Executive Assistant to Chief Executive Officer

Compass Health Systems, PA; Cherry Hills Village (CO); On-site; USD 75,000 - 110,000; Full time

Job summary

Compass Health Systems, PA seeks a seasoned Executive and Personal Assistant to support the CEO and family in a demanding, long-term role. The ideal candidate will manage complex calendars, travel, budgeting, and confidential communications with discretion and professionalism.

This on-site position in Cherry Hills Village requires 5+ years of high-level PA experience, healthcare familiarity being a plus. The role emphasizes loyalty, stability, and a long-term career with annual performance

Qualifications

• 5+ years of senior-level Executive/Personal Assistant experience; healthcare experience a plus.
• Proven track record supporting CEOs or high-net-worth families.
• Excellent written and verbal communication; strong attention to detail.
• Proficient with Microsoft Office; Excel and PowerPoint.
• Bilingual English/Spanish preferred.

Responsibilities

• Provide comprehensive admin support to the CEO, including calendars and meeting scheduling.
• Act as gatekeeper to the CEO, prioritizing urgent calls and emails.
• Oversee billing and expenses and handle basic financial administration.
• Prepare documents, reports, and presentations; proficient with Excel.
• Coordinate travel arrangements and logistics for business and personal needs.
• Prep the CEO for meetings with briefing materials.
• Maintain discretion in all professional and personal matters.
• Coordinate family schedules and events; manage vendors and services.
• Support special projects and initiatives for business growth.

Skills

Executive support

Calendar management

Travel arrangements

Budget & expenses

Bilingual English/Spanish

Tools

Microsoft Office Suite

Excel

PowerPoint

Job description

We are seeking a seasoned, career-minded Executive and Personal Assistant to support a busy CEO and his family. This is not an entry-level role- it requires a highly experienced professional who values discretion, loyalty and long-term stability. Salary will match that and may be higher than noted for very qualified candidates.

The right candidate will become a trusted partner in both professional and personal matters, managing executive responsibilities, household operations, and family logistics. We are looking for someone who wants to build a long-term career and remain with us for many years. This dynamic position requires exceptional organizational skills and the ability to manage complex tasks efficiently. Will serve as the primary point of contact for the CEO, coordinate business and personal schedules, and ensure the CEO’s time is managed effectively.

Key Responsibilities

Executive Support

• Provide comprehensive administrative support to the CEO, including managing complex professional and personal calendars, scheduling meetings, and ensuring timely follow-up.
• Act as the gatekeeper to the CEO, managing incoming communications (phone calls, emails, etc.) and prioritizing urgent requests.
• Oversee billing, expenses and financial administration.
• Prepare documents, reports, presentations, and correspondence for meetings, and external communications. Must be well versed with Excel.
• Coordinate travel arrangements (flights, accommodations, transportation) and ensure all logistics are handled seamlessly.
• Prepare the CEO for important meetings, providing briefing materials, and ensuring all required documents are ready.
• Serve as a trusted liaison, handling all matters with discretion.

Personal Support

• Coordinate family schedules, medical and personal appointments, and assist with special events.
• Oversee household vendors, contractors and service providers.
• Manage family vacations, school schedules and kid after school-logistics.
• Assist with planning and managing personal events, celebrations, and special requests.

Project Management & Special Initiatives

• Support the CEO in managing key projects and initiatives.
• Track deadlines, milestones, and deliverables, ensuring projects remain on schedule.
• Assist in research and special tasks as required for business growth or personal endeavors.

Qualifications

• 5+ years of experience as a senior-level Executive and/or Personal Assistant, with health care experience a plus.
• Proven success supporting CEO's, executives, or high-net-worth families.
• Strong ability to manage time effectively, prioritize tasks, and maintain a high level of attention to detail.
• Excellent communication skills, both written and verbal. Preferable if bilingual (English/Spanish).
• Proficiency in Microsoft Office Suite (Outlook, Word, Excel, PowerPoint) and other business tools.
• A proactive and flexible approach to work with a demonstrated ability to adapt to changing priorities.
• History of long-term, stable employment with excellent references. Must provide at least three excellent references (two professional, one personal).

Conduct

• Must be polished, respectful, and professional in demeanor and appearance.
• Must be drug-free and able to pass a drug screening.
• No personal phone use or social media engagement during work hours.
• Healthy personal boundaries and appropriate, professional conduct at all times.
• Comfortable working closely with a family while maintaining discretion and privacy.
• Must bass a comprehensive background check with no criminal record.
• Must maintain a strong credit history.
• Must sign and uphold a strict NDA (Non-Disclosure Agreement).

Why Join Us

This is a rare opportunity for a career professional to join a respected CEO and his family in a long-term, stable role. We are seeking someone who thrives on responsibility, values discretion and takes prime in making complex lives run seamlessly. For the right candidate, this position offers more than a job- it offers a meaningful and lasting career.