Director of Design Innovation – AI

Role Overview

• Define and own the design vision for ClassLink's AI-powered products
• Lead the design of novel AI interaction patterns including conversational interfaces
• Develop design frameworks that build trust with school districts, educators, and administrators
• Provide strategic and hands-on UI/UX design leadership across ClassLink's product suite
• Leverage AI-powered design and coding tools to accelerate prototyping
• Lead research initiatives to understand how educators, IT administrators, district leaders, and students perceive, trust, and interact with AI features
• Collaborate with security, compliance, and AI engineering teams to ensure AI interfaces surface appropriate guardrails
• Work closely with AI engineering, product management, security, compliance, and district-facing teams
• Build, lead, and mentor a design team focused on AI product experiences
• Establish design processes, review cadences, and quality standards for AI product design
• Ensure all AI-powered experiences meet WCAG accessibility standards
• Translate complex AI capabilities into clear, compelling narratives for stakeholders
• Stay current with the rapidly evolving landscape of AI interaction design

Requirements

• 8+ years of professional UI/UX design experience, with at least 3 years in a design leadership or management role overseeing a team of designers.
• At least 2 years of experience designing AI-powered product experiences, including conversational interfaces, intelligent assistants, agent-based workflows, or other LLM-driven features.
• Demonstrated hands-on proficiency with AI-assisted coding and design tools (e.g., Cursor, GitHub Copilot, Claude, Figma AI, v0, or similar) used to accelerate prototyping and product development.
• Strong portfolio demonstrating excellence in UI/UX design across complex, multi-user product ecosystems — ideally including SaaS or platform products.
• Experience establishing and scaling design systems and component libraries across product teams.
• Deep understanding of AI interaction design patterns including conversational UI, agent transparency, progressive trust, confidence visualization, human-in-the-loop controls, safe failure modes, and error recovery.
• Demonstrated experience designing and shipping complex SaaS products, ideally in enterprise or regulated environments.
• Experience conducting and leading user research, usability testing, and data-informed design iteration.
• Familiarity with front-end technologies (HTML, CSS, JavaScript, React, or similar) sufficient to collaborate effectively with engineers and to leverage AI coding tools for rapid prototyping.
• Experience designing for accessibility (WCAG compliance) and inclusive design principles.
• Experience working in regulated environments, preferably involving student data privacy (FERPA, COPPA) or similarly regulated industries (healthcare, finance, government).
• Strong understanding of how AI systems work at a conceptual level — including LLMs, RAG, agentic architectures, and tool use that is sufficient to design informed, technically grounded user experiences.
• Excellent communication and presentation skills, with the ability to articulate design vision and rationale to engineering, product, executive, and district stakeholders.
• Demonstrated ability to lead cross-functional initiatives and influence product direction at the organizational level.

Tech Stack

• JavaScript
• React

Benefits

• Generous Paid Time Off : 4+ weeks of vacation and 13+ paid holidays
• Parental Leave : 12 weeks fully paid for all parents
• Retirement : 401(k) with 0.5:1 company match
• Comprehensive Health Coverage : Medical, dental, and vision plans
• Insurance : Company-paid life, short-term disability, and long-term disability, plus voluntary options including supplemental life, accident, and pet insurance
• Volunteer Time Off: Give back through ClassLink Cares paid volunteer days
• Lifelong Learning: Tuition reimbursement for continued education
• Growth & Development: Coaching and internal programs to support career and personal growth
• Supportive Culture: A workplace that values curiosity, compassion, and continuous learning
• Connection & Community: Annual company retreats and team events with bright, fun coworkers