Principal Product Designer

📍 Job Overview

Job Title: Principal Product Designer Company: project44 Location: Chicago, Illinois, USA Job Type: Full-Time Category: Product Design / GTM Operations Date Posted: 2025-10-07 Experience Level: Principal / Senior Remote Status: On-site

🚀 Role Summary

• Lead end-to-end design initiatives for complex, interconnected systems within project44's Decision Intelligence Platform.
• Drive user-centered design strategies, leveraging research and data to solve real-world problems for enterprise B2B SaaS users in the logistics and supply chain industry.
• Champion design excellence and advocate for user-centric thinking across product, engineering, and other cross-functional teams.
• Contribute to and evolve the company's design system, ensuring scalability, consistency, and efficiency in product development.
• Mentor and guide junior designers, fostering a culture of high-performance and craft within the Product Design team.

📝 Enhancement Note: This role is a Principal Product Designer, indicating a senior-level position requiring extensive experience and strategic leadership. The emphasis on "complex systems," "systems design," and "AI fluency" suggests a focus on intricate B2B SaaS products where design significantly impacts operational efficiency and decision-making, aligning with GTM Operations principles by ensuring the user experience directly supports business objectives and revenue generation.

📈 Primary Responsibilities

• Own the complete product design lifecycle, from initial discovery and user research through to prototyping, visual design, interaction design, and final delivery.
• Translate intricate logistics data and complex system functionalities into intuitive, elegant, and user-friendly interfaces for a diverse range of B2B users.
• Conduct comprehensive user research, including usability testing and qualitative interviews, to deeply understand user needs, pain points, and workflows.
• Collaborate closely with Product Managers, Engineers, and other stakeholders to define product strategy, align on design visions, and co-create innovative solutions.
• Develop and maintain high-fidelity prototypes and detailed design specifications to effectively communicate design intent and facilitate seamless handoff to engineering teams.
• Actively contribute to and enhance project44's design system, ensuring its scalability, consistency, and adherence to best practices across all product surfaces.
• Advocate for the importance of design thinking, user empathy, and design excellence throughout the organization, influencing product strategy and roadmap decisions.
• Mentor and provide design guidance to junior designers, fostering their professional growth and ensuring the quality of design output.

📝 Enhancement Note: The responsibilities highlight a hands-on design role with significant strategic influence. The emphasis on "translating complex systems" and "designing for complex, interconnected systems" points to a need for strong systems thinking, which is crucial in operations roles for understanding and optimizing intricate business processes and technology stacks.

🎓 Skills & Qualifications

Education: Bachelor's or Master's degree in Design, HCI, Computer Science, or a related field, or equivalent practical experience.

Experience:

• Minimum of 15 years of progressive experience in product design, with a proven track record of delivering end-to-end design solutions for complex digital products.
• Demonstrated experience in designing for enterprise or B2B SaaS platforms, with a deep understanding of user needs in these contexts.

Required Skills:

• Portfolio Excellence: A strong, polished portfolio showcasing end-to-end product thinking, complex systems design, and exceptional UI/UX craft.
• Systems Thinking: Proven ability to design for intricate, interconnected systems and understand how to scale design solutions across multiple products and features.
• User-Centered Design: Deep understanding and application of user-centered design principles, grounded in user research, data analysis, and usability testing.
• Collaboration & Communication: Exceptional ability to collaborate effectively with cross-functional teams (Product, Engineering, Marketing, Sales) and build strong alignment.
• Craftsmanship: A high bar for visual and interaction design quality, with work that serves as a benchmark for peers.
• Proactiveness & Ownership: A self-directed, proactive approach with a strong sense of ownership over design initiatives in a fast-paced environment.
• AI/ML Design: Experience designing AI-powered features or workflows, with an understanding of how to make machine learning and automation intuitive, transparent, and valuable to users.

Preferred Skills:

• Familiarity or experience with the logistics, supply chain, or data-heavy platform industries.
• Experience contributing to or actively maintaining a comprehensive design system.
• Knowledge of user research methodologies and their application in B2B environments.

📝 Enhancement Note: The 15+ years of experience requirement for a Principal role is significant and indicates a need for a seasoned designer who can operate with a high degree of autonomy and strategic input. The "AI Fluency" requirement is particularly relevant for modern GTM and operations roles, as AI is increasingly integrated into operational platforms for predictive analytics and automation.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase of end-to-end design process, from problem definition and research to final polished UI and interaction design.
• Case studies demonstrating the ability to tackle complex, interconnected systems and scale design solutions.
• Examples of designing AI-powered features or workflows, highlighting how complexity was simplified for the user.
• Evidence of contributing to or evolving a design system, demonstrating an understanding of consistency and scalability.
• Projects that clearly articulate user problems, design decisions, and measurable outcomes or impact.

Process Documentation:

• Ability to articulate your design process clearly, including your approach to user research, ideation, prototyping, testing, and iteration.
• Examples of how you collaborate with Product Management and Engineering to define requirements and ensure successful implementation of designs.
• Demonstrations of how you leverage data and user feedback to inform and validate design decisions.

📝 Enhancement Note: For a Principal Designer role, the portfolio is critical. It must go beyond individual screens to showcase strategic thinking, systems-level design, and the ability to influence product direction, aligning with the operational impact of design choices.

💵 Compensation & Benefits

Salary Range: Given the Principal level and the specific requirements (15+ years of experience, AI fluency, enterprise SaaS design), a competitive salary range for a Principal Product Designer in Chicago, IL would typically fall between $170,000 - $220,000+ USD annually. This estimate is based on industry benchmarks for senior design leadership roles in major tech hubs, considering the company's focus on AI and supply chain technology, and the high demand for experienced designers in this specialized field.

Benefits:

• Comprehensive health, dental, and vision insurance plans.
• Generous paid time off (PTO) and holidays.
• 401(k) retirement savings plan with company match.
• Stock options or equity grants.
• Professional development budget for conferences, training, and certifications.
• Parental leave policy.
• Commuter benefits (for on-site work).
• Access to a new customer experience center and opportunities for executive interaction.

Working Hours:

• Standard full-time hours, approximately 40 hours per week.
• The role requires being on-site four days a week, with full days spent in the office to foster collaboration, immersion, and direct interaction with leadership and the team.

📝 Enhancement Note: The salary range is an estimate for a Principal level role in a major tech market like Chicago. The on-site requirement of four full days a week is a significant factor in the work environment and likely reflects a company culture that values in-person collaboration and idea exchange, which can be beneficial for complex problem-solving in operations.

🎯 Team & Company Context

🏢 Company Culture

Industry: Supply Chain Technology / Logistics Software / Decision Intelligence Platform Company Size: project44 is a rapidly growing company, indicative of a scale-up environment. Based on public information, they are a large enterprise with hundreds to thousands of employees, suggesting structured processes but also opportunities for impact. Founded: Founded in 2014, project44 has a history of innovation and growth, establishing itself as a leader in the Supply Chain AI and Decision Intelligence space.

Team Structure:

• The Product Design team likely comprises a mix of designers at various levels, including potentially other Principal Designers, Senior Designers, and UI/UX Designers.
• This role will report into a Head of Product Design or VP of Product, with close collaboration with Product Managers, Engineering Leads, and potentially other GTM teams (Sales, Marketing, Customer Success) who rely on the platform's usability.
• Cross-functional collaboration is central, with designers working closely with product and engineering to translate complex business logic into intuitive user experiences.

Methodology:

• Data-driven decision-making is paramount, with a strong emphasis on AI and real-time insights.
• Design processes are likely agile and iterative, focusing on rapid prototyping, user testing, and continuous improvement.
• The company champions a "better" mindset, challenging the status quo and driving innovation in the supply chain industry.

Company Website: https://www.project44.com/

📝 Enhancement Note: The company's focus on "Decision Intelligence Platform" and "Supply Chain AI" indicates a data-intensive and technologically advanced environment. This means the design team must be adept at working with complex data visualizations, AI-driven workflows, and B2B enterprise applications, directly impacting how users derive value and make critical business decisions.

📈 Career & Growth Analysis

Operations Career Level: Principal Product Designer. This level signifies a highly experienced individual contributor or potential leader who is expected to drive significant strategic initiatives, mentor others, and set design standards. They are key players in shaping the user experience of complex B2B products. Reporting Structure: The Principal Product Designer will likely report to a Director or VP of Product Design. They will work collaboratively with Product Managers and Engineering teams, influencing product roadmaps and strategy. Operations Impact: The design of project44's platform directly impacts operational efficiency, decision-making speed, and the overall effectiveness of global supply chains for their clients. A Principal Designer's work is instrumental in ensuring users can easily access and act upon critical logistics data, thereby driving customer success and revenue for project44.

Growth Opportunities:

• Leadership: Potential to grow into a Design Lead or Managerial role, overseeing a team of designers and setting design vision for product areas.
• Specialization: Deepen expertise in AI/ML design, complex data visualization, or specific areas of supply chain technology.
• Strategic Influence: Increased involvement in product strategy, roadmap planning, and cross-functional leadership initiatives.
• Mentorship: Continue to mentor and develop junior talent, contributing to the growth of the design organization.

📝 Enhancement Note: The "Principal" title suggests a path towards design leadership or deep technical expertise with significant strategic influence. The role's impact on customer success and revenue is a key differentiator for operations-focused design roles.

🌐 Work Environment

Office Type: The description mentions an office where "ideas spark, connections thrive, and innovation comes alive," suggesting a modern, collaborative workspace designed to foster creativity and teamwork. It also highlights a new "customer experience center." Office Location(s): Chicago, Illinois, USA (primary headquarters). The role requires being on-site four days a week. Workspace Context:

• Collaborative Hub: The on-site requirement emphasizes in-person collaboration, brainstorming, and direct interaction with colleagues, founders, and executives.
• Tooling: Access to industry-standard design tools and technologies will be available.
• Team Interaction: Frequent opportunities for direct interaction with product, engineering, and leadership teams, fostering a dynamic and integrated work environment.

Work Schedule:

• The role requires a commitment to being in the office four full days per week. This structured schedule is designed to maximize in-person collaboration and team synergy, crucial for complex design and product development.

📝 Enhancement Note: The strong emphasis on in-office presence (four full days) indicates a preference for high-touch collaboration, which is often beneficial for tackling complex operational challenges where nuanced communication and rapid feedback loops are essential.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Review of resume and portfolio, focusing on experience, craft, systems thinking, and AI design capabilities.
• Hiring Manager Interview: Discussion about your design philosophy, experience with complex systems, and approach to user research.
• Design Deep Dive/Portfolio Review: A comprehensive walkthrough of your portfolio, focusing on specific case studies that demonstrate your end-to-end process, problem-solving skills, and impact. Expect detailed questions about your design decisions and collaboration.
• Cross-functional Interviews: Meetings with Product Management, Engineering, and potentially other stakeholders to assess collaboration skills, communication, and alignment with company values.
• Executive/Leadership Interview: Final discussion with senior leadership to assess strategic thinking, leadership potential, and cultural fit.

Portfolio Review Tips:

• Focus on Impact: For each case study, clearly articulate the problem, your role, the process you followed, your key design decisions, and the measurable business or user impact. Quantify results where possible.
• Showcase Systems Thinking: Highlight projects where you designed for complexity, interconnectedness, or scaled design solutions. Explain how your design considered the broader system.
• Demonstrate AI/ML Design: If you have AI/ML design experience, clearly articulate how you approached designing for these features, focusing on transparency, user trust, and intuitive interaction.
• Tell a Story: Structure your case studies as narratives that guide the reviewer through your thought process and problem-solving journey.
• Tailor to project44: Research project44's platform and understand their industry. Be prepared to discuss how your skills align with their specific challenges in supply chain and logistics.

Challenge Preparation:

• Be prepared for potential design exercises or whiteboarding sessions that assess your problem-solving skills, systems thinking, and ability to articulate design solutions under pressure.
• Practice explaining complex design concepts clearly and concisely, as if presenting to both technical and non-technical stakeholders.

📝 Enhancement Note: The interview process for a Principal role is rigorous. The portfolio review is the most critical component, requiring a deep dive into the candidate's strategic thinking, problem-solving methodology, and ability to drive significant product impact.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma, Sketch, Adobe Creative Suite (Photoshop, Illustrator).
• User Research: Tools for conducting usability tests, user interviews, and surveys (e.g., UserTesting.com, Lookback, SurveyMonkey).
• Collaboration: Jira, Confluence, Slack, Miro/Mural for whiteboarding and team collaboration.

Analytics & Reporting:

• While not a direct design tool, familiarity with how analytics tools (e.g., Amplitude, Google Analytics) are used to track user behavior and measure product performance is beneficial.

CRM & Automation:

• Understanding of how design impacts CRM systems and automated workflows within B2B SaaS products is a plus.

📝 Enhancement Note: Proficiency in industry-standard design tools like Figma is expected. The mention of AI and complex systems implies that understanding how design integrates with data analytics and potentially automation platforms is a significant advantage.

👥 Team Culture & Values

Operations Values:

• Better: A core value focused on continuous improvement, challenging the status quo, and striving for excellence in all aspects, including product design.
• Impact: Driving meaningful change and delivering tangible value for customers and the business through innovative solutions.
• Urgency & Purpose: Approach work with a sense of purpose and a drive to solve critical logistics challenges efficiently.
• AI-Powered Innovation: Embracing and leveraging artificial intelligence to create smarter, more intuitive, and more powerful products.
• Collaboration: Working effectively across teams to achieve common goals and foster a shared understanding of user needs and product vision.

Collaboration Style:

• Highly collaborative, with a strong emphasis on cross-functional partnerships between Design, Product, and Engineering.
• Open communication and feedback are encouraged to ensure alignment and drive the best possible outcomes.
• The on-site work model facilitates spontaneous interactions and deeper team cohesion.

📝 Enhancement Note: The emphasis on "Better," "Impact," and "Urgency" suggests a culture that values high performance, continuous improvement, and a results-oriented approach, which is common and highly valued in operations and GTM roles.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Complexity: Translating intricate supply chain logistics and AI functionalities into simple, intuitive user experiences for a demanding B2B audience.
• Scaling Design: Ensuring design consistency and scalability across a rapidly evolving platform with diverse product surfaces.
• AI Integration: Designing AI-powered features that are transparent, trustworthy, and genuinely add value without overwhelming users.
• Cross-functional Alignment: Navigating complex stakeholder needs and driving consensus on design direction within a fast-paced, matrixed organization.

Learning & Development Opportunities:

• Industry Expertise: Deepen knowledge in supply chain management, logistics, and the application of AI in enterprise software.
• Design Leadership: Develop skills in mentoring, team leadership, and strategic design planning.
• Cutting-edge Technology: Work with advanced AI and data intelligence technologies, staying at the forefront of product design innovation.
• Professional Growth: Access to training, conferences, and resources to enhance design craft and strategic capabilities.

📝 Enhancement Note: The challenges are directly related to the operational complexity of the product and industry, presenting significant opportunities for a designer to hone their skills in strategic problem-solving and impact-driven design.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you designed for a highly complex system. What were the challenges, and how did you approach simplifying it for the user?" (Focus on your process, systems thinking, and user empathy.)
• "How do you balance the needs of different stakeholders (e.g., Product, Engineering, Sales) when designing a new feature or product?" (Highlight your collaboration and alignment strategies.)
• "Tell me about your experience designing AI-powered features. How do you ensure transparency and build user trust in AI systems?" (Prepare specific examples and your design philosophy for AI.)
• "Walk me through your process for conducting user research and how you translate those insights into design decisions." (Be ready to detail your research methodologies and how they informed your work.)

Company & Culture Questions:

• "Why project44? What excites you about our mission and the supply chain industry?" (Research project44's mission, platform, and recent news.)
• "How do you embody the 'Better' value in your work and interactions?" (Connect this to your personal work ethic and design philosophy.)
• "How do you approach mentorship and contributing to a positive team culture?" (Share examples of your leadership and collaborative style.)

Portfolio Presentation Strategy:

• Structure is Key: Organize your portfolio around 2-3 in-depth case studies that best represent your capabilities for this role (complex systems, AI, enterprise SaaS).
• Tell the Story: For each case study, clearly articulate: the problem, your specific role, the research and discovery phase, your design process and decisions, the challenges you overcame, and the final outcome/impact (quantified if possible).
• Highlight Systems Thinking: Explicitly call out how you approached interconnectedness, scalability, and the overall system architecture in your designs.
• Explain Your 'Why': Be ready to justify every design decision, linking it back to user needs, business goals, or technical constraints.
• Practice Your Pitch: Rehearse your presentation to ensure a smooth, confident, and concise delivery within the allotted time.

📝 Enhancement Note: Interview preparation for a Principal role should focus on demonstrating strategic thinking, leadership potential, and a deep understanding of the design process's impact on business objectives and operational efficiency.

📌 Application Steps

To apply for this Principal Product Designer position:

• Submit your application, including your resume and a link to your online portfolio, through the project44 careers portal.
• Portfolio Customization: Ensure your portfolio prominently features case studies demonstrating your experience with complex enterprise SaaS products, systems design, AI-powered features, and end-to-end product ownership. Tailor the presentation to highlight your understanding of the supply chain industry and project44's mission.
• Resume Optimization: Clearly articulate your 15+ years of experience, focusing on achievements and responsibilities relevant to complex systems, B2B design, AI fluency, and leadership/mentorship. Use keywords like "Product Design," "UX/UI," "Systems Thinking," "AI Design," "Enterprise SaaS," and "Design System."
• Prepare for Case Studies: Practice presenting 2-3 of your most relevant portfolio case studies, focusing on storytelling, design decisions, and measurable impact. Be ready to discuss your collaboration and problem-solving approach in detail.
• Research Project44: Understand their Decision Intelligence Platform, target industries, and company values. Be prepared to articulate why you are a strong fit for their specific culture and mission.

⚠️ 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.

---