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
Get notified about new Head of Design jobs in Greater Boston.
Burlington, MA $235,450.00-$280,000.00 1 week ago
Boston, MA $227,000.00-$283,000.00 1 day ago
Boston, MA $160,000.00-$205,000.00 6 days ago
Boston, MA $175,000.00-$225,000.00 23 hours ago
REMOTE - Director of Engineering - Security
Boston, MA $160,000.00-$210,000.00 2 weeks ago
Boston, MA $190,000.00-$230,000.00 2 weeks ago
Engineering Manager - Public Cloud, Python, Golang
Marlborough, MA $130,000.00-$170,000.00 1 month ago
We’re unlocking community knowledge in a new way. Experts add insights directly into each article, started with the help of AI.
#J-18808-Ljbffr