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Great Question (YC W21) Is Hiring Director of Product

About This Role: We’re hiring a Director or Senior Director of Product who can be both strategic and hands-on — a player-coach who thrives at the intersection of leadership, execution, and product innovation. You’ll report directly to the CTO and work closely with the CEO, Head of Design & Director of Engineering to refine our product org structure and build a world-class product culture. You’ll lead by doing: partnering with engineering and design, managing and mentoring PMs, and helping teams execute quickly and effectively. We believe in empowering squads with ownership and autonomy, and you’ll help set up the systems to make that work at scale. This is a high-impact, high-visibility role ideal for someone who’s taken a startup from Series A to B and beyond — and is ready to do it again, better and faster, with the wisdom of experience. What You’ll Do: Product Leadership: Guide and coach PMs while personally owning key product initiatives; grow the team from 2 to 4+ PMs over the next year. Organizational Design: Help define the right product org structure (e.g., squad zoning vs. centralized planning) to support autonomy and velocity. Strategy & Execution: Collaborate with the CEO, CTO, and Head of Design to drive the product roadmap, refine our strategic bets, and deliver impactful features quickly. AI Innovation: Leverage AI tooling and shape product experiences infused with AI. Ideally, you’ve built and shipped AI products and know how to evaluate emerging AI tech critically. Metrics & Measurement: Ensure the right data is tracked and used to inform decisions. Champion outcome-oriented thinking. Cross-Functional Alignment: Be the connective tissue between product, engineering, design, marketing, customer success, and go-to-market teams. Commercial Thinking: Bring a business mindset — thinking not just about UX and usability but also about growth, pricing, retention, and revenue impact. What We’re Looking For: 7–12 years of experience in product management, with at least 2–3 years in a leadership role (e.g., Head of Product, Director, or similar). Hands-on experience building AI-driven products or a strong portfolio using AI tools in product development. Experience at early-stage, fast-growing companies — ideally from Series A through B/C — and a desire to do it again. Strong product instincts with a founder’s mindset. Prior entrepreneurial experience (e.g., starting a company or building 0→1) is a bonus. Proven ability to hire, coach, and retain product talent. Highly organized with strong communication skills; you bring structure to chaos and clarity to ambiguity. Commercial acumen — you’re comfortable discussing growth models, pricing, and business strategy. Located in the North America and able to work Pacific Time Zone hours. (CEO is based in the Bay Area, CTO in Colorado.)

You’ll lead by doing: partnering with engineering and design, managing and mentoring PMs, and helping teams execute quickly and effectively. Organizational Design: Help define the right product org structure (e.g., squad zoning vs. centralized planning) to support autonomy and velocity. Strategy & Execution: Collaborate with the CEO, CTO, and Head of Design to drive the product roadmap, refine our strategic bets, and deliver impactful features quickly.

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