Head of Design

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.

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.

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

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

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.