Head of Design

Pilot is seeking a Head of Design to lead our Product Design team and champion the design function. This is a unique opportunity for a collaborative leader who can seamlessly blend high-level strategic thinking with hands-on execution to deliver truly intuitive and impactful product experiences.

You'll be at the forefront, instrumental in shaping cutting-edge financial tools that empower business owners and startup founders with unparalleled control and visibility into their finances. We're looking for a dynamic player-coach who thrives on balancing inspiring leadership, direct design contributions, and a relentless pursuit of operational excellence.

This is a hybrid position with the expectation to work in the San Francisco office on Mondays, Tuesdays, and Thursdays.

Key Responsibilities

• Define and Evolve Design Vision : Craft a holistic design vision that deeply aligns with our business strategy and user needs, with a keen focus on pioneering accounting automation and financial tools for startups and SMBs.
• Strategic Partnership : Collaborate closely with Product, Engineering, and Operations leadership, influencing crucial product decisions and roadmap priorities to drive our vision forward.
• Nurture and Grow Talent : Manage, mentor, and grow a small to mid-sized design team, fostering a vibrant culture, shaping our hiring strategy, and building robust professional growth frameworks.
• Lead End-to-End Design : Take ownership of the entire product design process, ensuring seamless and delightful interactions across all touchpoints within your product and service areas.
• Steward Our Design System : Develop and champion our design system, ensuring consistency, accelerating execution, and maintaining the highest quality standards.
• Optimize Design Operations : Establish scalable design operations, fostering efficient collaboration processes and tooling that support rapid execution without ever sacrificing quality.
• Champion Research-Informed Design : Lead the charge on research-informed design—through user interviews, testing, and prototyping—to drive truly intuitive, data-backed experiences that resonate with our users.
• Uphold Design Excellence : Maintain unparalleled excellence in visual and interaction design, encompassing information architecture, visual hierarchy, accessibility, and thoughtful layout.

About You

Our ideal candidate is deeply curious, highly analytical, and genuinely team-oriented, possessing the following essential qualifications and skills :

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 2,000 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?

The base pay range target for the role seniority described in this job description is $211,000 - $286,000 in San Francisco, CA. Final offer amounts depend on multiple factors such as candidate experience and expertise, geographic location, total compensation, and market data. In addition to cash pay, full-time regular positions are eligible for equity, 401(k), health benefits, and other benefits; some of these benefits may be available for part-time or temporary positions.

Pilot commits to provide a work environment free of discrimination and harassment, as well as equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements.

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