Executive Assistant / Strategic Operations Lead (Chief of Staff Track)

Job Title: Executive Assistant / Strategic Operations Lead (Chief of Staff Track) Contract Type: Full-time, Remote Salary Range: $2,000–$2,500/month (salary based on assessment) Working Hours: Monday to Friday, 9 AM - 5 PM ET Location: LATAM About the Role We are seeking a proactive, empathetic, and aligned Strategic partner to support a leadership team driving two core businesses.This is not a traditional administrative role. You will function as a high-impact partner, protecting the leaders’ time and energy while driving operational rhythm. The role starts as an Executive Assistant with a clear, 12-month advancement path to mature into a Chief of Staff position at the business scale. Key Responsibilities Calendar & Inbox Management: Own and safeguard executive calendars; optimize meetings for coaching sessions, strategic planning, and family commitments. Streamline communications, prioritizing urgent items and drafting responses with high discretion. Strategic Operations & Project Ownership: Identify activities tied to revenue and growth. Take initiative on special projects (e.g., AI product development) from conception to completion independently. Cross-Functional Coordination: Serve as the central communication hub and liaison between multiple business units, external partners, clients, and vendors. Process Improvement & AI Enablement: Build systems and lightweight operating systems to streamline recurring processes. Be AI-forward by identifying opportunities to automate repetitive tasks and leveraging new tools. Performance Management: Collaborate with leadership to define North Star KPIs; monitor progress, flag blockers, and ensure deliverables are completed with ownership and quality. Logistics & Travel: Manage all travel arrangements, meeting coordination, and logistics for internal and external engagements. Stakeholder & Family Alignment: Coordinate professional and family calendars to minimize conflicts, protecting personal energy and downtime. Qualifications Experience & Skills 3+ years of executive assistant, operations, or Chief of Staff-capable experience. Fluent English (written and verbal) with exceptional interpersonal skills. Proven Autonomy: Ability to work independently with minimal supervision and handle high-value, time-sensitive situations with composure. Technical Proficiency: Tech-savvy with an aptitude for learning new tools and comfort with AI-enabled workflows and project management methodologies. Strategic Judgment: Strong organizational skills and the ability to navigate ambiguity and "roll" with project timelines. Attitude & Fit Ownership Mindset: High emotional intelligence, empathy, and the proactive ability to complete tasks without constant oversight. Growth Orientation: Interest in scaling into a leadership role and supporting a visionary leader building multiple companies. Values-Driven: Aligned with a mission to help clients grow; a collaborative, non-siloed thinker. Preferred Qualifications Time zone alignment with Central or Latin America. Experience supporting founders or small business leadership. Familiarity with online coaching platforms, digital product launches, or professional services. Background in operations for service-based businesses (e.g., construction/contracting).