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Head of Design

Head of Design

ToolbxSan Diego, CA, United States
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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 industry—and 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

  • You’ll partner closely with Vishal (Co-founder & CEO, ex-Uber, Meta, Ethos) and Anshu (Co-Founder & CTO, ex-Meta, Ethos, 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
  • Salary : $180k - $200k + performance
  • Benefits : Great gear, equity plan, team retreat, modern tools, flex schedule, unlimited PTO and growth budget

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    Head Of Design • San Diego, CA, United States