Head of Design

PermitFlow is redefining how America builds. We’re an applied AI company serving the nation’s builders, tackling one of the largest information challenges in the economy: understanding what can be built, where, and how. Our AI agent workforce helps the fastest-growing construction companies navigate everything from permitting and licensing to inspections and project closeouts – accelerating housing, clean-energy, and infrastructure development across the country. Despite being a $1.6T industry, construction still suffers from massive delays, wasted capital, and lost opportunity. PermitFlow has already delivered unprecedented speed, accuracy, and visibility to over $20B in development, helping contractors reduce compliance time, de-risk projects, and scale with confidence. As the U.S. enters a new capex supercycle across data centers, factories, housing, and renewables, joining PermitFlow means building the AI infrastructure at the core of every construction project driving the next wave of reindustrialization. We’ve raised over $90M, most recently completing our Series B, https://www.permitflow.com/blog/permitflow-series-b from top-tier investors including Accel, Kleiner Perkins https://www.linkedin.com/feed/update/urn:li:activity:7401703305569275904/, Initialized, Y Combinator, Felicis, and Altos Ventures, with backing from leaders at OpenAI, Google, Procore, ServiceTitan, Zillow, PlanGrid, and Uber. Role Overview We are looking for an experienced and hands-on Head of Design to build and lead PermitFlow's design function. In this role, you will define how our product looks, feels, and works. You will evolve our design capabilities from a small team into a well-staffed, strategic organization that partners closely with Product, Engineering, and the founding team to ship work that directly moves the business. You'll be responsible for hiring and developing a team of product and brand designers, defining the company's design strategy and quality standards, and building the systems and processes that enable great design at scale. This is a player-coach leadership role that requires exceptional craft, strong product judgment, and the ability to operate both strategically and hands-on in a fast-paced startup environment. What You'll Do - Build and lead PermitFlow's design organization, evolving it into a strategic partner embedded across the business. - Hire and develop a team of product and brand designers to support stakeholders across Product, Engineering, GTM, Customer Success, Operations, and more. - Define PermitFlow's design strategy, including design system architecture, quality standards, critique processes, and cross-functional collaboration models. - Do hands-on design work yourself, particularly on the workflows and product areas that set the quality bar for the rest of the team. - Own and evolve the design system to ensure consistency, scalability, and coherence across the product as the company grows. - Establish consistent quality standards and review processes across the organization, ensuring what ships to production matches design intent. - Partner closely with leadership to drive design quality that directly impacts business metrics, including activation, retention, and customer satisfaction. - Set the vision for how AI transforms the design function, driving adoption of AI tools and evolving workflows across the team. What We're Looking For - 8+ years of product design experience, with deep expertise in B2B SaaS. Experience designing complex workflow products with data-dense interfaces and domain-expert users. - 3+ years of experience leading and managing design teams, ideally in a high-growth startup or technology company. - Proven experience building design teams and functions from early-stage to scale. - Exceptional craft across typography, layout, spacing, hierarchy, color, interaction, and polish. Systems thinking, not just good-looking screens. - Player-coach mentality with the ability to do hands-on desig