Head of Design ($200K - $250K + Equity) at Overtone

📍 Job Overview

Job Title: Head of Design

Company: Overtone (Recruited by Jack & Jill)

Location: New York City, New York, United States

Job Type: FULL_TIME

Category: Product Design / User Experience

Date Posted: March 13, 2026

Experience Level: Senior / Lead (Implied 10+ years)

Remote Status: On-site (with potential for flexibility, implied by "New York City, USA" location and AI recruiter context)

🚀 Role Summary

• Spearhead the end-to-end product design strategy for a novel AI-powered dating platform, Overtone, from its foundational stages.

• Define and execute the visual and interactive soul of a category-defining, 0-to-1 product, moving beyond traditional swipe models to foster deep personal connection.

• Collaborate intimately with the founder (ex-Hinge CEO) and engineering teams to translate complex human emotions and AI capabilities into intuitive, elegant digital interfaces.

• Establish Overtone’s comprehensive design language, visual identity, and user experience standards, ensuring a high-trust, sophisticated, and safe environment for users.

📝 Enhancement Note: While the original listing is for a "Head of Design," the context of a "founding Head of Design" and the responsibility scope strongly suggest a senior leadership role focused on Product Design and UX. The emphasis on "0-to-1" and "founding opportunity" indicates a pivotal strategic role, rather than purely tactical design execution. The mention of AI and voice-based tools points towards a need for forward-thinking UX research and design innovation. The "New York City, USA" location implies an on-site requirement, though early-stage startups often offer some flexibility.

📈 Primary Responsibilities

• End-to-End Design Ownership: Lead the entire design lifecycle, from conceptualization and user research through high-level UX strategy, systems thinking, detailed UI execution, and motion design.

• Product Vision Translation: Directly partner with the founding team and engineering to translate the product vision and AI capabilities into tangible, user-friendly prototypes, iterative testing cycles, and polished product releases.

• Brand & Identity Development: Architect Overtone’s unique visual identity, design system, and brand guidelines, ensuring a consistent, trustworthy, and emotionally resonant user experience across all touchpoints.

• User-Centric Innovation: Drive innovation in matchmaking interaction models, leveraging AI and voice technologies to create a deeply personal and high-trust dating experience that differentiates from existing platforms.

• Cross-Functional Leadership: Serve as the primary design leader, closely collaborating with product, engineering, and marketing to ensure design integrity and strategic alignment throughout the product development process.

📝 Enhancement Note: The primary responsibilities are inferred from the "Job Description" and "What you will do" sections, emphasizing the comprehensive nature of the role and the strategic impact expected from a founding Head of Design. The focus on "0-to-1," "AI," and "voice-based tools" highlights the need for innovative problem-solving and a forward-thinking approach to user experience.

🎓 Skills & Qualifications

Education:

Experience:

• 10+ years of progressive experience in product design, with a strong emphasis on mobile-first consumer applications.

• Demonstrated experience in leading design initiatives from conception through launch, ideally in a 0-to-1 or early-stage startup environment.

Required Skills:

• UX Strategy & Systems Thinking: Ability to define high-level user experience strategies and design complex, interconnected systems for consumer applications.

• Visual Craft & UI Execution: Exceptional proficiency in typography, layout, visual design principles, and pixel-perfect UI implementation.

• Interaction Design & Motion Graphics: Strong understanding of user interaction patterns and the ability to incorporate motion design to enhance user experience and convey emotion.

• Prototyping & User Testing: Expertise in rapid prototyping tools and methodologies, coupled with a robust approach to user research and iterative testing.

• Design Systems Development: Experience in creating and maintaining scalable design systems and style guides.

• Entrepreneurial Mindset: Thrives in ambiguous environments, demonstrates initiative, and can operate effectively with a bias for action in a fast-paced startup setting.

Preferred Skills:

• Experience with AI-driven product features or voice-based interfaces.

• Familiarity with the dating app industry or platforms from Match Group.

• Experience working directly with founders and engineering teams in a highly collaborative manner.

• Strong understanding of ethical design principles, particularly in sensitive contexts like dating.

📝 Enhancement Note: The "ideal candidate" section provides the core requirements. The emphasis on "hybrid skills" and "elite visual craft" points to a need for a designer who is both a strategic thinker and a meticulous executor. The implied "10+" years of experience is derived from the seniority of a "Head of Design" role and the expectation of leading "end-to-end" processes in a "founding" capacity.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A curated portfolio showcasing a minimum of 3-5 significant product design projects, with a strong emphasis on mobile-first consumer applications.

• Demonstrated experience in defining and executing UX strategy and systems thinking for complex products.

• Clear examples of UI execution, including high-fidelity mockups and interactive prototypes.

• Case studies that highlight your ability to translate complex user needs and business objectives into elegant design solutions.

Process Documentation:

• Detailed case studies that walk through your design process, from initial problem definition and user research to ideation, prototyping, testing, and final UI implementation.

• Examples of how you have established and utilized design systems or style guides to ensure consistency and scalability.

• Demonstrations of your approach to user testing and iterative design, showing how feedback was incorporated to improve the product.

• Showcase of your ability to collaborate with engineering and product teams, illustrating your role in bringing a product from concept to launch.

📝 Enhancement Note: The portfolio requirements are inferred from the "ideal candidate" qualifications and the "What you will do" responsibilities. For a founding Head of Design, the portfolio must demonstrate strategic thinking, end-to-end execution capabilities, and a strong understanding of consumer product design, especially in sensitive social contexts. The emphasis is on showcasing process, not just final deliverables.

💵 Compensation & Benefits

Salary Range: $200,000 - $250,000 USD per year

Benefits:

• Equity: Significant stock options package, reflecting the founding nature of the role and the company's early stage.

• Health Insurance: Comprehensive medical, dental, and vision coverage.

• Paid Time Off: Generous vacation, sick leave, and holiday policy.

• Professional Development: Opportunities for continued learning, conferences, and skill enhancement.

• Impactful Work: Opportunity to shape a category-defining product and build a company culture from the ground up.

Working Hours:

• Full-time, approximately 40 hours per week. Flexibility is expected in a startup environment, especially during critical development phases.

📝 Enhancement Note: The salary range is explicitly stated in the input. Equity is also explicitly mentioned. Other benefits are standard for a full-time role in a funded startup, particularly one backed by a major player like Match Group. The working hours are estimated based on the "FULL_TIME" employment type. The "On-site" nature of the role in NYC is assumed to require typical office hours, with the understanding that startup environments often demand more.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology (AI, Dating, Social Networking)

Company Size: Early-Stage Startup (Implied by "founding Head of Design," "0-to-1 product," and "startup environment")

Founded: Recently (Implied by the "founding" nature of the role and the "0-to-1 product" description. Founder is from Hinge, suggesting recent inception and significant backing).

Company Description: Overtone is an innovative AI-powered dating startup based in NYC, founded by the former CEO of Hinge. Backed by Match Group, Overtone aims to revolutionize modern matchmaking by moving beyond traditional swipe mechanics and leveraging AI and voice-based tools to create a more personal, high-trust, and emotionally resonant user experience.

Team Structure:

• Founding Team: You will work directly with the visionary founder (ex-Hinge CEO) and a core team of engineers.

• Cross-functional Collaboration: Design will be central to product development, requiring close partnership with engineering and product management.

• Lean & Agile: Expect a dynamic, fast-paced environment where agility, rapid iteration, and direct communication are paramount.

Methodology:

• Data-Driven Design: Utilizing user data, AI insights, and A/B testing to inform design decisions and optimize user experience.

• Iterative Development: Employing rapid prototyping and continuous user feedback loops to refine the product.

• Human-Centric Approach: Focusing on deep user understanding to create emotionally intelligent and trustworthy digital interactions.

Company Website: https://www.jackandjill.ai/jack/job-listing?utm_source=job_listing&utm_medium=job_board&utm_campaign=44687fbf-a684-4777-ae5e-858580465442 (Note: This is the Jack & Jill application portal, not Overtone's direct website, which is not publicly provided.)

📝 Enhancement Note: Information about Overtone is pieced together from the "Company Description" and the context of the role. The backing by Match Group and the founder's background with Hinge are significant indicators of the company's potential and the environment. The "AI Recruiter" context suggests a tech-forward approach.

📈 Career & Growth Analysis

Operations Career Level: Founding Head of Design. This is a pivotal leadership role, marking the inception of the design function within the company. It offers the opportunity to build and scale the design team and process from the ground up.

Reporting Structure: You will report directly to the Founder and CEO, providing a unique opportunity for direct influence and visibility at the highest level of the organization.

Operations Impact: As the founding Head of Design, your work will have a direct and profound impact on the product's success, user adoption, brand perception, and ultimately, the company's ability to achieve its mission of revolutionizing modern matchmaking. Your design decisions will shape the core user experience and differentiate Overtone in a competitive market.

Growth Opportunities:

• Team Building & Leadership: Opportunity to recruit, mentor, and lead the future design team as the company scales.

• Strategic Influence: Direct involvement in shaping the company's product strategy and long-term vision.

• Product Innovation: Chance to pioneer new interaction models and leverage cutting-edge AI in a consumer product context.

• Industry Recognition: Potential to build a highly visible, category-defining product that could significantly impact the dating tech landscape.

• Career Trajectory: Potential to grow into a VP of Design or Chief Product Officer role as the company matures.

📝 Enhancement Note: This analysis focuses on the career implications of a "founding" role at an early-stage startup. The direct reporting line and the opportunity to build a function from scratch are key growth drivers. The impact is tied directly to the product's success and the company's mission.

🌐 Work Environment

Office Type: Likely a co-working space or a small, dedicated office in New York City, typical for early-stage, funded startups. The environment will be dynamic, collaborative, and fast-paced.

Office Location(s): New York City, USA. Specific office details are not provided, but candidates should expect a physical presence in NYC.

Workspace Context:

• Collaborative Hub: Expect an open and interactive workspace designed to foster direct communication and rapid iteration between design, engineering, and the founder.

• Tooling: Access to industry-standard design and prototyping tools (e.g., Figma, Sketch, Adobe Creative Suite, prototyping software).

• Innovation Focus: The environment will encourage experimentation, risk-taking, and a continuous pursuit of innovative design solutions.

Work Schedule: Full-time, with an expectation of flexibility. While standard business hours are typical, startup demands may require extended hours during key development sprints or product launches. The emphasis is on delivering results rather than strict adherence to a clock.

📝 Enhancement Note: The work environment is inferred based on typical early-stage, funded startup settings in major tech hubs like New York City. The "on-site" nature implies a physical workspace, and the collaborative culture is a hallmark of such environments.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening (Jack & Jill): A conversation with "Jack" (AI) to understand your background and career aspirations, followed by Jill (AI Recruiter) assessing your fit for Overtone.

• Founder Interview: Likely a deep dive with the Founder/CEO to assess your vision, strategic thinking, cultural fit, and alignment with the company's mission. Expect discussions around your past experiences and approach to building products from scratch.

• Design Challenge/Portfolio Review: A session to present your portfolio, walk through key case studies, and potentially engage in a design exercise or discuss hypothetical problem-solving scenarios relevant to Overtone's challenges.

• Team/Engineering Interviews: Meetings with key engineering or product team members to evaluate technical understanding, collaboration style, and ability to work effectively in a cross-functional team.

• Final Round: May involve further discussions with the founder or other key stakeholders to finalize the decision.

Portfolio Review Tips:

• Storytelling is Key: For each case study, clearly articulate the problem, your role, the process you followed, the challenges you encountered, your solutions, and the measurable impact of your design decisions.

• Highlight 0-to-1 Experience: Emphasize projects where you built something from scratch, navigated ambiguity, and drove product definition.

• Showcase Strategic Thinking: Demonstrate how you moved beyond aesthetics to address user needs, business goals, and technical constraints.

• Focus on Impact: Quantify results wherever possible (e.g., user engagement lifts, conversion improvements, retention increases). If quantitative data is unavailable, articulate the qualitative impact on user experience and trust.

• Tailor to Overtone: Be prepared to discuss how your experience and approach align with Overtone's mission of creating a high-trust, AI-driven dating experience.

Challenge Preparation:

• Understand the Product: Research Overtone's mission, the founder's vision (from Hinge), and the competitive landscape of dating apps. Consider the unique challenges of AI and voice in a social context.

• Think Strategically: Be ready to discuss high-level UX strategy, systems thinking, and how you would approach designing for complex human emotions and trust.

• Design for Ambiguity: Prepare to tackle hypothetical design problems that may not have a clear "right" answer, showcasing your problem-solving process and ability to make reasoned decisions.

• Articulate Your Process: Clearly explain your design methodology, including how you incorporate user feedback, collaborate with engineers, and iterate on designs.

📝 Enhancement Note: The interview process is structured based on typical startup hiring practices and the unique "Jack & Jill" application funnel. Portfolio and challenge preparation advice is tailored to the specific requirements of a founding Head of Design role in a tech startup.

🛠 Tools & Technology Stack

Primary Design Tools:

• UI/UX Design & Prototyping: Figma (highly likely), Sketch, Adobe XD. Proficiency in at least one leading tool is essential.

• Prototyping & Animation: Principle, After Effects, Framer (for more advanced interactions).

• Collaboration & Project Management: Jira, Asana, Trello (for tracking design tasks and collaborating with engineering).

• Design Systems: Figma's component features, Zeroheight, or similar platforms for documentation.

Analytics & Reporting (Familiarity):

• Product Analytics: Mixpanel, Amplitude, Google Analytics (understanding how to interpret user behavior data is crucial).

• A/B Testing Tools: Optimizely, VWO (familiarity with how design impacts testable metrics).

CRM & Automation (Indirect Exposure):

• While not a direct design tool, understanding how user data flows from CRM and marketing automation platforms can inform design decisions related to onboarding and user engagement.

📝 Enhancement Note: The tools listed are standard for a Head of Design role in a modern tech startup. The emphasis is on design and prototyping tools, with an understanding of how data and collaboration tools support the design process.

👥 Team Culture & Values

Operations Values:

• Innovation & Boldness: A culture that encourages pushing boundaries, challenging the status quo, and embracing novel solutions (e.g., AI, voice).

• User-Centricity: A deep commitment to understanding and serving the user, prioritizing their emotional well-being and trust.

• Collaboration & Transparency: Open communication, shared ownership, and a strong partnership between design, engineering, and leadership.

• Agility & Iteration: A dynamic environment that values rapid learning, quick adaptation, and continuous improvement.

• High-Trust Environment: Creating a product and workplace where honesty, respect, and safety are paramount.

Collaboration Style:

• Direct & Frequent: Expect constant interaction with the founder and engineering team, with design integrated into the daily development cycle.

• Feedback-Oriented: A culture where constructive feedback is welcomed and actively sought from all team members.

• Shared Ownership: A collaborative approach where the entire team feels responsible for the product's success, with design playing a central role in guiding the user experience.

📝 Enhancement Note: These values and collaboration styles are inferred from the company's description (AI dating, founder's background, startup nature) and the role's emphasis on building a "high-trust" product.

⚡ Challenges & Growth Opportunities

Challenges:

• Defining a New Category: Building a truly novel dating experience that moves beyond established paradigms requires significant user education and market validation.

• AI Integration Complexity: Designing intuitive interfaces for complex AI functionalities and ensuring user understanding and trust in AI-driven recommendations.

• Balancing Innovation with Trust: Creating a safe, emotionally resonant, and trustworthy environment while leveraging new technologies like AI and voice.

• Navigating Ambiguity: Operating in a 0-to-1 environment means constant evolution, shifting priorities, and the need to define processes as you go.

• Scaling Design: Establishing scalable design processes, systems, and potentially a team from the ground up.

Learning & Development Opportunities:

• Pioneering AI in Dating: Gain cutting-edge experience in applying AI and voice technologies to human connection.

• Building from Scratch: Develop unparalleled experience in establishing design functions, teams, and processes within a high-growth startup.

• Strategic Leadership: Deepen strategic thinking and leadership skills by working directly with a seasoned founder and influencing company direction.

• Industry Impact: Contribute to a product that could significantly shape the future of online dating and human connection.

📝 Enhancement Note: The challenges are derived from the unique nature of Overtone's product (AI dating, new interaction models) and the inherent difficulties of a founding role in an early-stage startup. Growth opportunities are framed around these challenges and the leadership aspect of the role.

💡 Interview Preparation

Strategy Questions:

• "How would you approach designing an AI-powered matchmaking system that prioritizes user trust and emotional connection over simple compatibility scores?"

  • Preparation: Think about user control, transparency in AI decisions, progressive disclosure of information, and how to design for nuanced emotional responses.

• "Describe your process for establishing a design system and visual identity for a brand-new consumer product in a highly competitive market."

  • Preparation: Outline steps for foundational research, brand exploration, defining core visual elements, creating a component library, and ensuring scalability.

• "Imagine you have limited user data initially. How would you validate and iterate on your core interaction model for Overtone?"

  • Preparation: Discuss strategies like user interviews, concept testing, low-fidelity prototypes, and leveraging founder insights from Hinge.

Company & Culture Questions:

• "What excites you most about Overtone's mission, and how does your design philosophy align with building a high-trust dating experience?"

  • Preparation: Research Overtone's stated goals. Connect your personal design values to concepts of safety, authenticity, and emotional intelligence.

• "How do you envision collaborating with a founder and engineering team to rapidly iterate on a complex product like Overtone?"

  • Preparation: Emphasize your experience with agile methodologies, cross-functional communication, and a bias for action. Provide examples of successful collaborations.

• "Given your experience, what do you believe are the biggest design challenges in the modern dating app landscape, and how can Overtone differentiate?"

  • Preparation: Discuss common pain points (superficiality, ghosting, safety concerns) and how Overtone's AI and voice approach can offer unique solutions.

Portfolio Presentation Strategy:

• Focus on Narrative: Structure each case study as a compelling story with a clear beginning (problem), middle (your solution and process), and end (impact).

• Demonstrate Process, Not Just Polish: Show wireframes, user flows, research insights, and iterations, not just final UI screens. This reveals your thinking.

• Quantify Impact: Use metrics to showcase the success of your designs. If direct metrics aren't available, articulate the qualitative improvements in user experience or trust.

• Address the "Why": For each decision, explain the reasoning behind it, linking it back to user needs, business goals, or technical constraints.

• Be Prepared for Deep Dives: Anticipate detailed questions about your role, decisions, and the outcomes of your projects.

📝 Enhancement Note: Interview preparation advice is tailored to the specific challenges and context of Overtone, emphasizing AI, trust, and the startup environment. The questions are designed to probe strategic thinking, problem-solving skills, and cultural fit.

📌 Application Steps

To apply for this Head of Design position:

• Visit the Jack & Jill website and initiate a conversation with "Jack" (AI) to register your profile and career interests.

• Resume Optimization: Ensure your resume clearly highlights your experience in mobile-first consumer products, end-to-end design ownership, UI/UX strategy, and any experience in social connection or high-trust domains. Use keywords relevant to AI, product design, and startup environments.

• Portfolio Customization: Prepare a portfolio that prominently features 3-5 strong case studies demonstrating your process, strategic thinking, and impact, with a particular emphasis on your ability to build from scratch and design for complex human interactions.

• Interview Preparation: Thoroughly research Overtone, its founder's background, and the AI dating landscape. Practice articulating your design philosophy and how you would tackle the unique challenges of this role. Prepare to discuss your portfolio in detail, focusing on narrative and impact.

• Follow Instructions: Complete all steps outlined on the Jack & Jill website, including the "Talk to Jack" session, to ensure your application is properly channeled to Jill (the AI Recruiter) for consideration by Overtone.

⚠️ 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 or through the Jack & Jill application process before making application decisions. The application process is unique, relying on the Jack & Jill AI platform.