primary tool for UX/UI design, prototyping, and collaboration. Proficiency is highly desired, and the company is willing to train.

• Prototyping Tools: In-depth knowledge of prototyping capabilities within Figma or similar tools (e.g., InVision, Adobe XD).

• Wireframing Tools: Experience with tools for creating low-fidelity wireframes (e.g., Balsamiq, Sketch, or Figma itself).

Analytics & Reporting:

• While not explicitly a primary tool for the UX Designer, an understanding of how to interpret user analytics and reporting data (e.g., from Google Analytics, Adobe Analytics, or internal dashboards) to inform design decisions is beneficial.

CRM & Automation:

• Not directly applicable to this UX role, but awareness of how CRM systems and automation tools might interact with user-facing platforms could be helpful for context.

📝 Enhancement Note: Figma is the central tool. Candidates should emphasize their mastery of Figma for UI design, prototyping, and collaboration. An understanding of how design integrates with data analysis and development processes is also valuable.

👥 Team Culture & Values

Operations Values:

• User-Centricity: A core value driving all design decisions, prioritizing the needs and experiences of users.

• Collaboration: Emphasis on working effectively with cross-functional teams to achieve shared goals.

• Excellence & Quality: Commitment to delivering high-quality, pixel-perfect designs and outstanding user experiences.

• Data-Driven Approach: Utilizing research, analytics, and testing to inform design strategy and validate solutions.

• Continuous Improvement: Staying current with industry best practices and seeking opportunities to optimize processes and designs.

Collaboration Style:

• Cross-Functional Integration: Close partnership with Product Managers, Engineers, and Business stakeholders to ensure alignment and successful product delivery.

• Iterative Feedback: Openness to constructive criticism and iterative design cycles, involving regular feedback loops.

• Knowledge Sharing: Encouraging sharing of design insights, best practices, and lessons learned within the design team and broader organization.

📝 Enhancement Note: The culture values a blend of independent work within a hybrid model and strong collaborative effort. The emphasis on user-centricity, data, and continuous improvement aligns with modern UX best practices, while the insurance industry context suggests a need for professionalism and thoroughness.

⚡ Challenges & Growth Opportunities

Challenges:

• Complex Domain Navigation: Designing for the intricacies of the insurance industry requires a steep learning curve to understand policies, regulations, and diverse user needs.

• Balancing User & Business Needs: Effectively translating complex business requirements and technical constraints into intuitive and effective user experiences.

• Hybrid Work Management: Successfully collaborating and maintaining team cohesion in a hybrid work environment that requires proactive communication and coordination.

• Design System Adoption: Championing and implementing a design system across various product areas to ensure consistency and efficiency.

Learning & Development Opportunities:

• Deep Insurance Industry Expertise: Gain specialized knowledge in a high-demand niche sector.

• Advanced UX/UI Skills: Opportunities to hone skills in complex product design, design systems, and user research.

• Leadership & Mentorship: Potential to lead design projects, mentor junior designers, and influence product strategy.

• Industry Conferences & Training: Possibility of attending relevant UX conferences or training programs to stay current and expand skill sets.

📝 Enhancement Note: The primary challenge lies in navigating the complexity of the insurance domain. Growth opportunities are tied to developing specialized expertise and taking on leadership responsibilities within a growing digital solutions team.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you led the design for a complex feature or product area. What was your process, and what was the outcome?" (Prepare a case study highlighting leadership, process, and impact).

• "How do you balance user needs with business objectives and technical constraints, especially in regulated industries like insurance?" (Focus on your decision-making process and ability to find optimal solutions).

Company & Culture Questions:

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

• "How do you approach working in a hybrid environment, and what strategies do you use to stay connected with your team?" (Discuss communication tools, proactive engagement, and structured work habits).

Portfolio Presentation Strategy:

• Structure: For each project, clearly define the problem, your role and responsibilities, the design process (research, ideation, design, testing), key decisions and rationale, challenges encountered, and finally, the measurable results and impact.

• Visuals: Use high-quality mockups, interactive prototypes, user flows, and wireframes. Ensure visuals are clean and easy to understand.

• Narrative: Tell a compelling story about each project, focusing on your problem-solving journey and the value you delivered.

• Conciseness: Be prepared to present your key projects within a specified timeframe, focusing on the most relevant aspects for this role.

📝 Enhancement Note: Prepare to discuss your portfolio in depth, focusing on how your experience aligns with the requirements for designing complex, external-facing applications within a regulated industry. Be ready to articulate your understanding of the insurance business and how UX can drive value.

📌 Application Steps

To apply for this Senior UX Designer position:

• Submit your application through the provided Workday link.

• Portfolio Customization: Ensure your portfolio prominently features projects demonstrating robust UX/UI design, user research, and experience with complex or regulated domains. Highlight your work with Figma and any relevant insurance industry experience.

• Resume Optimization: Tailor your resume to highlight keywords such as "UX Design," "UI Design," "Figma," "Insurance," "Agile," "Product Design," "Information Architecture," and "User Research." Quantify your achievements wherever possible.

• Interview Preparation: Practice articulating your design process, problem-solving approach, and the impact of your work. Be ready to discuss your experience with hybrid work and your interest in the insurance sector.

• Company Research: Familiarize yourself with Ryan Specialty's business, RT Specialty's role, and the broader insurance landscape to demonstrate your understanding and engagement.

⚠️ 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.