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.

Youll 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. Were 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 designthrough user interviews testing and prototypingto 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 designs transformative role across the product platform the broader business and the intricate user journeysimplifying 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 teams 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 humbleand 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 2000 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 Fintechs 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 $211000 - $286000 in San Francisco CA. Final offer amounts depend on multiple factors such as candidate experience and expertise geographic location total compensation and market 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 Pilots recruiting notices here including our EEO policy recruitment agency policy recruitment scam notice and important E-Verify information.