Product Designer

📍 Job Overview

Job Title: Product Designer

Company: AwardSpring

Location: Chicago, Illinois, United States

Job Type: Full-Time

Category: Product Design / Engineering Operations

Date Posted: May 11, 2026

Experience Level: Mid-Level (3+ years)

Remote Status: Hybrid

🚀 Role Summary

• Drive end-to-end product design, including UX, UI, and interaction, leveraging AI-native development tools for direct production deployment.

• Collaborate closely with engineering and product teams, blurring traditional disciplinary lines in an AI-first development environment.

• Own and evolve the visual and interaction systems for key product surfaces, ensuring a cohesive and high-quality user experience.

• Actively contribute to product strategy by providing strong design opinions and proposing refined solutions based on user feedback and technical feasibility.

• Utilize advanced AI tooling and unlimited token budgets to accelerate development cycles and enhance design output.

📝 Enhancement Note: This role is highly specialized, focusing on "AI-native" development where designers actively participate in shipping code using AI-assisted tooling. This deviates significantly from traditional design roles and emphasizes a "designer as builder" ethos. The "Engineering Operations" category is added to reflect the deep integration of design with the production codebase and continuous deployment practices, which are core to operations in an AI-driven product development lifecycle.

📈 Primary Responsibilities

• Ship UX, UI, and interaction work end-to-end across AwardSpring's products, with tangible features demonstrable within the first three months.

• Prototype in code using agentic tooling (e.g., Claude Code, Cursor) rather than solely relying on static mockups, ensuring designs are production-ready.

• Own the complete visual and interaction system for assigned product surfaces, ensuring consistency, usability, and aesthetic appeal.

• Actively challenge and refine product framing, proposing tighter, more effective alternatives based on user insights and technical constraints.

• Maintain close proximity to users through observation and feedback, allowing direct influence on shipped product features and iterative improvements.

• Collaborate with engineering and product management to ensure seamless integration of design into the production codebase.

• Champion the adoption and effective use of AI tooling within the design and development process to maximize efficiency and output quality.

📝 Enhancement Note: The responsibilities emphasize a "production-first" and "code-centric" design approach, a key differentiator for this AI-native role. The expectation is for designers to be comfortable and proficient with AI-assisted coding tools and to contribute directly to the codebase, which is a significant deviation from traditional design responsibilities.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio and demonstrable experience in shipping production-quality design work are paramount. A background in Computer Science, Human-Computer Interaction, Graphic Design, or a related field is beneficial.

Experience: 3+ years of professional experience shipping product design work that has successfully reached production environments.

Required Skills:

• Proven experience shipping product design work (UX, UI, Interaction) directly into production.

• Fluency with AI-native development tools such as Claude Code, Cursor, GitHub Copilot, or comparable agentic tools used for shipping real product features.

• A robust portfolio showcasing not just visual design but also interaction design, system thinking, and craft in shipped products.

• Strong opinions and the ability to articulate and defend design and product decisions effectively.

• Stack-agnostic mindset, demonstrating comfort and adaptability in unfamiliar codebases.

• Experience presenting design work to diverse audiences, including customers, executives, and peers.

Preferred Skills:

• Direct experience with AwardSpring's specific AI tooling ecosystem (Claude Max, Cursor, GitHub Copilot).

• Familiarity with multi-tenant SaaS platforms and the unique design challenges they present.

• Experience in the higher education or foundation technology sector.

• Understanding of data-driven design principles and A/B testing methodologies for optimizing user experiences.

• Contributions to open-source projects or a strong presence in design communities.

📝 Enhancement Note: The emphasis on "agentic tools" and "prototyping in code" signifies a radical departure from traditional design roles. The "stack-agnostic" requirement suggests a focus on transferable skills in AI-assisted development rather than deep expertise in a specific tech stack. The portfolio requirement is also unique, demanding evidence of shipped code and system thinking over purely visual aesthetics.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase of 2-3 significant projects where you were instrumental in shipping features end-to-end, from concept to production.

• Demonstrations of your ability to prototype using AI-assisted coding tools, including examples of code generated and shipped.

• Evidence of system thinking, illustrating how you designed and maintained cohesive visual and interaction systems across a product.

• Case studies detailing your problem-solving approach, design decision-making process, and the measurable impact of your work on users and the business.

Process Documentation:

• Clearly articulate your workflow for taking a design from ideation through to production deployment using AI-native tooling.

• Document your approach to defining, building, and maintaining design systems within a codebase.

• Provide insights into how you gather user feedback and incorporate it into iterative design improvements in a production environment.

• Explain methodologies for collaborating with engineering and product teams in an AI-driven development cycle.

📝 Enhancement Note: The portfolio requirements are heavily skewed towards demonstrating hands-on production work using AI tools, including code contributions and system ownership within the codebase. This is a critical differentiator for operations professionals in this AI-native environment.

💵 Compensation & Benefits

Salary Range: $100,000 - $130,000 per year.

This range is estimated based on the mid-level experience requirement (3+ years), the specialized nature of AI-native product design, and the Chicago, IL location, which has a moderate to high cost of living. The company's provision of top-tier AI tooling and unlimited token budgets suggests a commitment to attracting and retaining high-caliber talent, supporting this competitive salary band.

Benefits:

• Comprehensive Health, Dental, and Vision Insurance plans.

• 401(k) with employer match to support long-term financial planning.

• Unlimited Paid Time Off (PTO) to promote work-life balance and employee well-being.

• Paid Parental Leave for new parents.

• Generous AI Tooling Budget, including access to top-tier AI models and tools like Claude Max, Cursor, and GitHub Copilot, with unlimited token budgets.

Working Hours: 40 hours per week, with a hybrid work arrangement. Specific in-office days will be determined with the manager, allowing for flexibility within the hybrid model.

📝 Enhancement Note: The salary range has been estimated based on industry benchmarks for mid-level Product Designers in major tech hubs like Chicago, adjusted for the highly specialized nature of AI-native development. The "AI Tooling Budget" and "Unlimited token budgets" are highlighted as significant, unique benefits reflecting the company's AI-centric operational model.

🎯 Team & Company Context

🏢 Company Culture

Industry: SaaS (Software as a Service) for scholarship and donor management, serving higher education institutions and foundations. The company operates on a mature, multi-tenant platform, indicating a focus on scalability and robust infrastructure.

Company Size: Based on the description, AwardSpring appears to be an established and growing company with a "small, focused team" and "hundreds of institutions" served. This suggests a mid-sized company (likely 50-200 employees) where individual contributions have a significant impact.

Founded: AwardSpring is described as an "established" company, implying it has been operating for several years, likely with a well-defined product and market presence.

Team Structure:

• The product team is small and intentionally blurs traditional disciplinary lines, with engineers, PMs, and designers all contributing across the stack.

• This role is an individual contributor reporting directly to the CTO, indicating a flat hierarchy and direct access to leadership.

Methodology:

• AI-Native Development: Nearly 100% of the product code is AI-generated, and all team members are expected to ship features end-to-end using agentic tooling.

• Production Shipping: A strong emphasis on shipping into production environments and working with real users and stakes.

• Data-Driven Iteration: User feedback directly shapes shipped features and product improvements.

Company Website: https://awardspring.com/ (Inferred from awardspring.breezy.hr and awardspring.com domain)

📝 Enhancement Note: The "AI-native" development methodology is the defining characteristic of AwardSpring's culture and operations. This implies a fast-paced, experimental, and highly collaborative environment where traditional roles are redefined around leveraging AI for end-to-end product development.

📈 Career & Growth Analysis

Operations Career Level: This is a Mid-Level Product Designer role, requiring 3+ years of experience. The role is an individual contributor with significant autonomy and direct impact on the product's production codebase. It represents a step into an advanced, AI-driven product development paradigm.

Reporting Structure: You will report directly to the Chief Technology Officer (CTO). This close proximity to top leadership provides visibility and opportunities to influence technical and product strategy from a design perspective.

Operations Impact: As a Product Designer in this AI-native environment, your impact extends beyond traditional design. You will directly contribute to shipping code, shaping product direction, and enhancing the efficiency of the entire development pipeline through your design and AI tooling expertise. Your work will directly influence the user experience of hundreds of institutions and the effectiveness of the company's AI development processes.

Growth Opportunities:

• Skill Specialization: Deepen expertise in AI-native product development, becoming a leader in the emerging field of AI-assisted design and engineering.

• Leadership Potential: With demonstrated success in shipping end-to-end features and influencing product direction, opportunities for leading design initiatives or mentoring junior team members may arise.

• Cross-Disciplinary Mastery: Develop a comprehensive understanding of the entire product development lifecycle, including coding and engineering best practices, by working directly within the production codebase.

• Tooling Evolution: Stay at the forefront of AI technology by having direct access to and influence over the selection and implementation of cutting-edge AI development tools.

📝 Enhancement Note: The growth trajectory here is unconventional, emphasizing mastery of AI-driven development and cross-disciplinary skills rather than traditional design career ladders. The direct reporting to the CTO offers a unique path for impactful contributions and potential leadership within a rapidly evolving tech landscape.

🌐 Work Environment

Office Type: AwardSpring offers a hybrid work environment, with a physical office located in Chicago's West Loop / Fulton Market area. This suggests a modern workspace designed to foster collaboration and in-person interaction.

Office Location(s): Chicago, Illinois (West Loop / Fulton Market). This location is known for its vibrant tech scene and accessibility.

Workspace Context:

• Collaborative Hub: The office provides a space for in-person collaboration, team meetings, and cross-functional work sessions, crucial for the hybrid model.

• AI Tooling Access: While not explicitly stated as office-based, the emphasis on cutting-edge AI tooling implies that employees will have access to powerful workstations and reliable internet connectivity to support these demanding applications.

• Team Interaction: The hybrid model is designed to balance focused individual work (potentially remote) with essential team interaction and brainstorming sessions held at the office.

Work Schedule: The standard work schedule is 40 hours per week. The hybrid arrangement allows for flexibility, with specific in-office days to be coordinated with the manager, accommodating the need for both focused individual work and team collaboration.

📝 Enhancement Note: The hybrid nature of the role is key, balancing the benefits of in-person collaboration in a specific tech hub location with the flexibility required for focused, AI-tool-intensive work.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Applications will be reviewed, potentially with AI assistance, for alignment with core requirements. Candidates are welcome to request AI-free review.

• Portfolio Review: A deep dive into your submitted portfolio, focusing on shipped production work, AI tooling usage, system design, and problem-solving approach. Be prepared to walk through specific examples of code you've shipped via agentic tools.

• Technical/Design Challenge: A practical exercise, likely involving prototyping or problem-solving using AI tools, to assess your hands-on capabilities and thought process in a production-like scenario.

• Team & Leadership Interviews: Conversations with engineering, product, and potentially the CTO to assess cultural fit, collaboration style, and strategic thinking.

• Customer/Executive Presentation: You may be asked to present your work or approach to stakeholders, demonstrating your communication skills.

Portfolio Review Tips:

• Highlight Production Impact: Focus on projects where your design directly led to shipped features and measurable outcomes. Quantify impact whenever possible (e.g., improved conversion rates, reduced task completion time).

• Showcase AI Tooling Proficiency: Clearly demonstrate how you've used AI tools (Cursor, Claude Code, etc.) to drive design and development. Include examples of code.

• Illustrate System Thinking: Present case studies that show your ability to design and maintain consistent, scalable design systems.

• Articulate Your Process: Be ready to explain your thought process, decision-making criteria, and how you handle constraints and feedback, especially in an AI-assisted workflow.

• Prepare for "Pushback": Have examples ready where you challenged product assumptions and proposed better alternatives.

Challenge Preparation:

• Practice with AI Tools: Become highly proficient with tools like Cursor and Claude Code. Familiarize yourself with common AI code generation patterns and limitations.

• Simulate Production Scenarios: Think about how you would approach designing and implementing a feature from start to finish in a hybrid environment.

• Develop Strategic Talking Points: Be ready to discuss how design integrates with AI development, how you measure success, and how you collaborate across disciplines.

📝 Enhancement Note: The interview process is heavily weighted towards practical application and demonstrating proficiency with AI-native development tools and processes, including direct code contribution. The portfolio review demands evidence of shipped production work and AI tooling usage.

🛠 Tools & Technology Stack

Primary Tools:

• Agentic AI Development Tools: Cursor, Claude Code, GitHub Copilot. Proficiency and fluency are critical, as these are central to the development workflow.

• Prototyping & Design Systems: Figma (for initial ideation and system definition), with a strong emphasis on translating these into production code.

• Version Control: Git and GitHub (implied by GitHub Copilot usage and standard development practices).

Analytics & Reporting:

• While not explicitly detailed, expect to work with product analytics tools to understand user behavior and measure the impact of your designs. This could include tools like Amplitude, Mixpanel, or similar platforms common in SaaS.

CRM & Automation:

• While this role is primarily design-focused, an understanding of the underlying SaaS platform and its CRM capabilities (likely related to scholarship management and donor tracking) would be beneficial.

• Awareness of workflow automation principles as applied to both user-facing features and internal development processes.

📝 Enhancement Note: The technology stack is heavily defined by AI-native development tools, with a practical, code-centric approach to design. Proficiency in these specific AI tools, rather than a broad range of traditional design software, is the primary technical requirement.

👥 Team Culture & Values

Operations Values:

• ACTION: Emphasizes taking initiative, being accountable for shipping features end-to-end, and actively sharing learnings within the team.

• DETERMINATION: Focuses on simplifying complex problems, creatively overcoming obstacles in development, and relentlessly improving processes and product features.

• HUMANITY: Stresses empathy and kindness in all interactions, fostering a supportive and collaborative team environment.

• IMPROVEMENT: Encourages continuous learning and capability growth, aiming to become an indispensable contributor to both clients and peers.

Collaboration Style:

• Cross-Functional Integration: A highly integrated team where designers, engineers, and PMs work closely together, with blurred lines between disciplines. Expectations are for active participation in code reviews and direct collaboration on the same codebase.

• Feedback-Rich Environment: Openness to constructive feedback on design decisions and product strategies, with an expectation of reciprocity.

• Knowledge Sharing: A culture that values sharing expertise, especially regarding AI tooling and development best practices, to uplift the entire team.

📝 Enhancement Note: The company values are deeply integrated with the AI-native operational model, emphasizing proactive contribution, problem-solving, and continuous growth in a highly collaborative, human-centric environment.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating AI-Generated Code: Adapting to and refining code that is largely AI-generated requires a different mindset than traditional coding, focusing on review, iteration, and integration.

• Bridging Design and Code: Effectively translating design intent into production code using AI tools and ensuring high-quality output can be challenging.

• Evolving AI Landscape: Staying abreast of the rapid advancements in AI models and tooling, and integrating them effectively into the workflow.

• Defining "Good" in AI-Native Design: Establishing and maintaining high standards for design quality, usability, and craft when the development process is fundamentally different.

Learning & Development Opportunities:

• AI Tooling Mastery: Become an expert in the latest AI development tools, potentially influencing tool selection and adoption.

• Cross-Disciplinary Expertise: Gain deep experience in coding and software engineering principles by working directly within the production codebase.

• Emergent Design Practices: Contribute to defining best practices for product design in an AI-native development environment.

• Industry Leadership: Position yourself at the forefront of a rapidly evolving field, potentially leading to speaking engagements or thought leadership opportunities.

📝 Enhancement Note: This role presents unique challenges and growth opportunities tied directly to the cutting edge of AI in software development, offering a chance to shape the future of product design and engineering workflows.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you used AI tooling (like Cursor or Claude Code) to ship a significant product feature. Walk us through your process, the challenges, and the outcome." (Focus on demonstrating end-to-end ownership and AI proficiency.)

• "How do you approach building and maintaining a design system when the underlying codebase is largely AI-generated? What are the unique challenges and how do you overcome them?" (Assess system thinking and adaptability.)

Company & Culture Questions:

• "What excites you most about AwardSpring's AI-native approach to product development, and what concerns do you have?" (Gauge your understanding and enthusiasm for their model.)

• "How do you see the role of a Product Designer evolving in an AI-first company, and how does your experience align with that evolution?" (Assess your forward-thinking perspective.)

Portfolio Presentation Strategy:

• Curate for Impact: Select 2-3 projects that best showcase your ability to ship production work using AI tools and demonstrate system thinking.

• Tell a Story: For each project, clearly outline the problem, your approach, the tools used (especially AI), your specific contributions, the challenges faced, and the measurable results.

• Show, Don't Just Tell: Be prepared to demo interactive prototypes or even snippets of code you contributed. Highlight the "before" and "after" of your work.

• Quantify Achievements: Wherever possible, use data and metrics to demonstrate the impact of your design decisions.

• Address AI Integration: Be explicit about how AI tooling amplified your capabilities and how you managed the output.

📝 Enhancement Note: Interview preparation should heavily focus on practical application of AI tools, end-to-end ownership of shipped features, and the ability to articulate a unique design process within an AI-native development framework.

📌 Application Steps

To apply for this Product Designer position:

• Submit your application via the provided link on AwardSpring's careers page.

• Portfolio Customization: Tailor your portfolio to highlight projects demonstrating end-to-end shipping of production features, specifically using AI-native development tools like Cursor or Claude Code. Showcase your system design thinking and any instances where you refined or challenged product framings.

• Resume Optimization: Ensure your resume clearly articulates your 3+ years of experience shipping product designs to production. Integrate keywords related to AI development, UX/UI, interaction design, and system thinking. Quantify achievements where possible.

• Interview Preparation: Practice articulating your design process, focusing on how you leverage AI tools to prototype and ship code. Prepare specific examples for strategy and behavioral questions, especially those related to collaboration and problem-solving in an AI-first environment.

• Company Research: Gain a deep understanding of AwardSpring's mission, their AI-native development philosophy, and their values. Be ready to discuss how your skills and approach align with their unique operational model.

⚠️ 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.