At Outmarket, we’re building the modern operating system for brokers, MGAs, and carriers. Our AI-powered platform transforms messy data into insight, replaces manual workflows with automation, and empowers users to move faster and smarter. We’re already live with some of the most forward-thinking agencies in the industry—and now we’re scaling.
We’re 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’s changing how an entire industry works.

Why This Role Is a Career-Defining Move

• You’ll partner closely with Vishal (Co-founder & CEO, ex-Uber, Meta, Ethos) and Anshu (Co-founder, early IBM Watson AI team)

• You’ll lead design across both product and marketing—setting the tone for user experience, interface, and storytelling

• You’ll shape how brokers, MGAs, and carriers interact with AI in their daily workflows

• You’ll work with engineering and product from concept through execution—every feature, every surface

What You’ll 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 action—wireframes, prototypes, hi-fidelity mocks

• Define Outmarket’s brand look and feel across all touchpoints

What You Bring

• 5+ years of experience in product design, with at least 1–2 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 mindset—you 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 You’ll 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

Ready to Build the UX That Changes an Industry?
Send your portfolio, resume, or LinkedIn to careers@outmarket.ai
Include a note on why you want to lead design at Outmarket and how you approach designing for complex systems.