Head Of Design

📍 Job Overview

Job Title: Head Of Design

Company: Quizlet

Location: San Francisco, California, United States

Job Type: FULL_TIME

Category: Design Leadership / Product Design

Date Posted: 2026-09-11

Experience Level: 10+ Years (Principal Level / Leadership)

Remote Status: Hybrid (2 days in office required)

🚀 Role Summary

• Lead the design vision and execution for an AI-native adaptive learning platform, impacting over 60 million learners globally.

• Drive the visual and experiential direction of next-generation learning experiences, leveraging AI-assisted design and development tooling for rapid prototyping and production-quality output.

• Build and maintain scalable design systems that empower cross-functional teams and contractors to contribute effectively across product, marketing, and internal tools.

• Transition from a hands-on Principal Designer role to leading and managing the design organization, fostering a culture of innovation and excellence.

📝 Enhancement Note: This role is unique in its phased approach, starting as a hands-on Principal Designer with a clear path to leadership. The emphasis on AI-assisted design and rapid prototyping suggests a forward-thinking design team that values efficiency and direct impact. Candidates should be prepared to demonstrate both exceptional craft and strategic leadership potential.

📈 Primary Responsibilities

• Define and execute the product design strategy for core learning experiences that power over 1 billion weekly interactions, focusing on impactful improvements for millions of students.

• Set and deliver the visual and experiential direction for Quizlet's future, utilizing AI tooling to create working, production-quality prototypes at an accelerated pace.

• Develop and evolve comprehensive design systems that extend across product, marketing, and internal tools, ensuring consistency and enabling self-sufficiency for various stakeholders.

• Own the design learning loop by collaborating with user research, data science, and product marketing to translate insights into actionable design standards and best practices.

• Execute high-visibility brand and marketing design initiatives, including campaigns, feature identities, executive presentations, and launch assets, as required by business needs.

• Lead, mentor, and develop a team of product designers and manage a network of contractors for brand and marketing design efforts, ensuring high-quality output company-wide.

• Foster strong partnerships with product, engineering, marketing, and executive leadership to align priorities, drive design velocity, and ensure successful product development.

• Champion an AI-first design methodology, elevating the capabilities of individual designers and enabling the entire team to operate with increased speed and efficiency.

📝 Enhancement Note: The responsibilities highlight a dual focus: deep individual contribution to core product features and strategic leadership of the entire design function. The expectation to leverage AI for rapid prototyping and production-quality output is a key differentiator for this role, requiring candidates to be at the forefront of design technology.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong educational foundation in Design, Human-Computer Interaction, or a related field is beneficial. Emphasis is placed on demonstrated skills and experience.

Experience: 15+ years of progressive experience in product design, with a significant portion focused on consumer products at scale. Proven experience in a Principal Designer capacity or equivalent, with a track record of setting strategic design direction and executing complex projects. Experience in a leadership role managing design teams is highly desirable, especially given the role's arc.

Required Skills:

• Principal-level product design craft with exceptional visual taste and a strong portfolio showcasing impact at scale.

• Proven expertise in designing and maintaining robust design systems that facilitate adoption and contribution from diverse teams.

• Fluency in operating at both strategic (design strategy, creative direction) and tactical (hands-on execution of polished work) levels.

• Demonstrated proficiency and eagerness to leverage AI tools for accelerated design, prototyping, and shipping of digital products.

• Strong cross-functional collaboration skills, adept at navigating complex stakeholder relationships and competing priorities with low ego and high effectiveness.

• Comfort and adaptability to a role that begins with hands-on individual contribution and evolves into leadership within a dynamic, small team environment. Preferred Skills:

• Experience in brand marketing or creative direction, including setting brand strategy, defining illustration systems, or leading rebranding initiatives.

• Agency background with a proven ability to deliver high-quality work across diverse categories and at speed.

• Proficiency in motion design and animation.

• Experience managing and project-managing contract designers.

• A genuine interest in learning science and education, understanding the "why" behind Quizlet's mission.

• Ambition to grow into a long-term leadership role, shaping the future of an AI-native design organization.

📝 Enhancement Note: The experience requirement of 15+ years at a "principal-level" signals this is a senior leadership role, even with the initial hands-on focus. The emphasis on AI-first practice is critical, suggesting candidates should have concrete examples of how they've integrated AI into their workflow and seen tangible benefits.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase a minimum of 15 years of product design experience, with a strong emphasis on consumer products at significant scale.

• Demonstrate principal-level craft, including sophisticated visual design, user experience, and interaction design across multiple platforms.

• Provide clear examples of designing, implementing, and maintaining scalable design systems that enabled others to build efficiently.

• Include case studies highlighting strategic design thinking, problem definition, and the impact of your design solutions on user behavior and business metrics.

• Present examples of how AI tools were integrated into the design and prototyping process, detailing the benefits and outcomes. Process Documentation:

• Document the process for setting design strategy and creative direction, including how you translate company vision into tangible design outcomes.

• Illustrate your approach to building and evolving design systems, detailing governance, contribution models, and maintenance strategies.

• Provide examples of how you've collaborated with user research, data science, and product marketing to inform design decisions and establish design standards.

• Detail your experience with rapid prototyping and shipping production-quality work, especially using AI-assisted tooling.

📝 Enhancement Note: The portfolio for this role should clearly articulate not just design output, but also the strategic thinking, process, and leadership capabilities. The emphasis on AI tooling and design systems means these should be prominent features in candidate portfolios.

💵 Compensation & Benefits

Salary Range: $212,000 - $289,000 per year. This range is competitive for a Head of Design role at a well-funded tech company in San Francisco, reflecting the significant experience and leadership responsibilities.

Benefits:

• Collaborative work-life balance initiatives with manager support.

• Generous 20 days of paid vacation.

• Comprehensive health, dental, and vision insurance (100% employee coverage, 75% dependent coverage for PPO, Dental, VSP Choice).

• Employer-sponsored 401k plan with a company match.

• Access to LinkedIn Learning and other professional development resources.

• Paid Family Leave, FSA, HSA, Commuter benefits, and Wellness benefits.

• 40 hours of annual paid time off for volunteer programs.

Working Hours: While the standard workweek is 40 hours, the hybrid model requires employees to be in the San Francisco office on Wednesdays and Thursdays to foster collaboration. Flexibility is encouraged within the team's overall goals.

📝 Enhancement Note: The salary range provided is based on the input data. For a Head of Design role in San Francisco, this range is typical for candidates with 15+ years of experience and proven leadership capabilities. The benefits package is comprehensive, offering strong support for employee well-being and professional growth.

🎯 Team & Company Context

🏢 Company Culture

Industry: Education Technology (EdTech) / Learning Platform. Quizlet operates in a rapidly evolving digital learning landscape, leveraging AI and cognitive science to personalize education for a global audience.

Company Size: While not explicitly stated in the raw data, Quizlet is described as a "$1B+ learning platform" with "60M+ users." This suggests a significant, growth-stage company with established infrastructure and a large user base, likely employing several hundred to over a thousand individuals.

Founded: Quizlet was founded with a mission to help learners achieve their outcomes. Its evolution into an AI-native platform indicates a commitment to innovation and adaptation within the EdTech space.

Team Structure:

• The Design team is described as "small but mighty," indicating a high-impact group where individual contributions are significant.

• Design works embedded with product, engineering, and user research in tight weekly cycles, suggesting a highly collaborative and agile environment.

• This role reports to the VP User Experience, placing it within a broader UX leadership structure.

• The Head of Design will manage product designers and a contractor network for brand and marketing work, indicating a hierarchical structure within the design department. Methodology:

• Emphasis on AI-native design and development, utilizing AI tooling for rapid prototyping and production-quality output.

• Agile development cycles with a focus on shipping working software, not static mockups.

• Data-driven decision-making, partnering with user research and data science to inform design.

• Systems thinking approach to design, building scalable design systems across multiple product surfaces.

Company Website: https://quizlet.com/

📝 Enhancement Note: Quizlet's focus on AI and learning science positions it as an innovative player in EdTech. The "small but mighty" design team implies a culture that values efficiency, direct impact, and strong individual contribution, with a clear growth path into leadership.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned at a senior leadership level, encompassing both Principal Designer responsibilities and the Head of Design title. It represents a significant step up for individuals with extensive individual contributor experience looking to transition into formal management and strategic oversight of a design function. The arc of the role—hands-on IC first, then leadership—is designed for individuals who want to deeply understand the product before leading its evolution.

Reporting Structure: The Head of Design reports to the VP User Experience. They will also work daily with product, engineering, and marketing leadership, indicating a highly cross-functional and visible position.

Operations Impact: The design team's work directly impacts over 60 million learners and over a billion learning interactions weekly. A Head of Design at Quizlet has the potential to shape the learning experience for a substantial portion of the global student population, driving user engagement, learning efficacy, and ultimately, the company's success.

Growth Opportunities:

• Leadership Development: Transitioning from an individual contributor to managing a team of designers and contractors provides direct leadership growth.

• Strategic Influence: Shaping the AI-native vision for Quizlet's design will offer significant strategic influence on the company's future product direction.

• Skill Expansion: Deepening expertise in AI-assisted design, learning science, and potentially brand strategy and creative direction.

• Organizational Growth: The long-term vision is for this individual to build and lead a world-class design organization for an AI-native company, offering substantial career progression.

📝 Enhancement Note: The role is structured for significant growth, moving from individual impact to organizational leadership. The emphasis on AI and learning science means opportunities to become a thought leader in these cutting-edge fields within EdTech.

🌐 Work Environment

Office Type: Hybrid. Quizlet maintains offices in San Francisco and New York City, with employees expected to be in the office a minimum of two days per week (Wednesday and Thursday) to facilitate collaboration.

Office Location(s): San Francisco, California, and New York City. The specific office for this role is San Francisco.

Workspace Context:

• The San Francisco office will provide a collaborative environment for in-person teamwork on core days.

• Designers will have access to modern tools and technologies, including AI-assisted design and development platforms, to enhance their workflow.

• Opportunities for daily interaction with product, engineering, marketing, and executive leadership, fostering a dynamic and cross-functional work setting.

Work Schedule: The role is full-time, with an expectation of 40 hours per week. The hybrid model requires specific in-office days, but flexibility is likely encouraged for remote work on other days, balanced with team needs and project deadlines.

📝 Enhancement Note: The hybrid model with specific in-office days is designed to balance the benefits of remote work with the advantages of in-person collaboration, crucial for design leadership and team cohesion.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio, focusing on the 15+ years of experience, principal-level craft, systems design, and AI proficiency.

• Portfolio Presentation & Deep Dive: Expect to present your portfolio, detailing specific case studies that showcase your strategic thinking, execution, design systems, and AI integration. This will likely involve discussions on your approach to problem-solving, collaboration, and leadership.

• Cross-Functional Interviews: Interviews with Product, Engineering, and Marketing leadership to assess your ability to collaborate effectively, understand technical constraints, and align design with business objectives.

• Leadership/VP Interview: A discussion with the VP User Experience to evaluate your strategic vision, leadership potential, and cultural fit with Quizlet's mission and values.

• Potential Case Study/Exercise: While not explicitly stated, a design challenge or exercise focused on a specific problem relevant to Quizlet's platform or AI initiatives may be part of the process.

Portfolio Review Tips:

• Curate Strategically: Select 3-5 of your most impactful projects that best demonstrate principal-level craft, systems thinking, AI integration, and leadership potential.

• Tell a Story: For each project, clearly articulate the problem, your role, the process, the constraints, your solution, and the measurable impact (metrics are key!).

• Highlight AI Usage: Explicitly detail how you used AI tools, what they enabled, and the outcomes. This is a critical differentiator for this role.

• Showcase Design Systems: Dedicate specific sections to your experience with design systems, including their architecture, governance, and impact on efficiency.

• Demonstrate Leadership: If you have prior leadership experience, use case studies to illustrate your mentoring, team management, and strategic decision-making abilities.

Challenge Preparation:

• Understand Quizlet: Research Quizlet's platform, user base, mission, and recent developments, especially their AI initiatives.

• Think AI-First: Prepare to discuss your perspective on the future of AI in learning and design, and how Quizlet can lead in this space.

• Process Optimization: Be ready to discuss how you would optimize design processes for speed, efficiency, and quality within a hybrid, AI-augmented environment.

• Stakeholder Management: Prepare examples of how you've managed competing priorities and driven consensus among diverse stakeholders.

📝 Enhancement Note: The interview process is designed to thoroughly vet candidates for both deep design expertise and emerging leadership capabilities. A strong, well-articulated portfolio that highlights AI integration and systems design is paramount.

🛠 Tools & Technology Stack

Primary Tools:

• AI-Assisted Design Tools: Proficiency with emerging AI tools for design generation, prototyping, and potentially code generation (e.g., tools like Uizard, Galileo AI, Midjourney for ideation, or internal/proprietary AI tools).

• Prototyping Tools: Expertise in industry-standard tools such as Figma, Sketch, Adobe XD, or similar, with a focus on rapid prototyping and interactive deliverables.

• Design Systems Tools: Experience with tools and methodologies for building and managing design systems, often integrated within Figma or similar platforms.

Analytics & Reporting:

• Familiarity with user analytics platforms (e.g., Google Analytics, Amplitude, Mixpanel) to understand user behavior and measure design impact.

• Ability to interpret data science outputs and user research findings to inform design decisions. CRM & Automation:

• While not directly a CRM role, understanding how design integrates with user acquisition and engagement funnels is beneficial.

• Familiarity with project management and collaboration tools (e.g., Jira, Asana, Notion) for team workflow and communication.

📝 Enhancement Note: The emphasis on AI-assisted design tools is a key requirement. Candidates should be prepared to discuss their experience and comfort level with these technologies, as they are central to the role's execution strategy.

👥 Team Culture & Values

Operations Values:

• Learner-Centricity: A deep commitment to helping every learner achieve their outcomes effectively and delightfully.

• Innovation & AI-First: Embracing cutting-edge technology, particularly generative AI, to redefine the learning experience and enhance design capabilities.

• Impact & Scale: Driving meaningful improvements that reach millions of users globally, understanding the significant impact of design decisions.

• Collaboration & Ownership: Working embedded with cross-functional teams, taking initiative, and owning outcomes with transparency and respect.

• Continuous Learning: A culture that encourages curiosity, learning through challenges, and staying open to new ideas and methodologies.

Collaboration Style:

• Embedded & Agile: Working closely with product, engineering, and research in tight weekly cycles, focused on shipping working software.

• Cross-Functional Partnerships: Building strong relationships with leadership across product, engineering, and marketing to navigate priorities and drive alignment.

• Open Communication: Valuing honest, respectful communication and thoughtful collaboration to foster a supportive environment.

• Empowering Others: Building systems and processes that enable contractors, PMs, and marketers to contribute effectively to design efforts.

📝 Enhancement Note: Quizlet's culture appears to value mission-driven work, technological innovation (especially AI), and a collaborative, agile approach. The "small but mighty" design team culture suggests a high degree of autonomy and responsibility for its members.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Hands-on Craft with Leadership: Effectively transitioning from a Principal Designer's deep individual contribution to the broader responsibilities of leading a team and setting company-wide design direction.

• Scaling Design Systems: Ensuring design systems remain robust, scalable, and maintainable as the product and company grow, while empowering diverse contributors.

• Pioneering AI in Design: Staying at the forefront of AI tooling and methodologies in design, and effectively integrating these into team workflows at scale.

• Navigating Competing Priorities: Managing diverse stakeholder needs and business objectives in a fast-paced environment to maintain design velocity and quality.

Learning & Development Opportunities:

• AI Design Leadership: Opportunity to become a leader in applying AI to product design and development within the EdTech space.

• Organizational Building: Experience in hiring, mentoring, and developing a design team, and building a design function from a foundational stage.

• Product Strategy: Deep involvement in shaping the strategic direction of a major consumer product with global reach.

• Industry Impact: Contributing to the evolution of learning and education through innovative AI-powered tools.

📝 Enhancement Note: The challenges are framed as opportunities for growth, particularly in areas of AI adoption, leadership, and strategic product development within the impactful EdTech sector.

💡 Interview Preparation

Strategy Questions:

• "Describe your approach to setting the design strategy for a product like Quizlet, especially in the context of it becoming an AI-native platform." (Focus on translating company vision, user needs, and AI capabilities into a cohesive design roadmap).

• "How would you build and maintain design systems that can be used effectively by product designers, marketing teams, and external contractors?" (Highlight governance, contribution models, and scalability).

• "Walk us through a time you used AI tools to significantly accelerate your design or prototyping process. What were the results?" (Be specific about the tools, your workflow, and the impact on speed and quality).

• "How do you balance hands-on design execution with the strategic and leadership demands of a Head of Design role?" (Explain your transition strategy and how you'd delegate and empower). Company & Culture Questions:

• "What interests you most about Quizlet's mission and our focus on AI in education?" (Show genuine passion for the domain and the company's direction).

• "How do you foster a collaborative and inclusive design culture within a hybrid team environment?" (Discuss your approach to team building, communication, and feedback).

• "Describe a time you had to navigate significant disagreements with product or engineering leadership. How did you reach a resolution?" (Emphasize low ego, data-driven arguments, and focus on shared goals). Portfolio Presentation Strategy:

• Structure is Key: Organize your presentation logically, starting with an overview of your experience and then diving into 2-3 in-depth case studies.

• Quantify Impact: For each project, clearly state the problem, your solution, and the measurable outcomes (e.g., increased engagement, conversion rates, efficiency gains).

• Showcase AI & Systems: Dedicate specific slides or sections to demonstrate your AI tool usage and your approach to design systems.

• Be Ready for Deep Dives: Anticipate detailed questions about your design decisions, process, and contributions.

• Enthusiasm for the Mission: Convey genuine excitement about Quizlet's role in education and its AI-driven future.

📝 Enhancement Note: Candidates should prepare to articulate their vision for AI in design and education, demonstrate their systems thinking, and clearly communicate their leadership philosophy and ability to execute at a high level.

📌 Application Steps

To apply for this Head Of Design position:

• Submit your application through the provided link on Ashby.

• Portfolio Customization: Tailor your portfolio to prominently feature projects demonstrating principal-level craft, comprehensive design systems, and significant contributions at scale. Critically, highlight your experience and strategic use of AI-assisted design tools and workflows.

• Resume Optimization: Ensure your resume clearly reflects 15+ years of relevant experience, emphasizing leadership roles, consumer product success, and any experience with AI technologies or design system implementation. Use keywords from the job description.

• Prepare Your Narrative: Practice articulating your design philosophy, leadership approach, and vision for AI in education design. Be ready to present your portfolio with confidence, detailing process, impact, and your unique contributions.

• Research Quizlet: Thoroughly understand Quizlet's mission, product, user base, and their stated commitment to AI. Familiarize yourself with their current design aesthetic and user experience.

⚠️ 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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