Head of Design

Summary

Join Puzzle Financial, a company reimagining accounting software, as their exceptional Head of Design. Lead the design organization, driving product excellence by architecting scalable design systems and building high-performing teams. Establish design as a strategic function, ensuring alignment with business objectives and exceptional user experiences. This hands-on leadership role reports to the VP of Product and involves shaping design culture and systems for effective product scaling. You will be responsible for developing and executing a comprehensive design strategy, partnering with various teams, and building a world-class design team. The role requires strong leadership, communication, and design skills, along with experience in SaaS or fintech products and building design teams in startup environments.

Requirements

• 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)
• 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
• 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
• 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
• 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

Responsibilities

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

Preferred Qualifications

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

Benefits

• 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