Head of Design

📍 Job Overview

Job Title: Head of Design

Company: Kikoff

Location: San Francisco, CA, United States

Job Type: Full-Time

Category: Design Leadership / Product Design

Date Posted: 2026-04-24

Experience Level: 10+ Years

Remote Status: On-site

🚀 Role Summary

• Spearhead the overall design vision, craft, and execution for a leading FinTech company, ensuring a cohesive and high-quality user experience across all touchpoints.

• Lead, manage, and develop a product design team, focusing on hands-on mentorship, talent strategy, and fostering a culture of user obsession and craftsmanship.

• Architect and build a robust design system from the ground up, defining and enforcing design patterns to minimize design debt and ensure brand consistency.

• Serve as a strategic partner to Engineering, Product, and Marketing, driving cross-functional impact and integrating brand and product design efforts for cohesive output.

• Innovate and define the team's approach to leveraging AI in design workflows, including hands-on experimentation and guiding the team in adopting new AI tools and processes.

📝 Enhancement Note: This role is positioned as a senior leadership opportunity within a growth-stage FinTech startup, emphasizing hands-on involvement, team building, and strategic influence. The "Head of Design" title, coupled with the responsibilities of building a design system from scratch and integrating AI, indicates a significant impact on the company's product strategy and user experience. The explicit mention of "close to the pixels, close to the product, and close to the team" highlights a "player-coach" expectation.

📈 Primary Responsibilities

• Manage, coach, and develop the product design team through hands-on mentorship, providing clear expectations, honest feedback, and career growth paths.

• Own the hiring and talent strategy for the design team, identifying and recruiting designers who elevate the team's capabilities and shaping an effective organizational structure.

• Establish and maintain a high bar for design craft, ownership, and user obsession, ensuring exceptional quality in all design outputs.

• Define the overarching design vision for Kikoff, encompassing visual aesthetics, interaction design, UX fundamentals, and the team's operational methodologies.

• Make critical design decisions to resolve ambiguity and drive progress when the design team encounters challenges, ensuring timely project advancement.

• Develop and implement a comprehensive design system from inception, making it usable and desirable for the entire company, including coding agents.

• Define and enforce consistent design patterns across the product to reduce design debt and enhance user experience coherence.

• Drive the standards for visual identity and user experience across product, marketing, and brand touchpoints, ensuring a unified "Kikoff feel."

• Act as a strategic peer to Engineering, Product, and Marketing leadership, influencing product direction and ensuring design considerations are integrated early.

• Foster collaboration between product design and creative functions, uniting them to deliver both brand-quality products and product-quality brand experiences.

• Translate company-wide strategic direction on design, brand, and creative into actionable work for product, marketing, and creative teams.

• Champion user insights by conducting journey workshops, incorporating user feedback, and ensuring the team designs for real user needs.

• Define and implement the Kikoff design team's AI strategy, including hands-on exploration of AI tools, prototyping, and guiding adoption.

• Experiment with new AI tools and workflows, identifying effective methods for the team to leverage AI while maintaining design craft and quality.

📝 Enhancement Note: The responsibilities are detailed and cover the full spectrum of a Head of Design role, from people management and strategic vision to hands-on execution and innovative adoption of new technologies like AI. The emphasis on "building the design foundation" and "defining and enforcing design patterns" suggests a need for someone who can establish scalable processes and components.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong foundation in design principles, potentially acquired through formal education (e.g., Bachelor's or Master's in Design, HCI, or related field) or equivalent practical experience, is expected.

Experience:

• Minimum of 10 years of progressive experience in product design, with a significant portion dedicated to consumer-facing, mobile-first products.

• A minimum of 7 years in a leadership capacity, managing and growing design teams, with a proven ability to develop designers into senior individual contributors and build teams that can operate autonomously.

Required Skills:

• Deep expertise in visual design, interaction design, and user experience (UX) principles, with the ability to provide detailed, pixel-level feedback and elevate design work.

• Proven track record of building and successfully implementing design systems that are adopted by the team and scale effectively with product growth.

• Strong experience partnering with Product Management and Engineering teams as a peer, influencing product strategy and successfully shipping impactful features.

• Hands-on proficiency and a clear point of view on modern AI tooling for design, including practical application and understanding of its impact on workflows and craft.

• Exceptional ability to improve team performance through clear communication, constructive feedback, and fostering trust with strong practitioners.

• Sharp eye for brand integrity, ensuring brand values are embedded in the product's DNA and aligning stakeholders on a unified brand vision.

• Strong understanding of how to ensure every UI element reflects the company's specific visual language.

• Demonstrated ability to make decisive calls in ambiguous situations, guiding the team to resolution.

Preferred Skills:

• Experience within the FinTech industry, particularly in consumer credit or other regulated consumer product environments.

• Experience leading both product design and brand/creative functions, or a proven ability to bridge these disciplines.

• Experience in building or scaling design systems that support a diverse range of surfaces, including native mobile applications and marketing websites.

📝 Enhancement Note: The experience requirements are substantial, indicating a need for a seasoned leader with a proven history of building and scaling design functions in fast-paced, consumer-focused environments. The emphasis on "growing designers into senior ICs" and "building a team that does great work without you in the room" highlights the need for a strong mentor and delegator. The explicit requirement for hands-on AI tooling experience is a key differentiator for this role.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A curated selection of case studies showcasing end-to-end product design ownership, from initial concept and user research to final execution and impact measurement.

• Evidence of leading design initiatives, demonstrating strategic thinking, problem-solving, and the ability to drive design vision.

• Examples of building or significantly contributing to design systems, illustrating their architecture, components, and adoption strategy.

• Projects that highlight cross-functional collaboration, detailing how you partnered with Product, Engineering, and Marketing to achieve business objectives.

• Case studies demonstrating experience with mobile-first, consumer-facing applications, with a focus on user experience and visual craft.

• Demonstrations of how you've integrated user insights and research into the design process to inform product decisions.

Process Documentation:

• Documented methodologies for user research, journey mapping, and insights synthesis.

• Frameworks for defining design patterns and ensuring their consistent application across product surfaces.

• Examples of design system documentation, including component libraries, style guides, and usage guidelines.

• Processes for fostering design team growth, including mentorship frameworks, feedback mechanisms, and career development planning.

• Strategies for integrating AI into design workflows, outlining adoption plans, tool evaluation, and team training.

• Cross-functional collaboration models and communication protocols for design, product, and engineering alignment.

📝 Enhancement Note: Given the leadership nature of this role and the emphasis on building foundational elements like a design system, candidates will be expected to present a portfolio that not only showcases their design skills but also their strategic thinking, leadership capabilities, and ability to establish scalable design processes. The inclusion of AI in design is a critical component that should be evident in their portfolio.

💵 Compensation & Benefits

Salary Range: The provided base salary range for this position is $260,000 to $374,000 USD annually. This range is competitive for a Head of Design role in San Francisco, reflecting the senior level of responsibility, extensive experience requirements, and the company's growth stage in the FinTech sector.

Benefits:

• Comprehensive health, dental, and vision insurance plans.

• Generous paid time off (PTO) and company holidays.

• Stock options or equity in a rapidly growing FinTech unicorn.

• 401(k) retirement savings plan.

• Professional development budget for conferences, courses, and learning opportunities.

• Opportunities for significant career growth and impact within a mission-driven company.

• Potential for performance-based bonuses.

Working Hours: The standard working hours are expected to be around 40 hours per week. However, given the leadership nature of the role and the startup environment, flexibility may be required to meet project deadlines and strategic objectives. The on-site requirement in San Francisco suggests a need for consistent availability during core business hours.

📝 Enhancement Note: The salary range is explicitly provided in the job description. The benefits listed are standard for senior tech roles in San Francisco and are inferred to support a high-performing design leader. The working hours are estimated based on typical full-time expectations, with an acknowledgment of potential startup-related flexibility needs.

🎯 Team & Company Context

🏢 Company Culture

Industry: FinTech (Financial Technology). Kikoff operates in a dynamic and rapidly evolving sector, focusing on providing affordable financial tools, credit building, and debt reduction solutions powered by AI. This industry is characterized by innovation, regulatory considerations, and a strong emphasis on user trust and security.

Company Size: Kikoff is described as a "FinTech Unicorn," indicating a significant valuation and a substantial, likely rapidly growing, employee base. Unicorn status typically implies hundreds of employees, often ranging from 200-1000+, suggesting a well-established but still agile operational structure. This size allows for significant impact but also requires robust processes and clear communication.

Founded: Founded in 2019, Kikoff is a relatively young company, positioning it as a growth-stage startup with a proven product-market fit and significant traction. This implies a culture that is likely fast-paced, innovative, and focused on scaling operations and user acquisition.

Team Structure:

• The design team is expected to grow, with the Head of Design responsible for shaping its structure and hiring strategy.

• The Head of Design will be a direct partner to senior leadership, indicating a flat or matrixed organizational structure where design has a voice in strategic decisions.

Methodology:

• Data-Driven Decisions: The company leverages AI extensively, implying a strong emphasis on data analysis and using insights to drive product development and strategy.

• Process Optimization: The need to build a design system from the ground up and define design patterns highlights a focus on efficiency, consistency, and reducing "design debt."

• AI Integration: A key methodological focus is redefining design workflows through AI, emphasizing hands-on experimentation and practical adoption.

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

📝 Enhancement Note: The description of Kikoff as a "FinTech Unicorn" founded in 2019 provides context for a dynamic, growth-oriented environment. The emphasis on "extreme ownership, clear communication, a strong sense of craftsmanship, and the desire to create lasting work" points to a culture that values high performance, collaboration, and a commitment to quality. The integration of AI is positioned as a core differentiator for their product and operations.

📈 Career & Growth Analysis

Operations Career Level: This role represents a senior leadership position, specifically at the "Head" level within the Design function. It is a strategic role responsible for setting the vision, building and managing a team, and significantly influencing the company's product and brand direction. The expectation of hands-on involvement and mentorship also positions it as a "player-coach" role, offering opportunities for both strategic leadership and direct contribution.

Reporting Structure: The Head of Design will be a direct partner to senior leadership, suggesting they will likely report to a C-level executive, such as the CEO, CTO, or CPO. This direct line of communication and influence is crucial for driving design strategy across the organization.

Operations Impact: The Head of Design will have a profound impact on Kikoff's success by:

• Shaping the core user experience of financial products, directly influencing customer acquisition, retention, and satisfaction.

• Building and scaling a high-performing design team that elevates product quality and innovation.

• Establishing a strong brand identity and visual language that differentiates Kikoff in the competitive FinTech market.

• Driving efficiency and consistency through a robust design system and optimized workflows, including the strategic adoption of AI.

Growth Opportunities:

• Leadership Expansion: Potential to grow the design function, potentially encompassing brand, creative, and UX research as the company scales.

• Strategic Influence: Opportunity to shape product roadmaps and company-wide strategic decisions, leveraging design expertise.

• Innovation Leadership: Lead the charge in adopting and integrating cutting-edge technologies like AI into design practices, setting industry trends.

• Team Development: Mentor and grow a team of talented designers, fostering their careers and building a strong design culture.

• Executive Development: Gain experience operating at the executive level, contributing to business growth and P&L considerations.

📝 Enhancement Note: This role is positioned as a critical leadership opportunity within a high-growth FinTech company. The growth path is clearly defined by the potential to expand the design function and increase strategic influence within the executive team, particularly given the company's unicorn status and focus on innovation.

🌐 Work Environment

Office Type: The role is based in San Francisco, CA, and is designated as "On-site." This indicates a traditional office-based work environment with a physical workspace designed for collaboration and in-person interaction.

Office Location(s): San Francisco, CA, United States. This location places the role within a major tech hub, offering access to a vibrant talent pool and industry events. Specific office details beyond the city are not provided but can be assumed to be a modern, collaborative workspace typical of tech startups.

Workspace Context:

• Collaborative Environment: The on-site requirement suggests a focus on in-person collaboration, team meetings, brainstorming sessions, and spontaneous interactions that foster innovation.

• Tools and Technology: As Head of Design, access to state-of-the-art design software, hardware, and potentially AI-powered design tools is expected. The company's FinTech nature and use of AI imply a technologically advanced environment.

• Team Interaction: The role emphasizes being "close to the team," indicating a work environment that encourages regular interaction, mentorship, and direct engagement with designers.

Work Schedule: While core working hours are implied for an on-site role, the emphasis on "extreme ownership" and "making the call when designers are stuck" suggests a culture where dedication and responsiveness are valued. Flexibility may be expected to accommodate critical project phases or strategic initiatives.

📝 Enhancement Note: The "On-site" designation in San Francisco points to a classic startup office environment. The emphasis on being "close to the pixels, close to the product, and close to the team" reinforces the idea of a hands-on, collaborative physical workspace rather than a remote setup.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A preliminary call with a recruiter or hiring manager to assess overall fit, experience, and alignment with the role's core requirements.

• Hiring Manager Interview: In-depth discussion with the hiring manager (likely a senior executive) focusing on leadership philosophy, team building, strategic vision, and experience with design systems and AI.

• Design Team/Peer Interviews: Meetings with current design team members and potentially peers from Product and Engineering to assess collaboration style, mentorship approach, and technical design acumen.

• Portfolio Review & Presentation: A dedicated session where candidates present their portfolio, walking through key case studies to demonstrate their design process, strategic thinking, leadership impact, and ability to handle ambiguity. This will also include discussion on their approach to AI in design.

• Executive/Final Interview: A final conversation with a senior leader (e.g., CEO, CTO) to discuss company vision, cultural fit, and long-term strategic alignment.

Portfolio Review Tips:

• Curate Strategically: Select 3-5 of your strongest, most relevant case studies that highlight leadership, team building, design system development, AI integration, and significant business impact in consumer-facing products.

• Structure for Impact: For each case study, clearly articulate the problem, your role and approach, the key decisions made (especially in ambiguous situations), the solutions developed, the process followed (including AI usage), and the measurable outcomes.

• Showcase Leadership: Emphasize your role in mentoring designers, shaping team strategy, and driving cross-functional alignment. Highlight instances where you elevated the team's craft and ownership.

• Highlight AI Integration: Clearly detail how you've used AI tools in your design process. Discuss your point of view on their benefits, limitations, and how you've guided teams in their adoption.

• Brand Integrity Focus: Demonstrate how you ensure brand consistency and visual language across product and marketing surfaces.

• Be Prepared for Ambiguity: Articulate how you navigate design challenges and make decisions when faced with uncertainty.

• Practice Your Presentation: Rehearse your presentation to ensure a smooth, engaging, and concise delivery within the allotted time.

Challenge Preparation:

• Be prepared to discuss hypothetical scenarios related to scaling a design team, building a design system from scratch, integrating AI into design workflows, and resolving design conflicts.

• Practice articulating your design philosophy, leadership style, and how you foster a culture of craftsmanship and user obsession.

• Research Kikoff's current product and brand to form informed opinions and potential areas for design enhancement.

📝 Enhancement Note: The interview process is typical for a senior leadership role, emphasizing strategic thinking, leadership capabilities, and hands-on design expertise. The portfolio review is a critical component, and candidates should be prepared to showcase their ability to lead, build, and innovate, with a specific focus on AI integration.

🛠 Tools & Technology Stack

Primary Tools:

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

• Design Systems: Figma (for component libraries and collaboration), Storybook (for code-based component documentation, if applicable).

• AI Design Tools: Candidates are expected to have hands-on fluency. This could include tools for AI-assisted image generation (e.g., Midjourney, DALL-E), AI-powered UI generation or optimization (e.g., Uizard, Galileo AI), AI for content creation, or AI for user research analysis. Specific tools are less important than the demonstrated understanding and application of AI in design.

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

Analytics & Reporting:

• User Analytics: Mixpanel, Amplitude, Google Analytics.

• A/B Testing Platforms: Optimizely, VWO.

• Data Visualization: Tableau, Looker (if integrated with product data).

CRM & Automation:

• While not directly design tools, an understanding of CRM (e.g., Salesforce, HubSpot) and marketing automation platforms is beneficial for cross-functional collaboration, especially with Marketing.

📝 Enhancement Note: The technology stack is inferred based on industry standards for a growth-stage FinTech company and the specific requirements of a Head of Design role. The emphasis on AI tooling is a key differentiator, and candidates should be prepared to discuss their experience with relevant AI applications in design.

👥 Team Culture & Values

Operations Values:

• Extreme Ownership: Taking full responsibility for design outcomes, from conception to execution and impact, and driving initiatives to completion.

• Clear Communication: Fostering transparent and effective communication within the design team and with cross-functional partners, ensuring alignment and shared understanding.

• Strong Sense of Craftsmanship: Upholding high standards for visual design, interaction design, and user experience, with meticulous attention to detail and a commitment to quality.

• User Obsession: Deeply understanding and empathizing with users, prioritizing their needs and feedback in all design decisions, and advocating for the user's voice.

• Scrappiness & Pragmatism: Moving fast, building efficiently, and making deliberate tradeoffs. Knowing when to innovate and when to leverage existing solutions without over-engineering.

• Risk-Oriented Decision Making: Making calculated bets and understanding the difference between valuable risks and unnecessary ones, especially in a FinTech context.

• Humility & Gratitude: Approaching work with an understanding of the effort and collaboration required for success, appreciating team members and opportunities.

Collaboration Style:

• Peer-Level Partnership: Working as an equal with Engineering, Product, and Marketing leaders, contributing strategically and influencing decisions collaboratively.

• Cross-Functional Integration: Actively seeking opportunities to bring design closer to other functions, ensuring a unified approach to product and brand.

• Feedback Culture: Encouraging open, honest, and constructive feedback within the design team and across departments to drive continuous improvement.

• Knowledge Sharing: Promoting a culture where learnings, best practices, and new methodologies (especially regarding AI) are shared openly to elevate the entire team.

📝 Enhancement Note: The company culture values are explicitly stated, providing a clear framework for what kind of behaviors and attitudes are expected. The emphasis on "extreme ownership," "craftsmanship," and "user obsession" aligns perfectly with a high-performing design team, while "scrappiness" and "risk-orientation" point to a dynamic startup environment.

⚡ Challenges & Growth Opportunities

Challenges:

• Scaling Design Systems: Building and maintaining a design system that effectively supports a growing product and diverse teams, ensuring adoption and evolution.

• Integrating AI Seamlessly: Defining and implementing AI workflows that enhance design efficiency and creativity without compromising craft or user experience, and navigating potential ethical or quality concerns.

• Balancing Craft and Speed: Maintaining high design standards and brand integrity in a fast-paced startup environment where rapid iteration is crucial.

• Cross-Functional Alignment: Ensuring consistent brand and design vision across product, marketing, and creative efforts, managing diverse stakeholder needs and priorities.

• Talent Acquisition and Development: Attracting and retaining top design talent in a competitive San Francisco market and developing a team that can meet evolving demands.

Learning & Development Opportunities:

• AI in Design Specialization: Deep dive into emerging AI tools and methodologies for design, becoming a recognized expert within the company and potentially the industry.

• FinTech Domain Expertise: Gain in-depth knowledge of consumer finance, credit building, and regulated product design, a valuable niche skill.

• Strategic Leadership Development: Grow into a broader leadership role, potentially overseeing multiple creative disciplines and contributing more significantly to executive strategy.

• Mentorship and Coaching: Hone leadership and coaching skills by developing a team of designers and fostering their career progression.

• Industry Exposure: Participate in FinTech and design conferences, staying abreast of industry trends and best practices.

📝 Enhancement Note: The challenges presented are typical for a senior design leader in a growth-stage tech company, particularly one focused on innovation like AI. The growth opportunities are substantial, focusing on expanding leadership scope and developing specialized expertise in high-demand areas like AI and FinTech.

💡 Interview Preparation

Strategy Questions:

• "Describe your philosophy on leading and growing a product design team. How do you foster a culture of craftsmanship and user obsession while maintaining agility?" (Preparation: Focus on your mentorship style, hiring strategies, feedback mechanisms, and how you balance quality with speed.)

• "Walk us through your experience building or scaling a design system from the ground up. What were the key challenges, how did you ensure adoption, and what was its impact?" (Preparation: Have a specific case study ready, detailing your process, component strategy, documentation, and adoption metrics.)

• "How do you see AI transforming the design process, and what is your hands-on experience with AI design tools? How would you integrate AI into our design workflow at Kikoff?" (Preparation: Be ready to discuss specific AI tools you've used, your opinions on their utility, and a practical plan for Kikoff, including potential pilot projects and team training.)

• "Describe a time you had to make a critical design decision when your team was stuck in ambiguity. What was the situation, how did you resolve it, and what was the outcome?" (Preparation: Use the STAR method to outline a scenario demonstrating your decisiveness and problem-solving skills.)

Company & Culture Questions:

• "What excites you most about Kikoff's mission and our position in the FinTech market?" (Preparation: Research Kikoff's product, mission, and recent news. Connect your personal values and career aspirations to their goals.)

• "How do you align with our stated values of extreme ownership, clear communication, craftsmanship, and user obsession?" (Preparation: Prepare specific examples from your career that demonstrate these values in action.)

Portfolio Presentation Strategy:

• Start with Your Vision: Begin by framing your overall design philosophy and leadership approach.

• Structure Case Studies Logically: For each case study, clearly outline the problem, your role, the process (including AI usage), the solution, and the impact/results. Quantify success whenever possible.

• Emphasize Leadership Moments: Highlight instances where you mentored designers, drove strategic decisions, or managed team growth.

• Showcase Design System Expertise: Dedicate specific time to explain your approach to design systems, their architecture, and adoption.

• Demonstrate AI Fluency: Clearly articulate how AI tools were used in your projects and the benefits realized.

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

• Conclude with Company Fit: Reiterate why you are a strong cultural and strategic fit for Kikoff.

Challenge Preparation:

• Expect scenario-based questions related to scaling design, managing team performance, and integrating new technologies.

• Prepare to discuss how you would approach building Kikoff's design system and AI strategy from day one.

• Practice articulating your vision for the Kikoff brand and user experience.

📝 Enhancement Note: The interview preparation focuses on showcasing leadership, strategic thinking, hands-on design skills, and a clear vision for AI integration. Candidates need to be prepared to present a compelling narrative of their experience and align it with Kikoff's values and business objectives.

📌 Application Steps

To apply for this Head of Design position:

• Submit your application through the provided link on the Greenhouse platform.

• Portfolio Customization: Curate your portfolio to prominently feature case studies demonstrating leadership, design system development, AI integration in design, and impactful consumer-facing product design. Ensure it clearly articulates your strategic approach and measurable results.

• Resume Optimization: Tailor your resume to highlight your 10+ years of product design experience and 7+ years of team leadership, using keywords like "Design Leadership," "Design Systems," "AI Tooling," "Consumer-Facing," "Mobile-First," and "FinTech." Quantify your achievements and leadership impact.

• Interview Preparation Practice: Rehearse your portfolio presentation, focusing on clearly articulating your design vision, leadership philosophy, and hands-on AI experience. Practice answering strategy and culture questions using the STAR method.

• Company Research: Thoroughly research Kikoff's mission, product, target audience, and recent company news. Understand their FinTech space and identify areas where design and AI can drive further innovation and user value, aligning your responses with their strategic goals and stated values.

⚠️ 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.