Executive Operations to Chief of Staff (12-18 months)

About the role

A fast-growing education and software business founded by Richard Yu is looking for an Executive Operations professional to act as his execution arm and second brain, protecting his time and eliminating operational drag. The role is described as a supercharged executive assistant with a path to Chief of Staff based on performance, and is remote with strong overlap to EST hours.

Key responsibilities

• Own the CEO's calendar: protect deep work blocks, batch meetings and turn chaos into an intentional weekly schedule
• Run the follow-up engine: action items, owners, due dates, reminders and escalations across Slack, WhatsApp and email
• Manage project accountability across the organization using tools such as Trello, Asana or Notion
• Run end-to-end hiring operations for key roles, including pipeline, scheduling, scorecards and Loom reviews
• Oversight of content operations so that YouTube, Instagram and email content ships on time
• Compile monthly P&L requests, KPI dashboards and weekly reports, including payroll analysis and compensation recommendations
• Help execute personal and local projects, such as building a home studio in Puerto Rico
• Use AI in daily workflows and advise other department leaders on its use

Required profile

• Highly organized, self-accountable operator who anticipates needs and makes good decisions without constant approval
• Detail-oriented, able to hold people accountable and write detailed, clear reports
• Discreet and comfortable with high access and confidential information
• Comfortable with unglamorous, repetitive tasks and tough conversations
• Spanish preferred but not required; fluency in Spanish is optional

Required skills

• Project management tools such as Trello, Asana or Notion
• Google Workspace, Slack, Calendly, Zoom and Loom
• Basic AI tool use (e.g., ChatGPT)

The application requires a 5-minute Loom video answering specific questions about the role, a hard problem solved for a CEO, a follow-up approach and dealbreakers, plus a final assignment based on a provided document and videos.