Director, Web UX & Design

📍 Job Overview

Job Title: Director, Web UX & Design

Company: Topstep

Location: United States

Job Type: Full-Time

Category: UX/UI Design & Web Strategy

Date Posted: 2025-10-17

Experience Level: 10+ Years

Remote Status: Hybrid

🚀 Role Summary

• Lead the strategic vision and execution for all Topstep-owned web experiences, including Topstep.com, TopstepBrokerage.com, and ProjectX.com, driving engagement and conversion through optimized user journeys.

• Manage and empower a team of UI/UX and web designers to deliver cohesive, high-performing digital experiences aligned with brand architecture and business objectives.

• Oversee the end-to-end UX process, from research and wireframing to prototyping and usability testing, ensuring seamless integration from web touchpoints to product engagement.

• Champion the development and maintenance of scalable web design systems and component libraries, ensuring consistency, efficiency, and adherence to brand guidelines across all digital properties.

• Integrate privacy-by-design and security-by-design principles into all UX and design workflows, ensuring compliance with cybersecurity standards and data protection regulations.

📝 Enhancement Note: This role is positioned as a leadership opportunity at a company operating in a regulated industry (implied by "NFA" and "fintech or regulated industries preferred"), requiring a strong emphasis on compliance, security, and seamless integration across multiple branded web properties. The "Hybrid" work arrangement suggests a need for strong remote collaboration skills alongside in-office presence.

📈 Primary Responsibilities

• Define and execute the overarching UX and design strategy for Topstep's entire web ecosystem, ensuring alignment with brand identity, performance goals, and user needs.

• Lead, mentor, and develop a team of UI/UX and web designers, fostering a collaborative environment that encourages innovation and consistent delivery of exceptional digital experiences.

• Drive comprehensive UX research initiatives, including user interviews, surveys, and competitive analysis, to translate insights into actionable wireframes, prototypes, and usability testing protocols.

• Develop, implement, and maintain robust, scalable web design systems and component libraries that ensure brand consistency, design efficiency, and cross-platform compatibility.

• Proactively embed privacy-by-design and security-by-design principles throughout the UX and design lifecycle, collaborating with IT Security and Product teams to mitigate risks and ensure compliance.

• Establish, monitor, and report on key UX success metrics (e.g., conversion rates, time-on-site, user satisfaction, task completion rates) to measure impact and inform iterative improvements.

• Champion and enforce accessibility standards (e.g., WCAG), mobile optimization, and performance best practices across all digital assets to enhance user experience and reach.

• Own the UX process for critical web initiatives, including major site redesigns, new product page development, sub-brand site launches, and targeted marketing landing pages.

• Manage relationships and deliverables with external agency partners, ensuring projects are completed on time, within budget, and to the highest strategic and creative standards.

• Continuously research and integrate emerging digital trends, technologies, and evolving user behaviors to drive ongoing innovation and improvement in the Topstep web experience.

• Ensure all digital experiences strictly adhere to legal, NFA (National Futures Association), and internal brand standards, working closely with compliance and legal teams.

• Partner with the Sr. Creative Director and Brand leadership to translate overarching brand identity and campaign strategies into cohesive, visually compelling, and high-performing digital experiences.

• Collaborate closely with Engineering, Product, Product Design, and Marketing teams to ensure pixel-perfect implementation of designs, seamless functionality, and efficient development workflows.

• Liaise with Product, Engineering, and IT Security teams to guarantee all web properties meet stringent cybersecurity best practices, data protection standards, and secure design protocols.

• Work hand-in-hand with Growth and Analytics teams to implement A/B testing, analyze data-driven insights, and facilitate continuous iteration and optimization of web performance.

📝 Enhancement Note: The responsibilities clearly indicate a strategic leadership role with significant cross-functional collaboration, emphasizing the need for strong communication, project management, and an understanding of both creative execution and technical implementation within a regulated environment.

🎓 Skills & Qualifications

Education: While not explicitly stated, a Bachelor's or Master's degree in Design, Human-Computer Interaction, Computer Science, or a related field is typically expected for a Director-level role. Relevant certifications in UX or design thinking can also be advantageous.

Experience: 12+ years of progressive experience in web design, UX/UI, or digital experience leadership roles, with a demonstrable track record of leading teams and driving impactful digital initiatives.

Required Skills:

• Proven success in leading and managing UI/UX and web design teams within brand-driven, performance-focused organizations, ideally in fintech or other regulated industries.

• A comprehensive portfolio showcasing exceptional UX thinking, creative visual and interaction design skills, and successful execution of digital brand storytelling.

• Deep understanding and practical application of UX methodologies, including user research, journey mapping, wireframing, prototyping, and usability testing.

• Proficiency in building and maintaining scalable design systems and component libraries that ensure brand consistency and design efficiency.

• Strong knowledge of digital accessibility requirements (e.g., WCAG 2.1 AA) and responsive design best practices for a seamless multi-device experience.

• Familiarity with cybersecurity principles, web security protocols, privacy regulations (e.g., GDPR, CCPA), and compliance requirements relevant to digital experiences.

• Demonstrated experience collaborating effectively with Product, Engineering, and IT Security teams to ensure secure, compliant, and scalable web infrastructure.

• Expertise in core design and prototyping tools, including Figma, Adobe Creative Suite (Photoshop, Illustrator, XD), and web analytics/user behavior tools (e.g., Hotjar, Google Analytics).

• Familiarity with Content Management Systems (CMS) such as Webflow, WordPress, or headless CMS solutions, and experience collaborating with developers for implementation.

• Excellent communication, presentation, and interpersonal skills, with the ability to articulate complex design concepts and strategies to diverse stakeholders.

• Proven ability to thrive in fast-paced, cross-functional environments, working effectively with creative, growth marketing, product, and engineering teams.

Preferred Skills:

• Experience with project management tools (e.g., Jira, Asana) for tracking design workflows and team progress.

• Knowledge of SEO best practices and how design impacts search engine visibility.

• Experience managing external agency partners and ensuring quality deliverables.

• Familiarity with A/B testing methodologies and data analysis for design optimization.

📝 Enhancement Note: The emphasis on "fintech or regulated industries" and "cybersecurity principles" alongside "compliance requirements" indicates a need for candidates who understand the unique challenges and stringent standards of these sectors, beyond standard UX/UI expertise.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A strong, curated portfolio is paramount, demonstrating a clear progression of thought from problem definition to solution execution for web-based user experiences.

• Showcase case studies that highlight strategic UX thinking, creative visual and interaction design principles, and successful digital brand storytelling.

• Include examples of how user research, wireframes, prototypes, and usability testing informed design decisions and led to measurable improvements in user engagement or conversion.

• Provide evidence of experience in building or contributing to design systems and component libraries, demonstrating an understanding of scalability and consistency.

Process Documentation:

• Demonstrate proficiency in documenting UX processes, including user journey maps, information architecture diagrams, and user flow charts.

• Showcase examples of wireframing, prototyping, and usability testing documentation that clearly articulate design iterations and rationale.

• Present documentation of design system components, style guides, and brand guidelines, illustrating adherence to established standards.

• Include examples of how data and analytics were used to inform design decisions and measure the impact of implemented solutions.

📝 Enhancement Note: For a Director-level role, the portfolio is expected to go beyond individual design work and showcase strategic leadership, team management, process ownership, and the ability to drive significant business impact through UX and design initiatives.

💵 Compensation & Benefits

Salary Range: $170,000 - $230,000 per year.

Benefits:

• Comprehensive health, dental, and vision insurance for full-time employees.

• Competitive 401(k) matching program.

• Generous paid time off (accrued monthly), with an encouragement bonus for taking 5 consecutive vacation days.

• 9 Company-paid holidays.

• Robust Family Leave policy.

• Employee referral bonuses.

• Food and groceries budget.

• Contributions towards health and wellness initiatives.

Working Hours: While not explicitly stated, the role is assumed to be a standard 40-hour work week, with flexibility often expected for leadership positions to meet project deadlines and team needs. The hybrid arrangement implies a structured schedule with days spent in the office and days remote.

📝 Enhancement Note: The provided salary range is a base salary. The "Bonus: This position is eligible for a performance-based bonus" indicates additional variable compensation potential. The statement about compensation considering "geographic region, job-related knowledge, skills, and experience" suggests that the final offer will be tailored to the individual candidate and their location within the United States.

🎯 Team & Company Context

🏢 Company Culture

Industry: Financial Technology (Fintech), specifically focused on trading and brokerage services. This industry is characterized by rapid innovation, a strong emphasis on security and compliance, and a focus on customer acquisition and retention through digital channels.

Company Size: While not explicitly stated by number, Topstep operates multiple distinct web properties (Topstep.com, TopstepBrokerage.com, ProjectX.com, and sub-brands), suggesting a medium to large-sized organization with a significant digital footprint and established operational processes.

Founded: The founding date is not provided, but the existence of multiple branded web properties and a clear organizational structure implies a company with a significant history and established market presence.

Team Structure:

• The Director, Web UX & Design will likely lead a team of UI/UX designers and web designers, potentially including specialists in areas like interaction design, visual design, and front-end development liaison.

• This role reports into a higher level of Creative or Product leadership (e.g., Sr. Creative Director, VP of Product), and collaborates extensively with cross-functional teams including Growth Marketing, Product Management, Engineering, IT Security, and Legal/Compliance.

Methodology:

• Data analysis and user behavior insights will be crucial for informing design decisions and optimizing web performance, driven by collaboration with Growth and Analytics teams.

• Workflow planning and optimization will be central to the role, particularly in managing multiple web projects and ensuring efficient design system implementation.

• Automation and efficiency practices are implied through the use of design systems and the need to work closely with engineering for seamless implementation.

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

📝 Enhancement Note: The company's focus on trading and brokerage, coupled with the mention of "NFA" and "regulated industries," highlights the critical importance of security, compliance, and a user-centric approach that builds trust and facilitates complex financial transactions.

📈 Career & Growth Analysis

Operations Career Level: Director, Web UX & Design is a senior leadership role, commanding significant autonomy and strategic influence over a critical customer-facing function. It signifies a move into management and strategic oversight, moving beyond individual contributor or team lead roles.

Reporting Structure: This role reports to a senior executive, likely within the Marketing, Product, or Creative departments. The Director will manage a team of designers and collaborate horizontally with other department heads (e.g., Product, Engineering, Marketing).

Operations Impact: The Director of Web UX & Design has a direct and measurable impact on Topstep's revenue and business success. By optimizing the digital front door, this role influences customer acquisition, conversion rates, user retention, and overall brand perception. The effectiveness of the web experience directly correlates with the ability to attract and onboard new clients, a key driver for a trading platform.

Growth Opportunities:

• Leadership Advancement: Potential to grow into VP-level roles overseeing broader digital experience, product design, or marketing technology functions.

• Strategic Impact: Opportunity to shape the digital strategy for a growing fintech company, influencing product direction and market positioning.

• Skill Specialization: Deepen expertise in UX strategy, design systems, and digital transformation within a specialized, high-growth industry.

• Mentorship: Develop leadership skills by mentoring and growing a team of talented designers.

📝 Enhancement Note: For a Director-level role, the emphasis is on strategic leadership, team development, and influencing business outcomes, rather than purely tactical design execution. This role offers a clear path for career progression within a dynamic industry.

🌐 Work Environment

Office Type: The company offers a hybrid work environment, indicating a blend of remote work and in-office collaboration. This suggests a modern office setup designed to support both focused individual work and team collaboration.

Office Location(s): While the specific office locations are not detailed, the timezone derivation of "America/Chicago" suggests a primary presence or significant operations in the Central United States, likely Chicago given Topstep's Chicago headquarters. Employees are expected to be located within the United States.

Workspace Context:

• The environment fosters collaboration with "cameras on during meetings" and a "robust Slack environment," indicating a culture that values connection and communication, even in a hybrid setting.

• Access to industry-standard design and collaboration tools (Figma, Adobe Creative Suite, etc.) is expected.

• Opportunities for interaction with diverse teams (Creative, Growth Marketing, Product, Engineering, IT Security) are abundant, facilitating a holistic understanding of the business.

Work Schedule: A standard 40-hour work week is implied, with flexibility often inherent in leadership roles to ensure project success and team support. The hybrid model requires careful time management to balance remote productivity with in-office collaboration needs.

📝 Enhancement Note: The hybrid model and emphasis on remote communication tools suggest a company that has adapted to flexible work arrangements while still valuing in-person interaction for strategic and team-building purposes.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter or hiring manager will review your resume and portfolio to assess alignment with the role's requirements.

• Portfolio Review & Presentation: Expect a dedicated session to walk through your portfolio. Be prepared to discuss your design process, strategic thinking, problem-solving approach, and the impact of your work. Focus on 2-3 key projects that best represent your leadership and UX expertise.

• Team Interviews: You will likely meet with potential peers, direct reports, and cross-functional stakeholders (e.g., Product Managers, Engineering Leads, Marketing Managers) to assess collaboration style, technical understanding, and cultural fit.

• Leadership Interview: A final interview with senior leadership (e.g., VP of Product, Creative Director) to discuss strategic vision, leadership philosophy, and alignment with company goals.

Portfolio Review Tips:

• Curate Strategically: Select projects that best showcase your leadership, UX strategy, design system implementation, and impact in regulated or performance-driven environments.

• Tell a Story: For each project, clearly articulate the problem, your role, the process you followed, the challenges encountered, your solutions, and the measurable results or business impact.

• Highlight Process: Emphasize your UX methodology, research insights, iterative design process, and how you collaborated with stakeholders.

• Showcase Leadership: Include examples of how you mentored designers, managed projects, influenced strategy, or contributed to team growth.

• Quantify Impact: Whenever possible, use data and metrics to demonstrate the success of your designs (e.g., increased conversion rates, improved user satisfaction scores, reduced support inquiries).

Challenge Preparation:

• Be prepared for a potential design challenge or case study. This could involve evaluating an existing web property, proposing improvements for a specific user flow, or outlining a strategy for a new feature.

• Focus on demonstrating your strategic thinking, problem-solving skills, and ability to articulate your design rationale clearly and concisely.

• Practice presenting your ideas under pressure, simulating a real-time design review or strategy session.

📝 Enhancement Note: Given the Director level, interviewers will be looking for strategic thinking, leadership capabilities, and a clear understanding of how UX and design contribute to business objectives, not just aesthetic execution.

🛠 Tools & Technology Stack

Primary Tools:

• UX/UI Design: Figma (primary), Adobe Creative Suite (Photoshop, Illustrator, XD).

• Prototyping & User Testing: InVision, Maze, Hotjar (for heatmaps and session recordings).

• Design Systems: Experience in building, maintaining, or utilizing established design systems.

• Collaboration: Slack, Zoom, Google Workspace/Microsoft 365.

Analytics & Reporting:

• Web Analytics: Google Analytics, Adobe Analytics (or similar).

• User Behavior Analysis: Hotjar, FullStory (or similar for session recording and heatmaps).

• Performance Monitoring: Tools for tracking site speed and core web vitals.

CRM & Automation:

• Familiarity with how web experiences integrate with CRM systems (e.g., Salesforce) and marketing automation platforms, though direct management may not be required.

• Understanding of CMS platforms like Webflow, WordPress, or headless CMS solutions is crucial for implementation collaboration.

📝 Enhancement Note: Proficiency in Figma and Adobe Creative Suite is explicitly stated. The mention of Hotjar and prototyping tools indicates a need for hands-on experience in user research and validation. Familiarity with CMS platforms is important for effective collaboration with development teams.

👥 Team Culture & Values

Operations Values:

• User-Centricity: A deep commitment to understanding and serving user needs, ensuring that every design decision prioritizes the user experience.

• Data-Driven Decision Making: Utilizing analytics, user research, and A/B testing to inform design strategy and measure impact.

• Collaboration & Teamwork: Fostering a supportive and communicative environment where cross-functional teams work together seamlessly to achieve common goals.

• Innovation & Continuous Improvement: Encouraging new ideas, embracing emerging technologies, and constantly seeking ways to enhance digital experiences.

• Integrity & Compliance: Upholding the highest standards of security, privacy, and regulatory compliance in all digital interactions, especially critical in the fintech sector.

Collaboration Style:

• Cross-functional Integration: Actively partnering with Product, Engineering, Marketing, and IT Security to ensure cohesive and aligned digital strategies.

• Open Communication: Encouraging transparent feedback, constructive critique, and open dialogue to drive better outcomes.

• Shared Ownership: Promoting a sense of collective responsibility for the success of web properties and user experiences.

• Agile Methodologies: Likely working within agile frameworks to facilitate iterative development and rapid response to market changes.

📝 Enhancement Note: The company's values likely mirror those of a modern, growth-oriented fintech firm, emphasizing user experience, data integrity, and cross-functional collaboration, with a strong undercurrent of regulatory adherence.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Multiple Brands: Effectively managing and differentiating user experiences and design systems across distinct web properties (Topstep.com, TopstepBrokerage.com, ProjectX.com, sub-brands).

• Regulatory Compliance & Security: Navigating stringent compliance requirements (NFA, cybersecurity) while delivering an intuitive and engaging user experience.

• Technical Constraints & Implementation: Collaborating with engineering teams to ensure pixel-perfect execution of designs within technical limitations and platform capabilities.

• Measuring ROI: Clearly demonstrating the business impact and ROI of UX and design initiatives to senior leadership.

• Evolving Digital Landscape: Staying ahead of rapid changes in user behavior, technology, and design trends while maintaining brand consistency and performance.

Learning & Development Opportunities:

• Industry Conferences & Training: Opportunities to attend leading UX, design, and fintech industry events.

• Skill Specialization: Deepening expertise in areas like design systems, accessibility, or user research methodologies.

• Leadership Development: Access to leadership training programs and mentorship to enhance management and strategic skills.

• Cross-Functional Exposure: Gaining a broader understanding of product development, marketing strategies, and business operations within a fintech environment.

📝 Enhancement Note: The challenges presented are typical for a senior design leadership role in a complex, regulated industry. Overcoming these challenges provides significant opportunities for professional growth and impact.

💡 Interview Preparation

Strategy Questions:

• "How would you approach developing a unified design system for multiple distinct web properties like Topstep.com, TopstepBrokerage.com, and ProjectX.com, ensuring both brand consistency and unique user experiences?"

• "Describe a time you had to balance stringent regulatory or security requirements with user experience goals. What was your strategy, and what was the outcome?"

• "How do you measure the success of UX and design initiatives, and how would you demonstrate the ROI of your team's work to senior leadership?"

Company & Culture Questions:

• "What interests you specifically about Topstep and the fintech industry?"

• "How do you foster a collaborative and innovative culture within a design team, especially in a hybrid work environment?"

• "How have you previously partnered with Product, Engineering, and Marketing teams to achieve common goals?"

Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly articulate the problem statement, your specific role and contributions, the design process followed, key challenges, innovative solutions, and quantifiable results.

• Focus on Impact: Emphasize how your design decisions directly contributed to business objectives like conversion rates, user engagement, or satisfaction.

• Showcase Leadership: Highlight instances where you led a team, mentored designers, managed stakeholders, or influenced strategic direction.

• Be Ready for Deep Dives: Anticipate detailed questions about your design choices, the rationale behind them, and how you handled trade-offs.

• Prepare for a Whiteboard/Digital Board Session: Be ready to sketch out ideas, map user flows, or discuss strategic approaches collaboratively.

📝 Enhancement Note: Interviewers will be assessing your strategic thinking, problem-solving abilities, leadership potential, and your understanding of how design contributes to business growth in a regulated environment.

📌 Application Steps

To apply for this Director, Web UX & Design position:

• Submit your resume and a link to your comprehensive online portfolio through the Topstep careers portal.

• Portfolio Customization: Tailor your portfolio to highlight projects demonstrating leadership in UX strategy, design systems, and experience in performance-driven or regulated industries. Showcase your ability to manage multiple web properties.

• Resume Optimization: Ensure your resume clearly articulates your 12+ years of experience, leadership achievements, specific UX methodologies used, and proficiency with key tools like Figma and Adobe Creative Suite. Quantify your impact with metrics.

• Interview Preparation: Practice articulating your design process, leadership philosophy, and strategic vision. Prepare to discuss specific case studies from your portfolio in detail, focusing on problem-solving and business impact.

• Company Research: Thoroughly research Topstep, its mission, its various web properties, and the fintech industry. Understand their competitive landscape and identify potential UX/design opportunities and challenges.

⚠️ 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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