Director of Product Designer

📍 Job Overview

Job Title: Director of Product Design

Company: Siro

Location: New York City, New York, United States

Job Type: FULL_TIME

Category: Product Design / GTM Operations Enablement

Date Posted: 2026-09-15

Experience Level: 8+ Years

Remote Status: On-site

🚀 Role Summary

• Lead end-to-end product design strategy and execution for a cutting-edge AI-powered sales enablement platform.

• Drive product craft, consistency, and user delight across all mobile and web application surfaces.

• Develop and scale a robust design system, establishing core principles and patterns for a growing organization.

• Champion customer insights and user needs, translating them into intuitive and impactful AI-driven interactions.

• Partner closely with Product, Engineering, and GTM leadership to influence the product roadmap and set strategic direction.

📝 Enhancement Note: While the title is "Director of Product Design," the description emphasizes a hands-on leadership role focused on execution and craft, aligning with a senior individual contributor or a design lead managing a small, high-impact team. The "GTM Operations Enablement" category is inferred due to Siro's focus on empowering field sales teams with technology, directly impacting Go-To-Market efficiency.

📈 Primary Responsibilities

• Own the product design craft, ensuring exceptional quality, consistency, and user delight across all user touchpoints.

• Architect and implement a scalable design system, defining patterns, principles, and guidelines for UI/UX consistency.

• Design intuitive and engaging mobile and web app interfaces, with a specific focus on novel AI interactions.

• Rapidly prototype concepts using modern AI tooling, iterating quickly to test ideas and involve the team.

• Plan and execute comprehensive user research, including direct customer visits and field ride-alongs to gather deep insights.

• Serve as the primary advocate for the customer's voice in product development debates and decision-making processes.

• Collaborate with senior leadership, including the Founder/CEO, to frame complex problems, influence product roadmaps, and define strategic product direction.

• Elevate the design thinking and decision-making capabilities of Product Managers and Engineers working alongside the design function.

📝 Enhancement Note: The responsibilities are directly extracted and organized from the provided description, with an emphasis on the strategic and hands-on nature of the role. The inclusion of "AI interactions" and "AI tooling" highlights the innovative aspect of the position.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio and demonstrated expertise in product design principles are paramount.

Experience: 8+ years of dedicated product design experience with a proven track record of delivering quantifiable success in product development.

Required Skills:

• Exceptional visual and interaction design craft, with the ability to articulate design decisions clearly and precisely.

• Proficiency in designing for both mobile and web application surfaces.

• Deep understanding and practical experience with modern AI prototyping tools.

• Fluency with coding concepts sufficient to translate designs into functional prototypes.

• Strong systems thinking capabilities, balanced with meticulous attention to detail (e.g., 4px decisions).

• Demonstrated customer obsession, evidenced by a willingness to conduct in-person research and fieldwork.

• Proven ability to influence senior leadership and stakeholders through well-reasoned arguments and robust research.

• Experience in mentoring or leading designers is a plus, but the primary focus is on craft, judgment, and influence.

• Comfort and effectiveness in ambiguous environments with high expectations and challenging problems. Preferred Skills:

• Experience in the SaaS industry, particularly with platforms integrating with CRMs like Salesforce.

• Familiarity with sales processes and the challenges faced by field sales teams.

• Experience building and evolving design systems from inception.

• Direct experience with AI-powered product features and their design implications.

• Understanding of Go-To-Market (GTM) strategies and how design can enable sales success.

📝 Enhancement Note: The experience requirement is explicitly stated as "8+ years." The "AI-native" requirement is interpreted as fluency with AI prototyping tools and understanding of AI's role in product design. The distinction between "hiring for craft, judgment, and influence" versus "headcount" suggests a focus on individual contribution and impact over team management size.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase a minimum of 8 years of product design work with clearly articulated outcomes and quantifiable successes.

• Demonstrate exceptional visual and interaction design quality through case studies, highlighting problem-solving and attention to detail.

• Feature examples of designing for both mobile and web applications, with a specific emphasis on innovative AI interactions.

• Include projects where AI tooling was used for rapid prototyping, illustrating efficiency and speed in the design process.

• Present evidence of customer-centricity through user research methodologies and how insights informed design decisions.

• Provide examples of influencing product strategy and roadmaps through design rationale and stakeholder engagement.

• Illustrate systems thinking by showcasing the development or significant contribution to a design system. Process Documentation:

• Detail the process undertaken for user research, including methodologies for customer visits and field ride-alongs.

• Explain the workflow for ideation to working prototype, emphasizing the use of AI tooling and iterative design.

• Document the approach to building and scaling a design system, including principles, patterns, and governance.

• Illustrate how customer feedback and insights were integrated into design iterations and product direction.

• Showcase how design decisions were communicated and defended to senior leadership and cross-functional teams.

📝 Enhancement Note: Given the emphasis on "craft, judgment, and influence" and the hands-on nature of the role, a strong portfolio is critical. The requirements focus on demonstrating a breadth of skills, from detailed execution to strategic influence, with a specific need to highlight AI tool proficiency and customer research.

💵 Compensation & Benefits

Salary Range: $250,000 per year.

Explanation for Estimate: The provided salary is a fixed amount of $250,000 USD per year, as indicated by the salary_raw data. This figure is presented as a definitive annual compensation.

Benefits:

• Equity: Opportunity to own a stake in a high-growth Series B company.

• Comprehensive health, dental, and vision insurance.

• Generous paid time off (PTO) policy.

• Professional development opportunities, including access to conferences and training.

• Direct access to the Founder CEO and senior leadership team.

Working Hours: 40 hours per week, with an expectation of flexibility and dedication given the demanding nature of a high-growth startup environment.

📝 Enhancement Note: The salary is explicitly stated as $250,000 USD annually. Benefits are inferred from typical offerings for senior roles at well-funded startups, with "Equity" being explicitly mentioned. Working hours are set at 40 hours/week, but the context suggests potential for longer hours typical in startup environments.

🎯 Team & Company Context

🏢 Company Culture

Industry: Software / AI / Sales Technology (SaaS) - Siro operates at the intersection of AI, sales enablement, and SaaS, focusing on transforming field sales operations through intelligent technology.

Company Size: Series B funded, lean team (specific employee count not provided, but implies a growing, dynamic startup environment).

Founded: Founded on the principle of improving field sales efficiency through AI coaching, evolving into a comprehensive intelligent companion for sales teams.

Team Structure:

• A lean, senior team comprised of experienced professionals from leading tech companies (Meta, McKinsey, DoorDash, Uber).

• Direct collaboration with Product, Engineering, and GTM leaders, including the Founder/CEO.

• Emphasis on cross-functional partnership to drive product innovation and market strategy. Methodology:

• AI-driven insights and automation to enhance sales performance and reduce administrative burdens.

• Focus on human-AI collaboration to create proactive and personalized sales experiences.

• Data analysis of in-person sales conversations to surface actionable insights and drive workflow automation.

• Agile product development with a strong emphasis on rapid prototyping and user feedback loops.

Company Website: https://siro.ai/

📝 Enhancement Note: The company context is derived from the "Description" and "Why join us?" sections, highlighting Siro's mission, funding, investor backing, and team composition. The "Methodology" section reflects the AI-centric approach and focus on data analysis.

📈 Career & Growth Analysis

Operations Career Level: Director level, signifying significant leadership and ownership. This role is pivotal in defining the design function's strategy and impact within the organization, moving beyond execution to strategic influence.

Reporting Structure: This role reports directly to senior leadership, likely a Head of Product or the CEO, given the "Founder/CEO" partnership mentioned. The designer is expected to influence strategy across Product, Engineering, and GTM.

Operations Impact: The Director of Product Design will have a profound impact on Siro's Go-To-Market strategy by shaping the user experience of a product designed to directly enhance field sales performance, efficiency, and revenue generation. Their work will define how sales teams learn, perform, and win, making them a critical driver of business outcomes.

Growth Opportunities:

• Define and establish the design function's identity, standards, and scope of influence at Siro.

• Shape the product language and user experience for a nascent but rapidly growing category in sales technology.

• Tackle complex, multi-faceted problems involving conversational AI, system integration, and field execution.

• Receive direct user feedback and gratitude from a highly engaged customer base.

• Benefit from operating within a high-growth Series B company with direct access to the Founder CEO and a small, senior team.

• Potential to grow into a VP of Design or Head of Design role as the company scales.

📝 Enhancement Note: The growth analysis focuses on the unique opportunity to define a design function from the ground up in a new product category, emphasizing strategic impact and leadership potential.

🌐 Work Environment

Office Type: On-site role in New York City, indicating a preference for in-person collaboration, team synergy, and a structured work environment.

Office Location(s): New York City, New York, United States. Specific office address details are not provided but are implied to be in a major metropolitan hub.

Workspace Context:

• A collaborative environment where design, product, and engineering teams work closely together.

• Access to modern AI tooling and prototyping software.

• Opportunities for direct engagement with sales teams through field visits and ride-alongs, providing a unique context for design work.

• A culture that values "taste" and high standards in product aesthetics and user experience.

Work Schedule: Standard full-time hours (40 hours/week) are expected, with a dynamic startup culture that may necessitate flexibility and dedication beyond nominal hours to meet ambitious goals.

📝 Enhancement Note: The "On-site" designation is key. The description emphasizes direct customer interaction, suggesting that the workspace context extends beyond the office to include field environments.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Review of resume and portfolio to assess experience, craft, and alignment with the role's requirements.

• Design Challenge/Portfolio Deep Dive: A hands-on exercise or in-depth review of portfolio case studies, focusing on problem-solving, design thinking, AI tool usage, and customer research. Expect to articulate your design process and rationale for key decisions.

• Cross-Functional Interviews: Meetings with Product, Engineering, and GTM leaders to evaluate collaboration style, strategic thinking, and ability to influence.

• Founder/CEO Interview: A final discussion to assess cultural fit, leadership potential, and alignment with Siro's vision and mission.

Portfolio Review Tips:

• Showcase Breadth and Depth: Include 3-5 strong case studies demonstrating 8+ years of experience, covering visual design, interaction design, AI prototyping, user research, and strategic influence.

• Highlight AI & Customer Focus: Explicitly detail your work with AI tools and how customer research (especially field research) informed your design decisions. Quantify impact where possible.

• Articulate Your Process: Clearly explain your design process, from problem framing to solutioning, and justify your choices with data and reasoning, not just aesthetics.

• Demonstrate Leadership Potential: Include examples of how you've influenced roadmaps, mentored others, or raised design standards, even if not in a formal management role.

• Prepare for Ambiguity: Be ready to discuss how you approach undefined problems and thrive in a fast-paced, evolving environment.

Challenge Preparation:

• Anticipate Design Problems: Prepare to tackle challenges related to designing AI interactions, optimizing mobile/web interfaces for field sales, or integrating complex data insights into user workflows.

• Leverage AI Tools: Be ready to demonstrate your proficiency with AI prototyping tools during a potential timed exercise or discussion.

• Think Strategically: Focus on how your design solutions align with business objectives and customer needs, demonstrating an understanding of product strategy.

• Practice Articulation: Clearly and concisely communicate your thought process, design rationale, and potential solutions, as if presenting to senior leadership.

📝 Enhancement Note: The interview process is structured based on typical senior design roles in startups, emphasizing portfolio strength, hands-on skills, and strategic influence. The "AI Tooling" and "Customer-Obsessed" aspects are critical focus areas for preparation.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma, Sketch, Adobe Creative Suite (standard design tools).

• AI Tooling: Modern AI-powered prototyping and design assistance tools (specifics to be discussed, but expect proficiency in tools like Midjourney, Stable Diffusion, Generative AI plugins for design software, or specialized AI design platforms).

• User Research Tools: UserTesting.com, Lookback, Maze, or similar platforms for remote and in-person user feedback.

• Collaboration Tools: Slack, Jira, Confluence for team communication and project management.

Analytics & Reporting:

• Product Analytics: Mixpanel, Amplitude, or similar for understanding user behavior within the app.

• CRM Integration: Familiarity with Salesforce or similar CRM platforms is highly beneficial, as Siro integrates with these systems.

CRM & Automation:

• CRM: Salesforce (Siro's integration target). Understanding of CRM data structures and workflows is advantageous.

• Automation: While not a direct tool for the designer, understanding how Siro automates workflows for sales reps is crucial for designing effective interfaces.

📝 Enhancement Note: The "AI Tooling" is highlighted as a specific requirement. Proficiency with standard design software is assumed, but the emphasis is on modern AI capabilities and understanding how the product integrates with core sales systems like Salesforce.

👥 Team Culture & Values

Operations Values:

• Craftsmanship & Quality: A deep commitment to high-quality design, consistency, and user delight in all product outputs.

• Customer Obsession: Prioritizing user needs and feedback, actively seeking out and incorporating insights from field sales teams.

• Innovation & AI-Native: Embracing cutting-edge AI technology to create novel and impactful user experiences.

• Systems Thinking: Designing with a holistic view, building scalable systems and principles that support growth.

• Influence & Impact: Driving product strategy and decisions through strong reasoning, research, and collaboration.

• Ambiguity & Grit: Thriving in uncertain environments, tackling tough problems with determination and a proactive attitude.

Collaboration Style:

• Cross-Functional Partnership: Close working relationships with Product, Engineering, and GTM teams, fostering a shared understanding of user needs and business goals.

• Direct Communication: Open and honest dialogue, with an emphasis on providing constructive feedback and challenging ideas respectfully.

• Data-Informed Decisions: Using research and analytics to guide design choices and influence product direction.

• Proactive Engagement: Actively seeking opportunities to contribute beyond core design tasks, influencing the product roadmap and team practices.

📝 Enhancement Note: These values are inferred from the "About you" and "Why Siro" sections, focusing on the emphasis of craft, customer focus, AI integration, and strategic influence.

⚡ Challenges & Growth Opportunities

Challenges:

• Defining a New Category: Designing for a product category that is still being invented, requiring significant foresight and innovation in defining user experiences.

• Complex Problem Space: Integrating AI coaching, administrative automation, real-time visibility, and human-AI collaboration into a cohesive and intuitive product.

• Balancing Craft and Scale: Maintaining high design quality and polish while rapidly scaling the design system and product features.

• Influencing Senior Leadership: Effectively communicating and advocating for design decisions to a founder-led executive team.

• Field Sales Realities: Designing for users in dynamic, often challenging field environments, requiring a deep understanding of their workflows and constraints.

Learning & Development Opportunities:

• Pioneering AI Design: Gain unparalleled experience in designing cutting-edge AI-powered product features.

• Category Definition: Play a key role in shaping the future of sales technology and defining best practices for AI in sales.

• Strategic Impact: Directly influence product direction and business outcomes at a fast-growing startup.

• Leadership Development: Opportunity to build and mentor a design team as the company scales.

• Deep Customer Immersion: Extensive opportunities for direct customer interaction and understanding of field sales operations.

📝 Enhancement Note: Challenges are derived from the unique nature of Siro's product and market position. Growth opportunities focus on the unique learning and impact potential of a pioneering role.

💡 Interview Preparation

Strategy Questions:

• "How would you approach designing the core AI interactions for a field sales representative, considering their need for speed and accuracy in real-time?"

  • Preparation: Think about AI conversational interfaces, proactive suggestions, and minimizing user input. Consider how data from Salesforce and sales conversations would be surfaced.

• "Describe a time you had to influence a founder or senior executive on a critical product decision. What was your approach, and what was the outcome?"

  • Preparation: Prepare a STAR method (Situation, Task, Action, Result) story focusing on data-driven arguments, clear communication, and impactful outcomes.

• "How would you design a system that balances the need for a consistent design language across mobile and web with the unique constraints and opportunities of each platform, especially with AI features?"

  • Preparation: Discuss your approach to design systems, component-based design, and adapting experiences for different contexts while maintaining brand and functional consistency.

Company & Culture Questions:

• "What excites you most about Siro's mission to redefine field sales, and how does your design philosophy align with that?"

  • Preparation: Research Siro's website, funding news, and understand the pain points of field sales teams. Connect your personal passion for design and user advocacy to their mission.

• "How do you foster collaboration between design, product, and engineering, especially in a fast-paced startup environment?"

  • Preparation: Discuss your experience with Agile methodologies, cross-functional team dynamics, and methods for transparent communication and shared ownership.

• "How do you measure the success of your design work, particularly concerning user engagement, adoption, and business impact?"

  • Preparation: Prepare to discuss relevant design metrics (e.g., conversion rates, task completion times, user satisfaction scores) and how you tie them back to business objectives.

Portfolio Presentation Strategy:

• Storytelling is Key: For each case study, craft a narrative that clearly articulates the problem, your role, the process, the solutions, and the measurable impact.

• Show, Don't Just Tell: Use visuals effectively to demonstrate your design process, wireframes, prototypes, and final UI.

• Highlight AI & Field Research: Dedicate specific slides or sections to showcase your AI tooling usage and insights gained from customer fieldwork.

• Be Prepared for Deep Dives: Anticipate detailed questions about your technical skills, design decisions, and problem-solving approach.

• Demonstrate Strategic Thinking: Connect your design work to broader business goals and product strategy.

📝 Enhancement Note: Interview questions are tailored to the specific requirements of the role, emphasizing AI, customer research, strategic influence, and the unique challenges of designing for a new product category.

📌 Application Steps

To apply for this Director of Product Design position:

• Submit your application through the provided link on Ashby.

• Portfolio Customization: Tailor your portfolio to highlight projects demonstrating 8+ years of product design experience, with a strong emphasis on visual/interaction craft, AI tooling proficiency, and customer-focused research. Showcase at least one case study that deeply involves AI-driven features or complex user workflows.

• Resume Optimization: Ensure your resume clearly articulates your experience in product design leadership, AI prototyping, user research, and influencing senior stakeholders. Quantify achievements and highlight your ability to drive product strategy.

• Interview Preparation: Practice articulating your design process, rationale, and impact using the STAR method. Prepare to discuss your approach to building design systems and your experience with AI tools. Rehearse presenting your portfolio case studies, focusing on storytelling and demonstrating your strategic thinking.

• Company Research: Thoroughly research Siro's mission, product, funding, and target market. Understand the challenges faced by field sales teams and how Siro addresses them. Prepare thoughtful questions for the interviewers that demonstrate your engagement and strategic thinking.

⚠️ 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.