Head of Design Job at Puzzle?? in San Francisco

At Puzzle, we’re not just building accounting software- we’re fundamentally reimagining it. Our cutting-edge platform seamlessly integrates with modern fintech tools, offering founders and finance teams a real-time and comprehensive view of their financial landscape like never before.

About the Role We're seeking an exceptional Head of Design to lead our design organization and drive product excellence. This role requires a rare combination of systems thinking, technical understanding, and leadership acumen. The ideal candidate will be someone who can architect design systems that scale, build high-performing teams, and navigate the complexities of a fast-growing startup environment.

You'll be responsible for establishing design as a strategic function that drives business outcomes while maintaining exceptional user experiences. Reporting directly to the VP of Product, this is a hands-on leadership role where you'll shape both the design culture and the systems that enable our product to scale effectively.

What You'll Do Strategic Leadership & Vision

Develop and execute a comprehensive design strategy that aligns with business objectives and technical constraints

Partner closely with Product, Engineering, and Executive teams to ensure design is integrated into all strategic decisions

Think architecturally about how design decisions impact the broader product ecosystem

Team Leadership & Development

Build, mentor, and lead a world-class design team in a fast paced, early stage environment

Develop design talent by building career development frameworks and creating an environment of continuous learning, feedback, and design excellence

Foster a culture of systems thinking and principled decision-making across the design organization

Operations & Process

Drive design operations and processes that improve velocity, consistency, and collaboration

Structure and facilitate design critiques, workshops, and cross-functional discussions that drive clarity and alignment with stakeholders

Navigate organizational change and introduce new design methodologies without disrupting existing workflows

Ensure design deliverables meet quality standards while moving at startup speed

Design Systems & Execution

Design and implement scalable design systems, components, and patterns that evolve with our product

Balance ideal design solutions with practical constraints including technical debt, timelines, and business needs

Anticipate design challenges and guide the team toward coherent, forward-thinking solutions

Communication & Collaboration

Communicate complex design concepts clearly to executives, product managers, and engineers

Qualifications Background & Experience

8+ years of design experience with 4+ years in senior design leadership roles

Strong background in SaaS or fintech products, with deep understanding of complex user workflows

Experience building 0-1 and scaling design teams in startup environments (Series A-C preferred)

Technical background preferred - ideally someone who transitioned from engineering to design and understands how products are built

Design & Strategic Capabilities

You architect beyond individual screens, designing interconnected systems that evolve over time

Deep understanding of how design intersects with engineering, product, data, and business strategy

Strong design convictions balanced with practical flexibility when constraints require trade-offs

Ability to identify design, behavioral, and organizational patterns that help anticipate and solve problems before they emerge

Leadership & Team Development

Proven track record of developing design talent and elevating team capabilities

Skilled at structuring discussions that clarify complexity and drive teams toward aligned decisions

Skilled at introducing new systems and methods into existing organizational structures

Cares deeply about how design is delivered, not just conceptualized

Communication & Adaptability

Ability to explain complex design systems and decisions to executives, PMs, engineers, and designers with precision

Comfortable with ambiguity and rapid iteration in startup environments, including strong intuition for when to move fast vs. when to push back and advocate for design quality

User-Centered Focus

Customer-obsessed - every systems decision is grounded in real user needs and behaviors

Experience with user research integration and data-driven design decisions

Strong opinions about user experience backed by evidence and clear reasoning

What’s in it for you? Join Puzzle Financial at a pivotal growth stage where you'll help redefine and reimagine how companies handle their financials while building your career in a flexible, remote-first environment. You'll have the opportunity to make a significant impact, work with innovative founders, and develop valuable expertise at the intersection of modern accounting and fintech.

Here is a preview of some of the amazing benefits here at Puzzle :

Competitive base pay and meaningful equity

100% paid employee health, dental, and vision plans (U.S. & Canada vary)

10 observed holidays and a flexible PTO policy so you can recharge

$1000 home office budget to get you set up for success

$2400 co-working budget for face time with your colleagues

$600 learning and development budget

401K so you can save for your future

And much more

Puzzle is an equal opportunity and affirmative action employer. We welcome and encourage diversity in the workplace regardless of gender, race or color, ethnicity or national origin, age, disability, religion, sexual orientation, gender identity or expression, veteran status, or any other characteristics protected by law.

Candidates should be currently residing in the U.S. or Canada to be eligible for this position. If hired, you will be required to present proof of work authorization. This employer is a participant of the E-Verify program.

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In Summary : We're seeking an exceptional Head of Design to lead our design organization and drive product excellence . The ideal candidate will be someone who can architect design systems that scale, build high-performing teams, and navigate the complexities of a fast-growing startup environment . You'll be responsible for establishing design as a strategic function that drives business outcomes .

En Español : En Puzzle, no estamos simplemente construyendo software de contabilidad - lo estamos reinventando fundamentalmente. Nuestra plataforma de vanguardia se integra perfectamente con herramientas modernas de fintech, ofreciendo a los fundadores y equipos financieros una visión en tiempo real e integral de su paisaje financiero como nunca antes. Sobre el papel Estamos buscando un Jefe de Diseño excepcional para liderar nuestra organización de diseño y impulsar la excelencia del producto. Este rol requiere una rara combinación de pensamiento sistémico, comprensión técnica y perspicacia de liderazgo. El candidato ideal será alguien que pueda diseñar sistemas que escalarán eficazmente, construir equipos de alto rendimiento y navegar por las complejidades de un entorno startup de rápido crecimiento. Usted será responsable de establecer el diseño como una función estratégica que guíe resultados empresariales mientras mantiene sistemas excepcionales. Informarse al VP del Producto, este producto es una cultura práctica donde usted puede moldear directamente nuestras experiencias de desarrollo y dirección. Desarrollar y ejecutar una estrategia de diseño integral que se alinee con los objetivos del negocio, la retroalimentación y la excelencia en el diseño Asociarse estrechamente con equipos de producto, ingeniería y ejecutivos para garantizar que el diseino esté integrado en todas las decisiones estratégicas Piense arquitectónicamente sobre cómo las decisiones de diseños afectan al ecosistema más amplio del producto Equipo Liderazgo & Desarrollo Construir, mentor, y liderar un equipo de diseñador de clase mundial en un entorno acelerado y temprano. ¿Cuándo empujar hacia atrás y abogar por la calidad del diseño Concentrado en el usuario Enfoque al cliente Obsesionado - cada decisión de sistemas se basa en necesidades y comportamientos reales de los usuarios Experiencia con la integración de investigación del usuario y decisiones de diseño basadas en datos opiniones fuertes sobre la experiencia del usuario respaldados por evidencia y razonamiento claro Qué hay para usted? Únete a Puzzle Financial en una etapa crucial de crecimiento donde ayudará a redefinir e reimaginar cómo las empresas manejan sus finanzas mientras construyen su carrera en un entorno flexible, remoto-primero. Tendrá la oportunidad de tener un impacto significativo, trabajar con los fundadores, y desarrollar valiosas experiencias innovadoras en la intersección de la contabilidad moderna y fintech. Aquí está una vista previa de algunos de los increíbles beneficios aquí en Puzzle : pago competitivo base sexual y equidad significativa 100% salarial orientada a la salud, odontología y visión de empleados (Estados Unidos) planes 401K. Los candidatos deben residir actualmente en los Estados Unidos o Canadá para ser elegibles para este puesto. Si son contratados, se les pedirá que presenten una prueba de autorización de trabajo.