Principal Product Designer

📍 Job Overview

Job Title: Principal Product Designer
Company: Pulley
Location: Sunnyvale, CA
Job Type: Full-Time
Category: Product Design / UX/UI
Date Posted: October 17, 2025
Experience Level: 8+ Years
Remote Status: Hybrid (1-2 days in-office)

🚀 Role Summary

• Lead the design of a new, AI-native product from conception to launch, redefining how startups manage equity and make strategic decisions in an AI-driven world.
• Drive end-to-end design processes, including discovery, user research, prototyping, and iterative development for innovative AI-powered features.
• Collaborate closely with engineering, product management, and leadership to influence product direction, strategy, and establish design best practices for AI-native business environments.
• Shape the long-term vision for Pulley's AI product strategy, ensuring an intuitive, delightful, and effective user experience that leverages AI capabilities.

📝 Enhancement Note: This role is explicitly focused on designing a "brand-new, AI-native product" and positions the Principal Product Designer as the "founding designer on this initiative." This implies a high degree of autonomy, strategic influence, and the need to establish foundational design principles for a novel product category within the company's offering. The emphasis on "AI-native business environments" and "agent-led workflows" suggests a forward-thinking approach to product development that goes beyond traditional SaaS.

📈 Primary Responsibilities

• Own the complete design lifecycle for a new, 0-1 AI-native product experience, from initial concept generation to final implementation.
• Design and develop innovative AI-powered products and features that extend Pulley's existing offerings or create entirely new product lines.
• Spearhead design discovery initiatives, conduct user research, create functional prototypes, and manage iterative design processes to define a compelling user experience tailored for AI-native business environments.
• Foster strong cross-functional collaboration with engineering, product, and leadership teams to effectively shape product direction, strategy, and ensure seamless execution.
• Contribute significantly to defining the long-term vision for Pulley's AI product strategy and champion the establishment of robust design best practices throughout the development process.

📝 Enhancement Note: The responsibilities emphasize a "0-1" product development, meaning the designer will be instrumental in creating something entirely new. This requires not only strong design execution but also strategic thinking, market understanding, and the ability to translate nascent AI capabilities into tangible user value. The role demands a proactive approach to defining "what company operations look like in a world of AI-native tools."

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio demonstrating design expertise and strategic thinking is paramount. Candidates are expected to possess a deep understanding of design principles and user-centered methodologies.
Experience: A minimum of 8+ years of hands-on product design experience is required, with a proven track record of successfully designing and launching complex B2B products.

Required Skills:

• Product Design Leadership: Demonstrated ability to lead the end-to-end design process for new products, particularly in a "0-1" or highly innovative context.
• B2B Product Design Expertise: Proven experience in designing and shipping complex, enterprise-grade B2B software products, understanding the unique user needs and workflows of business users.
• Strategic Thinking & Execution: A strong track record of balancing visionary thinking with pragmatic execution, capable of developing a clear product vision and building the necessary design strategies to achieve it.
• User Research & Discovery: Proficiency in leading design discovery, conducting user research, and translating insights into actionable design solutions that address complex user problems.
• Prototyping & Iteration: Expertise in creating high-fidelity prototypes and managing iterative design cycles based on user feedback and testing.
• Cross-Functional Collaboration: Excellent ability to partner effectively with engineering, product management, and leadership teams to drive product strategy and align on design outcomes.
• User Empathy & AI Intuition: Deep user empathy coupled with a creative imagination and a strong desire to understand and execute on the needs of professionals operating in AI-native business environments.

Preferred Skills:

• Experience designing products leveraging Artificial Intelligence (AI) or Machine Learning (ML) capabilities.
• Familiarity with equity management, financial technology (FinTech), or startup operations software.
• Experience working in fast-paced, startup environments with a focus on rapid iteration and product-market fit.
• Knowledge of current AI trends, agent-led workflows, and their implications for business operations.
• Experience in defining and establishing design systems and best practices for new product initiatives.

📝 Enhancement Note: The requirement for "8+ years" and the "Principal" title indicate a senior-level role. The emphasis on "balancing strategic thinking with execution" and "creative imagination coupled with deep user empathy" points to a need for a designer who can not only create beautiful interfaces but also drive product strategy and understand emerging technological paradigms like AI. The mention of "AI-native professionals" suggests the need for designers who can anticipate future user behaviors and needs in an AI-augmented workplace.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• End-to-End Product Design Case Studies: Showcase comprehensive case studies detailing your process from problem identification and user research through to final design solutions and their impact. Highlight at least one complex B2B product you've owned end-to-end.
• 0-1 Product Innovation: Include examples of projects where you've been involved in the early stages of product development, demonstrating your ability to define new product experiences from scratch.
• AI/Emerging Technology Integration: If possible, showcase projects that involve complex technologies, AI, or novel user experiences that required significant research and strategic design thinking.
• Strategic Impact & Collaboration: Demonstrate how your design decisions led to measurable business outcomes or improved user workflows, and illustrate your collaboration process with product and engineering teams.

Process Documentation:

• Discovery & Research: Detail methodologies used for user research, market analysis, and defining product requirements for new initiatives.
• Design & Prototyping: Showcase your approach to wireframing, interactive prototyping, and user testing, emphasizing how you iterate based on feedback.
• Collaboration & Strategy: Illustrate how you partner with cross-functional teams to align on product strategy, define roadmaps, and ensure design feasibility.
• Best Practice Establishment: Provide examples of how you've contributed to or established design systems, style guides, or design best practices within a team or organization.

📝 Enhancement Note: Given this is a "founding designer" role for a new AI-native product, the portfolio should strongly emphasize the ability to define and innovate in uncharted territory. Case studies demonstrating strategic thinking, user research rigor, and the ability to translate complex concepts (like AI) into intuitive user flows will be critical. The company's emphasis on "Principles over playbooks" and "Ideas over egos" suggests a portfolio that highlights adaptability, learning, and collaborative problem-solving.

💵 Compensation & Benefits

Salary Range: $200,000 - $235,000 USD per year.
Explanation of Range: This range is provided by the employer and reflects the typical compensation for a Principal Product Designer with extensive experience in a high-cost-of-living area like Sunnyvale, CA. The final offer will be determined by factors such as the candidate's specific experience, interview performance, demonstrated skills, and overall fit for the role and company.

Benefits:

• Competitive Salary and Equity: A strong base salary combined with equity options, reflecting the senior level and impact of the role.
• Comprehensive Health Coverage: Medical, Dental, and Vision insurance plans to support employee well-being.
• Work-Life Balance: Unlimited Paid Time Off (PTO) and a dedicated Winter holiday break to encourage rest and rejuvenation.
• Family Support: Generous parental leave policies to support new parents.
• Professional Development & Well-being: Significant stipends for home office setup, continuous learning, wellness activities, and AI tools, underscoring the company's investment in employee growth and modern work enablement.
• Retirement Planning: 401(k) match for US employees and Pension match for Canadian employees, supporting long-term financial security.

Working Hours: The role is full-time, typical for a Principal Designer. While not explicitly stated as flexible, the hybrid model and generous PTO suggest a culture that values work-life integration. Expect standard business hours with the understanding that project demands may occasionally require flexibility, particularly during critical development phases.

📝 Enhancement Note: The salary range is competitive for a Principal Product Designer in the Bay Area, especially for a founding role on a new initiative. The inclusion of stipends for "AI tools" is particularly noteworthy, aligning with the role's focus on AI-native products and suggesting the company actively supports exploration and adoption of cutting-edge technology. The hybrid requirement of 1-2 days in-office in Sunnyvale, CA, is a key factor for candidates considering this role.

🎯 Team & Company Context

🏢 Company Culture

Industry: FinTech / SaaS (Equity Management, Startup Operations)
Company Size: Pulley is a growing startup that has secured significant funding from prominent investors. While an exact employee count isn't provided, the company has over 4,000 customers and is actively expanding its team, indicating a stage beyond early-stage but still maintaining startup agility.
Founded: The founding date is not specified, but the company's trajectory, customer base, and investor backing suggest a relatively young but established and rapidly scaling organization.

Team Structure:

• Operations Focus: The company is building tools for startup operations, specifically equity management. This means the core operations team likely comprises individuals deeply familiar with startup finance, legal compliance, and founder needs.
• Design Integration: Design is explicitly stated to have a "seat at the table from day one," with designers partnering directly with engineering and product leadership. This suggests a collaborative, integrated structure where design is a key driver of product strategy, not an afterthought.
• Cross-Functional Collaboration: The role emphasizes close collaboration with engineering, product, and leadership. This indicates a flat hierarchy and a focus on team-based problem-solving, common in agile startup environments.

Methodology:

• Data-Driven & Principled: While the company values "Good taste over data" and "Conviction over consensus," they also operate with "Principles over playbooks" and "Momentum over speed." This suggests a balanced approach that values strategic intuition and bold bets, grounded in understanding core principles and driving forward progress.
• AI-Centric Vision: Pulley is actively exploring and building for an "AI-native world," indicating a forward-looking methodology that embraces new technologies and their potential to transform existing workflows.
• Agile Development: The mention of a "small, fast-moving team" and the need to "shape product direction and strategy" implies an agile development process focused on rapid iteration and responsiveness to user needs and market opportunities.

Company Website: https://pulley.com/

📝 Enhancement Note: Pulley's mission to simplify company formation and equity management, combined with their focus on AI, positions them as an innovative player in the startup ecosystem. The company culture described through their operating principles ("Principles over playbooks," "Momentum over speed," "Ideas over egos," etc.) indicates a preference for proactive, thoughtful, and collaborative individuals who can drive impact. The "AI-native" focus is a significant differentiator and will shape the product development and user experience.

📈 Career & Growth Analysis

Operations Career Level: This Principal Product Designer role represents a senior-most or near senior-most individual contributor position within the design function, particularly for this new AI initiative. It signifies a high level of autonomy, strategic influence, and ownership. The role is foundational for the AI product, implying the potential to shape the future of design at Pulley.
Reporting Structure: The Principal Product Designer will likely report to a Head of Design, VP of Product, or a CTO, given the close collaboration with leadership and the strategic nature of the role. They will be the primary design lead for the AI product initiative.
Operations Impact: The design of Pulley's AI-native product will directly impact how thousands of startups manage critical operational and financial aspects of their business. A successful design will enhance user efficiency, improve decision-making, and potentially redefine the standard for startup equity management in an AI-augmented future, directly contributing to Pulley's growth and market position.

Growth Opportunities:

• Foundational Leadership: Opportunity to be the founding designer for a significant new product line, establishing its design vision, principles, and best practices. This can lead to leadership opportunities within the AI product domain.
• Skill Specialization: Deepen expertise in designing for AI-native products, user experience in complex financial/operational tools, and contributing to cutting-edge technology adoption.
• Strategic Influence: Directly influence product strategy and company direction through design leadership, potentially growing into a more senior design leadership role as the company scales.
• Cross-Functional Development: Gain broad experience working across product, engineering, and leadership in a fast-paced, funded startup environment, enhancing overall product development acumen.

📝 Enhancement Note: The "Principal" title and "founding designer" status for a new AI product indicate a high-impact role with significant potential for career advancement. This isn't just about executing designs; it's about shaping a new product category and influencing the company's strategic direction. Candidates should be prepared to discuss their vision for AI in business operations and how they can translate that into user-centric design.

🌐 Work Environment

Office Type: Pulley operates a hybrid work model, requiring 1-2 days of in-person collaboration per week in their Sunnyvale, CA office. This suggests a blend of focused individual work (potentially remote) and collaborative team sessions in a physical workspace.
Office Location(s): Sunnyvale, California, USA. This location is in the heart of Silicon Valley, offering proximity to a vibrant tech ecosystem.
Workspace Context:

• Collaborative Hub: The office environment is designed to facilitate cross-functional collaboration, essential for a fast-moving product team. Expect a dynamic atmosphere where design, product, and engineering teams interact regularly.
• Technology-Enabled: As a tech company focused on AI, expect access to modern tools and technology required for design and development. The company also offers stipends for "AI tools," suggesting a commitment to equipping employees with the latest resources.
• Team Interaction: The hybrid model necessitates intentional interaction, fostering strong working relationships through planned in-office days for brainstorming, workshops, and team building.

Work Schedule: The role is full-time. While specific hours aren't detailed, the hybrid model and focus on outcomes suggest a degree of flexibility, balanced with the need for scheduled in-office collaboration and responsiveness typical of a startup environment.

📝 Enhancement Note: The hybrid model in Sunnyvale, CA, is a key characteristic of the work environment. Candidates should be comfortable with commuting to the office for collaborative sessions while also valuing the flexibility of remote work for focused tasks. The emphasis on "stunning colleagues" and the company's operating principles suggest an environment that prioritizes high-quality work and positive team dynamics.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio to assess foundational qualifications and alignment with the role's requirements.
• Hiring Manager/Design Lead Call: An initial conversation to discuss your background, experience, and initial thoughts on the AI product initiative.
• Design Challenge/Case Study Presentation: You will likely be asked to present a portfolio piece or tackle a design challenge that demonstrates your approach to complex problems, strategic thinking, and user empathy, particularly in the context of AI or B2B products. This is where your "0-1" product thinking will be crucial.
• Cross-Functional Interviews: Meetings with Product Management, Engineering, and potentially other P. Design or leadership members to assess collaboration style, strategic alignment, and technical understanding.
• Final Round: Potentially a discussion with senior leadership (e.g., CEO, CTO) to evaluate strategic fit, cultural alignment, and long-term vision.

Portfolio Review Tips:

• Prioritize AI/B2B/0-1: Showcase projects most relevant to this role – complex B2B products, new product initiatives (0-1), and ideally, any experience with AI or emerging technologies.
• Tell a Story: For each case study, clearly articulate the problem, your role, your process (research, ideation, iteration), the challenges faced, and the impact of your design solutions. Quantify results where possible.
• Highlight Strategic Thinking: Demonstrate how you contributed to product strategy, not just UI execution. Show your understanding of user needs, business goals, and how design bridges them.
• Showcase Collaboration: Explain how you worked with cross-functional teams, managed feedback, and navigated trade-offs.
• Prepare for AI Discussion: Be ready to articulate your thoughts on the future of AI in business operations and how design can shape this landscape.

Challenge Preparation:

• Understand Pulley's Mission: Research Pulley's product, target audience (startups), and competitive landscape. Think about the challenges startups face in equity management.
• Brainstorm AI Applications: Consider how AI could fundamentally change equity management or startup operations. Think about agent-led workflows, predictive analytics, or automated strategic guidance.
• Focus on User Needs: Frame any challenge response around solving a core user problem, leveraging AI as a tool to achieve that solution.
• Structure Your Approach: For any design challenge, outline your steps: understanding the problem, defining users, brainstorming solutions, prototyping, and testing.

📝 Enhancement Note: The interview process for a Principal Designer, especially a founding role, tends to be rigorous. Candidates should expect to deeply explore their strategic thinking, problem-solving skills, and ability to operate autonomously. The portfolio review will be a critical component, so ensure it's tailored to showcase the specific skills and experiences Pulley is seeking for this unique AI-focused initiative.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping Software: Proficiency in industry-standard tools such as Figma, Sketch, Adobe Creative Suite (Illustrator, Photoshop), and prototyping tools like InVision, Axure, or similar. Figma is likely a core tool given its prevalence in collaborative design environments.
• User Research Platforms: Experience with tools for user interviews, surveys, and usability testing (e.g., UserTesting.com, Lookback, SurveyMonkey).
• Collaboration & Project Management: Familiarity with tools like Jira, Asana, Trello, or Notion for managing design tasks, tracking progress, and collaborating with product and engineering teams.

Analytics & Reporting:

• Product Analytics: While not a direct responsibility, understanding how to interpret data from tools like Amplitude, Mixpanel, or Google Analytics is beneficial for informing design decisions and measuring impact.
• Reporting Dashboards: Familiarity with data visualization tools or principles to understand how user data is presented and used to drive product strategy.

CRM & Automation:

• CRM Understanding: Basic familiarity with CRM systems (like Salesforce, HubSpot) is helpful for understanding broader business workflows, though not a primary design tool.
• Automation Concepts: An understanding of workflow automation principles will be valuable given the company's focus on AI-native tools and agent-led workflows.

📝 Enhancement Note: The company's mention of "Generous stipends for... AI tools" suggests that candidates might be encouraged to explore and utilize new AI-powered design assistance tools. While core design software is standard, an awareness of emerging AI tools in the design workflow could be a plus. The emphasis on AI-native products means an understanding of how data and AI models influence user experience design will be highly valued.

👥 Team Culture & Values

Operations Values:

• Principles over Playbooks: This value emphasizes critical thinking and understanding the 'why' behind strategies. For operations professionals, this means not just following established procedures but questioning them, adapting them, and innovating based on core business principles.
• Momentum over Speed: Focus on sustainable progress and delivering value effectively, balancing short-term wins with long-term success. In operations, this translates to building robust, scalable processes rather than rushing through quick fixes.
• Good Taste over Data: While data is important, this value highlights the importance of intuition, creativity, and bold bets, particularly in design and strategy. For operations, it means not shying away from innovative solutions even if they deviate from purely data-driven approaches.
• Ideas over Egos: A culture where the best idea wins, encouraging open communication and psychological safety for all team members to contribute. Operations professionals are encouraged to propose improvements and challenge the status quo.
• Gladiator over Spectator: A bias for action and execution. Operations team members are expected to be proactive, hands-on, and driven to achieve results, taking ownership of their work.
• Conviction over Consensus: Having the courage to stand by well-reasoned ideas, even if they aren't universally agreed upon initially. This fosters strong decision-making and innovation.
• Proactive over Passive: Taking initiative, seeking clarity, and driving for understanding. Operations professionals should be self-starters who actively seek information and context.

Collaboration Style:

• Integrated & Cross-Functional: Design, Product, and Engineering work closely together from the outset, fostering a unified approach to product development.
• Iterative & Feedback-Oriented: The culture supports continuous feedback and iteration, allowing for adjustments and improvements throughout the design and development process.
• Principle-Guided Decision Making: Discussions and decisions are often framed around the company's core operating principles, ensuring alignment and a shared understanding of strategic direction.

📝 Enhancement Note: Pulley's operating principles are a strong indicator of their desired culture. They value individuals who are proactive, strategic, collaborative, and possess strong convictions. For an operations professional, this means being comfortable with ambiguity, driving initiatives forward, and contributing to a culture of continuous improvement and innovation. The emphasis on "Gladiator over spectator" suggests a high-performance culture where initiative and execution are highly prized.

⚡ Challenges & Growth Opportunities

Challenges:

• Defining a New Paradigm: As the founding designer for an AI-native product, you will be tasked with defining user experiences for a nascent category. This requires significant foresight, research into user adoption of AI, and the ability to translate abstract AI capabilities into tangible user value.
• Balancing Innovation with Usability: Creating cutting-edge AI features while ensuring the product remains intuitive, accessible, and addresses the core needs of startup founders will be a key challenge.
• Cross-Functional Alignment on Novel Concepts: Navigating product strategy and design direction with engineering and leadership when working with emerging AI technologies can present unique communication and alignment challenges.
• Establishing Design Best Practices: Being the first designer for this initiative means you'll be responsible for setting the initial design standards, processes, and potentially a design system for this new product area.

Learning & Development Opportunities:

• Pioneering AI Product Design: Gain unparalleled experience in designing for AI-native applications and shaping the future of startup operations through technology.
• Strategic Product Influence: Directly impact the company's product roadmap and long-term vision by leading the design of a critical new initiative.
• Building from Scratch: Develop expertise in "0-1" product development, from ideation and research to launch and iteration in a funded startup environment.
• Mentorship & Leadership: Opportunity to mentor future designers and potentially grow into a leadership role as the AI product line expands.
• Industry Exposure: Engage with cutting-edge AI technology and contribute to the evolving landscape of FinTech and startup operational tools.

📝 Enhancement Note: The challenges presented are inherent to groundbreaking product development. Candidates should view these not as obstacles but as opportunities to demonstrate their strategic thinking, problem-solving skills, and pioneering spirit. The growth opportunities are significant, offering a chance to build something new and have a substantial impact on both the company and the industry.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you designed a completely new product or feature from scratch (0-1). What was your process, and what were the key challenges and outcomes?" (Focus on discovery, user needs, and strategic decision-making.)
• "How do you envision AI transforming startup operations or equity management? What are the key design opportunities and challenges you see?" (Demonstrate foresight, understanding of AI capabilities, and user-centric application.)
• "Walk us through a complex B2B product you designed. How did you balance user needs with business objectives and technical constraints?" (Highlight your B2B design expertise, problem-solving skills, and collaborative approach.)

Company & Culture Questions:

• "Based on our mission and values, how do you see yourself contributing to Pulley's culture as a Principal Product Designer?" (Connect your personal values and work style to Pulley's operating principles like "Ideas over egos" and "Gladiator over spectator.")
• "How do you approach collaboration with product managers and engineers, especially when dealing with novel concepts like AI?" (Showcase your cross-functional communication and teamwork skills.)
• "How would you establish design best practices for a new AI product initiative with a small, fast-moving team?" (Demonstrate your leadership in setting standards and processes.)

Portfolio Presentation Strategy:

• Focus on Impact: For each case study, clearly articulate the problem, your specific role, the strategies you employed, and the measurable outcomes or impact of your design. Quantify results whenever possible.
• Narrate Your Process: Walk through your design journey, explaining your rationale at each step – from initial research and ideation to prototyping, testing, and iteration.
• Highlight Strategic Contributions: Emphasize how your design thinking influenced product strategy and addressed core user and business needs.
• Be Prepared for AI Questions: Specifically discuss any projects that involved AI or complex technology, and be ready to articulate your vision for AI-driven user experiences.
• Demonstrate Collaboration: Explain how you partnered with cross-functional teams and incorporated feedback.

📝 Enhancement Note: Candidates should prepare to discuss their understanding of AI's role in business operations and demonstrate how they can translate complex technological concepts into intuitive user experiences. The interview process will likely assess not only design craft but also strategic thinking, leadership potential, and cultural fit within Pulley's unique operating principles.

📌 Application Steps

To apply for this Principal Product Designer position:

• Submit your application through the provided link on Greenhouse.
• Tailor Your Resume: Highlight experience with B2B products, end-to-end design ownership, and any involvement with new product initiatives (0-1). Explicitly mention skills related to user research, prototyping, and cross-functional collaboration.
• Curate Your Portfolio: Select 2-3 of your strongest case studies that best represent your experience in designing complex B2B products, leading design from inception, and ideally, any work involving innovative technologies or AI. Ensure each case study clearly articulates the problem, your process, your role, and the impact.
• Prepare Your Pitch: Be ready to articulate your vision for AI in business operations and how you would approach designing for an AI-native product at Pulley. Practice presenting your portfolio case studies concisely and impactfully.
• Research Pulley: Understand their mission, target audience (startups), product offering, and company culture, particularly their operating principles. This will help you tailor your application and responses to demonstrate alignment.

⚠️ 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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