Senior/Staff Product Designer

📍 Job Overview

Job Title: Senior/Staff Product Designer

Company: Pulley

Location: San Francisco, CA, USA

Job Type: Full-Time

Category: Product Design

Date Posted: 2026-06-18

Experience Level: 5-10 Years

Remote Status: On-site

🚀 Role Summary

• Focus on designing the right product solutions before refining the execution, with a strong emphasis on user-centricity and problem-solving.

• Leverage AI throughout the design lifecycle, from initial research and ideation to high-fidelity prototyping and contributing to production code.

• Lead product design initiatives from concept to successful launch, ensuring a high standard of craft and execution for enterprise B2B software.

• Drive product definition and roadmap by advocating for the user through direct customer feedback and close collaboration with product and engineering teams.

📝 Enhancement Note: This role is positioned as a Senior/Staff level, indicating a need for significant autonomy, strategic thinking, and the ability to influence product direction. The emphasis on AI integration and a departure from traditional Figma workflows suggests a forward-thinking design team focused on efficiency and innovation.

📈 Primary Responsibilities

• Design and effectively communicate compelling user flows, wireframes, and detailed specifications for stakeholders and engineering teams, ensuring clarity and alignment.

• Integrate AI tools and methodologies across the entire design process, including desk research, rapid prototyping, and potentially contributing to the understanding of production code.

• Lead end-to-end design projects, taking ownership from initial concept exploration through to successful launch and post-launch iteration.

• Directly engage with customers through user interviews and feedback sessions to gather insights and validate design decisions for new and existing functionalities.

• Act as a strong advocate for the end-user, collaborating closely with product management and engineering to inform product strategy, requirements, and roadmap planning.

• Contribute to the development, maintenance, and evangelization of Pulley's design system, ensuring consistency and scalability across the product suite.

• Conduct thorough design QA to uphold a high standard of visual and interaction quality before features are released to production.

• Champion and evolve the product design lifecycle at Pulley, identifying opportunities for process improvement and innovation.

📝 Enhancement Note: The explicit mention of "designing the right thing before designing the thing right" suggests a strategic focus on product-market fit and problem definition, which is crucial for senior-level designers. The responsibility to "contribute to and evolve the design system" implies a need for a designer who can not only use but also shape design infrastructure.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio and relevant experience are paramount. A background in Design, Human-Computer Interaction, Computer Science, or a related field is often beneficial.

Experience: 5+ years of professional experience designing software products, with a preference for experience in enterprise or B2B product environments.

Required Skills:

• Product Design: Proven ability to conceptualize, design, and iterate on complex software products, with a strong understanding of user-centered design principles.

• Visual Design & Craft: Exceptional attention to detail in visual design, UI execution, and overall product polish.

• Prototyping (AI-driven): Expertise in utilizing AI tools to create working prototypes, demonstrating an ability to leverage emerging technologies for rapid iteration and user validation.

• User Flow Design: Skill in mapping out and designing intuitive user journeys for complex workflows.

• Stakeholder Communication: Ability to clearly articulate design decisions, rationale, and user insights to cross-functional teams, including product managers, engineers, and leadership.

• Design QA: Meticulous approach to design quality assurance, ensuring pixel-perfect execution and adherence to design standards.

Preferred Skills:

• B2B/Enterprise Software Design: Prior experience designing for business applications, understanding the unique needs and workflows of enterprise users.

• Design Systems: Experience contributing to, maintaining, and evangelizing design systems for consistency and scalability.

• User Research: Ability to conduct user research, synthesize findings, and translate them into actionable design improvements.

• Shipping Production Code: Familiarity or experience with collaborating with engineering teams on production code, understanding the development lifecycle.

• Agile/Startup Environments: Adaptability to fast-paced, iterative development cycles common in startup settings.

📝 Enhancement Note: The requirement for "Expert with Figma designs and prototypes" is immediately qualified by the statement that "We rarely use Figma at Pulley." This is a critical distinction. The emphasis shifts to AI-driven prototyping and a pragmatic approach to "drawing rectangles" as the core method for communicating solutions, rather than adherence to a specific tool. This suggests the company is prioritizing adaptability and a willingness to embrace novel workflows over traditional software proficiency.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrate end-to-end product design process, from problem definition and user research to final UI and interaction design.

• Showcase at least one significant project where AI was leveraged to accelerate the design process, improve prototype fidelity, or inform product decisions.

• Include case studies that highlight complex problem-solving for B2B or enterprise contexts, detailing the challenges, your approach, and the outcomes.

• Present examples of visual design craft and UI polish, illustrating a high standard for product aesthetics and user experience.

• Clearly articulate your role and contributions within collaborative team environments (product, engineering). Process Documentation:

• Detail your approach to user research and customer engagement, with examples of how feedback was incorporated into design iterations.

• Explain your methodology for translating complex business requirements into intuitive user flows and functional designs.

• Illustrate your contribution to or management of design systems, including principles of consistency, scalability, and component-based design.

• Showcase how you collaborate with engineering teams, including your process for delivering design specifications and ensuring successful implementation.

📝 Enhancement Note: Given the company's emphasis on AI and a non-Figma workflow, the portfolio should highlight projects that demonstrate innovative problem-solving using new tools and methodologies. The ability to rapidly prototype and communicate complex ideas efficiently will be key.

💵 Compensation & Benefits

Salary Range: $180,000 - $250,000 USD per year. This range reflects a senior/staff level position in a high-cost-of-living area like San Francisco, considering the company's funding and industry.

Benefits:

• Equity: Significant stock options package, aligning employee success with company growth.

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

• 401(k) Plan: Retirement savings plan to support long-term financial well-being.

• Paid Time Off: Generous PTO policy for work-life balance.

• Professional Development: Opportunities for learning and growth, potentially including conference attendance or training in new design technologies.

• Team Events: Regular team-building activities and offsites to foster collaboration and company culture.

Working Hours: Standard full-time hours (approximately 40 hours per week), with the expectation of flexibility to meet project deadlines and business needs, common in startup environments.

📝 Enhancement Note: The salary range is competitive for a Senior/Staff Product Designer in San Francisco. The inclusion of equity is a standard and significant component for roles at this level in well-funded startups, signaling potential for substantial financial upside.

🎯 Team & Company Context

🏢 Company Culture

Industry: Software / Technology, specifically focusing on AI-powered permitting intelligence and project lifecycle management for commercial construction and retail buildouts. The company operates within the PropTech (Property Technology) and ConstructionTech sectors.

Company Size: The company is likely in a growth phase, with a design and engineering team of "15+ people." This suggests a dynamic environment where individual contributions have a significant impact.

Founded: Founded in 2021, Pulley is a relatively young startup, indicating a fast-paced, innovative, and potentially high-growth culture.

Team Structure:

• The design and engineering teams are collocated, fostering close collaboration and rapid iteration.

• The role reports to the CEO, Charlie Jacobson, indicating a high level of visibility and direct access to leadership.

• A design and engineering team size of 15+ suggests a specialized but integrated unit where designers work closely with engineers. Methodology:

• AI-Driven Design: A core tenet is leveraging AI across the design lifecycle, moving beyond traditional tools for efficiency and innovation.

• Customer-Centricity: Direct customer engagement is a key part of the product definition and feedback loop.

• Outcome-Oriented: Focus on delivering tangible results like reduced approval timelines, improved forecasting accuracy, and reduced manual work for clients.

• Startup Agility: Embraces fast-paced, async collaboration, ownership, and adaptability.

Company Website: https://withpulley.com

📝 Enhancement Note: The company's focus on AI and its mission to streamline complex, often outdated processes (like permitting) suggests a culture that values innovation, efficiency, and problem-solving. The direct reporting to the CEO implies that this role will have significant strategic influence.

📈 Career & Growth Analysis

Operations Career Level: This role is at the Senior/Staff level, signifying a designer expected to operate with a high degree of autonomy, lead complex projects, mentor junior designers (if applicable), and contribute to strategic product decisions. The "Staff" designation often implies impact beyond a single team or product area, potentially influencing broader design strategy or cross-functional initiatives.

Reporting Structure: Reporting directly to the CEO, Charlie Jacobson, provides unparalleled visibility and direct influence on product strategy and company direction. This is a rare opportunity for a designer to be so closely integrated with executive leadership.

Operations Impact: The designer's work will directly impact the efficiency and predictability of commercial projects for Pulley's clients, which include major brands and large-scale buildouts. Success in this role means making complex permitting processes simpler and faster, directly contributing to revenue enablement and client satisfaction by reducing costly delays.

Growth Opportunities:

• Strategic Influence: Direct access to the CEO and leadership offers significant opportunities to shape product vision and company strategy.

• AI Design Leadership: Become a leader in applying AI to the design process within a growing company, building expertise in a cutting-edge field.

• Design System Ownership: Play a key role in building and scaling Pulley's design system as the company grows.

• Mentorship: Potential to mentor other designers as the team expands.

• Career Acceleration: High impact and visibility in a fast-growing startup environment can lead to rapid career advancement.

📝 Enhancement Note: The reporting structure to the CEO is a significant differentiator, offering a growth path that extends beyond traditional design leadership into product strategy and executive influence. The emphasis on AI also positions the designer for high-demand specialization.

🌐 Work Environment

Office Type: This is an on-site role based in San Francisco, CA. The description implies a collocated design and engineering team, suggesting a collaborative and interactive physical workspace.

Office Location(s): San Francisco, CA, USA. Specific office details beyond this are not provided but would likely be in a tech hub area.

Workspace Context:

• Collaborative Environment: The collocated design and engineering team fosters close working relationships, facilitating rapid communication, brainstorming, and problem-solving.

• Tools & Technology: Expect access to modern design and collaboration tools, with a specific emphasis on AI integration rather than traditional software like Figma for core design output.

• Team Interaction: Opportunities for direct interaction with product managers, engineers, leadership, and customers, creating a dynamic and engaging work environment.

Work Schedule: The role is full-time (approx. 40 hours/week). While on-site, the startup culture may offer some flexibility, but the emphasis on collaboration and rapid iteration suggests a need for consistent presence and availability during core working hours.

📝 Enhancement Note: The "on-site" requirement for a role emphasizing AI and async communication is interesting. It suggests that while AI tools are central, the company values the synergy and immediate feedback loops that come from in-person collaboration for complex problem-solving and strategic alignment.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Likely a brief conversation to assess alignment with the role's core requirements and company culture.

• Portfolio Review: A deep dive into your portfolio, focusing on your design process, problem-solving approach, strategic thinking, and how you leverage AI. Be prepared to discuss specific projects in detail, emphasizing your role and impact.

• Design Challenge/Case Study: You may be asked to present a hypothetical or past design challenge, demonstrating your approach to solving a complex problem relevant to Pulley's domain. Focus on your rationale, user-centricity, and how you would leverage AI.

• Team/Cross-functional Interviews: Meetings with engineering, product, and potentially other stakeholders to assess collaboration style and technical understanding.

• CEO Interview: A final conversation with Charlie Jacobson, focusing on strategic alignment, cultural fit, and your vision for the role.

Portfolio Review Tips:

• Highlight AI Integration: Clearly showcase projects where you've used AI to enhance your design process, from ideation to prototyping. Explain the benefits and outcomes.

• Focus on Process & Rationale: Go beyond pretty pictures. Detail why you made certain design decisions, what problems you were solving, and what trade-offs you considered.

• Demonstrate Strategic Thinking: Show how your designs align with business goals and user needs. For Pulley, this means understanding the B2B context and the impact on complex commercial projects.

• Articulate Collaboration: Provide examples of how you've worked effectively with engineering and product teams to ship successful products.

• Embrace the "Drawing Rectangles" Mentality: Be prepared to discuss how you translate ideas into clear, functional representations, even if not using traditional tools like Figma.

Challenge Preparation:

• Understand Pulley's Domain: Research permitting, commercial construction, and the challenges Pulley aims to solve.

• Think AI-First: Consider how AI can fundamentally change design workflows and product capabilities in this space.

• Focus on B2B User Needs: Think about the unique challenges and workflows of professionals using software for their jobs.

• Prepare to Discuss Trade-offs: Be ready to discuss how you balance user experience, technical feasibility, and business objectives, especially in a fast-paced startup environment.

📝 Enhancement Note: The interview process will heavily scrutinize the candidate's ability to adapt to non-traditional design workflows and leverage AI effectively. Demonstrating strategic product thinking and a deep understanding of B2B user needs will be critical.

🛠 Tools & Technology Stack

Primary Tools:

• AI Prototyping Tools: Specific tools are not named, but the role requires expertise in leveraging AI for generating prototypes and solutions. This could include AI-assisted design platforms, generative AI tools for UI elements, or AI-powered research assistants.

• Collaboration Tools: Slack for asynchronous communication, and likely other project management tools (e.g., Jira, Asana) for task tracking.

• Design Communication Tools: While not Figma, there will be tools for creating and sharing visual representations of designs (e.g., Miro for whiteboarding, potentially specialized AI design tools).

Analytics & Reporting:

• Product Analytics: Tools to understand user behavior within the product (e.g., Amplitude, Mixpanel, Pendo) to inform design decisions.

• Customer Feedback Platforms: Mechanisms for collecting and analyzing customer feedback (e.g., surveys, in-app feedback tools, CRM integrations).

CRM & Automation:

• CRM: Likely a system to manage customer relationships and sales pipelines (e.g., Salesforce, HubSpot) that product designers may interface with for customer insights.

• Internal Documentation: Tools like Notion or Confluence for documenting design processes, systems, and project information.

📝 Enhancement Note: The emphasis on AI-driven prototyping is the most significant technological differentiator. Candidates should be prepared to discuss their experience with or willingness to learn and master new AI design tools. The absence of a mandatory Figma requirement suggests that proficiency in the outcome of design (clear, functional solutions) is more important than adherence to a specific tool.

👥 Team Culture & Values

Operations Values:

• Design the Right Thing: Prioritize understanding and solving the core problem before focusing on execution details.

• Curiosity & Obsession: Foster a deep drive to understand "why" and obsess over nuanced problems.

• High Craft Bar: Maintain an infectious commitment to quality, detail, and polished product experiences.

• Methodical Problem-Solving: Employ principles and frameworks to tackle problems of varying scales, acknowledging that effective methods exist.

• Designing for Work: Focus on creating intuitive and efficient software for professional use, simplifying complex domains.

• Startup Energy: Embrace fast-paced environments, async collaboration, ownership, and adaptability with strong opinions held loosely.

Collaboration Style:

• Cross-functional Integration: Close collaboration with collocated design and engineering teams, and direct partnership with product management.

• Async Communication: Reliance on tools like Slack for efficient communication in a distributed or hybrid work context.

• Customer-Centric Feedback Loop: Active engagement with customers to inform design decisions and product direction.

• Iterative Development: A culture that embraces rapid iteration, feedback, and continuous improvement.

📝 Enhancement Note: The values highlight a blend of rigorous design thinking ("method," "craft") with a pragmatic, innovative startup ethos ("startup energy," "AI-driven"). The emphasis on "designing for work" is a key cultural indicator for B2B product companies.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating Uncharted Territory: Working with AI in design is an evolving field; designers will need to experiment, learn, and adapt quickly.

• Balancing Innovation with Pragmatism: Integrating cutting-edge AI solutions with the practical needs of enterprise users and the realities of shipping production software.

• Defining and Evolving Design Processes: As a relatively young company, the designer will play a role in shaping and refining design workflows, systems, and best practices.

• Communicating Complex Solutions: Effectively conveying intricate design solutions and AI-driven functionalities to diverse stakeholders.

Learning & Development Opportunities:

• Mastery of AI in Design: Become an expert in applying AI tools and methodologies to the entire product design lifecycle, a highly sought-after skill.

• Strategic Product Influence: Gain significant experience in product strategy and roadmap definition through direct collaboration with the CEO and leadership.

• Design System Development: Contribute to the foundational elements of a growing company's design infrastructure.

• Industry Exposure: Work in the dynamic PropTech/ConstructionTech space, understanding the challenges of digitizing complex, traditional industries.

📝 Enhancement Note: The primary challenge and growth opportunity lie in pioneering AI-driven design practices within a real-world B2B product context. This role offers a unique chance to shape the future of design tooling and processes.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you designed the 'right thing' before the 'thing right.' What was the problem, your process, and the outcome?" (Focus on problem definition, user research, and strategic alignment.)

• "How would you approach designing a new feature that leverages AI to simplify the permitting process for a builder? Walk us through your initial thoughts and process." (Demonstrate your AI-first thinking and B2B domain understanding.)

• "Tell us about a complex B2B product you've designed. What were the biggest challenges, and how did you ensure a high bar of craft and user experience?" (Showcase your experience with enterprise software and attention to detail.) Company & Culture Questions:

• "Why are you interested in Pulley and our mission to bring AI to commercial project management?" (Research Pulley's mission, market, and funding. Connect it to your passion for designing for work.)

• "How do you stay curious and obsess over problems? Can you give an example?" (Highlight your intrinsic motivation and problem-solving drive.)

• "Describe your ideal collaboration style with engineering and product teams in a fast-paced startup environment." (Emphasize adaptability, async communication skills, and ownership.) Portfolio Presentation Strategy:

• Structure Your Case Studies: Begin with the problem and business context, detail your unique approach (especially AI integration), showcase your design artifacts and rationale, and conclude with outcomes and learnings.

• Quantify Impact: Where possible, use metrics to demonstrate the success of your designs (e.g., improved efficiency, reduced errors, increased user adoption).

• Emphasize Your Role: Clearly define your contributions, especially in collaborative projects.

• Be Ready for "Why Not Figma?": Prepare to articulate your understanding of the company's AI-centric workflow and your comfort with evolving design tools.

📝 Enhancement Note: The interview will heavily weigh your ability to think strategically, adapt to new technologies (AI), and understand the nuances of B2B design. Be prepared to articulate your design philosophy and how it aligns with Pulley's innovative approach.

📌 Application Steps

To apply for this Senior/Staff Product Designer position:

• Submit your application through the provided link on Ashby.

• Customize Your Resume: Tailor your resume to highlight your 5+ years of experience in software product design, specifically mentioning B2B or enterprise experience if applicable. Emphasize any experience with AI tools, rapid prototyping, and design systems.

• Curate Your Portfolio: Select 2-3 of your strongest projects that best showcase your end-to-end design process, problem-solving skills, visual craft, and any AI integration. Ensure your portfolio clearly articulates your role and the impact of your work.

• Prepare Your Narrative: Practice articulating your design philosophy, your approach to problem-solving, and your excitement for Pulley's mission. Be ready to discuss specific projects in detail and how you've leveraged innovative tools like AI.

• Research Pulley: Understand their product, target market, company mission, and the challenges they are solving. This will enable you to ask insightful questions and demonstrate genuine interest.

⚠️ 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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