Product Designer

📍 Job Overview

Job Title: Product Designer Company: Sailplane.ai Location: San Francisco, California, United States Job Type: FULL_TIME Category: Product Design / UX/UI Design Date Posted: 2026-02-09 Experience Level: 10+ years Remote Status: Hybrid (2-3 days in office)

🚀 Role Summary

• Shape the entire product experience for an early-stage AI infrastructure startup, focusing on autonomous systems and self-driving cloud technology.
• Drive the definition and evolution of end-to-end product UX, embodying the company's product vision and contributing to transformative enterprise computing.
• Develop functional prototypes for AI workflows, leveraging a blend of design and coding skills in tools like Cursor, Figma, and AI development platforms.
• Collaborate closely with customers and engineering teams through research, workshops, and design critiques to enhance features and designs.

📝 Enhancement Note: This role is positioned as a senior individual contributor, emphasizing hands-on craft and systems thinking rather than team management. The focus on "design to code" and AI UX indicates a need for a highly technical and integrated design approach within a fast-paced startup environment.

📈 Primary Responsibilities

• Define and evolve the end-to-end product user experience (UX) across Sailplane's AI infrastructure platform, aligning with the company's product vision and strategic goals.
• Prototype complex AI workflows and build functional prototypes using a "design to code" methodology, employing tools such as Claude Code, Cursor, Framer, Storybook, and Figma Dev Mode.
• Inspire and guide the engineering and product teams by presenting compelling mocks, interactive prototypes, and detailed UX feature designs that drive innovation.
• Conduct user research and workshops, embed with cross-functional teams, and lead design critiques and functional reviews to foster a collaborative and iterative design process.
• Establish and maintain a high standard for design craft and polish, ensuring excellence in interaction design, visual details, and overall user interface quality.
• Develop and implement scalable design systems and reusable patterns to ensure a cohesive and unified product experience across all Sailplane offerings.
• Explore and strategically integrate AI capabilities across user journeys, identifying opportunities to enhance user efficiency and product effectiveness.

📝 Enhancement Note: The responsibilities highlight a deep involvement in both strategic product definition and hands-on execution, particularly the "design to code" aspect which is crucial for an AI infrastructure product. The emphasis on collaboration with customers and internal teams suggests a strong user-centric approach within a technically complex domain.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong understanding of design principles, human-computer interaction, and technical concepts is expected, often gained through formal education or equivalent practical experience.

Experience: 10+ years of experience designing product experiences across various platforms, with a proven track record of shipping high-quality work at scale.

Required Skills:

• 10+ years of experience in product design, with a strong portfolio showcasing shipped work and significant impact.
• Deep proficiency in prototyping, with a comfort level working in both code and design tools, enabling rapid iteration from design to functional code.
• Experience designing with Artificial Intelligence (AI) or working on AI-powered products is essential.
• Strong product thinking capabilities, including defining user flows, applying jobs-to-be-done frameworks, and translating user needs into effective visual design solutions.
• Systems-level thinking applied across UX, UI, and design infrastructure to ensure scalability and consistency.
• Technical product familiarity, particularly with developer tools, B2B SaaS platforms, data-heavy user interfaces, or AI products.
• Excellent communication and presentation skills, with the ability to articulate complex AI hardware and agentic concepts to diverse audiences.
• Collaborative approach to working with cross-functional teams, including engineers, product managers, and customers.

Preferred Skills:

• Fluency in AI UX and adeptness at designing agentic workflows.
• Proficiency in tools like Cursor, Framer, Storybook, Figma Dev Mode, and other AI development tools.
• Experience with design critique methodologies and functional review processes.
• Familiarity with building and maintaining design systems.
• Experience working within a startup environment and navigating ambiguity.

📝 Enhancement Note: The requirement for 10+ years of experience and a strong portfolio, combined with the emphasis on AI UX and "design to code" proficiency, positions this as a lead or principal-level design role. The technical familiarity with developer tools and B2B SaaS is critical for designing for an enterprise AI infrastructure product.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A strong portfolio is mandatory, showcasing high-quality, shipped product experiences and demonstrating significant user and business impact.
• Portfolio pieces should highlight your ability to tackle complex problems, particularly those involving AI, agentic workflows, or technical/developer tools.
• Evidence of systems-level thinking, including the creation or contribution to design systems, reusable patterns, or scalable UX frameworks.
• Demonstrations of your "design to code" capability, showing a seamless transition from design concepts to functional prototypes or implemented features.
• Case studies that detail your problem-solving process, user research insights, design iterations, and the measurable outcomes achieved.

Process Documentation:

• Showcase an understanding of user research methodologies and how insights are translated into actionable design improvements and feature definitions.
• Detail your approach to prototyping, including the tools used, the fidelity of prototypes, and how they were leveraged for user testing and stakeholder feedback.
• Examples of how you've collaborated with engineering teams, including your role in design critiques, functional reviews, and bridging the gap between design and implementation.
• Documentation of your experience in creating or contributing to design systems, illustrating how you ensure consistency and scalability across a product.

📝 Enhancement Note: The portfolio requirements emphasize not just visual design but also the strategic and technical aspects, especially the "design to code" capability and systems thinking. Candidates should be prepared to demonstrate how their work directly translates into functional product experiences and business value.

💵 Compensation & Benefits

Salary Range: For a Product Designer with 10+ years of experience in San Francisco, California, the estimated salary range is typically between $170,000 - $250,000 annually, depending on specific qualifications, the scope of responsibilities, and the company's compensation philosophy.

Benefits:

• Comprehensive Health, Dental, and Vision coverage for employees and their families, fully paid by Sailplane starting on day one.
• Equity grant participation, offering ownership in the company's growth and success.
• Flexible Paid Time Off (PTO) with no accrual or annual cap, complemented by 15 paid holidays per year.
• Annual Health and Wellness stipend of $3,000 to support personal health and well-being goals.
• Annual AI Tools stipend of $1,200 to encourage hands-on exploration and familiarity with emerging AI tools.
• 12 weeks of paid parental leave for new parents.

Working Hours: The standard working hours are approximately 40 hours per week, with flexibility expected within a hybrid work model.

📝 Enhancement Note: The salary estimate is based on industry benchmarks for senior Product Designers in the San Francisco Bay Area, considering the AI startup context and the company's backing. The benefits package is highly competitive, with a strong emphasis on health, well-being, and professional development, particularly the unique AI Tools stipend.

🎯 Team & Company Context

🏢 Company Culture

Industry: AI Infrastructure / Enterprise Computing. Sailplane is at the forefront of developing autonomous infrastructure for managing large-scale AI data centers, a highly innovative and rapidly evolving sector. Company Size: Early-stage startup. This implies a dynamic, fast-paced environment where individual contributions have a significant impact, and team members are expected to be adaptable and take ownership. Founded: The company was founded recently, indicated by its early-stage status and backing from prominent venture capital firms. This suggests a culture of rapid innovation, agility, and a focus on building foundational technology.

Team Structure:

• The core team is small and highly skilled, composed of experienced engineers and leaders from prominent tech backgrounds (e.g., Google Cloud, AI industry).
• The Product Designer will report directly to the CEO, indicating a high level of visibility and direct impact on strategic decisions.
• Cross-functional collaboration is central, with close interaction between design, engineering, product management, and customer-facing roles.

Methodology:

• Data-driven decision-making is expected, leveraging user feedback, performance metrics, and technical insights.
• Agile and iterative development processes are likely in place to manage the complexities of AI infrastructure development.
• A strong emphasis on "systems thinking" and "design to code" suggests a focus on building robust, scalable, and maintainable solutions.

Company Website: https://careers.kula.ai/sailplane

📝 Enhancement Note: The company's focus on "self-driving cloud" and autonomous AI infrastructure management positions it as a leader in a critical, emerging technology space. The culture is likely to be driven by innovation, technical excellence, and a lean, agile approach common in well-funded, early-stage startups.

📈 Career & Growth Analysis

Operations Career Level: This role is a Senior Individual Contributor (IC) position, equivalent to a Principal Product Designer or Lead Designer in terms of experience and expected impact. It requires deep expertise and the ability to set design direction independently, mentor others, and influence product strategy.

Reporting Structure: The Product Designer will report directly to the CEO. This close proximity to leadership provides significant visibility and the opportunity to influence high-level product and business decisions.

Operations Impact: The Product Designer will play a pivotal role in shaping the user experience of a groundbreaking AI infrastructure platform. Their work will directly impact the usability, efficiency, and adoption of autonomous cloud management systems, which are critical for large-scale AI operations and enterprise computing. Success in this role means creating intuitive interfaces for complex, high-value systems, thereby driving operational efficiency and enabling clients to scale their AI initiatives.

Growth Opportunities:

• Skill Advancement: Deepen expertise in AI UX, agentic workflows, and "design to code" methodologies through hands-on project work and the company's AI tools stipend.
• Leadership Potential: While not a management role, the position offers opportunities to mentor junior designers and engineers, lead design initiatives, and influence product strategy, which can pave the way for future leadership roles.
• Industry Expertise: Gain invaluable experience in a cutting-edge field (AI infrastructure) with a company backed by top-tier VCs, positioning oneself for future opportunities in high-growth tech sectors.
• Strategic Influence: Direct reporting to the CEO allows for significant input into product vision and roadmap, fostering strategic thinking and business acumen.

📝 Enhancement Note: The direct reporting line to the CEO and the focus on a transformative technology suggest a high-impact role with significant growth potential, not just in design skills but also in strategic product development and understanding of AI infrastructure business models.

🌐 Work Environment

Office Type: This is a hybrid position. Sailplane operates from an office in San Francisco, requiring employees to be present 2-3 days per week. The office environment is likely to foster collaboration, innovation, and a strong team connection, typical of a modern tech startup.

Office Location(s): San Francisco, California. This location provides access to a vibrant tech ecosystem, talent pool, and networking opportunities. Specific details regarding office amenities or exact location within San Francisco would typically be shared during the interview process.

Workspace Context:

• Collaborative Environment: Expect a dynamic workspace designed to encourage interaction, brainstorming, and knowledge sharing among team members. This includes opportunities for design critiques, cross-functional workshops, and informal discussions.
• Tools and Technology: Access to cutting-edge design and development tools, including AI-specific platforms, coding environments (like Cursor), and comprehensive design software (like Figma). The company also provides an AI tools stipend for personal exploration.
• Team Interaction: Regular opportunities to engage with engineers, product managers, and leadership, fostering a tight-knit team dynamic essential for an early-stage startup.

Work Schedule: The role is full-time, with an expected 40-hour work week. The hybrid model offers flexibility for in-office days, allowing for a balance between focused individual work and collaborative team activities.

📝 Enhancement Note: The hybrid model in San Francisco, combined with a focus on collaborative work and access to advanced tools, suggests a work environment that balances flexibility with the need for in-person synergy crucial for early-stage product development.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio to assess experience, skills, and cultural fit. Be prepared to highlight your most relevant projects, especially those involving AI, complex systems, or "design to code" capabilities.
• Hiring Manager Interview: Likely with the CEO (Sam Ramji), focusing on your product vision, strategic thinking, and how you approach complex design challenges in an AI context.
• Design Challenge/Portfolio Deep Dive: A session where you present your portfolio in detail, explaining your process, rationale, and impact. You may be asked to walk through specific case studies or solve a hypothetical design problem related to AI infrastructure.
• Cross-functional Interviews: Conversations with engineers and other team members to assess your collaboration style, technical understanding, and ability to integrate with the team.
• Final Interview: Potentially with other key stakeholders, focusing on your long-term vision and alignment with Sailplane's mission.

Portfolio Review Tips:

• Curate Selectively: Focus on 3-5 of your strongest projects that best demonstrate your skills in AI UX, systems thinking, and "design to code."
• Tell a Story: For each project, clearly articulate the problem, your role, your process (research, ideation, prototyping, testing), the solutions you designed, and the measurable outcomes.
• Highlight AI & Technical Aspects: Emphasize any experience with AI products, agentic workflows, developer tools, or complex data-heavy UIs. Showcase your "design to code" capabilities with clear examples.
• Demonstrate Systems Thinking: Include examples of how you've contributed to design systems, scalable patterns, or have thought holistically about the product experience.
• Be Ready for Technical Discussion: Given the role's technical requirements, be prepared to discuss your proficiency with coding for prototypes and your understanding of the underlying technology.

Challenge Preparation:

• Understand the Domain: Research AI infrastructure, autonomous systems, and the "self-driving cloud" concept. Familiarize yourself with companies like Waymo and their approach to autonomy.
• Practice "Design to Code": If possible, refresh your skills in prototyping tools that bridge design and code (e.g., Framer, Storybook with code integration, or Cursor's capabilities).
• Articulate Complex Concepts: Practice explaining intricate AI concepts and technical challenges in simple, clear terms.
• Prepare for Strategy Questions: Think about how you would approach defining user experiences for highly technical B2B SaaS products and autonomous systems.

📝 Enhancement Note: The emphasis on a "design to code" capability and AI UX suggests that candidates will be rigorously tested on their technical design skills and ability to translate complex technical concepts into user-friendly interfaces. Portfolio presentations should clearly link design decisions to tangible business and user outcomes.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (including Dev Mode), Cursor (for code-based prototyping and design iteration), Framer, Storybook.
• AI Development Tools: Claude Code (or similar AI-assisted coding tools), and other emerging AI platforms used for workflow prototyping and development.
• Collaboration & Project Management: Tools like Jira, Confluence, or similar platforms for team collaboration and project tracking.

Analytics & Reporting:

• While not explicitly listed for the designer, an understanding of how user behavior is tracked and analyzed via analytics platforms (e.g., Amplitude, Mixpanel, Google Analytics) would be beneficial for informing design decisions.
• Ability to interpret data to drive design improvements and measure the impact of UX changes.

CRM & Automation:

• Familiarity with B2B SaaS CRM systems (e.g., Salesforce, HubSpot) is likely helpful for understanding the broader customer journey in a B2B context.
• Understanding of automation principles in design and workflow creation.

📝 Enhancement Note: The explicit mention of Cursor, Framer, Storybook, and AI coding tools highlights a strong requirement for designers comfortable and proficient in a code-centric prototyping environment, moving beyond traditional static mockups to functional prototypes.

👥 Team Culture & Values

Operations Values:

• Innovation & Boldness: A drive to tackle transformative challenges in AI infrastructure, pushing the boundaries of autonomous systems and enterprise computing.
• Customer Focus: Deep engagement with customers to understand their needs and challenges, embedding design within their workflows.
• Technical Excellence: A commitment to high standards in design craft, coding proficiency, and building robust, scalable systems.
• Collaboration & Ownership: A strong sense of teamwork, shared responsibility, and individual accountability for driving projects forward.
• Agility & Speed: The ability to move quickly, iterate rapidly, and adapt to the fast-paced nature of an early-stage startup.

Collaboration Style:

• Cross-functional Integration: Seamless collaboration between design, engineering, and product management is paramount. Designers are expected to work closely with engineers, often embedding within teams.
• Open Feedback Culture: Regular design critiques and functional reviews are integral to the process, fostering an environment where constructive feedback is valued and used for improvement.
• Knowledge Sharing: A culture that encourages sharing insights, best practices, and learnings, especially around AI UX and "design to code" workflows.

📝 Enhancement Note: The culture emphasizes a blend of ambitious innovation with practical execution, driven by a strong sense of ownership and collaborative problem-solving, particularly between design and engineering.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating Ambiguity: As an early-stage startup, priorities and product directions may evolve rapidly, requiring adaptability and a proactive approach to defining solutions.
• Designing for Complexity: Creating intuitive user experiences for highly technical AI infrastructure and autonomous systems presents a significant design challenge.
• Bridging Design and Code: Mastering the "design to code" workflow and ensuring seamless integration between design artifacts and functional prototypes/features requires continuous learning and skill refinement.
• Scaling Design: Developing scalable design systems and patterns that can accommodate the rapid growth and evolving needs of the platform.

Learning & Development Opportunities:

• AI UX Specialization: Gain deep expertise in designing for AI-driven products and agentic workflows, a highly sought-after skill.
• "Design to Code" Mastery: Become proficient in advanced prototyping techniques that leverage coding, enhancing your technical design capabilities.
• Strategic Product Influence: Work directly with the CEO and a high-caliber team, influencing the product roadmap and strategic direction of a groundbreaking technology.
• Industry Exposure: Immerse yourself in the cutting-edge field of AI infrastructure, with potential for industry conferences, workshops, and networking.

📝 Enhancement Note: The challenges are directly tied to the innovative nature of the company and its technology, offering significant opportunities for professional growth and skill development in a high-demand area.

💡 Interview Preparation

Strategy Questions:

• "How would you approach designing the user experience for an autonomous AI infrastructure management system? What are the key considerations for users interacting with 'million-dollar agents'?" (Focus on your product thinking, user research, and understanding of complex systems.)
• "Describe your process for moving from a design concept to a functional prototype using code. Walk us through an example from your portfolio." (Be prepared to demonstrate your "design to code" workflow and proficiency with relevant tools.)
• "How do you ensure consistency and scalability in design across a complex B2B SaaS product, especially when dealing with cutting-edge AI features?" (Highlight your experience with design systems, pattern libraries, and systems thinking.)

Company & Culture Questions:

• "What excites you about Sailplane's mission to build a 'self-driving cloud' and autonomous AI infrastructure?" (Show genuine interest and understanding of the company's vision.)
• "How do you typically collaborate with engineers and product managers in a fast-paced startup environment?" (Emphasize your adaptability, communication skills, and collaborative approach.)
• "How do you measure the success of your design work, particularly in a technical or AI-focused product?" (Discuss your approach to UX metrics, user feedback, and demonstrating ROI.)

Portfolio Presentation Strategy:

• Structure for Impact: Organize your presentation around 3-5 key projects. For each, clearly outline the problem, your role and process, the design solutions, and the quantifiable results.
• Show, Don't Just Tell: Use interactive prototypes or live demos where possible to showcase your "design to code" capabilities. Clearly articulate the technical aspects and AI integrations.
• Emphasize Systems Thinking: Dedicate time to explaining how your designs contribute to a larger system, design language, or scalable framework.
• Connect to Sailplane: Tailor your examples to resonate with Sailplane's domain—AI infrastructure, autonomous systems, B2B SaaS. Explain how your past experiences prepare you for the challenges and opportunities at Sailplane.

📝 Enhancement Note: Interview preparation should heavily focus on demonstrating technical design skills, strategic product thinking, and a deep understanding of AI UX principles, alongside strong collaboration and communication abilities.

📌 Application Steps

To apply for this Product Designer position:

• Submit your application through the provided link on the Kula careers portal.
• Portfolio Customization: Ensure your portfolio prominently features projects demonstrating AI UX, "design to code" capabilities, systems thinking, and experience with technical or B2B SaaS products.
• Resume Optimization: Tailor your resume to highlight your 10+ years of experience, specific achievements in product design, and proficiency with relevant tools and technologies mentioned in the job description. Use keywords like "AI UX," "prototyping," "systems thinking," "design to code," and "B2B SaaS."
• Interview Preparation: Practice articulating your design process, the rationale behind your decisions, and the impact of your work. Prepare to discuss your experience with AI and complex technical products, and be ready to present your portfolio confidently.
• Company Research: Thoroughly research Sailplane.ai, understanding their mission, the technology they are building (autonomous AI infrastructure, self-driving cloud), and their market position. Familiarize yourself with the background of the CEO, Sam Ramji.

⚠️ 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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