Who We Are

For the 57 million freelancers (36% of the US workforce), the administrative burden of self-employment is a full-time job that doesn't pay. Wingspan is developing the first one-stop shop for knowledge-based freelancers that streamlines income, benefits, and taxes -- think Justworks for freelancers.  We've assembled a world-class team that has the HR, technology, and insurance expertise to execute this vision and build Wingspan into a big business with significant impact.

Your Role

We’re looking for a Product Design Lead to help us build the product that will empower millions and change the future of how we work. At Wingspan we believe that User Experience is the heart and soul of the product, and that great UX starts with Design. Working closely with the Head of Product, this role will design how our platform works and how our members engage with it. To that end, the ideal candidate is a great collaborator, working across disciplines in order to pull together a product experience that will delight our members and contribute directly to our growth. 

Your Contribution

  • You’ll define how our members see and use the Wingspan Platform. 
  • Work closely with other teams at Wingspan and external contacts to pull together everything you need to be effective.
  • Own the design system, working with internal and external resources to evolve it, and collaborating with other teams to implement it.
  • Review customer feedback, both directly and from internal teams, to incorporate the member’s voice in the experience and improve the product. 
  • Work across various platforms like Web, iOS and Android.
  • Over time scale up and lead the design team.

Who You Are

You’re an experienced product designer who thinks deeply about the customer problem and experience, embraces collaboration with different teams to design the right product, and empowers partner teams to be successful.

Minimum Requirements

  • 5+ years of experience in product design or user experience.
  • Experience with designing services platforms.
  • Experience working with and designing around user research.
  • Up to date on the latest design practices and trends.
  • Knowledge of and experience working with different design 
  • Strong attention to detail, but also flexible and pragmatic when necessary.
  • Excellent verbal and written communication skills.

Preferred Requirements

  • Familiarity with online payment systems, or online commerce.
  • Understanding of the small business, or freelancer domain.
  • Leadership of other designers (not necessarily in a management capacity).


Values + Benefits

We're proud to be a mission-driven company with an inclusive culture. We also offer significant equity allocations, healthcare coverage, and flexible vacation/PTO. 

Our values guide our team every day (see below). 

Members First: We are focused on serving the evolving needs of our members. This means building new products and services that actually help our members work the way they want to live. 

Make Magic: We challenge the prevailing assumption that choosing to work for yourself means living with uncertainty and chaos. Wingspan strives to provide freelancers with confidence, stability and flexibility through a transformative experience that surprises and delights.

New Standards: We believe the old paradigm of work has not kept up with the needs of the growing independent; and that new competitors isolate services, fragmenting the experience. We designed Wingspan to be the modern essentials (everything) our members need, all in one place. I 

Shared Purpose: We are stronger together. With the shared experience of working independently, we understand the value in building a common community that can advocate, connect, and support one another. 


We appreciate candidates who are open and honest about what they’re looking for so we can ensure it’s a fit on both sides. 

Sound interesting? We look forward to hearing from you. Join us to reimagine the future of work and money!

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