GOLDLEAF

Executive & Personal Assistant - Annapolis

Annapolis, MD
Gold Leaf MD is a state-licensed medical cannabis dispensary located in Annapolis, MD. Our knowledgeable staff provides the latest information on strain-specific uses.

Job Description

Executive & Personal Assistant (To President)

Posted: Monday, 10/20/2025

The Executive & Personal Assistant will serve as the right hand to the President of GOLDLEAF, providing comprehensive executive, operational, and personal support across multiple fast-paced business verticals.

This individual will be instrumental in helping streamline the President’s workload — from managing business operations, vendor relations, and creative projects to handling personal scheduling, travel, and organization with the utmost professionalism and confidentiality.

This is not a routine administrative role — it’s a high-level, immersive support position that requires excellent judgment, impeccable organization, and a passion for excellence in both execution and presentation.

Key Responsibilities

Executive Support

  • Manage the President’s complex calendar, meetings, communications, and travel logistics with precision and foresight.
  • Act as the main liaison between the President and internal leadership teams, external partners, investors, and collaborators.
  • Attend and take notes during key meetings, track follow-ups, and ensure timely execution of next steps.
  • Draft, review, and edit correspondence, presentations, proposals, and internal communications on behalf of the President.
  • Anticipate needs and proactively resolve issues before they arise to ensure the President’s time is maximized efficiently.
  • Support high-level business initiatives, vendor negotiations, and strategic planning.

Operational & Project Coordination

  • Track timelines and deliverables across construction, design, retail, and marketing projects, ensuring all teams stay on schedule.
  • Maintain oversight of project management systems, reports, and digital workflows for the President’s active ventures.
  • Interface with contractors, designers, vendors, and consultants to communicate the President’s directives accurately.
  • Assist with document preparation, permitting coordination, and research related to upcoming business initiatives.
  • Organize and maintain confidential business files, brand assets, and visual materials for internal and external use.
  • Coordinate creative and marketing projects, including brand shoots, event planning, and media communications as needed.
  • Conduct and Complete on-boarding of new softwares. 

Personal Assistance

  • Manage personal calendar, appointments, errands, and household coordination.
  • Book and coordinate personal and family travel, accommodations, dining, and entertainment.
  • Oversee property management tasks, including vendor coordination, maintenance scheduling, and deliveries.
  • Assist with wardrobe, event prep, and special personal projects as requested.
  • Maintain complete confidentiality and discretion at all times.
  • Administrative & Organizational Excellence
  • Develop and maintain highly efficient organizational systems for scheduling, documentation, and communication.
  • Prioritize competing demands while maintaining flawless execution under tight deadlines.
  • Monitor incoming requests, screen communications, and ensure the President’s time is focused on strategic priorities.
  • Manage expense reporting, reimbursements, and light bookkeeping or tracking for both business and personal use.
  • Create visually polished reports, agendas, and presentations aligned with GOLDLEAF’s luxury brand aesthetic.
  • Support planning and coordination for internal events, meetings, and company-wide initiatives.
Required skills:

Proven ability to handle confidential information with integrity and discretion.

Exceptional organization, time management, and multitasking skills.

Strong written and verbal communication skills; ability to represent leadership professionally.

Tech-savvy with the ability to adopt and manage new software or AI-driven tools quickly.

High emotional intelligence, strong problem-solving ability, and an anticipatory mindset.

Reliable transportation and a valid driver’s license.

Flexibility to work evenings, weekends, and travel as needed.

Desired skills:

Advanced proficiency in Google Workspace, Microsoft Office Suite, project management software, and cloud organization tools.

2 years of experience supporting a C-level executive, business owner, or creative entrepreneur.

Apply Now

Classet is a skilled trades network. Once you have applied, A Classet recruiter will reach out within 24 hours to learn more about your career search! Classet helps everyone from experienced crafstmen & women to eager apprentices find new opportunities. We are here to help you find the right fit for your career.