Executive Assistant | Remote | Orlando

Founder Support (EA++) / Executive Assistant

**Employment Type:** Full-Time

**Location:** Remote

**Availability:** Early weekday coverage with occasional evening/off-hours responsiveness for rare, time-sensitive matters

**Apply here:** https://operationsarmy.com/application

About The Role We are looking for a **high-performing startup operator who happens to own Executive Assistant responsibilities** to support the Founder of a fast-moving investment firm.

This is an **EA++ / Founder Support role** , not a traditional administrative EA position. The ideal candidate has worked directly with a founder or entrepreneur in a startup environment and is comfortable operating in a fast-moving, ambiguous setting where priorities can change quickly and wearing multiple hats is part of the job.

You will act as a trusted execution partner to the Founder—anticipating needs, protecting his time, staying ahead of priorities, and figuring things out independently without requiring constant direction.

As trust and context build, the role may expand beyond executive support into **operations, project coordination, process improvement, and broader business support** .

What You’ll Do

Founder & Executive Support

• Manage and prioritize the Founder’s inbox, including filtering, drafting, follow-ups, and identifying what requires his attention
• Own complex calendar management and proactively protect the Founder’s time
• Coordinate meetings across multiple time zones
• Stay ahead of upcoming meetings, deadlines, commitments, and follow-ups
• Prepare the Founder for meetings by ensuring relevant information, materials, and context are organized
• Manage travel, accommodations, reservations, and related logistics
• Provide light personal administrative support as needed
• Seamlessly coordinate personal and professional commitments
• Serve as a polished and professional representative of the Founder when communicating with external stakeholders

Communication & Stakeholder Management

• Draft clear, polished, and professional emails and correspondence
• Communicate with investors, partners, advisors, vendors, and other external stakeholders
• Handle sensitive and confidential information with discretion
• Understand when to act independently and when to escalate
• Maintain a high standard of professionalism across all written and verbal communication
• Follow through on commitments and ensure important conversations and tasks do not fall through the cracks

Startup Operations & Project Support

As you gain trust and context, your responsibilities may expand to include:

• Supporting operational processes and documentation
• Coordinating with internal team members and external partners
• Managing follow-ups and keeping projects moving
• Supporting events, meetings, and business initiatives
• Assisting with PR coordination and internal workflows
• Identifying opportunities to improve processes and make the Founder’s work more efficient
• Supporting the internal operations lead
• Taking ownership of projects and driving them to completion

AI & Technology

• Use AI tools and modern cloud-based software to work faster and more effectively
• Leverage technology to research, organize information, automate repetitive tasks, and solve problems
• Quickly learn new tools and systems as the business evolves
• Be comfortable operating in a highly digital, technology-driven environment

What We’re Looking For

Must-Haves

• Direct experience supporting a founder, entrepreneur, startup leader, or senior executive
• Strong startup experience in a fast-moving environment
• Excellent written and spoken English with highly polished communication skills
• Highly self-directed and proactive—you do not need constant hand-holding or step-by-step instructions
• Strong business judgment, resourcefulness, and problem-solving ability
• Comfortable with ambiguity, shifting priorities, and wearing multiple hats
• Able to anticipate needs rather than simply react to requests
• Strong organizational skills and exceptional attention to detail
• Comfortable receiving direct feedback, pivoting quickly, and continuing to execute
• Calm, composed, and reliable under pressure
• Comfortable with AI tools, cloud-based software, and modern technology
• Able to work early and stay ahead of the Founder, whose workday typically begins around 8:30 AM …