Head of Design

📍 Job Overview

Job Title: Head of Design Company: SUBSCRIBE Location: New York, New York, United States Job Type: Full-Time Category: Product Design / User Experience Date Posted: January 15, 2026 Experience Level: 10+ Years Remote Status: On-site

🚀 Role Summary

• Lead the strategic vision and establish design standards for all SUBSCRIBE products, ensuring a cohesive and high-quality user experience across the platform.
• Drive the discovery and definition of complex user problems, synthesizing research insights into actionable requirements in partnership with Product Management and Engineering leaders.
• Own and evolve the company's design system, including components, guidelines, and governance, to ensure scalability and consistency.
• Directly contribute to the design of critical user flows, creating wireframes, high-fidelity screens, and interactive prototypes using Figma, and collaborating closely with frontend engineers for implementation and quality assurance.
• Mentor and build a small, high-performing design team, supporting their professional development and contributing to hiring and onboarding processes.

📝 Enhancement Note: This role is situated within a small, growing team, offering significant influence on product design decisions. The "Head of Design" title, coupled with the responsibilities of setting vision, owning the design system, and mentoring, indicates a leadership position with both strategic and hands-on design expectations. The company's focus on enterprise software for alternative investments suggests a need for sophisticated, user-friendly interfaces in a complex financial domain.

📈 Primary Responsibilities

• Define and champion the overall design vision, principles, and standards to ensure a consistent, intuitive, and high-quality end-to-end user experience across all SUBSCRIBE products.
• Lead user research initiatives, including planning, execution, and synthesis of findings, to deeply understand user needs and translate them into well-defined product requirements and design solutions.
• Develop, maintain, and govern the company's design system, encompassing UI components, style guides, and interaction patterns, ensuring its adoption and evolution to support product scalability.
• Personally execute end-to-end design work for critical user journeys, producing detailed wireframes, high-fidelity mockups, and interactive prototypes in Figma, and collaborating closely with engineering for seamless implementation.
• Conduct design quality assurance (QA) to ensure that shipped products accurately reflect the intended design specifications and user experience goals.
• Partner cross-functionally with Product Management, Engineering, Go-To-Market (GTM), and Customer Success teams to prioritize design initiatives, sequence work effectively, and balance user needs with technical constraints and business objectives.
• Build, mentor, and manage a small team of designers, providing guidance, coaching, and support for their career growth, and actively participating in recruitment and onboarding.
• Articulate design strategy and present compelling narratives to executive leadership, customers, and internal stakeholders to align teams and gain buy-in on design decisions and trade-offs.
• Define and track design quality metrics, analyze user behavior and UX health, and proactively drive continuous improvement cycles for the product's user experience.

📝 Enhancement Note: The responsibilities emphasize a blend of strategic leadership and hands-on execution, typical for a Head of Design in a growing SaaS company. The emphasis on "system thinking," "design system at scale," and "partnering with frontend on implementation" highlights the need for a strong technical design background and a collaborative approach with engineering. The requirement to "measure impact" and "define design quality metrics" points towards a data-informed design process.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong understanding of design principles, user-centered design methodologies, and visual communication is essential, often gained through formal education or equivalent professional experience. Experience: 7-10+ years in product, UI, and UX design, with a minimum of 2-3 years spent leading designers or managing significant design workstreams for complex SaaS products.

Required Skills:

• Product Design & UX Strategy: Proven ability to define design vision, set standards, and lead the discovery of complex user problems.
• Design Systems Expertise: Deep experience in creating, scaling, and governing design systems, including component architecture and best practices for collaboration with frontend developers.
• Figma Proficiency: Mastery in using Figma for wireframing, high-fidelity design, and interactive prototyping.
• User Research & Synthesis: Strong capabilities in designing research studies, synthesizing qualitative and quantitative insights, and translating findings into strategic product roadmaps.
• Interaction Design: Skill in crafting elegant and effective user interactions that enhance usability and user satisfaction.
• Mentorship & Team Leadership: Demonstrated experience in coaching designers, managing design capacity, and supporting career development.
• Stakeholder Management & Storytelling: Excellent ability to communicate design strategy, present to executives and customers, and align diverse stakeholders.
• Accessibility & Responsive Design: Solid understanding and practical application of accessibility standards (WCAG) and responsive design principles.
• Collaboration with Engineering: Comfort and experience partnering closely with frontend engineers on design implementation and ensuring design quality through QA.

Preferred Skills:

• Fintech/Alternative Investments Domain Knowledge: Familiarity with the financial services industry, particularly alternative investments, is a plus.
• Analytics for UX Measurement: Experience using analytics tools to measure UX performance and drive continuous improvement.
• Experimentation Design: Familiarity with A/B testing and other experimentation methodologies to validate design decisions.
• Performance Considerations: Awareness of how design impacts application performance.

📝 Enhancement Note: The experience requirement of "7-10+ years" with a specific emphasis on "2-3+ years leading designers or major workstreams" clearly positions this as a senior leadership role. The portfolio requirement is crucial, emphasizing "system thinking" and "measurable outcomes," which are key indicators of a candidate's ability to contribute strategically and tangibly.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• System Thinking Demonstration: Showcase projects where you've approached design holistically, considering the interconnectedness of features, user journeys, and the overall product ecosystem.
• Elegant Interaction Design: Highlight examples of innovative and intuitive interaction patterns that solve complex user problems effectively.
• Measurable Outcomes at Scale: Present case studies that clearly articulate the business and user impact of your design work, supported by quantifiable data (e.g., conversion rate improvements, task completion time reduction, user satisfaction scores).
• Design System Contributions: Include examples of your involvement in building, maintaining, or scaling design systems, detailing component design, guideline creation, and collaboration with development teams.

Process Documentation:

• Workflow Design and Optimization: Demonstrate your ability to map out existing user workflows, identify pain points, and design optimized processes that enhance efficiency and user satisfaction.
• System Implementation Standards: Provide evidence of your experience in translating design specifications into actionable plans for engineering, ensuring a smooth implementation process and adherence to design intent.
• Measurement and Performance Analysis: Illustrate how you have defined key performance indicators (KPIs) for design, collected data, and used insights to iterate and improve product experiences.

📝 Enhancement Note: For a Head of Design role, the portfolio is paramount. It must not only showcase visual and interaction design skills but also strategic thinking, system-level understanding, leadership capabilities, and a data-driven approach to measuring design impact. The focus on "complex SaaS products" and "measurable outcomes" indicates that candidates should be prepared to discuss the business impact of their design decisions.

💵 Compensation & Benefits

Salary Range: While not explicitly stated, for a Head of Design role in New York City with 7-10+ years of experience leading design for complex SaaS products, the estimated annual salary range is typically between $180,000 to $250,000 USD. This range accounts for the seniority of the position, the high cost of living in New York City, and industry benchmarks for leadership roles in the enterprise software sector.

Benefits:

• Comprehensive Health Insurance: Medical, dental, and vision coverage to support employee well-being.
• Stock Options/Equity: Potential for ownership in a growing company, aligning employee success with business growth.
• 401(k) Retirement Plan: With potential company match to aid in long-term financial planning.
• Paid Time Off: Generous vacation days, sick leave, and paid holidays for work-life balance.
• Professional Development Budget: Funds allocated for training, conferences, and learning opportunities to support continuous skill enhancement.
• Commuter Benefits: Assistance for transportation costs in New York City.

Working Hours: Standard full-time hours are expected, likely around 40 hours per week. However, given the leadership nature of the role and the small team environment, flexibility may be required to meet project deadlines and strategic objectives, especially during critical launch phases.

📝 Enhancement Note: The estimated salary range is based on industry data for similar roles in major tech hubs like New York City, considering the specified experience level and the responsibilities of a Head of Design. Benefits are typical for a full-time position at a growing tech company, with a focus on employee well-being, financial security, and professional growth.

🎯 Team & Company Context

🏢 Company Culture

Industry: Enterprise Software, specifically focusing on electronic subscription document technology and order management systems for alternative product transactions. This places SUBSCRIBE at the intersection of FinTech and enterprise SaaS. Company Size: Small, growing team. This implies a dynamic, fast-paced environment where individual contributions have a significant impact and cross-functional collaboration is essential. Founded: The founding date is not specified, but the company is positioned as a growing entity, suggesting a relatively young or recently scaled-up organization.

Team Structure:

• Reporting: The Head of Design reports directly to the Head of Product, indicating a close partnership in product strategy and execution.
• Design Team: Expected to build and mentor a small design team, suggesting a foundational stage for the design function within the company.
• Cross-functional Collaboration: Close partnerships with Product Management, Engineering, Go-To-Market (GTM), and Customer Success (CS) are explicitly mentioned, highlighting a collaborative and integrated approach to product development.

Methodology:

• Data-Driven Product Development: Emphasis on using research and analytics to define requirements, measure impact, and drive continuous improvement.
• Agile/Iterative Design: The role involves rolling up sleeves, designing critical flows, and pairing with frontend on implementation, suggesting an iterative and hands-on approach.
• Systemic Design Approach: Strong focus on design systems, component architecture, and ensuring consistency across products.

Company Website: https://subscribe.breezy.hr

📝 Enhancement Note: The company's mission to "reduce friction for a very painful investment process" suggests a culture focused on problem-solving, efficiency, and user-centric innovation within a complex financial domain. The "small but growing team" environment means individuals will likely wear multiple hats and have significant autonomy.

📈 Career & Growth Analysis

Operations Career Level: This role is a senior leadership position, equivalent to a Director or VP level within a larger organization, but tailored to a smaller, high-impact setting. It involves strategic oversight, team building, and direct contribution to product development. Reporting Structure: Reports directly to the Head of Product, indicating a close strategic alignment and collaboration at the leadership level. The Head of Design will be responsible for building and managing the design team reporting to them. Operations Impact: The Head of Design will have a direct and significant impact on the company's success by shaping the user experience of its enterprise software. This includes influencing customer acquisition and retention through intuitive design, reducing onboarding friction for alternative investments, and ensuring the platform's usability for sophisticated financial professionals.

Growth Opportunities:

• Team Expansion: Opportunity to grow the design team from its nascent stage into a robust function, defining its structure and processes.
• Strategic Influence: Directly influence the product roadmap and overall company strategy through design leadership and compelling storytelling.
• Domain Expertise: Develop deep expertise in the complex and high-value niche of alternative investment technology.
• Leadership Development: Hone leadership, mentorship, and strategic communication skills in a high-growth startup environment.
• Potential for Equity Growth: As a key member of a growing company, there's potential for significant equity appreciation.

📝 Enhancement Note: The "Head of Design" title in a small, growing company often presents a unique growth trajectory. Candidates can expect to build a function from the ground up, with the potential for significant career acceleration as the company scales. The role offers a blend of strategic impact and hands-on design leadership.

🌐 Work Environment

Office Type: On-site in New York City. This suggests a traditional office-based work environment where in-person collaboration is prioritized. Office Location(s): New York, New York, United States. This provides access to a vibrant tech and finance ecosystem.

Workspace Context:

• Collaborative Environment: The emphasis on cross-functional partnership and a small team size suggests a highly collaborative workspace where designers work closely with product managers, engineers, and other stakeholders.
• Tools & Technology: Likely equipped with modern design tools (Figma is specified) and potentially other collaborative software essential for enterprise SaaS development.
• Direct Interaction: Opportunities for direct interaction with leadership, customers, and team members are high, fostering a connected and engaged work atmosphere.

Work Schedule: Full-time, on-site. While standard business hours are expected, the nature of a growing tech company and a leadership role may require flexibility to meet business needs, particularly around product launches or critical deadlines.

📝 Enhancement Note: The on-site requirement in New York City suggests a company that values in-person collaboration and team cohesion. This environment can be highly beneficial for design teams, fostering spontaneous ideation and stronger working relationships with engineering and product counterparts.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio to assess qualifications and experience.
• Portfolio Presentation: A session where you present your portfolio, focusing on system thinking, design system experience, and measurable outcomes. Be prepared to discuss your design process and strategic decision-making.
• Cross-functional Interviews: Meetings with Product Management, Engineering leads, and potentially other stakeholders to evaluate collaboration skills, technical understanding, and cultural fit.
• Leadership Interview: A discussion with senior leadership (e.g., Head of Product, potentially CEO/CTO) to assess strategic vision, leadership potential, and alignment with company goals.
• Design Challenge (Potential): You may be asked to complete a take-home design exercise or participate in an on-site design workshop to demonstrate your problem-solving and design skills.

Portfolio Review Tips:

• Curate Strategically: Select 3-4 of your strongest projects that best demonstrate system thinking, design system experience, leadership, and quantifiable impact.
• Tell a Story: For each project, clearly articulate the problem, your role, the process you followed, the trade-offs you made, and the measurable results. Use visuals effectively.
• Highlight System Design: Emphasize your experience with design systems, component architecture, and how you've ensured consistency and scalability.
• Showcase Leadership: If possible, include examples of mentoring, leading workstreams, or influencing product strategy.
• Be Prepared for Questions: Anticipate questions about your design philosophy, how you handle feedback, your collaboration style, and your approach to metrics.

Challenge Preparation:

• Understand the Domain: Familiarize yourself with SUBSCRIBE's business (alternative investments, enterprise software) and its target users.
• Focus on Process: If given a design challenge, emphasize your process: research, ideation, prototyping, testing, and iteration.
• Think Systemically: Consider how your solution would integrate with existing systems or a design system.
• Prioritize and Justify: Be prepared to explain your design choices and justify trade-offs based on user needs, business goals, and technical constraints.

📝 Enhancement Note: The emphasis on "system thinking" and "measurable outcomes" in the portfolio review suggests that candidates should prepare to discuss the strategic impact of their design work, not just the visual execution. The interview process will likely assess not only design craft but also leadership and cross-functional collaboration abilities.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Explicitly mentioned as the primary tool for wireframing, high-fidelity design, and interactive prototyping. Proficiency is essential.
• Design System Management Tools: While not specified, tools for managing component libraries, style guides, and design tokens are implicitly required for design system ownership. This could include Figma's built-in features, Zeplin, Storybook, or similar.

Analytics & Reporting:

• UX Analytics Platforms: Familiarity with tools like Google Analytics, Amplitude, Mixpanel, or Pendo would be beneficial for measuring user behavior and UX performance.
• Data Visualization Tools: Experience with tools that can help visualize user data and performance metrics to inform design decisions.

CRM & Automation:

• Not Directly Applicable to Design Role: While the company uses enterprise software with order management and subscription documents, the Head of Design's primary tools will be design-focused. However, understanding how design integrates with CRM and automation workflows in a B2B context is advantageous.

📝 Enhancement Note: The explicit mention of Figma indicates a modern design stack. The role requires not just proficiency in design tools but also the ability to manage and scale a design system, which often involves understanding how design components are implemented and maintained in code.

👥 Team Culture & Values

Operations Values:

• User-Centricity: A core value likely embedded in the company's mission to "reduce friction." The design team will be expected to champion the user's needs.
• Excellence & Craft: The role calls for raising the bar on "craft" and ensuring "high-quality end-to-end experience," suggesting a commitment to detailed, polished design work.
• Collaboration: Close partnerships with Product, Engineering, GTM, and CS highlight a value placed on teamwork and shared ownership.
• Data-Informed Decision Making: The emphasis on research, metrics, and measuring impact points to a culture that values evidence-based strategies.
• Innovation & Problem-Solving: The nature of the business – solving complex investment process pain points – suggests a culture that embraces creative solutions to challenging problems.

Collaboration Style:

• Partnership Model: Close collaboration with Product and Engineering is key, involving joint discovery, requirement shaping, and implementation pairing.
• Cross-Functional Integration: Seamless integration with GTM and CS teams to ensure market fit, customer satisfaction, and effective product adoption.
• Feedback Loops: An environment that encourages constructive feedback, both giving and receiving, to elevate the quality of design and product outcomes.
• Open Communication: Given the small team size, direct and open communication is likely essential for efficient decision-making and problem-solving.

📝 Enhancement Note: The company's mission to reduce friction in a complex financial process implies a culture that values efficiency, clarity, and technological solutions. The design team will be instrumental in translating these values into a user-friendly product experience.

⚡ Challenges & Growth Opportunities

Challenges:

• Building a Design Function: Establishing design processes, standards, and a team culture from a relatively early stage.
• Complexity of the Domain: Designing for alternative investments requires understanding a sophisticated financial landscape and user base.
• Balancing Vision and Execution: Leading the design vision while also rolling up sleeves to execute on critical design tasks.
• Cross-Functional Alignment: Ensuring design priorities are effectively communicated and integrated with the roadmap of other departments in a growing company.
• Scaling the Design System: Evolving and maintaining a design system that supports rapid product development and a growing component library.

Learning & Development Opportunities:

• Strategic Leadership: Developing skills in setting design vision, managing teams, and influencing executive-level decisions.
• Domain Specialization: Gaining deep expertise in FinTech and alternative investment workflows.
• Scale-Up Experience: Contributing to and learning from the process of scaling a technology company.
• Mentorship & Coaching: Enhancing leadership capabilities by guiding and developing junior designers.
• Industry Exposure: Potential to attend relevant industry conferences or workshops focused on FinTech, enterprise SaaS, or design leadership.

📝 Enhancement Note: The primary challenge will be establishing and scaling the design function within a growing company. This presents a significant opportunity for the Head of Design to shape the future of product design at SUBSCRIBE and gain invaluable experience in a high-growth environment.

💡 Interview Preparation

Strategy Questions:

• "How would you approach defining the design strategy for a new feature in our alternative investment platform?" (Focus on user research, problem definition, and strategic alignment)
• "Describe a time you had to balance conflicting priorities from Product, Engineering, and business stakeholders. How did you reach a decision?" (Emphasize negotiation, data-driven rationale, and stakeholder management)
• "Walk us through your process for designing and scaling a design system. What are the key components and governance considerations?" (Detail system thinking, component architecture, and collaboration with development)

Company & Culture Questions:

• "What excites you about SUBSCRIBE's mission and the challenges in the alternative investments space?" (Show research and genuine interest)
• "How do you foster a collaborative and high-performing design team culture?" (Discuss mentorship, feedback, and team dynamics)
• "How do you measure the impact of design on business outcomes, particularly in a B2B SaaS context?" (Prepare to discuss specific metrics and case studies)

Portfolio Presentation Strategy:

• Structure for Impact: Organize your presentation logically: Problem -> Your Role -> Process -> Solution -> Impact (Quantified Results).
• Focus on Systems: Dedicate specific slides or sections to showcasing your design system work and how you approach systemic design.
• Showcase Leadership: If applicable, include a project where you led a team or a significant workstream, detailing your leadership approach.
• Quantify Everything: Use numbers and data to demonstrate the measurable outcomes of your design decisions.
• Be Conversational: Engage with the interviewers, ask clarifying questions, and be open to discussion.

📝 Enhancement Note: Interview preparation should heavily focus on demonstrating strategic thinking, leadership, and a deep understanding of design systems and their impact. Candidates should be ready to articulate their design process, justify decisions with data, and showcase their ability to collaborate effectively across functions.

📌 Application Steps

To apply for this Head of Design position:

• Submit your application through the provided link on subscribe.breezy.hr.
• Tailor your Resume: Highlight experience in SaaS product design, design leadership, design systems, and any relevant FinTech or enterprise software experience. Use keywords from the job description like "design vision," "design system," "stakeholder management," and "mentoring."
• Prepare Your Portfolio: Ensure your portfolio is up-to-date and showcases 3-4 strong projects that demonstrate system thinking, interaction design, and measurable outcomes. Be ready to present this virtually or on-site.
• Research SUBSCRIBE: Understand their business, mission, and the challenges within the alternative investments sector. This will help you tailor your answers and demonstrate genuine interest.
• Practice Your Presentation: Rehearse your portfolio walkthrough, focusing on clear storytelling, quantifying impact, and articulating your design process and strategic approach.

⚠️ 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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