Head of Design

📍 Job Overview

Job Title: Head of Design

Company: Opto Investments

Location: New York, New York, United States

Job Type: Full-Time

Category: Product Design / Design Leadership

Date Posted: May 07, 2026

Experience Level: 10+ Years

Remote Status: On-site

🚀 Role Summary

• Lead the product design function at Opto Investments, focusing on building exceptional, AI-native product experiences for the private markets industry.

• Drive the strategic vision for product design, ensuring it influences roadmap, prioritization, and problem-solving from inception.

• Foster a culture of design excellence, establishing principles for simplicity, clarity, and trust across all user touchpoints.

• Directly contribute to critical product surfaces, setting high standards for quality, usability, and human-AI interaction.

• Build and mentor a high-performing design team, cultivating strong product sense and a bias for action.

📝 Enhancement Note: This role is positioned at a senior leadership level, requiring not only hands-on design expertise but also significant strategic influence and team-building capabilities. The emphasis on "0-1 product design experience" and "contributing to or reaching product-market fit" suggests a critical phase of company growth where design is pivotal to defining and scaling core product offerings. The AI-native focus is a key differentiator for this role.

📈 Primary Responsibilities

• Personally lead design efforts on the most critical product surfaces, establishing a benchmark for craft, usability, and overall user experience.

• Define and champion a clear point of view on designing AI-native products, with a specific focus on building trust, transparency, and effective human-AI interaction models.

• Establish overarching principles for product experience design, ensuring simplicity, clarity, and trust from user onboarding through complex core workflows.

• Collaborate closely with product management and engineering teams to define product direction, challenge assumptions, and ensure the development of coherent, end-to-end user journeys.

• Advocate for simplification, scope reduction, and a relentless focus on user value drivers within product development cycles.

• Integrate design thinking into strategic decision-making processes early and consistently, influencing the product roadmap and prioritization.

• Develop and implement scalable design systems, patterns, and best practices that enhance consistency and efficiency across the entire product.

• Lead, mentor, and grow the design team, fostering a culture of high standards in craft, strategic thinking, and execution.

📝 Enhancement Note: The responsibilities highlight a dual focus on hands-on design execution and strategic leadership. The explicit mention of "living in the app" and not considering the job "over once something ships" indicates a deep commitment to product iteration and continuous improvement, a hallmark of successful design leaders in early-stage tech companies.

🎓 Skills & Qualifications

Education: Not explicitly stated, but a strong portfolio and relevant experience are implied to be more critical than a specific degree.

Experience: Minimum of 0-1 product design experience, meaning the ability to build products or significant features from scratch, demonstrating a deep understanding of the entire product lifecycle from ideation to iteration and scaling.

Required Skills:

• Strong Product Sense & High Quality Bar: Demonstrated ability to recognize and advocate for exceptional product design, pushing teams to achieve high standards of quality and usability.

• Comfort with Ambiguity: Proven capability to create clarity and drive progress in evolving, fast-paced environments, guiding teams through uncertainty.

• AI-Native Design Mindset: Experience integrating AI deeply into personal workflows and a well-defined perspective on the evolving role of design in AI-driven products, including human-AI interaction.

• 0-1 Product Design Expertise: Tangible experience building products or major features from the ground up, with the ability to articulate design decisions, trade-offs, and their impact on product outcomes.

• Product-Market Fit Contribution: Experience contributing to or achieving product-market fit, understanding how design facilitates learning, iteration, and user adoption.

• B2B Product Experience: Demonstrated experience designing for business-to-business environments, preferably within fintech or data-intensive sectors characterized by complex workflows.

• Leadership Potential/Experience: Proven experience leading designers or a strong senior individual contributor with a history of operating at a leadership level and readiness to own a design function.

Preferred Skills:

• Experience in the Fintech or Private Markets industry.

• Prior experience in a founder role or early-stage startup environment.

• Experience building or shaping user discovery and research practices.

📝 Enhancement Note: The requirements emphasize a blend of strategic vision, hands-on execution, and leadership acumen. The "0-1 product design experience" is a critical differentiator, suggesting the company is looking for someone who can establish design foundations and drive growth from an early stage, rather than optimizing an existing mature product. The AI-native mindset is a forward-looking requirement crucial for Opto's product direction.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• End-to-End Product Design Case Studies: Showcase at least one significant project where you led the design of a product or major feature from inception (0-1) through to launch and iteration. Clearly articulate the problem, your design process, the challenges faced, key decisions made, and the measurable outcomes achieved.

• Systems Thinking Demonstration: Include examples that illustrate your ability to think in terms of systems, not just individual screens. This could involve demonstrating how your design decisions impact broader workflows, data models, or user journeys across multiple touchpoints.

• AI Integration Examples: Highlight projects where you've incorporated AI into your design process or product solutions. Detail how you approached building trust, transparency, and effective human-AI interaction within these experiences.

• B2B Workflow Optimization: Present case studies from B2B environments, ideally in fintech or complex data-heavy domains, focusing on how your designs simplified complex workflows and drove user value.

• Design System Contribution (if applicable): If you have experience building or contributing to design systems, showcase how you established patterns, principles, and components that improved consistency and efficiency.

Process Documentation:

• Problem Definition & Ideation: Examples of how you define user problems, conduct research (discovery, user interviews), and generate innovative solutions.

• Design Iteration & Validation: Showcase your process for iterating on designs based on feedback, prototyping, and user testing, demonstrating how you validate design directions.

• Cross-Functional Collaboration: Illustrate how you collaborate with product managers and engineers, including artifacts like user flows, wireframes, interactive prototypes, and design specifications that facilitate clear communication and alignment.

• Outcome Measurement: Demonstrate how you track and measure the impact of your design decisions on key business and user metrics, linking design efforts to tangible results.

📝 Enhancement Note: For a Head of Design role, particularly one focused on "0-1" product development, the portfolio is paramount. It needs to clearly demonstrate strategic thinking, end-to-end ownership, and the ability to build and scale design functions and systems from the ground up, with a strong emphasis on measurable outcomes and complex B2B/Fintech environments.

💵 Compensation & Benefits

Salary Range: $250,000 - $290,000 USD per year. This range is dependent on skills, experience, and expected contribution.

Benefits:

• Significant Equity: Opportunity to share in the company's success through substantial stock options or grants.

• Comprehensive Health Coverage: Includes health, dental, and vision insurance plans for employees and potentially dependents.

• Unlimited Paid Time Off (PTO): Flexible approach to time off, encouraging work-life balance and autonomy.

• Retirement Savings Plan: 401(k) plan to support long-term financial planning.

• Professional Development Stipends:

  • Learning Stipend: Funds for courses, workshops, conferences, or other learning opportunities to enhance skills.
  • Fitness Stipend: Support for gym memberships, fitness classes, or wellness activities.
  • Commuter Stipend: Assistance with transportation costs to and from the office.

• Paid Holidays: Standard company-observed holidays are paid time off.

Working Hours: While not explicitly stated, the "On-site" work arrangement and the nature of a leadership role in a startup suggest a demanding schedule, likely exceeding a standard 40-hour work week, with an expectation of flexibility to meet business needs.

📝 Enhancement Note: The salary range provided is competitive for a senior leadership role in Product Design in New York City, especially within the tech and fintech sectors. The comprehensive benefits package, including significant equity and various stipends, indicates a strong focus on employee well-being and professional growth, typical of well-funded startups aiming to attract top talent.

🎯 Team & Company Context

🏢 Company Culture

Industry: Financial Technology (Fintech), specifically focused on Private Markets and Wealth Management technology. Opto is aiming to disrupt and modernize a large, growing, and traditionally opaque industry ($30T forecast by 2029).

Company Size: The description implies an early-stage, growth-focused company, likely between 50-200 employees, given the need to build out functions like design leadership from the ground up. This size offers the potential for significant impact but also requires adaptability.

Founded: Opto was founded with the mission to engineer the future of private markets, suggesting a relatively recent founding date with a strong vision for technological innovation. The company emphasizes "exceptional Silicon Valley engineering talent" and "experienced investors and industry specialists."

Team Structure:

• Design Function: This role is to establish and lead the design function. It implies that design is currently nascent or needs significant strategic direction. The Head of Design will be responsible for growing this team.

• Cross-functional Collaboration: The Head of Design will work "alongside product and engineering" and must "push teams to simplify, cut scope, and focus on what actually drives user value." This indicates a highly collaborative, integrated approach where design is not siloed.

• Leadership Integration: Design is intended to be "core to the strategy," meaning the Head of Design will be a key voice in strategic decision-making, influencing the roadmap and prioritization alongside product and engineering leadership.

Methodology:

• Data-Driven Product Development: The company's mission to fix a "broken system" through technology suggests a strong reliance on data to identify inefficiencies and measure impact. Design decisions are expected to be informed by user data and business objectives.

• Agile & Iterative Development: The emphasis on "0-1 product design," "reaching product-market fit," and "shaping product decisions" implies an agile, iterative approach where continuous learning and adaptation are key.

• Systems Thinking: The role explicitly requires thinking "in systems, not just screens," indicating a methodology focused on understanding and designing holistic user journeys and interconnected product components.

Company Website: www.optoinvest.com (inferred from domain_derived)

📝 Enhancement Note: Opto Investments is positioned as an ambitious, tech-forward company tackling a massive market opportunity. The culture appears to value boldness, clear communication, purposeful execution, and a strong emphasis on design as a strategic driver, not merely an execution layer. The early-stage nature means significant opportunity for impact and shaping the company's trajectory.

📈 Career & Growth Analysis

Operations Career Level: This role is at the highest individual contributor or early leadership level within the Design function. As "Head of Design," it implies responsibility for setting the vision, strategy, and execution standards for all product design activities. It's a critical role in a growth-stage company, offering the chance to build a function from the ground up.

Reporting Structure: The Head of Design will likely report directly to a C-level executive, such as the CEO, CTO, or CPO, given the strategic nature of the role and its integration into core business decisions. They will be responsible for building and managing their own team of designers.

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

• Defining the User Experience: Shaping how clients interact with and perceive the Opto platform, directly influencing adoption, retention, and client satisfaction.

• Driving Product Strategy: Guiding product development by ensuring user needs and market opportunities are translated into effective, intuitive, and differentiated product features.

• Enhancing Operational Efficiency: Through well-designed, self-serve onboarding and streamlined workflows, the design function can reduce operational overhead for Opto and its clients.

• Building Brand Perception: A high-quality, cohesive user experience contributes significantly to the brand's reputation for innovation, trust, and professionalism in the complex private markets space.

Growth Opportunities:

• Build and Scale a Design Team: Opportunity to recruit, mentor, and develop a team of talented designers, establishing best practices and a strong design culture.

• Shape Product Vision: Play a pivotal role in defining the future of private markets technology, influencing the product roadmap and strategic direction of the company.

• Become a Design Leader: Advance to a VP of Design or Chief Design Officer role as the company scales, potentially overseeing broader design initiatives beyond product.

• Deep Domain Expertise: Develop specialized knowledge in the complex and high-value private markets and wealth management sectors.

• Influence Company Strategy: As a key member of the leadership team, contribute to broader business strategy and company growth initiatives.

📝 Enhancement Note: This role offers a significant opportunity for an experienced design leader to make a substantial impact. The "0-1" nature of the product and the strategic importance placed on design mean that the Head of Design will be instrumental in shaping the company's future, with clear pathways for growth into larger leadership roles.

🌐 Work Environment

Office Type: The role is explicitly "based primarily onsite in either our San Francisco or New York City offices." This indicates a commitment to in-person collaboration and a traditional office-based work environment for this position.

Office Location(s): San Francisco, California, and New York City, New York. Candidates are expected to work from one of these primary locations.

Workspace Context:

• Collaborative Hub: The office environment is likely designed to foster collaboration, with shared spaces, meeting rooms, and potentially open-plan areas conducive to spontaneous interactions between design, product, and engineering teams.

• Tooling and Technology: Access to modern design software, collaboration tools, and potentially specialized hardware necessary for prototyping and user testing. The company's focus on "Silicon Valley engineering talent" suggests a tech-forward environment.

• Team Interaction: Being onsite facilitates direct, face-to-face communication, brainstorming sessions, design critiques, and team-building activities, which are often crucial for effective product development in a fast-paced startup.

Work Schedule: While specific hours are not detailed, the expectation for an "On-site" role at a startup, especially a leadership position, implies a demanding and flexible schedule. This would likely involve standard business hours but with the expectation to work extended hours or be available outside of them as needed to drive product initiatives and meet deadlines.

📝 Enhancement Note: The emphasis on "On-site" work in major tech hubs like NYC and SF suggests a company that values in-person collaboration and team cohesion, which can be particularly beneficial for design leadership roles that require deep integration with product and engineering.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Application Review: Submission of Resume, Cover Letter, and Portfolio. The Cover Letter is specifically requested to be creative and speak directly to the candidate's motivation for joining Opto.

• Portfolio Deep Dive: A thorough review of the candidate's portfolio is expected, focusing on "0-1" product design experience, AI integration, B2B context, and systems thinking. Expect to discuss specific case studies in detail.

• Skills & Experience Assessment: Interviews will likely assess product sense, comfort with ambiguity, AI-native design thinking, and leadership capabilities through behavioral and situational questions.

• Cross-functional Interviews: Opportunities to meet with members of the Product and Engineering teams to evaluate collaboration style, communication clarity, and strategic alignment.

• Leadership & Vision Discussion: A discussion with senior leadership (potentially CEO, CTO, CPO) to assess strategic thinking, vision for design at Opto, and cultural fit.

• Potential Design Challenge: A design exercise or case study presentation might be involved, either pre-interview or during the process, to evaluate problem-solving skills and design execution under pressure.

Portfolio Review Tips:

• Curate Strategically: Select 3-5 of your strongest case studies that best showcase your experience in "0-1" product design, AI integration, B2B fintech, and systems thinking.

• Tell a Story: Structure each case study with a clear narrative: problem statement, your role and responsibilities, design process (research, ideation, prototyping, testing), key decisions and trade-offs, and quantifiable outcomes.

• Highlight Impact: Emphasize the business value and user impact of your work. Use metrics where possible (e.g., conversion rates, user engagement, efficiency gains).

• Showcase AI-Native Thinking: Clearly articulate your approach to designing with AI, including considerations for trust, transparency, and human-AI interaction.

• Demonstrate Systems Thinking: Explain how your designs fit into a larger product ecosystem and how you considered broader workflows and data flows.

• Be Ready to Defend Decisions: Prepare to discuss why certain design choices were made, what alternatives were considered, and how you would iterate further.

Challenge Preparation:

• Understand Opto's Business: Research Opto Investments, its mission, target market (wealth managers, family offices, private banks), and the private markets industry. Understand the core problems they are solving.

• Anticipate Design Problems: Consider common challenges in B2B fintech, wealth management platforms, and AI-native product design. Think about user onboarding, workflow optimization, data visualization, and building trust in financial applications.

• Practice Articulating Strategy: Be prepared to discuss your design philosophy, your approach to building design systems, and how you would scale a design team.

• Prepare Questions: Have thoughtful questions ready for the interviewers about the product roadmap, design team structure, challenges, and company culture.

📝 Enhancement Note: The application process emphasizes a strong cover letter and a portfolio that directly addresses the key requirements of the role, particularly the "0-1" and AI-native aspects. Candidates should prepare to articulate their strategic thinking and demonstrate a deep understanding of Opto's business context.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping Software: Proficiency in industry-standard tools such as Figma (highly probable given current trends), Sketch, Adobe Creative Suite (Illustrator, Photoshop), and prototyping tools like InVision, Principle, or Axure.

• Design Systems Tools: Experience with tools for creating, managing, and documenting design systems (e.g., Zeroheight, Storybook, or built within Figma).

• Collaboration & Project Management: Familiarity with tools like Jira, Asana, Trello, or Monday.com for tracking design tasks and collaborating with development teams.

• Communication Tools: Slack, Microsoft Teams, or similar for daily team communication.

Analytics & Reporting:

• User Analytics Platforms: Experience with tools like Amplitude, Mixpanel, Google Analytics, or Pendo to track user behavior, feature adoption, and product engagement.

• Data Visualization Tools: Familiarity with tools like Tableau, Looker, or Power BI, or the ability to work with data analysts to interpret and visualize key performance indicators (KPIs) relevant to design impact.

CRM & Automation:

• While not directly a design tool, understanding how CRM systems (e.g., Salesforce) and automation platforms integrate with the user experience can be beneficial for B2B product design.

📝 Enhancement Note: While specific tools are not listed, the role's emphasis on modern product development, AI integration, and collaboration points towards a tech stack that is current and integrated. Figma is highly likely to be the primary design tool. The Head of Design should be adept at leveraging analytics to inform design decisions and understanding how their work impacts broader business metrics.

👥 Team Culture & Values

Operations Values:

• Boldness & Courage: Opto is "unapologetically bold" and not afraid to "do things differently." This suggests a culture that encourages taking calculated risks and challenging the status quo.

• Clear Communication: Emphasis on "clear communication" implies a value placed on transparency, directness, and articulate expression of ideas and feedback.

• Purposeful Execution: A focus on "purposeful execution" means that actions should be deliberate, aligned with objectives, and drive tangible results, avoiding busywork.

• High Bar for Talent: Opto has a "high bar for talent" and is committed to building the best teams, suggesting a culture of excellence, continuous improvement, and high performance.

• User Value Focus: The role is expected to "push teams to simplify, cut scope, and focus on what actually drives user value," indicating that user needs and impact are central to decision-making.

• Design as Strategy: The explicit statement that "Design is core to the strategy" highlights a fundamental company value where design is integrated into business planning, not just execution.

Collaboration Style:

• Integrated Teams: Collaboration with product and engineering is expected to be close and continuous, working together to define direction and challenge decisions.

• Constructive Debate: The value of "strong opinions" suggests a culture where different viewpoints are encouraged and debated constructively to arrive at the best solutions.

• Outcome-Oriented: Collaboration will likely be focused on achieving shared goals and delivering measurable outcomes, rather than simply completing tasks.

• Iterative Feedback Loops: The nature of building "0-1" products implies a culture of frequent feedback, rapid iteration, and learning from both successes and failures.

📝 Enhancement Note: The company culture appears to be dynamic, ambitious, and focused on impact. It values innovation, directness, and a high standard of work, with design playing a central, strategic role in achieving business objectives.

⚡ Challenges & Growth Opportunities

Challenges:

• Defining "0-1" Product Experience: Establishing the foundational design principles, patterns, and systems for a product that is still being defined and brought to market. This involves significant ambiguity and the need to make high-stakes decisions early.

• Shaping AI-Native Interaction: Designing for AI presents unique challenges in building trust, ensuring transparency, managing user expectations, and creating intuitive human-AI collaboration models.

• Balancing Strategy and Execution: As Head of Design, needing to simultaneously lead the team, mentor individual designers, and remain hands-on with critical product surfaces requires excellent time management and prioritization.

• Scaling the Design Function: Building a design team from scratch or near-scratch, defining its processes, and integrating it effectively into a growing engineering and product organization.

• Navigating Complex Domain: Understanding and designing for the intricacies of the private markets and wealth management industry, which involves sophisticated financial concepts and demanding users.

Learning & Development Opportunities:

• Strategic Leadership Development: Gain experience in shaping company-wide product strategy and influencing business decisions at a senior level.

• Building a Design Function: Develop skills in organizational design, talent acquisition, team building, and establishing operational best practices for a design team.

• Deep Fintech & Private Markets Expertise: Become a subject matter expert in a rapidly growing and complex financial domain.

• Cutting-Edge AI Design: Become a leader in designing for AI-native products, contributing to the evolution of human-AI interaction design principles.

• High-Leverage Impact: Contribute to a product that aims to fundamentally change a massive industry, offering significant professional satisfaction and visibility.

📝 Enhancement Note: The challenges presented are significant but are directly tied to the growth opportunities. This role is ideal for a leader who thrives in ambiguity, enjoys building from the ground up, and is passionate about leveraging design and AI to solve complex problems in a high-impact industry.

💡 Interview Preparation

Strategy Questions:

• Vision & Roadmap: "What is your vision for product design at Opto, and how would you translate that into a roadmap for the first 6-12 months?" (Focus on building foundational systems, defining principles, and demonstrating early impact.)

• AI Design Philosophy: "How do you approach designing AI-native products? What are the key considerations for building trust and transparency in human-AI interactions, especially in a financial context?" (Prepare specific examples of AI integration in your work.)

• Balancing Trade-offs: "Describe a situation where you had to make difficult trade-offs between design quality, scope, and development speed. How did you approach this, and what was the outcome?" (Highlight your ability to simplify and focus on user value.)

• Cross-functional Collaboration: "How do you ensure effective collaboration between design, product, and engineering teams, especially when there are differing opinions on direction or priority?" (Emphasize communication, empathy, and data-driven advocacy.)

Company & Culture Questions:

• Design's Strategic Role: "How do you see design integrating into Opto's overall business strategy, beyond just UI/UX execution?" (Connect design to business outcomes, market differentiation, and client acquisition/retention.)

• Leadership Style: "Describe your approach to leading and growing a design team. How do you set expectations, provide feedback, and foster a culture of excellence?" (Showcase your ability to mentor and build talent.)

• Handling Ambiguity: "Opto is an early-stage company with a lot of unknowns. How do you operate and lead effectively in ambiguous environments?" (Provide examples of creating clarity and driving progress.)

• Company Values Alignment: "We value boldness, clear communication, and purposeful execution. How do these values resonate with your own professional principles and how would you embody them as Head of Design?" (Connect your experience to Opto's stated values.)

Portfolio Presentation Strategy:

• Narrative Arc: For each case study, structure your presentation with a clear beginning (the problem), middle (your process and solutions), and end (the impact and learnings).

• Quantify Impact: Whenever possible, use data and metrics to demonstrate the success of your designs. If exact metrics aren't available, discuss the potential impact and how it would be measured.

• Focus on "Why": Explain the rationale behind your design decisions. Why did you choose a particular approach? What alternatives did you consider and reject?

• Showcase AI & B2B Nuances: Specifically highlight elements of your work that demonstrate your AI-native mindset and your understanding of complex B2B workflows.

• Interactive Elements: If possible, use interactive prototypes or screen recordings to bring your designs to life. Be ready to answer questions about the user experience in real-time.

• Conciseness: Be mindful of time. Focus on the most critical aspects of each case study and be prepared for follow-up questions.

📝 Enhancement Note: Interview preparation should focus on demonstrating strategic thinking, leadership potential, and a deep understanding of Opto's business and the challenges of designing for AI in a complex B2B fintech environment. The portfolio presentation is a critical opportunity to showcase these capabilities.

📌 Application Steps

To apply for this Head of Design position:

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

• Curate Your Portfolio: Select 3-5 of your most impactful case studies that best highlight your experience in 0-1 product design, AI-native product development, B2B fintech environments, and systems thinking. Ensure each case study clearly articulates the problem, your role, process, decisions, and measurable outcomes.

• Craft a Compelling Cover Letter: Write a creative cover letter that directly addresses why you are passionate about Opto Investments, the private markets industry, and this specific Head of Design role. Speak to your unique value proposition for building a foundational design function.

• Optimize Your Resume: Ensure your resume clearly outlines your experience in product design leadership, B2B product development, and any relevant experience in fintech or AI. Use keywords from the job description to highlight your qualifications.

• Prepare for Portfolio Presentation: Practice walking through your chosen case studies, focusing on storytelling, demonstrating strategic thinking, and quantifying impact. Be ready to discuss your approach to AI design and systems thinking.

• Research Opto Investments: Thoroughly understand Opto's mission, product offering, target market, and the competitive landscape in private markets technology. This research will inform your cover letter and interview responses.

⚠️ 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.