Head of Design

📍 Job Overview

Job Title: Head of Design

Company: Luminary

Location: New York, New York, United States

Job Type: FULL_TIME

Category: Design Leadership / Product Design

Date Posted: 2026-08-06

Experience Level: 10+ Years

Remote Status: Hybrid

🚀 Role Summary

• Lead and evolve Luminary's design organization, setting the vision and quality bar for product and brand design.

• Manage and grow a team of Principal Designers, fostering a user-centric design culture.

• Partner closely with Product and Engineering leadership to shape product strategy, roadmap priorities, and execution.

• Drive end-to-end design for strategic initiatives, from research and product definition through high-fidelity design and launch.

• Establish scalable design processes, critiques, and feedback loops to enhance team velocity and design quality.

📝 Enhancement Note: While the job title is "Head of Design," the description emphasizes a strong focus on product design leadership, with brand design being a secondary focus. The role requires a hands-on approach, meaning the candidate will not only manage but also actively contribute to design execution. The "AI-native system of action for wealth transfer services" context suggests a need for sophisticated, data-driven design solutions within the financial technology sector.

📈 Primary Responsibilities

• Lead Luminary’s design function, encompassing both product and brand design, with a strategic emphasis on product design excellence.

• Oversee the management of current Principal Designers and develop a strategic plan for growing the design team to meet company expansion needs.

• Define and champion the overall design vision and quality standards across the organization, ensuring a consistent, intuitive, and polished user experience.

• Collaborate strategically with Head of Product and Head of Engineering to influence product strategy, prioritize roadmap initiatives, and guide successful execution.

• Cultivate a deep, empathetic understanding of Luminary's customer base, their intricate workflows, and the specific challenges within wealth management to inform and direct UX efforts.

• Spearhead the complete design lifecycle for the company's most critical initiatives, from initial user research and product concept definition to the creation of high-fidelity designs and successful product launches.

• Implement and refine scalable design processes, including robust critique sessions and effective feedback mechanisms, to empower the design team to operate with both speed and exceptional quality.

• Continuously enhance Luminary's design system, aiming to improve consistency, accelerate design velocity, and elevate usability across all product offerings.

• Actively promote and embed a culture of deep customer empathy, iterative experimentation, and continuous improvement within the design team and across the broader organization.

📝 Enhancement Note: The responsibilities highlight a blend of strategic leadership and hands-on execution. The emphasis on "strategic initiatives" and "end-to-end design" indicates a need for a candidate who can manage complex projects from conception to delivery. The requirement to "partner closely with Product and Engineering leadership" underscores the importance of strong cross-functional collaboration skills.

🎓 Skills & Qualifications

Education: While specific educational requirements are not detailed, a strong foundation in design principles, user experience, and visual communication is implied, likely acquired through a Bachelor's or Master's degree in Design, HCI, or a related field, or through equivalent professional experience.

Experience: 12+ years of progressive experience in product design, with a significant portion dedicated to leading and managing high-performing product design teams. Proven experience in building and scaling design functions within fast-paced environments, particularly in complex B2B SaaS product development.

Required Skills:

• Product Thinking & Strategy: Demonstrated ability to translate complex business requirements and user needs into elegant, effective product solutions. Experience in shaping product strategy and roadmaps.

• Team Leadership & Management: Proven track record of building, mentoring, and developing design teams, fostering a collaborative and high-performance culture.

• User Experience (UX) Design: Deep expertise in user-centered design methodologies, information architecture, interaction design, and user research.

• Visual Design & UI: Exceptional visual design skills with a keen eye for aesthetics, layout, typography, and brand consistency across digital interfaces.

• Design Systems: Experience in creating, maintaining, and scaling robust design systems to ensure consistency, efficiency, and quality across products.

• B2B SaaS Product Design: Hands-on experience designing complex enterprise software, ideally within financial technology or similar regulated industries.

• Cross-functional Collaboration: Proven ability to partner effectively with Product Management, Engineering, and other stakeholders to drive product vision and execution.

• Communication & Influence: Excellent verbal and written communication skills, with the ability to articulate design decisions, influence stakeholders, and advocate for user needs.

• Process Development: Experience establishing and optimizing scalable design processes, including critiques, feedback loops, and workflow efficiencies.

Preferred Skills:

• Brand Design: Experience in developing and evolving brand identity and its application across digital and physical touchpoints.

• Financial Technology (Fintech) or Enterprise Software: Specific domain expertise in designing for wealth management, private banking, or complex enterprise workflows.

• Web and Mobile Platform Design: Experience designing for both web and mobile applications, understanding platform-specific design patterns and constraints.

• Familiarity with HTML/CSS: Basic understanding of front-end technologies to facilitate better collaboration with engineering teams.

• User Research & Usability Testing: Advanced skills in conducting user research, usability testing, and synthesizing findings to inform design decisions.

📝 Enhancement Note: The "12+ years of product design experience" combined with "leading and managing high-performing product design teams" strongly suggests this is a senior leadership role, likely reporting to C-suite or VP-level executives. The emphasis on B2B SaaS and financial technology experience is critical for candidates to highlight.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Product Thinking & Problem Solving: Showcase a minimum of 3-5 comprehensive case studies demonstrating your approach to solving complex user problems within B2B SaaS environments. Clearly articulate the problem, your process, key decisions, and the impact of your solutions.

• End-to-End Design Process: Illustrate your involvement across the entire design lifecycle, from initial user research, ideation, and wireframing to high-fidelity UI design, prototyping, and collaboration with engineering for implementation.

• Interaction & Visual Design Excellence: Provide examples of sophisticated interaction design patterns and pixel-perfect visual design that highlight attention to detail, usability, and aesthetic appeal.

• Design System Contribution: Include examples of how you have contributed to, or utilized, design systems, demonstrating an understanding of scalability, consistency, and efficiency.

• Impact & Metrics: Quantify the impact of your design work whenever possible. This could include improvements in user engagement, conversion rates, task completion times, or customer satisfaction scores.

Process Documentation:

• Workflow Design & Optimization: Be prepared to discuss how you have mapped, analyzed, and optimized complex user workflows, particularly in enterprise or financial software contexts.

• Design Process Implementation: Detail your experience in establishing and refining design processes, including critique frameworks, feedback mechanisms, and collaboration protocols with product and engineering.

• Measurement & Analysis: Demonstrate how you have used data and user feedback to measure the success of design initiatives and iterate on solutions.

📝 Enhancement Note: For a "Head of Design" role, the portfolio should not only showcase individual design craft but also strategic thinking, leadership capabilities, and the ability to build and scale design operations. Case studies should highlight leadership and process improvement contributions.

💵 Compensation & Benefits

Salary Range: Given the seniority of the role (Head of Design, 12+ years experience) and the location (New York City), a competitive salary range is expected. Based on industry benchmarks for Head of Design roles in major tech hubs like NYC, for a company in the FinTech/SaaS space, the estimated range is $200,000 - $300,000+ annually, with potential for equity.

Benefits:

• Comprehensive Health Coverage: 100% employee health insurance coverage, with 50% dependent coverage, indicating a strong commitment to employee well-being.

• Wellness Stipend: A monthly stipend dedicated to employee wellness, supporting physical and mental health initiatives.

• Generous Paid Time Off (PTO): 20 days of PTO per year, in addition to public holidays, offering ample opportunity for rest and rejuvenation.

• Prime Office Location: Access to a well-situated office space in NYC near Bryant Park, facilitating collaboration and providing a central hub for hybrid work.

• Retirement Savings Plan: A 401(k) plan to support long-term financial planning and retirement savings.

• Supportive Parental Leave: A comprehensive parental leave policy to support employees during significant life events.

Working Hours: The role is listed as FULL_TIME, implying a standard 40-hour work week. However, given the leadership nature and hybrid work arrangement, flexibility is likely expected, with a focus on outcomes rather than strict adherence to hours, particularly for a hybrid model.

📝 Enhancement Note: The salary estimate is based on data from industry salary aggregators (e.g., Levels.fyi, Glassdoor) for Head of Design roles in New York City at companies of comparable size and industry, factoring in the extensive experience required. Equity is a common component for leadership roles in growth-stage tech companies.

🎯 Team & Company Context

🏢 Company Culture

Industry: Luminary operates in the Financial Technology (FinTech) sector, specifically focusing on AI-native systems for wealth transfer services. This places them at the intersection of advanced AI technology and the highly regulated, complex world of wealth management, estate planning, and private client services. The market they serve ($90 trillion in assets) is a high-net-worth segment, indicating a need for sophisticated, secure, and high-trust solutions.

Company Size: Luminary is a growth-stage technology company. While an exact number isn't provided, the description mentions backing from significant investors and serving over 1,000 customers, including major players in private client services. This suggests a company that has moved beyond the startup phase, likely employing between 50-200 individuals, with ambitions to scale rapidly. This size implies a dynamic, fast-paced environment where design can have a significant impact on product direction and company culture.

Founded: Founded and led by CEO David Barnard, former Head of Wealth Management at AllianceBernstein, Luminary benefits from experienced leadership with deep industry knowledge. This background suggests a company culture that values expertise, strategic vision, and a strong understanding of the financial services landscape.

Team Structure:

• Design Team: Currently comprises two Principal Designers. The Head of Design will be responsible for managing these individuals and building out the team.

• Product & Engineering: Close partnership is expected with Head of Product and Head of Engineering, indicating a collaborative, integrated product development approach.

• Cross-functional Collaboration: Luminary serves a broad ecosystem of wealth managers, trust companies, and tax advisors, implying that design will need to facilitate collaboration between these external stakeholders and Luminary's internal teams.

Methodology:

• AI-Native Approach: Luminary leverages AI to transform complex documents into structured data, powering agent-driven workflows. This suggests a data-centric and technologically advanced approach to problem-solving.

• Customer-Centricity: The company emphasizes a deep understanding of customers and their workflows, indicating a strong commitment to user-centered design and iterative product development based on customer feedback.

• Systems Thinking: The description mentions "structured, proprietary data asset" and "core infrastructure," pointing to a company that values robust, scalable systems and holistic solutions.

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

📝 Enhancement Note: The company's mission to serve high-net-worth individuals and their advisors means design solutions must exude trust, sophistication, and precision. The "AI-native" aspect suggests opportunities for innovative, data-driven user experiences.

📈 Career & Growth Analysis

Operations Career Level: This role is at the highest level of the design function, designated as "Head of Design." It represents a significant leadership opportunity, moving beyond individual contribution to strategic oversight, team building, and influencing company-wide product direction. This is a critical role for someone looking to shape a design organization from a foundational stage within a rapidly growing, innovative company.

Reporting Structure: The Head of Design will likely report directly to a C-level executive, such as the Chief Product Officer (CPO), Chief Technology Officer (CTO), or even the CEO, given the strategic importance of design at Luminary. This ensures high visibility and direct influence on company strategy.

Operations Impact: The Head of Design will have a profound impact on Luminary's success by ensuring that the product experience is intuitive, elegant, and effectively addresses the complex needs of wealth advisors and high-net-worth individuals. Exceptional design is positioned as a competitive advantage, directly influencing customer adoption, retention, and the company's ability to scale its services. This role is pivotal in translating complex financial services into user-friendly, efficient, and trusted digital experiences.

Growth Opportunities:

• Team Building & Scaling: A primary growth opportunity involves building and scaling the design team from its current two Principal Designers to a robust, high-performing organization. This includes defining hiring profiles, recruiting top talent, and establishing a strong design culture.

• Strategic Product Influence: The role offers a chance to significantly influence Luminary's product strategy and roadmap, working directly with C-suite leadership to define the future of their AI-native system of action for wealth transfer.

• Domain Expertise Development: Deepen expertise in FinTech, wealth management, and AI-driven workflows, becoming a thought leader in designing for complex financial services.

• Leadership Development: Hone leadership skills in managing design functions, cross-functional collaboration, and driving organizational change within a fast-paced, high-growth environment.

• Equity Participation: As a key leadership hire, there is a strong likelihood of significant equity participation, offering substantial financial upside as the company grows.

📝 Enhancement Note: The emphasis on "building the design team as we grow" and partnering with C-suite leadership highlights the strategic and developmental aspects of this role, appealing to experienced design leaders looking to make a significant mark.

🌐 Work Environment

Office Type: Luminary offers a Hybrid work environment, with a physical office located in New York City near Bryant Park. This setup balances the benefits of in-person collaboration, team building, and dedicated workspace with the flexibility and autonomy of remote work.

Office Location(s): The primary office is situated in New York City near Bryant Park. This location is a prime business district, offering excellent accessibility via public transportation and proximity to amenities, making it a convenient and desirable location for employees.

Workspace Context:

• Collaborative Hub: The NYC office likely serves as a central point for team meetings, brainstorming sessions, design critiques, and fostering a strong sense of team cohesion.

• Modern Technology: As a technology company, expect a modern workspace equipped with the necessary tools and technology to support design and development efforts, including high-speed internet, collaboration software, and potentially advanced display and prototyping tools.

• Cross-functional Interaction: The hybrid model and close collaboration with Product and Engineering mean designers will have ample opportunities to interact with colleagues from various departments, fostering a dynamic and integrated work environment.

Work Schedule: The standard work schedule is likely aligned with a full-time, 40-hour week, but the hybrid arrangement offers flexibility. Core working hours may be established to ensure team availability for meetings and collaborative sessions, with the remaining time adaptable to individual work preferences and productivity peaks, especially for focused design work.

📝 Enhancement Note: The hybrid model is typical for tech companies aiming to balance flexibility with the need for in-person collaboration. The NYC office location near Bryant Park is a significant perk, offering convenience and access to a vibrant business environment.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A brief call with a recruiter or HR representative to assess basic qualifications and cultural fit.

• Hiring Manager Interview: Discussion with the CEO (David Barnard) or another C-level executive, focusing on strategic vision, leadership philosophy, and alignment with Luminary's mission.

• Design Team & Cross-functional Interviews: Meetings with the Principal Designers and leaders from Product and Engineering. These sessions will delve into design process, collaboration style, and problem-solving approaches.

• Portfolio Presentation: A dedicated session where the candidate presents their portfolio, showcasing key case studies, design leadership, and strategic thinking. This is a critical component to evaluate product thinking, execution, and impact.

• Executive/Final Interview: A final conversation, potentially with the CEO, to confirm overall fit, address any remaining questions, and discuss compensation and offer details.

Portfolio Review Tips:

• Curate Strategically: Select 3-5 of your strongest case studies that best represent your leadership, product strategy, and complex B2B SaaS design experience. Prioritize projects that align with Luminary's domain (FinTech, wealth management, AI).

• Structure for Impact: For each case study, clearly articulate the business problem, your specific role and responsibilities, the design process followed, key decisions made (and why), challenges encountered, and the measurable outcomes achieved. Use visuals (wireframes, mockups, prototypes) to illustrate your work.

• Highlight Leadership & Process: Emphasize your experience in leading teams, mentoring designers, establishing design processes, and collaborating effectively with product and engineering. Showcase how you've scaled design functions or improved design operations.

• Quantify Results: Wherever possible, use data and metrics to demonstrate the impact of your design solutions. This could include improvements in user engagement, conversion rates, efficiency, or customer satisfaction.

• Tell a Story: Present your work as a narrative. Connect your design decisions to business goals and user needs, demonstrating your strategic thinking and ability to drive value. Be prepared to discuss your thought process and defend your design choices.

Challenge Preparation:

• Design Strategy Exercise: You might be asked to outline a strategy for approaching a specific design challenge Luminary faces, or to critique an existing product feature and propose improvements. Focus on your process, user empathy, and business alignment.

• Team Collaboration Scenarios: Be ready to discuss how you would handle common team dynamics, such as disagreements on design direction, managing underperforming team members, or integrating new designers into the team.

• Stakeholder Management: Prepare to discuss how you communicate design decisions to non-design stakeholders, manage expectations, and build consensus across departments.

📝 Enhancement Note: The portfolio presentation is a crucial part of the process. Candidates should be prepared to discuss not just their individual contributions but also their strategic thinking, leadership approach, and ability to drive design impact at an organizational level.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly probable as industry standard), Sketch, Adobe Creative Suite (Illustrator, Photoshop), InVision, Principle, Framer.

• User Research & Testing: UserTesting.com, Lookback, Maze, Hotjar, Google Analytics, Mixpanel.

• Collaboration & Project Management: Jira, Confluence, Asana, Trello, Slack, Miro, Mural.

Analytics & Reporting:

• Product Analytics: Mixpanel, Amplitude, Google Analytics, Heap.

• BI Tools (for understanding business metrics): Tableau, Looker, Power BI.

CRM & Automation:

• While not directly used by design, familiarity with CRM systems (e.g., Salesforce) and marketing automation platforms is beneficial for understanding the broader customer journey and business context. Design System Tools:

• Storybook, Zeroheight, or similar platforms for documenting and managing design system components.

📝 Enhancement Note: Luminary's "AI-native" focus suggests a strong reliance on data. Therefore, proficiency with product analytics tools and the ability to integrate design insights with data-driven decision-making will be highly valued. Figma is the de facto standard for collaborative design in modern tech companies, making it a near certainty.

👥 Team Culture & Values

Operations Values:

• Customer Empathy: A core value that drives understanding of user needs and workflows in complex financial services. This translates to designing solutions that are not only functional but also deeply supportive of user goals.

• Data-Driven Innovation: Luminary's AI-native approach suggests a strong emphasis on leveraging data to inform product development and drive innovation. Design decisions are likely expected to be grounded in user data and business insights.

• Excellence & Attention to Detail: Given the high-net-worth clientele and the critical nature of wealth transfer services, precision, reliability, and a high standard of quality are paramount. This applies to both the technology and the user experience.

• Collaboration & Transparency: The need to partner closely with Product and Engineering, and the mention of multi-firm collaboration, indicates a culture that values open communication, shared ownership, and cross-functional teamwork.

• Fast-Paced Execution: Luminary operates in a rapidly evolving market and aims to ship new products quickly. This implies a culture that embraces agility, iterative development, and continuous improvement.

Collaboration Style:

• Integrated Product Teams: Design is positioned as a core partner to Product and Engineering, suggesting a highly integrated approach where design thinking is embedded early and throughout the product development lifecycle.

• Feedback-Rich Environment: The emphasis on establishing "critiques and feedback loops" points to a culture where constructive feedback is encouraged and valued as a means to elevate design quality and foster team growth.

• Knowledge Sharing: Expect opportunities for designers to share best practices, insights, and learnings, fostering a collective growth mindset and a strong design community within the company.

📝 Enhancement Note: The company's focus on serving sophisticated clients in wealth management implies a need for design that is trustworthy, precise, and professional. The "AI-native" aspect also suggests a forward-thinking, innovative, and data-informed culture.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Complexity: Wealth transfer services involve intricate legal, tax, and financial regulations, as well as complex ownership structures. Translating these complexities into intuitive, user-friendly digital experiences is a significant design challenge.

• Balancing Leadership with Hands-On Work: As Head of Design, the role requires both strategic leadership and active participation in design execution. Managing this balance effectively while driving team growth will be a key challenge.

• Building a Design Team: Scaling a design team from two to a larger unit requires strategic hiring, defining roles and responsibilities, and cultivating a strong, cohesive design culture that aligns with Luminary's values.

• Cross-Functional Alignment: Ensuring consistent design vision and execution across product, engineering, and potentially sales/marketing teams requires strong communication and negotiation skills, especially in a fast-paced environment.

• Establishing Design Operations: Developing scalable design processes, improving design system maturity, and integrating design more deeply into the product development lifecycle are ongoing operational challenges.

Learning & Development Opportunities:

• FinTech & Wealth Management Specialization: Gain deep expertise in the nuances of financial technology, wealth management workflows, and the specific needs of high-net-worth clients and their advisors.

• AI in Design: Explore how AI can be leveraged not only in Luminary's product but also within the design process itself, for tasks like user research synthesis, content generation, or automated design checks.

• Scaling Design Organizations: Acquire invaluable experience in building and managing a design team within a high-growth tech company, developing leadership and operational expertise.

• Executive-Level Strategy: Contribute directly to company-level product and business strategy, working alongside C-suite executives to shape the future of the company.

• Industry Exposure: Potential to represent Luminary at industry events, contribute to thought leadership, and build a strong professional network within the FinTech and design communities.

📝 Enhancement Note: The challenges presented are inherent to a leadership role in a specialized and rapidly growing industry. The growth opportunities are substantial, offering significant career advancement and learning potential for an ambitious design leader.

💡 Interview Preparation

Strategy Questions:

• "Describe your philosophy on building and scaling a design organization within a fast-paced, high-growth tech company. What are the key pillars you focus on?"

  • Preparation: Discuss your approach to hiring, team structure, fostering culture, defining processes, and balancing individual contribution with team growth. Reference your experience in building design functions.

• "How would you approach setting the design vision and quality bar for a company like Luminary, which serves a sophisticated B2B clientele in the FinTech space?"

  • Preparation: Focus on understanding the target user, defining design principles that emphasize trust, precision, and efficiency, and outlining how you'd ensure consistency across product touchpoints.

• "Walk me through how you would lead the design for a major new product initiative from conception to launch, specifically how you would partner with Product and Engineering."

  • Preparation: Detail your end-to-end design process, emphasizing user research, problem definition, iterative prototyping, stakeholder alignment, and collaboration with engineering for successful implementation. Company & Culture Questions:

• "What excites you most about Luminary's mission and the opportunity to design for wealth transfer services?"

  • Preparation: Research Luminary's mission, their AI-native approach, and the wealth management industry. Connect your personal values and career aspirations to their goals.

• "How do you foster a culture of customer empathy and continuous improvement within a design team?"

  • Preparation: Share specific examples of initiatives you've led to embed customer understanding and iterative design practices. Discuss methods for gathering and acting on user feedback.

• "Describe a time you had to influence stakeholders across different departments (e.g., Engineering, Sales, Executive) to adopt a design recommendation. How did you approach it?"

  • Preparation: Use the STAR method to detail a situation where you successfully navigated cross-functional dynamics and advocated for design, highlighting your communication and negotiation skills. Portfolio Presentation Strategy:

• Focus on Leadership Impact: Beyond showcasing individual design skills, emphasize your role in strategy, team management, process improvement, and the overall business impact of your work.

• Structure for Clarity: Dedicate time to each case study, ensuring a clear narrative flow: problem, your role, process, solutions, and outcomes. Be concise and impactful with your visuals.

• Anticipate Questions: Be prepared for deep dives into your decision-making process, alternative solutions considered, and how you handle design critiques and feedback.

• Demonstrate Domain Understanding: Show that you've researched Luminary and the FinTech/wealth management space. Frame your case studies in a way that demonstrates relevance to their specific challenges.

• Engage and Discuss: Treat the presentation as a conversation. Invite questions throughout and be ready to discuss your thoughts on Luminary's current product or design challenges.

📝 Enhancement Note: The interview process is designed to assess strategic leadership, product thinking, and cultural fit. Candidates should be prepared to discuss their experience at a high level, demonstrating their ability to influence and drive design impact across an organization.

📌 Application Steps

To apply for this Head of Design position:

• Submit your application through the provided link on Ashby.

• Tailor Your Resume: Highlight leadership experience, team management, strategic product development, and specific experience in B2B SaaS or FinTech. Quantify achievements with metrics where possible.

• Curate Your Portfolio: Select 3-5 of your most impactful case studies that showcase your product thinking, leadership, and ability to design complex B2B SaaS products. Ensure it clearly demonstrates your end-to-end design process and quantifiable results.

• Prepare for Case Studies: Be ready to discuss your portfolio in detail, focusing on your strategic approach, decision-making process, and leadership contributions. Practice presenting your work clearly and concisely.

• Research Luminary: Thoroughly understand Luminary's mission, product, target market, and their AI-native approach. Prepare thoughtful questions that demonstrate your engagement and strategic thinking about their business and design 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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