Executive Assistant to Chief Executive Officer

Job Title: Executive Assistant Location: Candidates located in the Miami area will only be considered Reports To: Chief Executive Officer (CEO) CheckedUp is a dynamic and growing organization committed to putting people first. Due to the expansion of the firm, the Executive Assistant position has been newly created to support our leadership team. Job Summary We are seeking an energetic, highly organized, proactive, and polished Executive Assistant who embodies professionalism, attention to detail, and a commitment to excellence, aligning with the CEO’s values and success. The Executive Assistant provides high-level administrative support to the CEO, managing schedules, handling correspondence, preparing reports, assisting with meeting preparation, and occasional personal requests. This role requires a proactive, organized individual capable of handling multiple tasks while maintaining confidentiality and professionalism. Light travel may be required for this role. Key Responsibilities: Calendar Management – Accurate and timely management of calendars, including personal appointments, meetings, events, and travel, working with the Chief of Staff to coordinate General Administration - Maintain accuracy of principal’s contact database, schedule appointments and meetings, mail receipt, draft, proof and finalize correspondence; brief principals on matters to be considered. Communication – Participate in daily/weekly meetings to review projects, events, travel and principal calendar. Prepare a weekly pending report for the principal. Act as a liaison with the Chief of Staff on behalf of the CEO. Standard Documentation – Assist with manuals, procedures, and checklists for operations, events, travel, etc., and conduct annual reviews & updates. Maintained schedules on all pertinent information regarding the principal and family members, such as passport renewals, credit card expirations, valuables policy etc. Must be able to read and translate legal documents and adjust as needed. Reading and Interpreting Contracts : Reviewing and interpreting contracts, agreements, and other legal documents to ensure accuracy and compliance. Special Projects – Oversee projects as assigned, membership information, and holiday preparations. Travel Planning & Logistics – Collaborate with the principal on creating unique and custom travel experiences and perform travel-related research as needed. As required, assist with itinerary planning and coordinate meal reservations or delivery at various properties and locations. Event Coordination – Collaborate on planning and managing all incoming event invitations, RSVP’ing on behalf of the CEO, and updating the calendar as needed. Meeting Preparation – Organize and coordinate meetings, including preparing agendas, taking minutes, and ensuring follow-up on action items. Help coordinate arrangements for internal and external meetings (location, catering, technology needs). Other duties as assigned – Support additional tasks as needed to assist the CEO and executive leadership team. Key Competencies Professionalism: Maintain a high level of professionalism in all interactions, reflecting the CEO's values and the company's standards. Exceptional Organizational Skills: Proven ability to manage multiple priorities, with outstanding attention to detail and time management. Communication Skills: Strong verbal and written communication skills, must be able to read and write in English proficiently. Discretion and Confidentiality: Handle all matters carefully, always maintaining confidentiality. Technology Proficiency: High proficiency in Google Workspace, Microsoft Office, and other relevant tools. Problem-Solving: Ability to quickly assess situations and make informed decisions to resolve issues effectively. Proactive Mindset: Self-starter with an entrepreneurial spirit who thrives in a fast-paced environment, takes initiative, and can anticipate the needs of executives. Interpersonal Skills: Ability to work with senior-level executives and manage relationships across departments. Required Qualifications Experience: 4 years of experience in an executive support role, preferably within a corporate environment. Education: Bachelor's degree in business administration, communications, or a related field. Must be able to read and write in English proficiently. Preferred Qualifications Paralegal Experience : Preference will be given to candidates with paralegal experience or legal expertise, particularly in reviewing and interpreting contracts. Benefits Three weeks of paid time off to start 50% company-paid medical insurance plan option Dental and vision insurance Short-term and long-term disability benefits Life insurance 401(k) plan Discount program Tuition Reimbursement CheckedUp Culture We are high growth physician-founded, physician-run patient education company offering tech-enabled patient engagement solutions. As the only physician-founded specialty technology platform, we are trailblazers, embracing technology to develop new products and services that enhance the Point of Care. In our ever-changing world, CheckedUp stays ready to adapt and evolve so we can best serve patients, healthcare providers, our team, and our partners.