EXECUTIVE ASSISTANT TO CEO

We’re looking for a highly adaptable Executive Assistant / Operations Partner to support a fast-moving CEO across multiple businesses. This is not a traditional EA role. It’s hands-on, dynamic, and ideal for someone who enjoys variety, ownership, and learning through action. You’ll be a true operational partner—managing day-to-day execution, communication, and follow-ups while helping bring structure to a constantly evolving environment. Schedule: Monday–Friday, 9:00 AM–5:00 PM Central Time (CT) Location: Remote

What You’ll Do Executive Support & Operations

Own inbox and calendar management across 4+ calendars and multiple businesses Handle client communications, scheduling, and follow-ups (payroll, tax optimization, advisory, coaching) Coordinate logistics for 1:1 and group coaching sessions, workshops, and networking events Book regional travel, manage expenses, and organize itineraries Draft and send emails in the CEO’s voice—clear, natural, and human Prepare agendas, meeting summaries, reports, and internal materials Consolidate calendars and identify efficiency improvements

Client, CRM & Administrative Work

Maintain CRM records, leads, and sales pipeline updates Track client deliverables, deadlines, and next steps Manage sensitive financial, payroll, and compliance-related documentation Build simple presentations, spreadsheets, and internal documentation Handle accurate data entry and basic reporting

Projects & Special Initiatives

Support experimental projects that may change direction quickly Assist with tasks across tech, HR, marketing, and finance as needed Take ownership of operational tasks the CEO shouldn’t be spending time on Provide weekly updates and move initiatives forward independently

What We’re Looking For

3+ years supporting founders, CEOs, or senior executives (less is okay if you’re highly coachable) Experience working in fast-paced, changing environments Strong written and verbal English C1< Comfortable with CRMs, Google Workspace, and/or Microsoft 365 Excellent organization, prioritization, and follow-through Ability to work independently, problem-solve, and make decisions Comfortable handling confidential business, payroll, and financial data Experience with payroll, HR, tax basics, or advisory work is a plus—not required

Personality Fit Matters Here You’ll do well in this role if you are:

Highly adaptable and calm under pressure Coachable and eager to learn through experimentation Comfortable making mistakes and iterating quickly Resilient, confident, and not easily overwhelmed Proactive, honest, and able to push back respectfully Comfortable with ambiguity and unstructured workflows A clear, direct communicator who values transparency

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