The Role
The Chief of Staff will support the CEO in various aspects of the business including hiring, operations, and product management, while working on cross-functional projects.
Summary Generated by Built In
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.
- 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
Top Skills
AI
Automation
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The Company
What We Do
Caddi uses AI to revolutionize the way service professionals work. Say goodbye to non-billable hours and unnecessary overhead costs — Caddi empowers you to focus on what matters most, your clients.








