About the Client:
The Executive is a business owner, investor, and operator who manages a diversified portfolio of businesses across behavioral healthcare, real estate, and service sectors. His primary operating role is as President & Co-CEO of a leading addiction treatment center, where he spends approximately 60% of his time. The remaining 40% is spent overseeing other investments, evaluating opportunities, directing leadership teams, engaging partners, and supporting multiple businesses at varying levels of involvement.
He operates at both strategic and high-touch levels combining mission-driven leadership, financial and operational oversight, and long-term vision-building. He requires a high-achieving, strategic Executive Assistant, someone who creates leverage, reduces friction and decision fatigue, supports communication, and builds durable workflows and systems that help him operate at his highest value.
About the Role:
This is not a traditional administrative support role. It is a strategic operations and personal leverage role, requiring judgment, anticipation, communication expertise, and emotional intelligence. The Executive Assistant will oversee complex scheduling and inbox management, conduct research, prepare deliverables and financial summaries, coordinate travel, manage meetings, screen calls, and serve as a first-line representative across stakeholders — including investors, partners, leadership team members, guests, and vendors. The ideal candidate is deeply organized, proactive, and resourceful — someone who does not just complete tasks, but actively improves systems, solves problems, makes recommendations, and protects the Executive’s time, focus, and energy.
Key Responsibilities
Calendar & Priority Management
- Fully manage the Executive’s calendar, coordinating across time zones, investments, leadership teams, and personal commitments.
- Protect focus time and optimize scheduling based on energy, priority, strategic value, and long-term planning.
- Anticipate conflicts and proactively reschedule or consolidate meetings.
- Set agendas, prepare briefing packets, and coordinate meeting follow-up.
Email & Communications Management
- Build intelligent email systems that sort and triage incoming messages to appropriate folders, levels of priority, or response pathways.
- Draft, refine, and respond to messages on behalf of the Executive using context, tone, and sound judgment.
- Function as a first-line filter, screening inbound requests, managing follow-ups, and when appropriate, conducting first-touch calls with partners, vendors, or stakeholders.
- Maintain clear records of communication threads, decisions, and commitments.
Research & Meeting Preparation
- Conduct focused research on people, companies, opportunities, and market context ahead of meetings or calls, gathering key facts, relational insight, and relevant financial or strategic background.
- Prepare clear, executive-ready briefings summarizing who we’re meeting, why it matters, what they want, and what we should know, including talking points, risks, and recommended positioning.
- Anticipate information needs before meetings and follow up after by capturing key decisions, commitments, next steps, and assigned actions.
- Bring judgment, not just research by filtering what is relevant, connecting dots, and highlighting what requires attention or decision-making.
Deliverable Creation & Presentation Development
- Produce high-quality, professional deliverables using PowerPoint, Word, Excel, or other tools including board presentations, investor updates, loan communications, and strategic proposals.
- Demonstrate financial literacy, including working knowledge of balance sheets, income statements, and cash flow reports.
- Assist with financial modeling, recap summaries, deal structures, and performance tracking across ventures.
Project, Process & Systems Setup
- Build foundational systems for managing follow-through, task tracking, email organization, document control, scheduling, and accountability.
- Develop sustainable workflows for both recurring and ad hoc tasks.
- Use intuition and judgment to refine how systems evolve as the business grows.
Travel & Remote Coordination
- Plan and coordinate professional and personal travel, including itineraries, lodging, meetings, scheduling, and dining arrangements.
- Support the Executive while traveling coordinating with leadership teams, managing priorities, and maintaining communication continuity.
Stakeholder & Customer Service Coordination
- Serve as a professional liaison with investors, leadership teams, bankers, vendors, and project partners.
- Occasionally interface with guests at short-term rental properties to resolve minor issues, including after-hours when necessary.
- Represent the Executive on Zoom calls, vendor introductions, or investor communications, when appropriate.
Desired Candidate Qualities
- Highly proactive: Takes initiative without waiting for direction
- Quick-processing: Able to identify key data points, evaluate issues, and take action
- Light, personable, and easy to work with while operating with professionalism and poise
- Emotionally intelligent and highly aware of audience and able to adapt tone
- Low ego, high competence, and responsible / trustworthy
Soft Skills & Personality (CRITICAL)
- Years of supporting a CEO, entrepreneur or principal in a fast-moving environment
- Proven track record of managing sensitive and confidential financial, operational, and personal information with references to support
- Experience establishing systems (email, process automation, project tracking) from scratch
- Clear financial literacy, capable of interpreting financial reports and performance metrics
- Comfortable managing multiple long-term / short-term projects at once with competing deadlines
- Confident presenting, drafting communication, and representing the Executive in Zoom meetings, calls, and written correspondence
- Availability for occasional after-hours responsiveness, travel coordination, or urgent communication needs
- Critical Thinking: Must be a critical thinker who can bring their own skills and perspective to the business.
- Adaptability & Temperament: Must be Adaptable, Easygoing, and Not Uptight, maintaining composure and a collaborative spirit in a high-pressure environment.
- Autonomy & Proactivity: Must possess the drive and ability to perform tasks with minimal supervision, taking initiative to save the Owner time.
- Communication: Must have excellent English fluency and communication skills.
- Commitment: Seeking a long-term partnership who views the role as an opportunity to grow with the company.
Technical & Execution Skills
- Analytical Skills: Strong comfort level with reviewing and summarizing critical KPIs and metrics.
- Software Familiarity: Experience with or ability to quickly learn short-term rental management software (Host Away) and internal business systems.
- Advanced proficiency in Microsoft 365 (Outlook, Excel, OneNote, PowerPoint, Teams, SharePoint, Planner, and OneDrive)
- Remote Readiness: Must have a reliable remote setup, including a backup power supply and good fiber optic internet connection.
