Senior Product Designer

📍 Job Overview

Job Title: Senior Product Designer

Company: Decagon

Location: San Francisco, CA, United States

Job Type: FULL_TIME

Category: Product Design / UX/UI

Date Posted: 2026-08-26

Experience Level: 6+ Years (with 2+ years in complex B2B/Enterprise)

Remote Status: On-site

🚀 Role Summary

• Spearhead the design of novel interaction patterns for autonomous AI agents, defining the future of conversational AI user experiences.

• Drive end-to-end design initiatives from deep customer discovery and problem framing to polished feature launches and adoption.

• Collaborate intensely with product management and engineering to translate complex business needs and technical constraints into intuitive, scalable enterprise SaaS solutions.

• Leverage a blend of traditional design tools (Figma) and emerging AI-powered tools (Cursor, Claude Code) to rapidly prototype and iterate on innovative product concepts.

• Contribute significantly to the foundational design system and shape the culture and practices of a growing, high-impact design team.

📝 Enhancement Note: This role is positioned as a senior, early-stage design hire within a rapidly growing AI company. The emphasis is on defining new product paradigms rather than iterating on established ones, requiring a high degree of autonomy, strategic thinking, and comfort with ambiguity. The unique blend of traditional design craft with AI tool fluency is a critical differentiator for candidates.

📈 Primary Responsibilities

• Lead the discovery, ideation, and design of user interfaces and interaction models for Decagon's core conversational AI platform, focusing on agent authoring, control, and trust.

• Translate complex user needs and business requirements into clear, actionable design specifications, wireframes, prototypes, and high-fidelity mockups.

• Conduct user research, interviews, and usability testing to gather insights, validate design decisions, and inform product strategy.

• Collaborate closely with product managers and engineers in small, autonomous project teams to ensure seamless execution from concept to launch.

• Develop and maintain robust design systems and components to ensure consistency, scalability, and efficiency across the product.

• Prototype using Figma and actively explore and integrate AI-powered design tools (e.g., Cursor, Claude Code) to accelerate the design and development cycle.

• Articulate design rationale clearly and persuasively to cross-functional stakeholders, building alignment and driving consensus.

• Contribute to the growth of the design team by participating in hiring, mentoring, and shaping design processes and culture.

📝 Enhancement Note: The responsibilities highlight a blend of strategic product definition and hands-on execution. The emphasis on "defining what great agent UX looks like" and "inventing" new patterns suggests a significant opportunity for innovation. The requirement to prototype directly on the codebase with AI tools points to a highly integrated design and engineering workflow.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio demonstrating equivalent knowledge and experience in product design, UX/UI, or a related field is paramount.

Experience: 6+ years of professional product design experience, with a minimum of 2 years focused on complex systems, B2B SaaS, or enterprise-level products where the designer is not the primary user.

Required Skills:

• Proven experience driving design initiatives end-to-end, from initial discovery and problem framing through to successful launch and adoption.

• Exceptional visual and interaction design craft, with a strong portfolio showcasing complex problem-solving and elegant solutions.

• Fluency in Figma for wireframing, prototyping, and high-fidelity design.

• Demonstrated ability to prototype rapidly, ideally with experience in AI-powered design tools such as Cursor or Claude Code.

• Strong understanding of user-centered design principles and methodologies, including user research and usability testing.

• Ability to articulate design decisions and rationale clearly and persuasively to cross-functional teams (Product, Engineering, Marketing).

• An ownership mindset with a proactive approach to identifying and solving problems. Preferred Skills:

• Experience creating, maintaining, or significantly contributing to design systems.

• Technical understanding of Large Language Models (LLMs) and hands-on experience building on top of them, shaping their behavior.

• Direct experience with voice technology, including conversational AI, speech synthesis, or audio production.

• Breadth of design experience, enabling systems thinking and strategic vision, coupled with an ability to execute at the pixel-perfect level.

• Experience working in fast-paced, agile startup environments.

• Courage to experiment, advocate for ideas, and humility to iterate based on feedback.

📝 Enhancement Note: The "even better if you have" section provides valuable insights into areas where candidates can differentiate themselves. Technical understanding of LLMs and experience with voice technology are particularly relevant given Decagon's focus on conversational AI. The emphasis on systems thinking and the ability to contribute to a design system are also key indicators of a senior-level contributor.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A curated selection of 3-5 case studies that demonstrate ownership of complex design challenges from discovery to launch.

• Focus on projects involving B2B SaaS, enterprise products, or complex systems where user needs, technical constraints, and business goals were balanced.

• Showcase your process for framing ambiguous problems, conducting user research, and iterating on solutions based on feedback and data.

• Highlight your visual and interaction design craft with high-fidelity mockups and interactive prototypes.

• Include evidence of your ability to collaborate effectively with product managers and engineers. Process Documentation:

• For each case study, clearly articulate the problem statement, your role and responsibilities, the design process followed, key decisions made, and the impact of your work.

• Demonstrate how you leveraged design systems or contributed to their development.

• If applicable, showcase your experience with AI-powered design tools or your approach to integrating AI into the design workflow.

• Quantify the impact of your designs where possible, using metrics related to user adoption, task completion, efficiency gains, or business outcomes.

📝 Enhancement Note: For a senior product design role, especially in an emerging field like AI-driven customer experience, the portfolio is critical. It needs to go beyond just showcasing polished UIs and demonstrate a deep understanding of the design process, problem-solving capabilities, and the ability to drive significant impact. The emphasis on AI tools and LLM understanding suggests that case studies involving these technologies will be highly valued.

💵 Compensation & Benefits

Salary Range: $212,000 - $265,000 USD per year. This range reflects the senior nature of the role, the demand for specialized AI design skills, and the cost of living in San Francisco.

Benefits:

• Comprehensive Medical, Dental, and Vision insurance for employees and their families.

• Life Insurance and Disability Benefits to provide financial security.

• Retirement Plan (e.g., 401K) for long-term financial planning.

• Generous Parental Leave to support new parents.

• Fertility and family building benefits through Carrot.

• Monthly stipend to support wellness, lifestyle, and work-life balance.

• Daily lunches and snacks provided in the office, fostering a collaborative and convenient work environment.

• Take-what-you-need vacation policy, promoting work-life balance and employee well-being.

• Significant Equity offering, providing ownership and upside in the company's growth.

Working Hours: The standard work week is 40 hours, typical for a full-time role in the US tech industry. The company culture emphasizes velocity and excellence, suggesting a dynamic and potentially fast-paced work environment.

📝 Enhancement Note: The salary range is competitive for a Senior Product Designer in San Francisco, especially for a role at a well-funded startup in the AI space. The equity component is particularly significant for senior hires. The benefits package is robust and includes several modern perks like fertility support and a wellness stipend, aligning with typical startup offerings.

🎯 Team & Company Context

🏢 Company Culture

Industry: Conversational AI Platform / Enterprise SaaS. Decagon operates at the intersection of AI, customer experience, and enterprise software, providing a cutting-edge solution for businesses.

Company Size: Decagon is a growing company, likely between 50-250 employees, indicated by its funded status and the mention of building out teams. This size typically offers a balance between the agility of a startup and the structure needed for enterprise-level operations.

Founded: While the founding date isn't explicitly stated, the company's backing by prominent investors suggests it is a relatively young but established startup, likely founded within the last 5-10 years.

Team Structure:

• The design team is early and growing, reporting to a Senior Director of Product Design. This implies a lean, high-impact team where individual contributions are highly visible.

• Designers work in small, autonomous project teams, pairing closely with engineers and product managers. This structure fosters agility, rapid iteration, and shared ownership.

• Collaboration extends across product, engineering, and go-to-market functions, ensuring a holistic approach to product development. Methodology:

• Data-Driven Insights: Emphasis on customer research, user interviews, and usability testing to inform design decisions.

• Agile Development: Small, autonomous teams suggest an agile or lean development methodology, prioritizing speed, flexibility, and continuous delivery.

• AI-Centric Innovation: A core part of the company's DNA is leveraging AI to redefine customer experiences, influencing product strategy and design approach.

Company Website: https://decagon.ai/

📝 Enhancement Note: Decagon's culture is characterized by "Just Get It Done," "Invent What Customers Want," "Winner's Mindset," and "The Polymath Principle." This suggests a results-oriented, innovative, and collaborative environment that values broad skill sets and a proactive approach. The "in-office" policy indicates a preference for in-person collaboration and team building.

📈 Career & Growth Analysis

Operations Career Level: Senior Product Designer. This level signifies a high degree of autonomy, the ability to own significant product areas end-to-end, and a key role in shaping product strategy and design direction. It involves not just execution but also problem framing, strategic thinking, and mentoring.

Reporting Structure: Reports to the Senior Director of Product Design. This provides a clear reporting line to experienced design leadership, offering mentorship and guidance.

Operations Impact: The role has a direct and substantial impact on the core product offering, which is central to Decagon's mission of redefining customer experiences through AI. The design of agent UX and authoring interfaces will be critical to the platform's adoption and success with enterprise clients, directly influencing revenue and market position.

Growth Opportunities:

• Leadership: Potential to grow into a Lead Product Designer role, managing specific product areas or mentoring junior designers as the team expands.

• Specialization: Opportunity to become a deep expert in Conversational AI UX, a rapidly evolving and high-demand field.

• Foundational Contribution: As an early design hire, there's a unique chance to shape the design team's culture, processes, and foundational design systems, offering significant influence and visibility.

• Cross-functional Advancement: Exposure to product strategy, engineering challenges, and go-to-market efforts can broaden skill sets and open doors to broader product leadership roles.

📝 Enhancement Note: The "Senior" title and the emphasis on "founding member" indicate a significant growth trajectory. Candidates should expect to not only contribute design expertise but also help build the design function itself. The unique domain of AI agent UX presents a significant opportunity for specialization and career advancement.

🌐 Work Environment

Office Type: Decagon is an "in-office company," indicating a preference for a physical workspace rather than fully remote. This suggests a collaborative environment with opportunities for spontaneous interaction.

Office Location(s): San Francisco, CA. This location places the company within a major tech hub, offering access to talent, resources, and a vibrant ecosystem.

Workspace Context:

• Collaborative Environment: The in-office policy suggests dedicated collaboration spaces and a culture that values face-to-face interaction for brainstorming, problem-solving, and team building.

• Tools and Technology: Access to modern design tools (Figma) and cutting-edge AI development tools (Cursor, Claude Code) will be integral to the daily workflow, supporting rapid prototyping and iteration.

• Team Interaction: Close pairing with product managers and engineers in small project teams will facilitate constant communication, feedback loops, and shared problem-solving.

Work Schedule: Standard full-time hours (approximately 40 hours per week) are expected. The company culture's emphasis on "velocity" and "excellence" may imply a dynamic work pace, but the "take what you need" vacation policy aims to balance this with employee well-being.

📝 Enhancement Note: The on-site requirement is a key differentiator. Candidates must be willing to work from the San Francisco office, suggesting that in-person collaboration is highly valued by Decagon for fostering innovation and team cohesion in the complex AI space.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your application and portfolio to assess alignment with the role's requirements and experience level.

• Design Challenge/Portfolio Review: A deeper dive into your portfolio, likely involving a presentation of 1-2 case studies. Be prepared to discuss your process, rationale, challenges, and impact. You may also be given a design exercise or prompt to assess your problem-solving and design skills.

• Cross-functional Interviews: Meetings with Product Managers and Engineers to assess collaboration style, technical understanding, and ability to work effectively in autonomous teams.

• Hiring Manager/Director Interview: A discussion with the Senior Director of Product Design to evaluate strategic thinking, leadership potential, cultural fit, and alignment with Decagon's values.

Portfolio Review Tips:

• Focus on Process, Not Just Polish: Clearly articulate the problem, your role, your design process, the trade-offs you made, and the outcomes. Use visuals to support your narrative.

• Highlight Ambiguity and Problem Framing: Given the role's focus on inventing new patterns, showcase instances where you tackled ill-defined problems and successfully framed them for design.

• Showcase AI Tool Fluency: If you have experience with AI-assisted design tools or have experimented with them, be prepared to discuss your findings and potential applications.

• Quantify Impact: Whenever possible, use data and metrics to demonstrate the success and impact of your designs.

• Tailor to Decagon: Research Decagon's product and mission thoroughly. Frame your case studies to highlight relevant skills and experiences, especially those related to enterprise SaaS, AI, or complex systems.

Challenge Preparation:

• Problem-Solving: Be ready for hypothetical scenarios related to designing AI interfaces, improving complex workflows, or balancing competing user needs.

• Design Thinking: Practice articulating your approach to user research, ideation, prototyping, and iteration.

• Communication: Prepare to present your ideas clearly, concisely, and persuasively, anticipating questions from both design and technical perspectives.

📝 Enhancement Note: The interview process emphasizes not just design skills but also strategic thinking, collaboration, and adaptability, particularly in the context of AI. The portfolio review is a critical gate, so candidates should invest significant time in preparing compelling case studies that demonstrate their ability to handle ambiguity and innovate.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The core tool for UI design, wireframing, and prototyping. Proficiency is essential.

• AI-Powered Design Tools: Explicitly mentioned are Cursor and Claude Code. Familiarity or a strong willingness to learn and integrate these into the workflow is expected. These tools likely assist with code generation, rapid prototyping, and potentially AI model interaction.

Analytics & Reporting: While not explicitly listed, expect to work with product analytics tools to understand user behavior and measure design impact. This could include tools like Amplitude, Mixpanel, or similar platforms.

CRM & Automation: Not directly relevant to the design role, but awareness of the enterprise SaaS context and how design impacts customer experience and sales enablement could be beneficial. Understanding how AI agents interact with customer data would be a plus.

📝 Enhancement Note: The explicit mention of Cursor and Claude Code is a significant indicator of the technology stack and the type of work expected. Candidates who can demonstrate experience or a strong aptitude for using AI tools to augment their design process will have a distinct advantage. This reflects Decagon's commitment to leveraging AI across all aspects of product development.

👥 Team Culture & Values

Operations Values:

• Just Get It Done: A strong bias for action and execution. This means taking initiative, overcoming obstacles, and delivering results efficiently.

• Invent What Customers Want: A deep focus on user needs and innovation. Design decisions should be driven by a genuine understanding of customer problems and a desire to create novel solutions.

• Winner's Mindset: A competitive drive and a commitment to excellence. This translates to striving for the best possible outcomes and pushing boundaries.

• The Polymath Principle: Valuing individuals with diverse skills and knowledge. This encourages learning across disciplines and fosters a collaborative environment where different expertise can be shared.

Collaboration Style:

• Tight-Knit Project Teams: Designers work closely with Product Managers and Engineers in small, autonomous units, fostering a highly collaborative and integrated workflow.

• Cross-Functional Partnership: Collaboration extends beyond the immediate project team to Product, Engineering, and Go-to-Market functions, ensuring a holistic product perspective.

• Open Communication: The emphasis on "velocity" and "excellence" in an "in-office" setting suggests frequent, direct communication and feedback loops are encouraged.

📝 Enhancement Note: The company values paint a picture of a high-performance, innovative, and collaborative culture. The "Polymath Principle" is particularly interesting for a design role, suggesting that a broad curiosity and willingness to engage with technical aspects (like AI) are highly valued.

⚡ Challenges & Growth Opportunities

Challenges:

• Defining New Paradigms: The primary challenge is inventing and establishing user experience patterns for designing, controlling, and trusting autonomous AI agents, a field with few established best practices.

• Balancing Ambiguity and Execution: Navigating the inherent ambiguity of working on cutting-edge AI technology while maintaining a focus on delivering tangible, high-quality product features.

• Technical Integration: Effectively integrating AI tools into the design workflow and understanding the technical nuances of LLMs to inform design decisions.

• Scaling Design Practices: As an early member of a growing team, contributing to the development of scalable design processes, systems, and culture.

Learning & Development Opportunities:

• Deep AI Expertise: Gaining specialized knowledge in Conversational AI UX, a rapidly growing and in-demand field.

• Product Strategy Influence: Directly impacting the product roadmap and strategic direction of a company at the forefront of AI customer experience.

• Leadership Development: Opportunities to mentor junior designers, lead design initiatives, and shape the future of the design team.

• Cross-Disciplinary Learning: Working closely with engineering and product on complex AI challenges offers significant opportunities to expand technical and strategic understanding.

📝 Enhancement Note: The challenges are directly tied to the innovative nature of Decagon's product. Successfully navigating these challenges presents significant growth and learning opportunities, particularly in the burgeoning field of AI UX.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to define a user experience for a completely new product category or technology. How did you approach it?" (Focus on problem framing, research, and iterative design).

• "How would you design an interface for enterprise users to build, manage, and trust autonomous AI agents? What are the key considerations?" (Assess understanding of B2B needs, AI trust, and complexity).

• "Walk us through a complex B2B SaaS product you designed. What were the biggest challenges, and how did you overcome them?" (Highlight problem-solving, stakeholder management, and impact). Company & Culture Questions:

• "Based on our values (Just Get It Done, Invent What Customers Want, Winner's Mindset, The Polymath Principle), how do you see yourself contributing to Decagon?" (Connect your experience to their stated values).

• "What are your thoughts on working in an in-office environment, and how do you see it benefiting your work and team collaboration?" (Show enthusiasm for their collaborative culture).

• "How do you approach learning new technologies, especially in rapidly evolving fields like AI?" (Demonstrate curiosity and a proactive learning approach). Portfolio Presentation Strategy:

• Structure: Begin with a high-level overview of Decagon and the specific problem your case study addresses. Clearly state your role and the project's goals.

• Process Narrative: Detail your design process, emphasizing critical decision points, user research insights, and how you iterated based on feedback. Use visuals effectively.

• AI Integration: If applicable, showcase how you incorporated AI tools or considered AI's role in the user experience.

• Impact & Learnings: Conclude with the quantifiable impact of your design (metrics, user feedback) and your key learnings from the project. Be prepared for deep dives into any aspect of your work.

📝 Enhancement Note: Interview preparation should focus on demonstrating not just design execution but also strategic thinking, comfort with ambiguity, and a proactive approach to innovation, especially concerning AI. The ability to articulate a clear design process and quantify impact will be crucial.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the provided link on Ashby.

• Tailor Your Resume: Highlight experience with B2B SaaS, enterprise products, complex systems, and any direct or indirect experience with AI technologies or conversational interfaces. Quantify achievements where possible.

• Curate Your Portfolio: Select 3-5 strong case studies that best showcase your end-to-end design process, problem-solving skills, visual/interaction craft, and ability to handle ambiguity. Pay special attention to projects involving complex systems or innovative technology.

• Prepare Your Presentation: Practice walking through 1-2 key case studies, focusing on your process, rationale, challenges, and impact. Be ready to discuss your experience with Figma and any AI design tools.

• Research Decagon: Understand their product, mission, target customers, and company values. Prepare thoughtful questions to ask the interviewers.

⚠️ 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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