Assistant Remote Data Protection Jobs in Winter Springs, FL

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 DoFounder & 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 ForMust-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 EST
• Comfortable with occasional evening or off-hours responsiveness for rare, time-sensitive matters

Strong Plus

• Chief of Staff experience
• Startup operations or business operations experience
• Experience working closely with entrepreneurs or high-growth companies
• Experience managing projects or cross-functional initiatives
• Experience improving processes or building systems from the ground up
• Experience coordinating with external vendors, advisors, partners, or other stakeholders
• Interest in growing into broader operations and project management responsibilities

Finance, private equity, venture capital, or investment experience is not required. We are primarily looking for someone with strong startup experience, excellent judgment, and the ability to operate as a true execution partner to a Founder.

Working Style

The Founder moves quickly, has a heavy meeting schedule, and may generate new work and messages throughout the evening. This role requires someone who can get online early, quickly catch up on what happened overnight, anticipate what is coming next, and stay ahead of the Founder throughout the day.

You should be comfortable working with someone who is direct, moves quickly, and expects a high level of ownership. You should be able to take feedback without being overly sensitive, adjust quickly, and keep moving.

Most importantly, you should be the type of person who thinks:

I'll figure it out.

rather than waiting for someone to tell you exactly what to do.

What Success Looks Like

Success means becoming a trusted extension of the Founder.

You anticipate needs before they become urgent, protect the Founder's time, keep communication moving, ensure commitments are followed through, and handle important details without constant oversight.

Over time, you become someone the Founder can rely on to take a problem, figure out the best path forward, and execute.

This is an opportunity for a high-performing startup operator who wants to grow beyond traditional EA responsibilities and become a key part of a scaling investment firm.

If you're proactive, resourceful, tech-savvy, highly organized, and thrive in fast-moving startup environments, we'd love to hear from you.

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