Head of Design (Chicago)

About our client

At Outmarket , they are building the modern operating system for brokers, MGAs, and carriers. Their AI-powered platform transforms messy data into insight, replaces manual workflows with automation, and empowers users to move faster and smarter. They are already live with some of the most forward-thinking agencies in the industryand now they are scaling.

They are looking for a Head of Design to own product and brand design from the ground up. This is a rare opportunity to set the visual language and UX strategy for a product that is changing how an entire industry works.

Why This Role Is a Career-Defining Move

• Youll partner closely with Vishal (Co-founder & CEO, ex-Uber, Meta, Ethos) and Anshu (Co-Founder & CTO, ex-Meta, Ethos, early IBM Watson AI team)
• Youll lead design across both product and marketingsetting the tone for user experience, interface, and storytelling
• Youll shape how brokers, MGAs, and carriers interact with AI in their daily workflows
• Youll work with engineering and product from concept through executionevery feature, every surface

What Youll Own

• Lead and scale the design function across product, web, and brand
• Build a design system that balances speed, consistency, and flexibility
• Own user experience across key workflows: quote comparison, policy review, proposal generation, and more
• Drive user research and distill insights into clean, intuitive flows
• Create artifacts that inspire actionwireframes, prototypes, hi-fidelity mocks
• Define Outmarkets brand look and feel across all touchpoints

What You Bring

• 5+ years of experience in product design, with at least 12 years in a leadership or founding designer role
• Strong portfolio showcasing complex workflows and clean UX
• Ability to move seamlessly between big-picture thinking and pixel-perfect execution
• Collaborative mindsetyou know how to partner with engineers, PMs, and execs
• A passion for simplifying complex information and workflows

Bonus If You Have

• Experience in SaaS, enterprise, data, or AI products
• Familiarity with insurance workflows or B2B tools
• Experience working in an early-stage or zero-to-one product environment

What Youll Get

• Founding-level influence on product and company brand
• Competitive compensation and meaningful early equity
• A high-trust environment focused on outcomes, not bureaucracy
• Opportunity to build something from scratch that users rely on daily
• Remote-friendly setup and a team that ships fast
• Salary: $180k - $200k + performance
• Benefits: Great gear, equity plan, team retreat, modern tools, flex schedule, unlimited PTO and growth budget