FreedUp is seeking a highly proactive and detail-oriented Executive Assistant (EA) to support the Founder & CEO of a fast-growing, systems-driven organization. This role is ideal for someone who thrives on structure, accountability, and clarity — and who can act as a true extension of the executive by turning complexity into calm, repeatable execution.

We are a high-performance team built around ownership, responsiveness, and continuous improvement. The Executive Assistant will play a critical role in stabilizing and scaling the CEO’s day-to-day operations, acting as his “functioning memory,” improving written communication quality, and ensuring nothing slips through the cracks.

This role goes beyond traditional administrative support. You will own core operational processes, manage communication systems, coordinate recruiting pipelines, and help implement tools and SOPs that reduce cognitive load for the CEO and leadership team.

This is a full-time, remote position requiring exceptional written communication, strong follow-through, comfort with sensitive information, and the ability to proactively manage both professional and limited personal tasks.

Location: Fully Remote

Job Type: Full-Time

Salary: $800 - $1,600 per month (based on experience)

Requirements

3+ years of experience supporting senior executives as an EA, Operations Coordinator, or similar role.
Exceptional written communication skills — must be a stronger writer than the executive.
Highly responsive, proactive, and detail-oriented.
Comfortable acting as a “memory system” for a fast-moving CEO.
Strong organizational instincts and follow-through.
Able to handle confidential and sensitive information responsibly.
Tech-comfortable and adaptable to evolving systems and tools.
Thrives in high-accountability, high-clarity environments.
Technical Requirements: Reliable high-speed internet and a modern home office setup.

Key Responsibilities

Email & Communication Management

Manage and organize three inboxes (personal, work, shared investor inbox).
Implement follow-up systems to prevent missed replies and recurring “email bankruptcy.”
Draft routine and logistical emails for CEO review, reducing workload while preserving control.
Proofread and edit all outgoing communications to improve clarity and accuracy.
Prioritize investor, recruiting, and vendor communications.

Meeting & Calendar Coordination

Coordinate weekly and bi-weekly internal meetings (all-hands, leadership, C-suite).
Prepare and maintain agendas, collect participant notes, and track follow-ups.
Attend meetings as needed to capture action items and enforce accountability.
Help implement calendar rules to protect focus time and avoid unnecessary meetings.
Conduct a daily end-of-day check-in (5:00–5:30 PM) to review upcoming meetings and open loops

Process Optimization & SOPs:

Document, organize, and improve company workflows and Standard Operating Procedures (SOPs) in Notion.
Support the creation of internal systems for accountability, task tracking, and delegation across Trotta’s operations and team structure.

Task Delegation & Tracking

Manage delegated tasks and ensure timely follow-up using Linear.
Close feedback loops and prevent lost action items.
Support the rollout of structured task and delegation systems across the organization.
Assist with daily reminders, priorities, and workload balancing.

Operational & Personal Support

Manage operational tasks such as office lunch orders, events, offsites, and travel coordination.
Assist with personal scheduling, including medical appointments on recurring cycles.
Handle sensitive information in compliance with HIPAA and related agreements.
Support monthly outreach to patients with high NPS scores and assist with review collection workflows.
Research and implement tools for reviews, CRM, and process optimization.

Systems & Tools

Communicate daily via Slack with structured updates.
Track tasks and delegation in Linear.
Help expand Notion usage for SOPs, documentation, and a lightweight CRM.

Benefits

International experience
Opportunity to work remotely from anywhere
Supportive and collaborative team environment
Learning and development opportunities
Potential Performance Bonuses
PTO
HMO after 3 months

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