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: 5-10 Years

Remote Status: Hybrid

🚀 Role Summary

• Lead the design of complex, external-facing digital products, including client platforms and quoting systems, with a strong emphasis on user experience (UX) and user interface (UI) design.

• Drive user-centered design processes from concept to pixel-perfect, development-ready deliverables, ensuring alignment with business objectives and technical constraints within an agile framework.

• Collaborate extensively with product management, engineering, marketing, and business stakeholders to translate user needs and business requirements into intuitive and impactful digital experiences.

• Conduct user research and leverage data-driven insights to inform design decisions, validate concepts, and continuously improve existing user journeys and product offerings.

📝 Enhancement Note: While the job title is "Senior UX Designer," the description emphasizes "full-stack" skills, including strong UI capabilities, and mentions leading design efforts for specific product areas. This indicates a hands-on role requiring a blend of strategic UX thinking and detailed UI execution, rather than a purely strategic or management-focused position. The "External Facing" designation highlights the critical importance of customer-centric design in this role.

📈 Primary Responsibilities

• Spearhead the design and execution of user experiences for external-facing platforms, such as quoting systems and client portals, ensuring they are intuitive, efficient, and meet user needs and business goals.

• Develop comprehensive design documentation, including wireframes, storyboards, process flows, sitemaps, high-fidelity prototypes, and polished final designs, to effectively communicate design direction to cross-functional teams.

• Collaborate closely with product managers and engineers to thoroughly understand product requirements, iteratively refine the visual and interactive experience, and ensure designs can be implemented within technical limitations.

• Conduct and/or partner with UX researchers to plan, execute, and interpret user testing insights, translating findings into actionable design improvements.

• Identify, catalog, and systematically address UX pain points and opportunities within the current digital product landscape, driving continuous optimization.

• Actively contribute to the development, optimization, and implementation of a robust design system to ensure consistency and efficiency across all digital touchpoints.

• Present design concepts and rationale to team leadership and external partners, effectively using data, research, and user insights to justify recommendations.

• Juggle multiple projects simultaneously, making informed decisions that balance design quality, project timelines, and available resources in a fast-paced environment.

• Stay abreast of emerging design trends, competitive landscapes within the insurance industry, and evolving UX best practices to bring innovative solutions to the team.

📝 Enhancement Note: The responsibilities highlight a blend of strategic ownership ("Lead design efforts") and tactical execution ("concept; plan; and execute pixel-perfect, development-ready deliverables"). The emphasis on "gathering, cataloging, and addressing UX problems" and "optimizing and implementing a design system" points to a proactive approach to improving the existing digital ecosystem and establishing foundational design practices.

🎓 Skills & Qualifications

Education: Bachelor’s degree in design, technology-related field, or equivalent industry experience.

Experience: 6+ years of experience in UX/Product Design, with a proven track record in the final development and execution process of digital products. Experience designing for complex domains like insurance or e-commerce within an agile development environment is essential.

Required Skills:

• User-Centered Design: A strong user-centered approach to problem-solving, effectively leveraging research, analytics, and empathy combined with robust design intuition.

• UI & Interaction Design: Competence in all aspects of interaction and UX design, from information architecture and workflows to micro-interactions, alongside strong UI design skills.

• Prototyping & Wireframing: Proficiency in rapidly producing high-fidelity prototypes and detailed wireframes to explore concepts and communicate design intent.

• Cross-Functional Collaboration: Excellent communication, presentation, and interpersonal skills, with the ability to tailor communication effectively to diverse audiences including engineers, product owners, marketing, and business partners.

• Agile Methodology: Experience working within agile development frameworks, understanding iterative design and development cycles.

• Complex Domain Experience: Demonstrated experience designing for complex industries such as insurance, e-commerce, or other regulated sectors.

• Time Management & Prioritization: Excellent time management skills, with the ability to operate independently, prioritize tasks, multi-task effectively, and manage shifting deadlines in a fast-paced environment.

• Attention to Detail: Ability to consider the "big picture" while also maintaining a keen eye for granular details in design execution.

Preferred Skills:

• Figma Proficiency: Expertise in Figma for UX/UI design, prototyping, and collaboration.

• Design Systems: Experience in documenting, optimizing, and implementing design systems for consistency and scalability.

• Insurance Industry Experience: Specific knowledge and experience within the insurance industry, understanding its unique user needs and regulatory landscape.

• UX Research: Experience conducting or partnering with UX researchers to plan, interpret, and apply user testing insights.

• Service Design: Understanding of service design principles and their application to create holistic user experiences.

📝 Enhancement Note: The requirement for "6+ years of experience with UX/Product Design, including the final development and execution process" strongly suggests a candidate who can not only conceptualize but also deliver polished, production-ready designs. The portfolio requirement specifically asks for demonstrated impact, collaboration, and learnings, indicating that the company values practical application and measurable outcomes over theoretical exercises. Insurance industry experience is explicitly stated as required, making it a critical filter for candidates.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase a minimum of 6 years of UX/Product Design work, emphasizing the complete design lifecycle from initial concept to final development and execution.

• Highlight specific challenges encountered in complex domains (e.g., insurance, e-commerce) and detail how these were overcome through user-centered design and collaboration.

• Provide clear examples of how designs have impacted user satisfaction and business outcomes, supported by relevant metrics or qualitative feedback.

• Demonstrate experience collaborating with cross-functional teams (engineers, product managers, business stakeholders) and illustrate your role within those teams.

Process Documentation:

• Document your approach to identifying user needs and business requirements, including methodologies for opportunity assessment and JTBD (Jobs-To-Be-Done) analysis.

• Illustrate your workflow for concept generation, rapid prototyping, and iterative design refinement, showing how you balance exploration with timely delivery.

• Detail your methods for presenting design concepts and recommendations to leadership and stakeholders, including how you leverage data and user insights to build consensus.

• Showcase your experience in creating and utilizing design documentation such as wireframes, storyboards, process flows, and sitemaps.

• Provide examples of your involvement in the development, maintenance, or implementation of design systems and style guides.

📝 Enhancement Note: The explicit requirement for portfolios to "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 problem-solving, teamwork, and measurable results. This means candidates should prepare case studies that not only showcase aesthetics but also demonstrate strategic thinking and the ability to drive positive outcomes within a team and for the business.

💵 Compensation & Benefits

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

Benefits:

• Comprehensive Health & Wellness: Mental health services, and other well-being support.

• Paid Time Off: Generous provisions including company holidays, vacation days, sick days, and personal days.

• Family Support: Paid parental leave.

• Financial Well-being: Eligibility for bonuses (for full-time roles).

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

Working Hours: Full-time position, likely aligning with standard business hours in Chicago (e.g., 9:00 AM - 5:00 PM CT), with a hybrid work arrangement.

📝 Enhancement Note: The provided salary range of $104,000 - $130,000 annually for a Senior UX Designer in Chicago, IL, aligns with industry benchmarks for experienced professionals in major metropolitan areas. This range reflects the "Senior" level designation and the requirement for specialized skills in a complex domain like insurance. The benefits package is described as comprehensive, with specific mentions of mental health services, paid parental leave, and bonus eligibility, which are attractive perks for experienced professionals.

🎯 Team & Company Context

🏢 Company Culture

Industry: Specialty Insurance Distribution. Ryan Specialty, through its division RT Specialty, is a prominent wholesale distributor of specialized insurance products and services. This industry context is crucial, as it implies a need for designers to understand complex financial products, regulatory environments, and the specific workflows of insurance brokers and clients.

Company Size: Ryan Specialty is a significant organization, indicated by its presence on WD5 MyWorkdayJobs and the comprehensive benefits package. While exact employee numbers aren't provided in the snippet, the scale suggests a structured environment with established processes but also opportunities for impact.

Founded: The founding date is not explicitly stated, but the company's established position in the insurance industry suggests a history of growth and evolution, likely building upon foundational expertise.

Team Structure:

• The UX Design team is part of the "Digital Solutions group," indicating a focus on technology-driven innovation and product development.

• This role involves close partnership with a "cross-discipline team," including Engineers, Product Owners, Marketing, and Business partners, highlighting a collaborative and integrated approach to product development.

Methodology:

• The team operates within an agile environment, requiring designers to be adaptable and responsive to evolving requirements and feedback.

• Emphasis is placed on user-centered design, driven by user needs, jobs-to-be-done (JTBD), and business objectives.

• Data and research are key components, with designers expected to "leverage available data and research to justify recommendations" and "apply user testing insights."

• A focus on creating "pixel-perfect, development-ready deliverables" underscores a commitment to design quality and seamless handover to engineering.

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

📝 Enhancement Note: The company operates within the specialized insurance sector, which is often characterized by complex regulations, unique terminology, and a need for high levels of trust and accuracy. A Senior UX Designer here must be comfortable navigating these complexities, translating them into user-friendly interfaces, and understanding the distinct needs of both internal users (brokers, underwriters) and external clients. The hybrid model suggests a company that balances in-office collaboration with employee flexibility.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as "Senior UX Designer," indicating a mid-to-senior level of expertise. It requires at least 6 years of experience and the ability to lead design efforts for product areas, collaborate autonomously, and mentor or guide junior designers implicitly through leading by example and design system contributions.

Reporting Structure: The Senior UX Designer will likely report to a Design Lead, UX Manager, or Director within the Digital Solutions group. They will work in close partnership with Product Owners and Engineering Leads within their assigned product teams.

Operations Impact: The UX Designer's impact is critical to the success of external-facing platforms. By improving user experience, they directly influence customer satisfaction, client retention, operational efficiency (e.g., faster quoting, easier policy management), and ultimately, revenue generation and market competitiveness. Their work bridges user needs with business goals, ensuring digital products are not just functional but also desirable and effective.

Growth Opportunities:

• Leadership Development: Opportunity to lead design initiatives for key product areas, influencing product strategy and design direction.

• Skill Specialization: Deepen expertise in complex domains like insurance, design systems, and advanced UX research methodologies.

• Cross-Functional Exposure: Gain broader understanding of product development lifecycle and business operations by working closely with diverse teams.

• Mentorship: Potential to mentor junior designers and contribute to the overall growth of the UX practice within Ryan Specialty.

• Career Advancement: Path to Lead UX Designer, UX Manager, or specialized roles within product or design strategy.

📝 Enhancement Note: The "Senior" title implies a level of autonomy and ownership. Candidates should anticipate being responsible for defining UX strategies for their product areas, not just executing tasks. The growth opportunities are tied to taking on more strategic responsibility, deepening domain expertise, and potentially moving into leadership or specialized design roles, aligning with typical career progression in UX design within established companies.

🌐 Work Environment

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

Office Location(s): The primary office location for this hybrid role is Chicago, Illinois, with a secondary option in Buffalo, NY. This offers geographical flexibility for candidates.

Workspace Context:

• The office environment is likely designed to foster collaboration among cross-functional teams (engineers, product owners, marketing, business partners).

• Access to modern UX/Service Design tools, with Figma being the primary tool mentioned, will be available.

• Opportunities for direct interaction and knowledge sharing with other designers and digital solutions team members, fostering a supportive design community.

• The hybrid model allows for focused individual work at home, balancing personal productivity with team synergy.

Work Schedule: While not explicitly stated, a typical full-time work schedule of approximately 40 hours per week is expected, with the hybrid arrangement allowing for flexibility on remote days.

📝 Enhancement Note: The hybrid model with 3 days in-office is a key aspect of the work environment. Candidates should be prepared for in-person collaboration, team meetings, and design workshops on designated office days, while leveraging remote days for focused individual work, prototyping, and research. The specific office locations (Chicago/Buffalo) provide options for where the in-office days will be spent.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio to assess experience, skills, and alignment with the role requirements.

• Hiring Manager/Team Interview: Discussion focused on your UX/UI design philosophy, experience with complex domains, and approach to user-centered design. Expect to walk through portfolio case studies.

• Design Challenge/Workshop: A practical exercise, potentially involving a design problem related to the insurance industry or a given product area. This may be a take-home assignment or an in-session activity.

• Cross-Functional Stakeholder Interviews: Meetings with Product Owners, Engineers, and potentially Marketing or Business representatives to assess collaboration style, communication skills, and understanding of business needs.

• Final Interview: A concluding discussion, possibly with senior leadership, to evaluate cultural fit, strategic thinking, and overall suitability for the Senior UX Designer role.

Portfolio Review Tips:

• Highlight Impact: Clearly articulate the user and business impact of your design work, using metrics or specific outcomes.

• Showcase Process: Detail your design process, including research, ideation, prototyping, testing, and iteration. Explain why you made certain decisions.

• Demonstrate Collaboration: Provide examples of how you worked with engineers, product managers, and other stakeholders.

• Address Challenges: Be prepared to discuss challenges faced and lessons learned from your projects.

• Focus on External Facing: Tailor your portfolio to showcase experience with client-facing platforms and complex domains like insurance.

• Figma Examples: If possible, include examples of work done in Figma, especially if it relates to design systems or complex interactive prototypes.

Challenge Preparation:

• Research Ryan Specialty and RT Specialty's digital offerings to understand their current user experience and business goals.

• Prepare to articulate your understanding of the insurance industry's user needs and design considerations.

• Practice presenting your portfolio case studies concisely, focusing on the problem, your solution, your role, and the outcome.

• Be ready to discuss how you would approach designing for a specific insurance-related product or workflow.

📝 Enhancement Note: The interview process will likely involve a multi-stage approach, typical for senior roles. The portfolio review is paramount, with a specific emphasis on demonstrating impact, collaboration, and handling complexity within domains like insurance. Candidates should prepare to articulate their design rationale and problem-solving methodologies thoroughly.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: This is explicitly mentioned as the primary UX/Service Design tool used by the team. Proficiency in Figma for wireframing, prototyping, UI design, and potentially design system management is essential.

• General UX/Service Design Tools: While Figma is primary, familiarity with other industry-standard tools for prototyping, wireframing, and user flow mapping may be beneficial.

Analytics & Reporting:

CRM & Automation:

• The role involves designing for "internal workflow tools for policy management" and "external quoting platforms." This implies an understanding of how UX design integrates with CRM systems and potentially business process automation tools to streamline user journeys and operational efficiency. Familiarity with how users interact with such systems is key.

📝 Enhancement Note: Figma is the core tool. Candidates should be ready to demonstrate advanced proficiency. While other tools aren't listed, a Senior UX Designer is expected to be tool-agnostic and capable of learning new technologies. The mention of "internal workflow tools" and "external quoting platforms" suggests the design work will integrate with backend systems and business processes, requiring an awareness of how design impacts operational workflows.

👥 Team Culture & Values

Operations Values:

• User-Centricity: A deep commitment to understanding and serving user needs, ensuring that design decisions prioritize the end-user experience.

• Data-Driven Decision Making: Utilizing research, analytics, and user testing to inform design choices and validate solutions.

• Collaboration & Partnership: Working effectively with cross-functional teams, valuing diverse perspectives, and building strong working relationships.

• Excellence & Quality: Striving for pixel-perfect execution, robust design systems, and outstanding user experiences that reflect positively on the company.

• Adaptability & Agility: Embracing iterative processes, responding to feedback, and navigating shifting priorities in a fast-paced environment.

• Innovation: Bringing fresh ideas and best practices to the team to continuously improve digital products and user journeys.

Collaboration Style:

• Integrated Teams: Designers are embedded within cross-disciplinary teams alongside product managers and engineers, fostering close collaboration throughout the product development lifecycle.

• Open Communication: Encouragement of clear, constructive communication and feedback exchange to ensure alignment and drive continuous improvement.

• Shared Ownership: A culture where design, product, and engineering share responsibility for delivering successful user experiences and business outcomes.

• Design System Advocacy: Promoting consistency and efficiency through the adoption and maintenance of a shared design system.

📝 Enhancement Note: The emphasis on "partnership with a cross-discipline team" and "collaborating closely with Engineers, Product Owners, Marketing, and Business partners" points to a highly collaborative and integrated team environment. Candidates should be prepared to actively contribute to team discussions, share their expertise, and be receptive to feedback from various perspectives.

⚡ Challenges & Growth Opportunities

Challenges:

• Complex Domain Navigation: Understanding and simplifying the intricacies of the insurance industry for both internal users and external clients is a significant challenge. This requires deep dives into policy management, quoting processes, and regulatory compliance.

• Balancing Stakeholder Needs: Juggling the diverse requirements of product management, engineering, marketing, and business stakeholders, while ensuring the user remains at the center of design decisions.

• Technical Constraints: Designing within the limitations of existing technology stacks and development processes, requiring creative problem-solving and negotiation with engineering.

• Design System Implementation & Adoption: Ensuring a design system is effectively implemented, maintained, and consistently adopted across multiple product areas and teams.

• Remote/Hybrid Collaboration Dynamics: Optimizing communication and collaboration effectiveness within a hybrid work model to maintain team cohesion and design quality.

Learning & Development Opportunities:

• Domain Expertise: Develop specialized knowledge in the insurance industry, a valuable niche in the B2B digital product space.

• Design Leadership: Opportunities to lead design for significant product areas, influencing strategic direction and potentially mentoring junior designers.

• Advanced Tooling & Systems: Deepen expertise in Figma, design systems, and potentially explore new UX research or prototyping tools.

• Cross-Functional Acumen: Enhance understanding of product management, agile development, and business operations through close collaboration.

• Industry Best Practices: Continuously learn and apply evolving UX/UI best practices, especially as they relate to financial services and complex B2B platforms.

📝 Enhancement Note: The primary challenge will be translating the complexity of the insurance industry into user-friendly digital experiences. Growth opportunities are abundant for a proactive designer willing to dive deep into the domain, take ownership of design initiatives, and contribute to building mature design practices like comprehensive design systems.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you led the design for a complex external-facing digital product. What was the user problem, your approach, and the business impact?" (Focus on process, collaboration, and outcome)

• "How do you balance user needs with business objectives and technical constraints when designing? Provide an example." (Demonstrate strategic thinking and pragmatism)

• "Walk us through your process for designing and implementing a design system or contributing to an existing one." (Assess understanding of consistency, scalability, and collaboration)

Company & Culture Questions:

• "What interests you about Ryan Specialty and the insurance industry?" (Show genuine curiosity and industry awareness)

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

• "Describe your experience working within agile development teams. How do you collaborate with product managers and engineers?" (Evaluate agile process understanding and cross-functional collaboration)

Portfolio Presentation Strategy:

• Structure: For each case study, clearly define the Problem, Your Role, The Solution, and The Impact (metrics/outcomes).

• Narrative: Tell a compelling story that showcases your problem-solving skills, design thinking, and collaborative efforts.

• Visuals: Use high-quality mockups, prototypes, user flows, and wireframes to illustrate your design process and final outcomes.

• Metrics: Quantify the impact of your work whenever possible (e.g., increased conversion rates, reduced task completion time, improved user satisfaction scores).

• Tailor: Emphasize projects that demonstrate experience with complex domains, external-facing products, and strong UI execution, aligning with the job description.

📝 Enhancement Note: Interview preparation should focus on demonstrating a blend of strategic UX thinking and hands-on UI execution, with a clear understanding of how design drives business outcomes in a complex industry. Be ready to discuss your portfolio in detail, highlighting your problem-solving process, collaborative approach, and the tangible impact of your work.

📌 Application Steps

To apply for this Senior UX Designer position:

• Submit your application through the provided link on workdayjobs.com.

• Portfolio Customization: Ensure your portfolio prominently features projects showcasing your experience with complex domains (especially insurance, if applicable), external-facing platforms, and a strong blend of UX strategy and UI execution. Highlight your process and the measurable impact of your work.

• Resume Optimization: Tailor your resume to highlight keywords from the job description, such as "UX Design," "UI Design," "Information Architecture," "UX Research," "Figma," "Agile," "complex domains," and "insurance industry." Quantify achievements where possible.

• Interview Preparation: Practice articulating your design process, decision-making rationale, and collaborative experiences. Prepare to discuss specific portfolio projects in detail and be ready for potential design challenges.

• Company Research: Familiarize yourself with Ryan Specialty and RT Specialty, their mission, values, and digital presence. Understand the general landscape of the specialty insurance industry to demonstrate informed interest and potential.

⚠️ 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.