Director, AI Design & Experience

Accordion • Chicago, IL

26d • Hybrid

About The Position

We're looking for a designer who understands that AI changes everything about how humans interact with software, and especially is obsessed with getting those interactions right. You won't be adding chatbots to existing interfaces. You'll be reimagining what's possible when intelligence is embedded into every touchpoint. This role sits at the intersection of design, AI, advanced data analytics, and product strategy. You'll work hand-in-hand with our Accordion Intelligence Lab (a team of expert software engineers building the AI capabilities that power our solutions) translating complex model outputs into experiences that feel intuitive, trustworthy, and genuinely useful to finance professionals who don't have time for friction.

Requirements

• The AI-Native Mindset: You've been designing for AI long enough to have strong opinions about what works and what doesn't. You understand the unique challenges of AI interfaces: uncertainty, latency, explainability, trust calibration — and have developed approaches to address them. You're thinking about copilots, agents, and multimodal interactions, not just chat windows.
• The Technical Fluency: You can have substantive conversations with ML engineers about model capabilities and limitations. You understand enough about LLMs, embeddings, retrieval systems, and agent architectures to design experiences that work with these technologies rather than against them. You've seen how prompt design affects UX and vice versa.
• The Craft Excellence: Your visual and interaction design skills are exceptional. You can take complex, data-dense financial workflows and make them elegant. You prototype at high fidelity and can articulate the reasoning behind every design decision. You've built and maintained design systems that scale.
• The Research Rigor: You ground your designs in real user behavior. You know how to run effective user research with busy professionals, extract actionable insights, and translate findings into design improvements. You measure the success of your work and iterate accordingly.
• The Strategic Influence: You can advocate for design at the leadership level and shape product direction. You build strong partnerships with product, engineering, and business stakeholders. You know how to make the case for design investments and demonstrate their impact.
• 8+ years of product design experience, with 3+ years focused on AI-powered or data-intensive applications
• Demonstrated portfolio of AI/ML interface design showing sophisticated approaches to human-AI interaction
• Deep experience with design systems, prototyping tools (Figma, Framer, or equivalent), and front-end collaboration
• Track record of shipping AI features that users actually adopt and value
• Strong user research skills and evidence-based design practice
• Excellent communication skills with both technical and executive audiences
• Experience leading design direction and mentoring designers

Nice To Haves

• You might come from a product design leadership role at a company pushing the boundaries of AI interaction, a design agency doing cutting-edge AI work, or a startup where you owned the entire design experience for AI-native products. What matters most is that you've wrestled with the hard problems of human-AI interaction and have the portfolio to prove it.
• Bonus points if you've designed for enterprise finance, CFO tools, or other high-stakes professional contexts where accuracy and trust are paramount.

Responsibilities

• You'll define the design language for AI-native experiences across Accordion's solution portfolio. This means moving beyond traditional UI patterns to create new interaction paradigms: how users prompt and guide AI systems, how they interpret and validate AI-generated insights, how they maintain appropriate oversight without drowning in alerts, and how they build trust in outputs they can't fully verify themselves.
• Your day-to-day will involve deep collaboration with engineers building LLM-powered features, RAG systems, and agentic workflows. You'll prototype rapidly, test with real users, and iterate based on what you learn about how finance professionals actually want to work with AI. You'll establish design principles and patterns that scale across products while remaining flexible enough to evolve as AI capabilities advance.
• You'll own the end-to-end experience strategy for AI interactions: from first-time onboarding that builds user confidence, to progressive disclosure of AI capabilities, to graceful handling of uncertainty and errors. You'll think deeply about when AI should act autonomously versus when it should ask for guidance, and design the interfaces that make those handoffs seamless.
• Travel to client sites as needed.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 1,001-5,000 employees