Executive Assistant to the CEO

• 2.9 Tampa, FL 33610 Remote $90,000 a year - Full-time Job Summary Sr Executive Assistant to the CEO Are you the kind of Executive Assistant who makes a CEO dramatically more effective? We're looking for an exceptional, seasoned Senior Executive Assistant to the CEO of a small, growth-oriented entrepreneurial venture with businesses in real estate investment and wealth education. This is not a traditional administrative assistant position. We're seeking an accomplished professional who has spent years working alongside successful entrepreneurs and executives — someone who knows how to protect a CEO's time, drive accountability, manage competing priorities, and turn ideas into completed results. We don't want to train you to become a great Executive Assistant. We're looking for someone who already is one. Our ideal candidate has 10+ years of progressively responsible experience supporting successful CEOs, founders, or business owners and can bring proven executive-support systems and best practices to our organization. You should be confident enough to challenge the CEO constructively, assertive enough to hold senior staff accountable, and experienced enough to know what needs to be done without waiting for instructions. The Opportunity Our founder is an experienced entrepreneur, real estate investor, author, and innovator building two complementary businesses:  A growing portfolio of small apartment communities, primarily in Oklahoma City.  A wealth education and investment platform that helps everyday people build lasting wealth through small apartment investing. We're a relatively small entrepreneurial organization with ambitious growth plans, multiple initiatives, and a founder whose greatest contributions come from creating opportunities, building relationships, making strategic decisions, and developing innovative business systems. Your mission is to make the CEO dramatically more effective by taking ownership of the details, communications, follow-through, and projects that otherwise compete for his attention. You will become his trusted professional and personal right hand. What You'll Own 1. Protect the CEO's Time and Attention  Serve as the primary gatekeeper for operational communications, requests, and interruptions.  Independently determine what requires the CEO's attention and what should be handled elsewhere.  Organize incoming issues into concise, actionable decision briefs.  Proactively manage priorities, scheduling, travel, and executive commitments.  Establish and improve systems that allow the CEO to focus on his highest-value activities. 2. Drive Accountability and Execution This is a particularly important part of the position.  Track important commitments made by managers, employees, and outside partners.  Follow up assertively to ensure deadlines and deliverables are met.  Challenge vague answers, missed deadlines, and incomplete work.  Identify execution problems before they become expensive emergencies.  Verify that commitments have actually been fulfilled — not merely discussed.  Escalate unresolved performance issues appropriately. You must be comfortable holding people accountable, including senior managers, without requiring the CEO to intervene. 3. Manage Special Projects from Concept to Completion Our CEO generates opportunities and initiatives rapidly. You'll help turn selected ideas into completed projects.  Translate broad objectives into actionable plans.  Identify and coordinate the people and resources needed.  Establish milestones, deadlines, and accountability.  Monitor progress, remove coordination obstacles, and report exceptions.  Deliver completed outcomes without requiring constant supervision. You'll coordinate execution through others rather than personally performing every task. Who We're Looking For Required qualifications:  Extensive experience directly supporting a CEO, founder, or senior business executive, ideally 10+ years.  Demonstrated success supporting an entrepreneurial leader in a fast-moving business.  A proven ability to drive accountability and follow-through across multiple people and projects.  Exceptional judgment, organizational discipline, written communication, and discretion.  Confidence in confronting underperformance professionally and constructively.  Strong project coordination and problem-solving capabilities.  High proficiency with modern business technology, productivity software, and AI tools.  Ability to work independently, establish priorities, and take initiative without detailed instructions.  Willingness to travel periodically to business events and properties.

Especially attractive backgrounds:

 Senior Executive Assistant to a founder or owner of a privately held business.  Executive Business Partner to a successful entrepreneur.  Senior Executive Assistant with substantial project management and cross-functional accountability experience.  Long-term right hand to a CEO who successfully scaled or managed multiple businesses. Experience in real estate is helpful but not required. The Person Who Will Thrive Here You're naturally proactive, highly resourceful, and exceptionally dependable. You enjoy creating order from complexity. You don't need recognition for every accomplishment, but you take personal satisfaction in seeing things completed correctly. You're diplomatic but not timid. You can politely tell a senior manager that an excuse is unacceptable and obtain a concrete recovery commitment. You know when to make a decision, when to delegate, and when to escalate. You're comfortable working with a creative, fast-moving entrepreneur who generates ideas and opportunities faster than most organizations can execute them.

And perhaps most importantly:

You know how to manage a CEO's attention and effectiveness better than the CEO knows. You bring proven methods, not just a willingness to follow instructions. This Position Is NOT for You If...  Your experience is primarily calendar management, scheduling, travel booking, and general administrative support.  You need detailed instructions before taking action.  You're uncomfortable challenging senior employees or confronting missed commitments.  You consider sending reminders equivalent to ensuring results.  You prefer a predictable corporate environment with narrowly defined responsibilities.  You are looking for an entry point into executive support rather than bringing substantial prior mastery. We're looking for a seasoned executive partner, not a glorified administrative assistant.

Compensation Base Salary:

$90,000 annually

Performance Bonuses:

Additional compensation based on demonstrated results, including execution reliability, successful special projects, and measurable improvements in CEO effectiveness. The CEO maintains residences in Florida and Houston and travels between locations regularly. The position offers flexibility in day-to-day work arrangements, with availability for in-person collaboration and periodic business travel. Travel may include Oklahoma City apartment properties and Houston-based educational events. This is a full-time, long-term opportunity with the potential to become an indispensable part of a growing entrepreneurial organization. How to Apply In addition to your resume, please accompany it with an explanation of why you consider yourself the ideal candidate. We will give particular consideration to candidates who provide specific, credible examples rather than general statements about being organized, proactive, or detail-oriented.

Pay:

$90,000.00 per year Application Question(s): Why do you consider yourself the ideal candidate?

Work Location:

Remote