Join to apply for the Head of Design role at JOBS by allUP 1 day ago Be among the first 25 applicants Join to apply for the Head of Design role at JOBS by allUP Get AI-powered advice on this job and more exclusive features. This range is provided by JOBS by allUP. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more. Base pay range $180,000.00/yr - $200,000.00/yr 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 Benefits: Great gear, equity plan, team retreat, modern tools, flex schedule, unlimited PTO and growth budget Seniority level Seniority level Mid-Senior level Employment type Employment type Full-time Job function Job function Design Industries Insurance Referrals increase your chances of interviewing at JOBS by allUP by 2x Sign in to set job alerts for “Head of Design” roles. Director, Design Systems & Operations, Remote McLean, VA $250,000.00-$300,000.00 2 months ago Arlington, VA $185,000.00-$205,000.00 1 day ago Engineering Manager - Public Cloud, Python, Golang Principal Partner Solutions Architect - GSI Washington, DC $210,600.00-$304,325.00 1 week ago Columbia, MD $125,000.00-$135,000.00 2 weeks ago Washington, DC $110,000.00-$165,000.00 1 week ago We’re unlocking community knowledge in a new way. Experts add insights directly into each article, started with the help of AI.

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