Head of Design

The Role

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.

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:

• Experience: 8+ years of impactful experience in product/UX design or a related field, including at least 2+ years in a manager or player-coach role.
• Domain Fit: Previous experience with accounting, finance, tax tools, small business SaaS, or a background in founding/designing within early-stage product environments is highly preferred.
• Strategic & Systems Thinking: You possess an innate ability to see design's transformative role across the product platform, the broader business, and the intricate user journey—simplifying complexity with remarkable clarity.
• Design Craft: A profound grounding in detailed visual and interaction design, expert-level prototyping in Figma, and a natural inclination for systems thinking.
• Leadership Style: You inspire and mentor with clarity, provide and receive direct feedback with grace, and secure your team's consistent progress through a powerful combination of positive culture and insightful coaching.
• Business Acumen: You deeply understand how exceptional design directly drives key product metrics, elevates customer satisfaction, and ultimately achieves impactful company outcomes.
• Soft Skills: You are inherently collaborative, a natural communicator, insatiably curious, genuinely humble—and possess a natural talent for influencing effectively across diverse functions.

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?

• 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
• Competitive benefits package including wellness benefits such as Modern Health, Headscape, One Medical, Aaptiv and Rightway
• Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
• 401(k) plan

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. You may view all of Pilot’s recruiting notices here, including our EEO policy, recruitment agency policy, recruitment scam notice, and important E-Verify information.