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Executive Assistant

Executive Assistant

Dropout CompaniesNashville, TN, US
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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

  • 4+ years of experience as an Executive Assistant or in a similar high-level support role
  • Prior experience supporting a CEO, founder, or senior executive in a fast-paced environment
  • Exceptional organizational skills and meticulous attention to detail
  • Strong written and verbal communication abilities; able to draft polished correspondence and documents
  • Tech-savvy : proficient in Google Workspace, Slack, and scheduling / project management tools
  • Ability to prioritize, pivot quickly, and execute under tight deadlines
  • High level of professionalism, discretion, and judgment
  • Executor at heart — thrives on action, not just planning

    • Nice to Have

  • Experience in startups, CPG, or creative industries
  • Familiarity with investor communications and board materials
  • Event and logistics coordination experience

    • Benefits

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

  • 10 days Paid Time Off
  • Medical, dental, and vision benefits
  • Technology allowance
  • Quarterly Dropout product benefit (Jams, Bronco, and future brands)
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    Executive Assistant • Nashville, TN, US