Executive Assistant

Our client is seeking a high-capacity Executive Assistant / Chief of Staff to work directly alongside the Founder of a growing, multi-entity organization with core business lines in pharmacy, mobile primary care, assisted living, and real estate holdings.

This is not a traditional "admin" role. This person will be the Founder's right hand, serving as a force multiplier across multiple companies—organizing his time, driving follow-through on key initiatives, coordinating communication, and creating systems that keep many moving parts running smoothly.

The ideal candidate is:

• Exceptionally organized and proactive
• A strong written and verbal communicator
• Comfortable in a fast-moving, entrepreneurial environment
• Trusted with sensitive information and high-level relationships

Experience in healthcare, pharmacy, or medical practice administration is helpful but not required. What matters most is a proven track record of supporting a busy executive and bringing order to complexity

Key Responsibilities1. Strategic Support & Prioritization

• Act as a thought partner to the Founder to help translate vision and priorities into clear plans, timelines, and action steps.
• Maintain and regularly update the Founder's priority list, ensuring his time aligns with the most important initiatives across entities.
• Anticipate needs and issues before they arise; proactively surface options and recommendations.

2. Calendar, Email, and Communication Management

• Own and manage the Founder's calendar: schedule, prioritize, and protect time based on business priorities.
• Triage the Founder's email and communication (where appropriate), drafting, editing, and sending messages on his behalf.
• Prepare the Founder for meetings with briefing docs, agendas, background materials, and key questions.
• Ensure timely and professional follow-up after meetings with clear action items and next steps.

3. Meeting Preparation, Execution, and Follow-Through

• Plan and coordinate leadership, board, and cross-functional meetings (virtual and onsite).
• Create and distribute agendas, take high-quality notes, and capture decisions and action items.
• Track and follow up on action items with accountable parties, ensuring outcomes are driven to completion.
• Help design and maintain recurring rhythms (weekly leadership meetings, monthly reviews, quarterly planning, etc.).

4. Project & Initiative Coordination

• Support and sometimes lead special projects across the businesses (e.g., new location launches, process rollouts, strategic partnerships).
• Build simple project plans, track progress, and keep stakeholders aligned and informed.
• Coordinate with internal leaders and external partners (attorneys, CPAs, consultants, vendors, etc.) to move initiatives forward.

5. Operational & Systems Support

• Identify opportunities to create systems and structure (templates, checklists, SOPs, recurring processes) that make recurring work more efficient.
• Help improve and maintain organization of digital files, shared drives, and key documents.
• Assist with preparation of presentations, reports, and documents as needed (board packets, lender packets, proposals, summaries).

6. Relationship & Stakeholder Management

• Serve as a professional, warm point of contact for key internal and external stakeholders.
• Help manage and nurture relationships with leaders, partners, vendors, and community contacts.
• Represent the Founder and the organization's values in all interactions.

7. Personal & Logistics Support (as needed)

• Handle select personal logistics that directly affect the Founder's ability to focus (e.g., travel arrangements, key appointments, occasional family or household coordination).
• Ensure smooth travel experiences: bookings, itineraries, confirmations, and post-travel follow-up.

First-Year Success Looks Like…

Within the first 12 months, success in this role will look like:

• The Founder spends 70–80% of his time on high-value activities (strategy, key relationships, major decisions), not logistics or firefighting.
• The Founder's calendar and inbox are structured, intentional, and under control.
• Key meetings are consistently well-prepared and well-documented, with clear decisions and follow-up.
• Important initiatives across multiple entities move forward predictably because of your coordination and follow-through.
• Recurring processes (meetings, travel, communication rhythms, reporting) are systematized and documented, not reinvented each time.
• The Founder and leadership team experience a noticeable reduction in dropped balls and last-minute crises that could have been anticipated.

Qualifications

Required:

• 5+ years in a high-level Executive Assistant, Chief of Staff, Operations, or similar role supporting a senior executive, founder, or business owner.
• Demonstrated ability to work in a fast-paced, multi-entity, entrepreneurial environment.
• Exceptional organization, attention to detail, and follow-through.
• Strong written and verbal communication skills; ability to draft clear, concise, professional emails and documents.
• High level of discretion and integrity in handling confidential and sensitive information.
• Strong tech literacy: calendars, email, spreadsheets, shared drives, basic project/task tools, and common business software.
• Proven ability to manage multiple priorities, deadlines, and stakeholders simultaneously.

Preferred / Nice-to-Have:

• Experience in healthcare, pharmacy, medical practice, senior living, or other regulated industries.
• Experience supporting an executive who leads multiple businesses or entities.
• Experience building basic systems/SOPs and improving operational workflows.
• Bachelor's degree in business, communications, healthcare administration, or a related field (or equivalent experience).

Personal Characteristics & Fit

We're looking for someone who is:

• Service-minded but not a pushover – humble enough to serve, confident enough to protect the Founder's time and priorities.
• Proactive and anticipatory – sees around corners, doesn't wait to be told every step.
• Calm under pressure – steady, composed, and solutions-oriented when things are busy or messy.
• Systems thinker – naturally turns chaos into checklists, templates, and repeatable processes.
• Relationally savvy – can communicate effectively with everyone from front-line staff to board members and external partners.
• Values-driven – aligned with a mission-oriented, ethical, and community-focused organization.
• Loyal and trustworthy – someone the Founder can rely on deeply and build a long-term working relationship with.

Who you'll be supporting:

• Our company is founded by a Christian business owner who values integrity, service, and community impact.

Work Environment & Schedule

• Onsite role in the Brownsville and Chalybeate, Kentucky area; in-person presence with the Founder is expected most days.
• Standard business hours with reasonable flexibility; occasional early/late hours based on meetings, travel, or urgent priorities.
• Some local or regional travel may be required for meetings, site visits, or events.

Compensation & Benefits

• Competitive salary commensurate with experience and role scope.
• Benefits package (health, retirement, PTO, etc.) to be discussed and tailored based on candidate and internal structure.

Pay: $60, $80,000.00 per year

Benefits:

• 401(k)
• Health insurance
• Paid time off

Work Location: In person