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).