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Job Details

Sr. Product Designer

The Role

Pilot is looking for Product Designers to help build the future of the financial back office.

Key Responsibilities 

  • Taking broad conceptual ideas and turning them into delightful solutions.
  • Partnering with Product, Engineering, Research, and Operations to uncover user insights.
  • Directly interfacing with our users to conduct interviews, research, and data gathering to inform design decisions.
  • Contributing to your overall product area by designing end-to-end workflows.
  • Bringing your ideas to life through brainstorming, sketching, prototyping, and high-fidelity mocks.

About you

Our ideal candidate will have at least 3 years of product design experience, and can additionally demonstrate the following:

  • You care deeply about customers and enjoy creating delightful experiences
  • Experience working with an established design system.
  • Highly proficient with design tools (Figma, Sketch, Photoshop, Illustrator, etc.)
  • Excellence in design craft
  • Ability to work with a low-ego, highly collaborative, cross-functional team
  • Excited about working in a fast-paced, dynamic startup environment

About Pilot

Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts - which Pilot hires as full-time, U.S.-based employees - who learn the ins-and-outs of their business. Pilot integrates directly with the billing, banking, expense, and payroll systems customers already use. With a special blend of custom software and expert bookkeepers, Pilot delivers accurate, consistent bookkeeping and financial management and tax services that give entrepreneurs the freedom to focus on their business.


Pilot has over 1,000 customers and has raised over $170 million in financing from Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock. Our investors also include a long list of world-class entrepreneurs, including Patrick and John Collison, Drew Houston, and Diane Greene. Our most recent funding round doubled our valuation to $1.2 billion – Meet Fintech’s Newest Unicorn.

Why Pilot?

  • We invest in our employees’ development and happiness because our employees are the keys to our success and ensuring happy customers
  • The opportunity to join a seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox).
  • Flexible vacation/time-off policy
  • All federal holidays are observed
  • 100% coverage of employee only (individual) benefits
  • Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
  • 401(k) plan