Executive Assistant

Job Description

Job Description

As Executive Assistant to the CEO , you’ll be the right hand to Dropout’s founder and leader. This role is about more than managing schedules — you’ll help the CEO stay focused on the highest priorities by managing time, communication, and follow-through with speed and precision.

You’ll handle sensitive information with discretion, coordinate across teams and stakeholders, and take ownership of operational details that keep the CEO and the company moving forward. If you thrive on anticipating needs, creating order out of chaos, and executing with excellence, this role is for you.

If you thrive in a fast-paced environment, anticipate needs before they’re voiced, and balance meticulous organization with creativity, you’ll excel here.

What You’ll Do

• Provide direct, high-level administrative support to the CEO
• Manage calendar, schedule meetings, and coordinate logistics with internal and external stakeholders
• Prepare the CEO for meetings with agendas, briefs, research, and follow-up notes
• Monitor and prioritize the CEO’s inbox and communications, drafting responses and flagging critical items
• Handle travel arrangements, itineraries, and logistics for both business and investor-facing needs
• Maintain absolute confidentiality with sensitive company and personal information
• Track and follow up on action items from meetings to ensure deadlines are met
• Support in preparing investor updates, presentations, and internal memos
• Anticipate the CEO’s needs, proactively solving problems and removing roadblocks
• Serve as a trusted partner who keeps the CEO organized, efficient, and focused on high-impact work

Requirements

Must Have

Nice to Have

Benefits

Dropout offers a comprehensive benefits package for full-time employees, including :