Principal Designer

Job Description

As our first Principal Designer, you’ll lay the foundation for design excellence across our entire product suite—from the mobile app that returning citizens use to launch new lives, to the internal case management tools that support them, to the dashboards that connect us to workforce boards, trucking companies, and educational partners.

This role blends individual craft with operational leadership. You’ll be designing key flows yourself while building a scalable design practice that can serve many stakeholders for years to come. We’re especially focused on innovative UX for users with low technical literacy, and we see AI/agentive UX as a key part of the future.

What you’ll do (Job Responsibilities)

• Design end-to-end product experiences across mobile, web, and dashboard tools
• Lead user research, usability testing, and participatory design with nontraditional users
• Build an accessible and maintainable design system from scratch
• Incorporate genAI/agentive design patterns into our core product UX
• Create documentation, rituals, and workflows for a future team of designers
• Collaborate with engineers, PMs, coaches, and end users to prioritize and ship features
• Advocate for user dignity and simplicity at every stage of the design process
• Help recruit, onboard, and mentor future design teammates

What you’ll have (Minimum Qualifications)  

• 6+ years experience in UX or product design, including mobile
• Portfolio showing intuitive, modern, and inclusive design
• Demonstrated experience with design systems and accessibility best practices
• Experience designing for complex or multi-sided products
• Passion for AI-native design thinking
• Empathy for users from marginalized backgrounds

Bonus Points if… (Preferred Qualifications)  ‍‍

• Experience working with non-native English speakers or users with low digital literacy
• Personal connection to the criminal justice system or re-entry
• Experience in a tech-based nonprofit or public-sector adjacent org
• Familiarity with ReactNative, Figma Tokens, or prototyping tools (e.g. Framer, ProtoPie)

Hiring Process

1. Read our FreeWorld Culture FAQ and our FreeWorld Core Values, and if you still think you are a fit… 
2. Submit an application and cover letter. If your qualifications are a match…  
3. We have a short introductory call. If we love each other, then…
4. You'll have a call with the CTO to walk through your work history, highlighting your proudest triumphs and the biggest mistakes you've made (i.e. the mistakes that made you).
5. One hour take-home exercise.  
6. Three one-hour panel interviews over video, focusing on Design Systems & Operational Excellence, Human-Centered Design & Accessibility, and Cross-Functional Collaboration & Product Thinking.
7. References- we talk to a few of your previous managers to learn more from the folks who knew you best.
8. We agree to terms, and get to work!
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Compensation and Benefits

This is a full-time position. Compensation is based on experience, but we are targeting the compensation range provided below.

FreeWorld is dedicated to caring for our team. For an up-to-date list of employee benefits, view our 2025 FreeWorld Benefits. A few key benefits are listed below:

• Remote flexibility
• A supportive, mission-driven culture
• Medical, dental, vision, and mental health insurance
• 401k and high-yield savings
• Unlimited PTO, 14+ holidays, and paid parental leave
• Quarterly wellness stipend & professional development fund