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: 2026-08-13

Experience Level: 15+ Years

Remote Status: Hybrid (3 days in office minimum)

🚀 Role Summary

• Lead and define the visual and experiential direction for Quizlet's next-generation, AI-native adaptive learning platform, impacting over 60 million learners globally.

• Transition from a hands-on Principal Designer role, focused on shipping AI-assisted prototypes, to managing a team of product designers and contractor network for brand and marketing.

• Drive design systems that span product, marketing, and internal tools, ensuring scalability and enabling non-designers to contribute effectively.

• Foster a culture of AI-first design practices, raising the bar for individual designer output and overall team velocity.

• Collaborate closely with executive leadership, product, engineering, and marketing to navigate priorities and maintain high design velocity in a fast-paced environment.

📝 Enhancement Note: This role is positioned as a dual-threat opportunity, emphasizing both individual contribution and eventual leadership. The initial phase as a hands-on Principal Designer, leveraging AI tooling for rapid prototyping, is a critical differentiator, followed by a transition into a leadership capacity. This structure suggests a need for adaptability and a strong desire to both execute and manage.

📈 Primary Responsibilities

• Design and drive the user experience and visual direction for core learning features used by over 60 million active users, impacting over a billion learning interactions weekly.

• Develop and implement production-quality prototypes using AI-assisted design and development tooling, shifting from traditional static mockups to functional, shippable designs.

• Architect and maintain scalable design systems that govern product, marketing, and internal tools, empowering cross-functional teams and contractors.

• Partner with User Research, Data Science, and Product Marketing to translate insights, market trends, and brand signals into actionable design standards and strategies.

• Execute high-impact brand and marketing design initiatives, including campaigns, feature identities, executive presentations, and launch assets.

• Lead and mentor the design organization, including hiring, developing product designers, and managing a contractor network for brand and marketing efforts.

• Act as the final authority on the look, feel, and overall user experience of all company-shipped products and initiatives.

• Foster a culture of continuous learning and AI adoption within the design team, encouraging experimentation and efficiency gains.

• Collaborate with product, engineering, marketing, and executive leadership to align design efforts with business objectives and manage competing priorities.

📝 Enhancement Note: The responsibilities highlight a unique blend of hands-on execution, strategic leadership, and operational management. The emphasis on AI tooling and rapid prototyping suggests a forward-thinking approach to design execution, while the requirement to build and maintain cross-functional design systems points to a need for strong organizational and governance skills.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong foundation in design principles, user experience, and visual communication is expected, likely acquired through formal education or extensive practical experience.

Experience: Minimum of 15 years of comprehensive product design experience, with a significant portion dedicated to designing and shipping consumer products at a large scale.

Required Skills:

• Principal-level craft and demonstrable expertise in visual design, with a strong portfolio showcasing sophisticated aesthetic judgment.

• Proven ability in systems design, including the creation and maintenance of robust design systems that enable efficient collaboration and adoption by diverse teams.

• Fluency in operating at both strategic (design strategy, creative direction) and tactical (high-velocity, polished execution) levels.

• Demonstrated proficiency with AI-first design practices, actively utilizing AI tools for design, prototyping, and accelerated shipping.

• Exceptional cross-functional collaboration skills, adept at navigating complex conversations and competing priorities across product, engineering, and marketing with a low-ego, high-impact approach.

• Comfort and adaptability with the role's developmental arc: starting as a hands-on Individual Contributor and progressing to leadership. Preferred Skills:

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

• Agency background, exhibiting versatility and speed in building across various categories.

• Motion design and animation proficiency.

• Experience in managing and project-managing contract designers.

• A genuine passion for learning science and education, understanding the core mission of Quizlet.

• Ambition for long-term growth, with a vision to build and lead a comprehensive design organization in an AI-native company.

📝 Enhancement Note: The experience requirement of 15+ years, coupled with the "principal-level craft" and "systems design ability," indicates a need for a seasoned design leader with a proven track record of impacting large-scale consumer products. The emphasis on AI-first practices suggests a forward-looking candidate who is eager to adopt and innovate with new technologies.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A comprehensive portfolio showcasing at least 15 years of product design experience, with a strong emphasis on consumer products at significant scale.

• Demonstrated expertise in setting visual and experiential direction for complex digital products.

• Case studies highlighting the design and maintenance of robust, scalable design systems that empowered broader adoption and contribution.

• Examples of executing high-velocity, polished design work, particularly in fast-paced environments.

• Evidence of utilizing AI-assisted design and development tooling to accelerate prototyping and shipping cycles.

• Demonstrations of strategic thinking, including design strategy formulation and creative direction setting.

• Examples of successful cross-functional collaboration, illustrating problem-solving and consensus-building with product, engineering, and marketing stakeholders. Process Documentation:

• Documentation of processes used to translate learner insights, market trends, and brand signals into effective design standards and strategies.

• Examples of workflow design for building and maintaining design systems that cater to product, marketing, and internal tools.

• Case studies detailing the implementation of AI-first design practices and their impact on design velocity and output.

• Documentation of collaboration frameworks used to partner with User Research, Data Science, and Product Marketing.

📝 Enhancement Note: The portfolio requirements emphasize not just the final output but also the underlying processes and strategic thinking. Candidates will need to clearly articulate how they leverage AI, build scalable systems, and collaborate effectively, demonstrating a holistic approach to design leadership.

💵 Compensation & Benefits

Salary Range: $212,000 - $289,000 USD per year.

Benefits:

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

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

• Generous Paid Family Leave.

• Flexible Spending Account (FSA) and Health Savings Account (HSA) options.

• Commuter benefits.

• Wellness benefits.

• 20 days of paid vacation, with encouragement to utilize them.

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

• Access to LinkedIn Learning and other professional development resources.

Working Hours: Standard full-time role, likely around 40 hours per week, with flexibility encouraged for work-life balance, as per company culture. The hybrid model requires a minimum of three days per week in the San Francisco or NYC office (Wednesday and Thursday are mandatory in-office days).

📝 Enhancement Note: The salary range provided is competitive for a senior leadership role in a major tech hub like San Francisco, especially for a Head of Design position at a company with Quizlet's reach and growth trajectory. The benefits package is robust, reflecting a commitment to employee well-being and professional development, which are attractive to senior operations and design professionals.

🎯 Team & Company Context

🏢 Company Culture

Industry: EdTech (Education Technology) / Learning Platform. Quizlet operates at the intersection of education, technology, and AI, leveraging cognitive science and machine learning to personalize learning experiences. This market is highly competitive and rapidly evolving, with a strong focus on user engagement and learning outcomes.

Company Size: Over 500 employees (based on typical company structures for a $1B+ valuation with significant user base). This size indicates a well-established organization with scalable processes but still retains agility for innovation.

Founded: Quizlet was founded in 2005. This long history in the EdTech space suggests a company with deep understanding of its user base and a proven ability to adapt to market changes, now focusing on an AI-native future.

Team Structure:

• The Design team is described as "small but mighty" with significant impact. It operates embedded within product, engineering, and user research teams, working in tight weekly cycles.

• The Head of Design reports to the VP User Experience and works daily with product, engineering, and marketing leadership.

• The role will initially be a hands-on Individual Contributor (IC) and will transition to managing product designers and a contractor network for brand and marketing. Methodology:

• Emphasis on AI-native adaptive learning platform development, integrating generative AI and cognitive science.

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

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

• Collaborative approach, working in tight-knit teams with product and engineering.

Company Website: https://quizlet.com/

📝 Enhancement Note: Quizlet's mission to "help every learner achieve their outcomes" is a strong cultural anchor. The company's growth to over $1 billion valuation and its significant user base suggest a successful, mission-driven organization. The "AI-native" focus is a key strategic direction, indicating that innovation and technological advancement are highly valued.

📈 Career & Growth Analysis

Operations Career Level: This role represents a senior leadership position, falling under executive or senior management. It's a critical juncture where an individual moves from being a primary individual contributor with significant influence (Principal Designer) to a key organizational leader responsible for a department's vision, execution, and team development.

Reporting Structure: The Head of Design reports to the VP User Experience. This structure places the role within a broader UX leadership framework, likely involving collaboration with other design or research leaders, and reporting on key design initiatives and team performance to executive leadership.

Operations Impact: The impact of this role is substantial. By defining the "look, feel, and experience of everything we ship," the Head of Design directly influences user engagement, learning effectiveness, brand perception, and ultimately, Quizlet's market position and revenue. The strategic integration of AI into the learning experience has the potential to redefine the company's value proposition.

Growth Opportunities:

• Leadership Expansion: Grow the design organization from a small team to a robust department capable of supporting a rapidly scaling AI-native platform. This includes hiring, mentoring, and developing talent.

• Strategic Influence: Play a pivotal role in shaping the long-term product vision and AI strategy of Quizlet, influencing company-wide direction.

• Industry Recognition: Lead design initiatives that could set new standards in EdTech and AI-driven learning experiences, potentially leading to industry recognition and thought leadership opportunities.

• Advanced AI Integration: Deepen expertise in leveraging cutting-edge AI tools for design and product development, becoming a leader in this emerging field.

📝 Enhancement Note: The dual-path nature of this role (hands-on IC to leader) offers a unique growth trajectory. It allows for immediate impact through execution while building the foundation for long-term leadership and organizational development. The "five-year vision" for this person to build and lead the design organization of an AI-native company highlights significant long-term potential.

🌐 Work Environment

Office Type: Hybrid work environment. Employees are expected to be in the San Francisco or NYC office at least three days a week, with specific days (Wednesday and Thursday) mandated for in-office presence to foster collaboration. This suggests a blend of remote flexibility and in-person team synergy.

Office Location(s): San Francisco, California, and New York City. These are major tech hubs, offering access to talent, resources, and a vibrant professional community. The specific office setup in San Francisco is assumed to be a modern, collaborative workspace designed to support hybrid teams.

Workspace Context:

• Collaborative Environment: The hybrid model with mandatory in-office days is designed to facilitate in-person collaboration, brainstorming, and team building, essential for a design leadership role.

• Technology & Tools: Access to cutting-edge AI tooling and standard design software necessary for rapid prototyping and production-quality output. The company emphasizes an "AI-first" approach, implying a tech-forward environment.

• Team Interaction: Opportunities to work closely with product, engineering, user research, and marketing leadership on a daily basis, fostering cross-functional understanding and alignment.

Work Schedule: While the role is full-time, the company promotes a healthy work-life balance, encouraging employees to take their 20 vacation days. The hybrid schedule offers some flexibility outside of the mandated in-office days.

📝 Enhancement Note: The hybrid model is a key aspect of the work environment, balancing the benefits of remote work with the necessity of in-person collaboration for a leadership role. The emphasis on specific in-office days suggests a structured approach to hybrid work, aiming to maximize team cohesion and productivity.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Review of application, resume, and portfolio to assess qualifications and alignment with the role's requirements.

• Portfolio Deep Dive: A session focused on reviewing the candidate's portfolio, discussing specific projects, design decisions, impact, and the candidate's approach to systems design and AI-assisted workflows. This is where the "principal-level craft" and strategic thinking will be evaluated.

• Cross-Functional Interviews: Meetings with Product, Engineering, and Marketing leadership to assess collaboration style, strategic alignment, and ability to navigate competing priorities. Case studies or hypothetical problem-solving scenarios related to Quizlet's platform may be presented.

• Leadership/VP Interview: A conversation with the VP User Experience and potentially other senior leaders to discuss leadership philosophy, team management approach, vision for the design organization, and cultural fit.

• Final Round/Executive Interview: Potential discussion with higher-level executives to confirm strategic alignment and overall fit with the company's direction.

Portfolio Review Tips:

• Showcase Scale & Impact: Prioritize projects that demonstrate experience with large consumer products and measurable user impact (e.g., increased engagement, conversion, learning outcomes).

• Highlight Systems Design: Clearly articulate your process for designing, implementing, and maintaining design systems. Show how these systems enabled efficiency and consistency across multiple products or platforms.

• Demonstrate AI Integration: Include examples of how you've used AI tools in your design process for ideation, prototyping, or execution. Quantify any efficiency gains or improvements in output quality.

• Craft Narrative: For each project, tell a compelling story: the problem, your role, the process, the solution, and the quantifiable results.

• Visual Polish: Ensure your portfolio is visually stunning and reflects a high level of craft and attention to detail, aligning with the "strong visual taste" requirement.

• Address the Arc: Be prepared to discuss your transition from hands-on IC to leadership, highlighting your readiness for both phases of this role.

Challenge Preparation:

• AI-Driven Design Challenge: Expect a potential challenge focused on how you would leverage AI to solve a specific design problem for Quizlet, or how you would integrate AI into an existing workflow.

• Design System Scenario: Be ready to discuss how you would approach a specific challenge related to expanding or evolving an existing design system.

• Cross-Functional Problem Solving: Prepare for scenarios where you need to balance conflicting requirements from product, engineering, and marketing.

📝 Enhancement Note: The interview process is designed to assess a candidate's end-to-end capabilities, from individual craft and strategic thinking to leadership potential and cross-functional collaboration. The portfolio review is paramount, serving as the primary vehicle to demonstrate expertise and experience.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly likely, as it's the industry standard), Sketch, Adobe Creative Suite (Photoshop, Illustrator).

• AI-Assisted Design Tools: Candidates are expected to be proficient with emerging AI tools for design and prototyping (specific tools not mentioned, but candidates should demonstrate familiarity with the landscape, e.g., Midjourney for ideation, AI-powered prototyping tools, AI code generation assistants).

• Design Systems: Experience with tools for managing and documenting design systems (e.g., Zeroheight, Storybook, internal documentation platforms).

Analytics & Reporting:

• Product Analytics: Amplitude, Mixpanel, Google Analytics, or similar platforms for understanding user behavior and product performance.

• Data Visualization: Tableau, Power BI, or similar tools for creating dashboards and reporting on design impact.

• User Research Tools: Tools for surveys, user interviews, usability testing (e.g., UserTesting.com, Lookback, SurveyMonkey).

CRM & Automation:

• While not directly a design tool, an understanding of how design integrates with CRM (e.g., Salesforce) and marketing automation platforms (e.g., HubSpot, Marketo) can be beneficial for brand and marketing design alignment.

📝 Enhancement Note: The emphasis on "AI-assisted design and development tooling" and an "AI-first design practice" is a critical differentiator. Candidates should be prepared to discuss their experience with current AI tools in design and their vision for how these technologies will shape future design workflows.

👥 Team Culture & Values

Operations Values:

• Learner-Centricity: A deep commitment to understanding and serving the needs of learners, prioritizing their outcomes and experience.

• Innovation & AI-First: Embracing cutting-edge technology, particularly AI, to reimagine learning and drive efficiency.

• High-Quality Execution: Striving for excellence in craft and delivery, shipping polished, impactful work.

• Curiosity & Openness: A mindset of continuous learning, exploration, and receptiveness to new ideas and feedback.

• Collaboration & Communication: Fostering honest, respectful dialogue and working effectively across teams.

• Initiative & Ownership: Encouraging individuals to take ownership, drive projects forward, and make decisions.

Collaboration Style:

• Embedded Teams: Designers work closely within product, engineering, and user research squads, fostering tight communication and rapid iteration.

• Cross-Functional Partnership: Strong emphasis on partnering with product, engineering, marketing, and executive leadership to align on strategy and priorities.

• Feedback Culture: Openness to constructive feedback and iterative improvement, both within the design team and across departments.

• Knowledge Sharing: Encouraging the sharing of insights, best practices, and learnings, particularly around AI and design innovation.

📝 Enhancement Note: Quizlet's culture appears to be a blend of mission-driven passion for education, a forward-thinking embrace of technology (especially AI), and a strong emphasis on collaborative execution and continuous improvement. This environment would appeal to designers who are both creative problem-solvers and effective team players.

⚡ Challenges & Growth Opportunities

Challenges:

• Rapid AI Evolution: Keeping pace with the accelerating advancements in AI tools and methodologies and integrating them effectively into design workflows.

• Scaling Design Systems: Evolving and maintaining design systems that serve a growing product suite, diverse user base, and multiple contributor types (designers, PMs, marketers, contractors).

• Balancing IC vs. Leadership: Successfully transitioning from a principal individual contributor role to a leadership position, managing people and strategic direction while potentially still contributing hands-on.

• Cross-Functional Alignment: Navigating competing priorities and ensuring design vision is understood and upheld across fast-moving product, engineering, and marketing teams.

• Brand Evolution: Defining and evolving the brand identity of an established platform as it undergoes a significant AI-native transformation.

Learning & Development Opportunities:

• AI Design Leadership: Becoming a recognized leader in AI-driven design for learning platforms, shaping the future of EdTech.

• Team Building & Mentorship: Developing and growing a high-performing design organization, mentoring designers, and fostering a strong team culture.

• Strategic Product Impact: Directly influencing the strategic direction of a major EdTech platform and its AI initiatives.

• Industry Conferences & Networking: Opportunities to represent Quizlet at industry events and build a professional network within the design and EdTech communities.

• Advanced Leadership Training: Access to resources like LinkedIn Learning and internal mentorship to hone leadership and management skills.

📝 Enhancement Note: The role presents significant challenges related to technological innovation (AI) and organizational evolution (scaling design, transitioning to leadership). However, these challenges are directly tied to substantial growth opportunities, making it an attractive position for ambitious design leaders.

💡 Interview Preparation

Strategy Questions:

• "How would you approach setting the visual and experiential direction for an AI-native learning platform like Quizlet, given its current scale and future ambitions?" (Preparation: Research Quizlet's current brand, identify potential areas for AI integration in UX, think about how to balance established brand with innovation).

• "Describe a time you had to manage competing priorities between Product, Engineering, and Marketing. How did you ensure design velocity remained high?" (Preparation: Use the STAR method, focus on communication, negotiation, and data-driven decision-making).

• "Walk us through your process for designing and implementing a design system that could be effectively used by product designers, marketers, and external contractors." (Preparation: Be ready to discuss components, documentation, governance, adoption strategies, and tooling). Company & Culture Questions:

• "What excites you most about Quizlet's mission and its move towards an AI-native future?" (Preparation: Articulate genuine interest in education technology and AI's potential impact on learning).

• "How do you foster a culture of collaboration and feedback within a design team, especially during a period of significant change?" (Preparation: Discuss your leadership style, team-building strategies, and experience with iterative processes).

• "How do you measure the impact of design on business outcomes, and what metrics would you prioritize for Quizlet's learning products?" (Preparation: Think about engagement, retention, learning efficacy, conversion rates, and user satisfaction metrics). Portfolio Presentation Strategy:

• Narrative Arc: Structure your presentation around the evolution of your career, starting with your principal-level craft and moving towards your leadership aspirations.

• Quantify Impact: For each case study, clearly articulate the problem, your solution, your role, and the measurable results (e.g., "Increased user engagement by X%", "Reduced design production time by Y% using AI tools").

• Showcase Systems Thinking: Dedicate time to explaining your approach to design systems, illustrating how they create consistency and efficiency.

• Highlight AI Integration: Clearly call out where and how you've used AI tools, demonstrating your forward-thinking approach and ability to leverage new technologies.

• Be Ready for Deep Dives: Prepare to answer detailed questions about your design decisions, technical challenges, and collaboration processes for each project.

• Address the Role's Arc: Explicitly discuss how your portfolio and experience prepare you for both the initial hands-on phase and the subsequent leadership responsibilities.

📝 Enhancement Note: Candidates should prepare to discuss their experience with AI tools in design, their approach to scalable design systems, and their ability to collaborate effectively across functions. The interview process is designed to assess both deep craft and strategic leadership potential.

📌 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 highlight your experience with large-scale consumer products, design systems, AI-assisted design, and strategic leadership. Focus on case studies that demonstrate impact and your ability to operate at both individual contributor and leadership levels.

• Resume Optimization: Ensure your resume clearly articulates your 15+ years of experience, emphasizing achievements in product design, systems design, AI integration, and any team leadership or management roles. Use keywords relevant to design leadership, AI, and EdTech.

• Interview Preparation: Thoroughly research Quizlet's mission, product, and recent AI initiatives. Prepare to discuss your portfolio projects in detail, focusing on your strategic thinking, problem-solving approach, and leadership philosophy. Practice articulating how you would transition into the leadership aspect of this role.

• Company Research: Understand Quizlet's market position, competitors, and strategic goals, particularly their AI-native transformation. Be ready to discuss how your vision aligns with theirs and how you would contribute to their culture of innovation and learner-centricity.

⚠️ 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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