Product Designer

📍 Job Overview

Job Title: Product Designer

Company: Arrive Logistics

Location: Chicago, IL

Job Type: Full-time

Category: Product Design / UX Design

Date Posted: 2026-09-16

Experience Level: Mid-Level (3-5 years)

Remote Status: Hybrid

🚀 Role Summary

• Design and own end-to-end product features within a dedicated sprint team, focusing on a proprietary transportation management platform.

• Collaborate closely with Product Managers and Engineers to define requirements, explore innovative solutions, and iterate rapidly based on user feedback and research.

• Conduct problem discovery and leverage user research to deeply understand user needs and pain points within complex, data-dense interfaces.

• Engage directly with expert users (trucking reps, operations teams) to gather insights and translate them into actionable design decisions for a high-pressure, information-rich environment.

• Contribute to and maintain a mature design system, ensuring consistency and efficiency across the platform's user experience.

📝 Enhancement Note: This role is specifically focused on designing for a B2B SaaS transportation management platform where users operate under significant time pressure. The emphasis is on designing for speed, information hierarchy in dense interfaces, and reducing friction in repetitive tasks, which are critical aspects for operations and sales enablement tools.

📈 Primary Responsibilities

• Take ownership of the design process for features and flows within your assigned sprint team, from initial problem framing through to shipped UI.

• Partner effectively with product managers and engineers to meticulously define feature requirements, ideate on potential solutions, and conduct rapid iterations based on gathered feedback.

• Proactively engage in problem discovery and user research activities to thoroughly understand and refine design challenges before solution ideation.

• Conduct direct user interviews, usability tests, and feedback sessions with onsite users to inform and drive design decisions in a fast-paced environment.

• Create comprehensive design artifacts, including wireframes, interactive prototypes, and high-fidelity mockups using industry-standard tools like Figma.

• Contribute to the evolution of the company's design system by creating and refining components and patterns, ensuring adherence to established standards.

• Clearly articulate design rationale and present work effectively to cross-functional teams, stakeholders, and the broader design community.

• Actively participate in design critiques, providing constructive feedback to peers and thoughtfully receiving feedback to enhance design outcomes.

📝 Enhancement Note: The responsibilities highlight a hands-on approach to product design within an agile development cycle. The emphasis on "spending real time with our users" and "problem discovery" indicates a strong user-centered design methodology, crucial for optimizing operational efficiency within the transportation sector.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong foundation in Design, Human-Computer Interaction (HCI), or a related field is expected, demonstrated through experience and portfolio.

Experience: 3-5 years of professional experience in Product Design or UX Design, with a preference for experience on B2B or SaaS products.

Required Skills:

• Proven experience as a Product or UX Designer, ideally within B2B or SaaS environments.

• A strong portfolio showcasing a thoughtful design process, including exploration of options and rationale behind final design decisions.

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

• Experience working with and contributing to established design systems.

• Solid understanding of interaction design principles and usability best practices, particularly for data-dense or workflow-heavy interfaces.

• Demonstrated ability to clearly communicate design decisions and rationale to both technical and non-technical audiences.

• Experience working in agile or sprint-based product development environments.

• Familiarity with leveraging AI tools in the design process (e.g., Figma Make, Claude, or similar). Preferred Skills:

• Prior experience designing for logistics, supply chain, or other complex operational technology platforms.

• Experience with collaborative design tools such as Miro.

• Familiarity with conducting lightweight user research, including interviews and usability testing.

📝 Enhancement Note: The requirement for a portfolio that shows "how you think, not just final screens" and the emphasis on "data-dense or workflow-heavy interfaces" are critical indicators for this role. Candidates should be prepared to demonstrate their problem-solving approach and ability to design for complex operational scenarios, aligning with the needs of a transportation management system.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase the end-to-end design process for at least 2-3 significant features or projects, demonstrating problem identification, user research, ideation, iteration, and final UI.

• Clearly articulate the design challenges, the options considered, and the strategic rationale behind the chosen solutions, especially for complex or data-intensive problems.

• Highlight contributions to or creation of design system components, demonstrating understanding of scalability and consistency.

• Include examples of how user feedback and research insights directly influenced design decisions and led to measurable improvements.

• Detail interactions with product managers and engineers throughout the design lifecycle. Process Documentation:

• Demonstrate experience in conducting problem discovery and framing design challenges effectively.

• Illustrate the use of wireframes, prototypes, and high-fidelity mockups to communicate design intent and gather feedback.

• Provide examples of how user research (interviews, usability tests) was synthesized and applied to refine designs.

• Show evidence of working within an agile or sprint-based development cycle, including collaboration with engineering teams.

📝 Enhancement Note: The portfolio should explicitly demonstrate the candidate's ability to tackle complex B2B SaaS design challenges, particularly those involving dense information displays and intricate workflows common in operational software. The inclusion of AI tool usage is a modern requirement that should be featured if applicable.

💵 Compensation & Benefits

Salary Range: $130,000 - $150,000 per year.

Explanation: This range is provided directly by the company and reflects typical compensation for a mid-level Product Designer in a major metropolitan area like Chicago, considering the specialized nature of B2B SaaS and operational technology design. Individual pay will be determined by factors such as work location, specific skills, experience, and relevant education.

Benefits:

• Comprehensive medical, dental, and vision insurance.

• Life, disability, and supplemental coverage options.

• Matching 401(k) program for retirement savings.

• Employee Resource Groups (ERGs) for community building and professional development.

• Generous paid time off, including company holidays, vacation time, and wellness days.

• 100% paid parental leave for new parents.

• Employee Assistance Program offering free counseling sessions.

• Office-wide engagement activities, team events, and happy hours.

• Casual dress code.

• Access to an onsite gym with Peloton bikes and personal training options.

• Referral program for employees who refer successful candidates.

• Relocation assistance for candidates not local to the area.

Working Hours: The role is full-time, with an expected 40 hours per week. The company emphasizes a hybrid work model, allowing for flexibility while maintaining in-office collaboration.

📝 Enhancement Note: The salary range is competitive for a mid-level Product Designer in Chicago. The extensive benefits package, including significant paid parental leave and relocation assistance, suggests a strong focus on employee well-being and support for attracting talent to their Chicago hub.

🎯 Team & Company Context

🏢 Company Culture

Industry: Transportation & Technology. Arrive Logistics operates as a leading transportation and technology company, leveraging its proprietary platform to manage freight movements across North America. This industry context means the product design work directly impacts real-time operational efficiency and business outcomes.

Company Size: Not explicitly stated but implied to be significant and growing, with multiple offices and employee resource groups. This suggests a structured but dynamic environment with opportunities for impact.

Founded: Not explicitly stated, but the company's growth trajectory and award-winning culture point to an established and evolving organization.

Team Structure:

• The Product Design team is part of a larger product development organization, working in a hybrid model with designers and partners in other offices.

• Designers are embedded within sprint teams, closely partnering with Product Managers and Engineers.

• There is a wider design team for critique and support, indicating a collaborative design community within the company. Methodology:

• Agile or sprint-based product development environment is standard.

• Emphasis on user-centered design, with direct user interaction and research playing a key role.

• Design system is mature but actively expanding, requiring contributions and adherence.

• A culture of early idea sharing and regular critique is encouraged.

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

📝 Enhancement Note: Arrive Logistics is positioned as a tech-forward company within the logistics sector. The culture appears to value collaboration, continuous improvement, and employee well-being, as evidenced by their numerous workplace awards and comprehensive benefits. The design team's integration into agile sprint teams suggests a fast-paced, iterative development process.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a Mid-Level Product Designer. It involves contributing to and owning designs for features within specific product areas, requiring a solid understanding of design principles, tool proficiency, and collaborative development processes. The opportunity to design for expert users in a complex domain offers significant depth for skill development beyond entry-level roles.

Reporting Structure: The Product Designer will report into a design leadership role, likely a Design Manager or Director, and will work closely with Product Managers and Engineering Leads within their assigned sprint team.

Operations Impact: The designs created directly impact the efficiency and effectiveness of Arrive Logistics' core business operations – moving freight. By improving the transportation management platform, this role directly influences revenue generation, operational cost reduction, and user productivity for internal teams.

Growth Opportunities:

• Skill Specialization: Deepen expertise in designing for complex B2B SaaS, data-dense interfaces, and operational workflows.

• Design System Contribution: Take on more responsibility in evolving and governing the design system, potentially leading initiatives.

• Mentorship & Leadership: As experience grows, opportunities may arise to mentor junior designers or lead design efforts for larger features or product areas.

• Cross-functional Exposure: Gain deeper understanding of the logistics industry and operational challenges by working closely with product, engineering, and potentially operations stakeholders.

📝 Enhancement Note: The role offers a strong foundation for specializing in operational technology design. The direct impact on business operations and the opportunity to work on a mature, in-house platform provide a solid career path. Growth opportunities are likely tied to increasing ownership and complexity of design challenges within the logistics domain.

🌐 Work Environment

Office Type: Hybrid work environment, with employees expected to work alongside colleagues in other offices. This suggests a blend of remote collaboration and in-office presence.

Office Location(s): The primary office for this role is in the heart of downtown Chicago, IL. The company also has other offices, facilitating a distributed team dynamic.

Workspace Context:

• The Chicago office is described as having a casual dress code and access to an onsite gym with modern equipment.

• Collaboration is key, with opportunities to work with designers and partners across different locations.

• The work environment supports direct user interaction and feedback loops, integrating designers closely with the operational realities of the business.

• Access to tools like Figma and Miro facilitates digital collaboration and design execution.

Work Schedule: Standard full-time hours (approx. 40 hours/week) are expected, with a hybrid arrangement offering some flexibility. The focus is on output and collaboration within the sprint structure, rather than strict hour-by-hour monitoring.

📝 Enhancement Note: The hybrid model in a downtown Chicago office provides a blend of flexibility and collaborative opportunities. The emphasis on a casual environment and access to amenities like a gym suggests a focus on employee well-being and a modern work setting.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Likely a brief call with a recruiter or hiring manager to assess basic qualifications and cultural fit.

• Portfolio Review & Design Exercise: Candidates will present their portfolio, focusing on their design process, problem-solving approach, and rationale behind key decisions. A design challenge or case study may be presented, requiring candidates to articulate how they would approach a specific problem relevant to the platform.

• Team Interviews: Discussions with Product Managers, Engineers, and potentially other designers to assess collaboration skills, technical understanding, and alignment with team methodologies.

• Final Interview: A meeting with senior leadership (e.g., Head of Product, Head of Design) to discuss overall fit, strategic thinking, and long-term potential.

Portfolio Review Tips:

• Focus on Process: Clearly articulate the problem, your research, the different solutions you explored, and why you made the choices you did. Don't just show final screens.

• Quantify Impact: Wherever possible, include metrics or outcomes that demonstrate the success of your designs, even if they are estimates or based on user feedback.

• Highlight Collaboration: Show how you worked with PMs, engineers, and other stakeholders.

• Demonstrate Tool Proficiency: Be ready to discuss your experience with Figma, Miro, and any AI tools used in your workflow.

• Address B2B/SaaS Specifics: If you have experience with complex, data-dense interfaces or operational workflows, emphasize it.

Challenge Preparation:

• Understand Arrive Logistics' business: Research their role in the transportation industry and the challenges of managing freight.

• Familiarize yourself with B2B SaaS design principles: Focus on efficiency, information hierarchy, and user productivity for expert users.

• Practice articulating design decisions: Be ready to explain your thought process clearly and concisely.

• Prepare questions: Develop thoughtful questions about the team, product, and challenges.

📝 Enhancement Note: The interview process emphasizes a deep dive into the candidate's design thinking and problem-solving capabilities, especially within the context of complex B2B operational software. The portfolio review is a critical component, requiring candidates to demonstrate not just aesthetic skill but also strategic decision-making and collaborative execution.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The core tool for wireframing, prototyping, and high-fidelity UI design. Advanced proficiency is required.

• Miro: Likely used for brainstorming, user journey mapping, wireframing, and collaborative workshops.

• AI Tools: Explicit mention of Figma Make, Claude, or other AI-powered design assistants, indicating an openness to leveraging AI for efficiency and ideation.

Analytics & Reporting:

• While not explicitly listed, expect to work with data provided by product analytics tools (e.g., Amplitude, Mixpanel, internal dashboards) to understand user behavior and measure design impact. CRM & Automation:

• The platform itself acts as a Transportation Management System (TMS), which integrates various operational workflows. Experience with or understanding of similar operational software is beneficial.

📝 Enhancement Note: Proficiency in Figma is non-negotiable. The inclusion of AI tools suggests that candidates who can demonstrate innovative uses of AI in their design workflow will be highly regarded. Familiarity with how design impacts operational efficiency and data flow within a TMS is a significant advantage.

👥 Team Culture & Values

Operations Values:

• User-Centricity: Deeply understanding and designing for the needs of expert users in high-pressure operational roles.

• Efficiency & Speed: Designing solutions that enable users to complete tasks quickly and accurately, directly impacting business operations.

• Collaboration: Working closely with product managers, engineers, and other designers to achieve shared goals.

• Data-Driven Decisions: Using research, user feedback, and analytics to inform design choices and measure impact.

• Continuous Improvement: Embracing iteration, critique, and learning to constantly enhance the product and design process.

Collaboration Style:

• Embedded Teamwork: Designers are integrated into agile sprint teams, fostering close daily collaboration with PMs and engineers.

• Open Critique: A culture of giving and receiving constructive feedback within the design team to elevate the quality of work.

• Early & Often: Encouragement to share rough ideas early in the process to facilitate quicker iteration and alignment.

• Cross-Functional Communication: Ability to present and discuss design rationale clearly with both technical and non-technical stakeholders.

📝 Enhancement Note: The culture emphasizes practical problem-solving and direct impact on the business. The values align with a fast-paced, operational environment where design decisions have tangible consequences. Collaboration is structured through agile teams, but also supported by a broader design community for feedback and growth.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Complexity: Tackling the inherent complexity of a transportation management platform with dense data and intricate workflows.

• Balancing Speed and Depth: Creating intuitive designs for expert users who need speed and efficiency, without sacrificing necessary depth of information or functionality.

• User Empathy in a Niche Industry: Developing deep empathy for users in the logistics and freight industry, who have specialized knowledge and high-stakes daily tasks.

• Integrating AI Seamlessly: Exploring and implementing AI tools in a way that genuinely enhances the user experience and design process, rather than being a superficial addition.

Learning & Development Opportunities:

• Deep Domain Expertise: Gaining in-depth knowledge of the logistics and supply chain industry, a complex and critical sector.

• Advanced B2B SaaS Design: Honing skills in designing for operational efficiency, data visualization, and high-density interfaces.

• Design System Evolution: Contributing to and potentially leading efforts to expand and refine a mature design system.

• Cross-Functional Impact: Seeing the direct impact of design decisions on business operations and revenue through an in-house platform.

📝 Enhancement Note: The primary challenge lies in mastering the intricacies of operational software design for a demanding user base. Growth opportunities are strong for individuals who thrive on solving complex problems and want to specialize in a critical, high-impact industry.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to design for a complex, data-dense interface. What were the challenges, and how did you approach them?" (Focus on information hierarchy, usability, and your process.)

• "How do you balance user needs with business requirements and technical constraints in a B2B SaaS environment?" (Highlight your collaboration with PMs and Engineers.)

• "Walk us through a project where user research significantly changed your initial design direction. What was the outcome?" (Demonstrate your user-centric approach and ability to adapt.)

• "How have you used AI tools in your product design process? What benefits did they provide, and what were the limitations?" (Be specific about tools and impact.) Company & Culture Questions:

• "What interests you about Arrive Logistics and our mission in the transportation industry?" (Research their business and show genuine interest.)

• "How do you approach contributing to and working within an established design system?" (Emphasize your understanding of consistency and collaboration.)

• "Describe your experience working in an agile or sprint-based development environment." (Highlight your adaptability and iterative process.) Portfolio Presentation Strategy:

• Structure: Organize your presentation logically, starting with the business problem or user need, followed by your research, ideation, chosen solution, and finally, the outcomes or learnings.

• Narrative: Tell a compelling story about each project, emphasizing your role and the impact of your design decisions.

• Visuals: Use clear, high-quality visuals of your work, including sketches, wireframes, prototypes, and final UI.

• Interaction: Be prepared to demonstrate interactive prototypes and discuss user flows in detail.

• Q&A: Anticipate questions about your design choices, trade-offs, and how you handle feedback. Be confident and articulate.

📝 Enhancement Note: Candidates should prepare to articulate their design process with a focus on problem-solving, user empathy, and collaborative execution within a B2B SaaS context. Demonstrating an understanding of operational efficiency and the specific challenges of the logistics industry will be highly beneficial.

📌 Application Steps

To apply for this Product Designer position:

• Submit your application through the provided Lever.co application link.

• Curate Your Portfolio: Select 2-3 of your most impactful B2B SaaS or complex operational design projects. Ensure each case study clearly outlines the problem, your research, design process, iterations, final solution, and any measured outcomes or user feedback. Highlight your Figma proficiency and any use of AI tools.

• Optimize Your Resume: Tailor your resume to highlight relevant experience in Product Design, UX Design, B2B/SaaS products, design systems, and agile methodologies. Use keywords from the job description and quantify your achievements where possible.

• Prepare Your Presentation: Practice walking through your portfolio with a focus on clear storytelling, design rationale, and collaborative interaction. Be ready to discuss your experience with data-dense interfaces and operational workflows.

• Research Arrive Logistics: Understand their business, their role in the logistics industry, and their company culture. Prepare thoughtful questions about the product, team, and challenges you might face.

⚠️ 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.