Staff Designer - Design Systems

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 We're hiring our first Design Systems Designer and Architect to build Cornerstone: the visual and interaction foundation that keeps design, engineering, and an increasingly AI-driven product moving as one. This isn't a maintenance role. You're establishing the standards PermitFlow's next stage of product complexity gets built on. We need someone who can hold the full system in their head and still catch a four-pixel misalignment without missing a beat, with real conviction about brand and visual quality baked into every call. You'll work side by side with frontend and platform engineering leadership to design, ship, and iterate on the components, patterns, and tokens the product runs on, and you'll have the mandate to grow a team around this practice as Cornerstone's footprint expands. How fast our teams can build, how consistently the product behaves, and how much trust our users place in high-stakes permitting, licensing, and inspection workflows all trace back to this foundation. What You'll Do Build and continually refine Cornerstone's core building blocks, components, patterns, and tokens designed for complex, workflow-heavy, AI-enabled experiences, with a strong eye for brand cohesion and polish. Set a multi-year direction for the design system and turn it into a roadmap that design, engineering, and product leadership can develop in concert. Design, prototype, and ship production-ready components hand in hand with a dedic Define how contribution, governance, and deprecation work in an AI-native working environment; balance shipping speed against system integrity; and adjust the model as the org grows. Bake accessibility, responsiveness, and performance into every part of the system from day one. Create the documentation, onboarding materials, and reference resources that make Cornerstone the quickest route to shipping well. Advocate for the system & guild in planning, design reviews, and roadmap conversations, and hold firm when speed and integrity are in tension. Mentor others in design systems craft as the practice grows, shaping what that craft looks like at PermitFlow for years ahead. Build real expertise in construction permitting, licensing, and inspections, leading with curiosity even if pre-construction is new territory for you. What We're Looking For A portfolio with real point of view, not just system diagrams: craft, quality, accessibility, and visual cohesion are all a must. 10+ years in product design, with meaningful ownership of a design system across a multi-product environment; brand or visual design background is a plus. Strong command of component architecture, design tokens, and what it takes for a system to total adoption across teams and surfaces. A history of working shoulder to shoulder with frontend engineers to ship production-grade systems, not just handing off specs and moving on. A track record of setting & reinforcing accessibility standards. Clear communication about system tradeoffs, whether you're talking to designers, engineers, or executives. Mastery of Figma, Notion, and Linear; actively experimenting with the next best tool to add to our stack. What We Offer Competitive salary and meaningful equity in a high-growth company 100% company-paid base medical, dental, and vision coverage for employees + healthcare FSA 401(k) savings plan Unlimited PTO and paid family leave Home office & equipment stipend Daily in-office lunch and dinner provided Commuter benefits (pre-tax transit and parking) 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.