Caddi

Compensation

Full Description

Chief of Staff job at Caddi. Seattle, WA. We’re hiring a Chief of Staff to work directly with the CEO and accelerate every part of the business. This is a high-ownership, founder-track role for someone who is relentlessly resourceful, organized, and energized by solving problems across hiring, GTM, product, and operations. What You’ll Do • Identify and research target firms • Support outbound with basic account insights • Manage CEO priorities, meetings, and coordination • Run cross-functional projects across sales, product, hiring, and ops • Prepare materials for customers, investors, and internal alignment • Build lightweight systems for pipeline, recruiting, and ops metrics • Support customer success and implementation workflows Requirements • 2–5 years in startups • Clear, concise communicator with strong writing skills • Comfortable operating in high ambiguity with minimal instruction • Operationally disciplined and highly reliable — able to manage many threads simultaneously • Scrappy, resourceful, and organized to an extreme • Interest in AI, automation, and the professional services landscape • Wants to be deeply embedded with founders and learn how companies scale from day zero Benefits • Work directly with the founders and meaningfully shape the company’s foundation • High-ownership, founder-track role with exposure across GTM, product, sales, and operations • Competitive base salary ($100,000–$120,000) + meaningful early equity • Medical (platinum PPO), dental, and vision — 100% covered for employees; subsidized dependents • In-person, fast-paced environment with a technical, ambitious, mission-driven team