Principal Product Designer

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, from top-tier investors including Accel, Kleiner Perkins, Initialized, Y Combinator, Felicis, and Altos Ventures, with backing from leaders at OpenAI, Google, Procore, ServiceTitan, Zillow, PlanGrid, and Uber. Our HQ is in New York City with a hybrid schedule (3 in-office days per week). We prefer NYC-based candidates or those open to relocation. About the Role As a Principal Product Designer at PermitFlow, you are the most senior individual contributor on the design team. You set the vision and the craft bar for our most complex, highest-leverage product surfaces, and you raise the ceiling for what design at PermitFlow can be. This is a hands-on role: you'll go deep on the hardest problems in construction permitting, and your influence felt in the quality of the product and in the impact of the designers around you. Permitting is a workflow-dense, high-stakes, historically manual industry, and we are rebuilding that industry as an intelligent product. You will define how automation and AI show up in moonshots & strategic big-bet experiences. In our core product offerings, you'll ensure our users understand what the product is doing, trust its output, and stay in control of decisions that carry real financial and regulatory weight. What You'll Do Own the design vision for our highest-impact product areas, from framing the problem through pixel-perfect execution. Set the strategic direction for how permitting workflows, automation, and AI-assisted decisions are designed, ensuring users can read, trust, and guide the product's output. Partner with the Head of Design, product, and engineering leadership to shape the roadmap, not just execute against it, bringing a strong and well-reasoned point of view on where the product should go. Raise the craft bar across the whole design team by modeling exceptional work, strengthening our critique culture, and mentoring designers without managing them. Evolve the design language and systems thinking that let a small team ship cohesive, scalable experiences as our surface area grows. Move fluidly between deep detail and big-picture direction while holding a high quality bar and a high pace of execution. Become a functional expert on construction permitting, licensing, and inspections, leading with curiosity even if this is your first time in the pre-construction industry. Collaborate with sales and marketing on collateral and branding as needed, and help us build a permitting product that is beautiful, that works, and that scales. What We're Looking For All applications must link to or include a portfolio. We want to see a track record of leading high-craft, complex products from concept through launch, with clear evidence of design decisions you drove and their impact. 10+ years designing dense B2B software, with deep experience in workflow-heavy products and real complexity. A demonstrated ability to operate as a force multiplier: elevating the work of other designers, defining what great looks like, and bringing structure to problem spaces that do not yet have any. Strong systems thinking paired with exceptional interaction and visual craft. You sweat the details just as well as you guide strategy. Experience designing AI-powered or highly technical products, or a clear point of view on how to make AI legible, trustworthy, and controllable for users. High tolerance for ambiguity. We are moving fast, and our design, product, and engineering processes are constantly in flux. We want someone who thrives in that and helps improve it. Excellent communication and storytelling. You can articulate design rationale and win alignment across designers, engineers, executives, and customers. Technical fluency. We value designers who understand the realities of implementation and can partner deeply with engineers. Hands-on comfort with code is a plus. Our team primarily uses Figma, Notion, and Linear. You should be comfortable with those or similar tooling, with comfort making tooling recommendations to leadership as new horizon models & solutions become available. PermitFlow provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, gender expression, or family status, as protected by applicable law. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities. All employment decisions are based on merit, qualifications, and business needs. PermitFlow