Chief Of Staff

Summary

Join Woolf, a global collegiate university, as a startup operator working closely with the CEO and executive leadership team. This hands-on role involves managing operations, working with technical software and regulatory requirements, and collaborating with a globally distributed, remote team. You will be responsible for high-throughput, high-communication, and high-precision work, often involving privileged information. The position requires extensive operational management experience and a readiness to work in a smaller, fast-paced environment. You will hire and manage additional operators to support the CEO's functions and execute key initiatives. The ideal candidate is highly organized, detail-oriented, and possesses excellent communication skills.

Requirements

• 10+ years of operational management (5+ with elite MBA) or elite management consulting with significant, extensive executive responsibilities
• Readiness to get back into a smaller operating environment where you will do hands-on work
• Willingness to work PST hours – occasionally long hours, occasionally a brief weekend touchpoint, e.g., Sunday night PST
• Understanding that as a long-term Chief of Staff, you will both have an attitude of service and adopt some COO functions as you build out an operations team within the CEO office and beyond
• Highly proactive approach, translating ideas into actions with high horsepower, high energy, high precision
• Highly organized and detail-oriented
• Ability to work in a role requiring high levels of trust and confidentiality
• Self-starter with an entrepreneurial flair and a team player willing to roll up sleeves
• Flexibility and resourcefulness
• Excellent verbal and written communication skills

Responsibilities

• Manage operations within the CEO office and across Woolf
• Work with highly technical software and regulatory requirements
• Collaborate with a globally distributed, remote team
• Maintain high-throughput, high-communication, and high-precision work
• Handle privileged legal, commercial, and financial information
• Hire and manage 1-3 additional operators to support CEO functions
• Execute key initiatives (e.g., creating a new subsidiary for payments processing)
• Translate complex discussions in meetings with CEOs, venture capitalists, and government officials into actionable plans
• Provide frequent concise communication

Benefits

• MacBook and WFH stipend
• 401(k) with company match
• Medical, dental, and vision coverage
• Flexible PTO and working hours