Executive & Personal Assistant (To President) - Now Hiring

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.

Salary

$65000 - $90000 USD per year

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.

About GOLDLEAF

GOLDLEAF is a luxury cannabis dispensary and lifestyle brand headquartered in Annapolis, Maryland, recognized for redefining the standard of service, sophistication, and design in cannabis retail. Known for its high-volume operations and five-star hospitality, GOLDLEAF delivers an elevated experience that blends innovation, culture, and modern luxury.

This position will work directly under the President of GOLDLEAF, providing both executive and personal support across the company's daily operations and an array of related ventures. Beyond GOLDLEAF, the President oversees multiple projects spanning hospitality, design, real estate development, marketing, and brand collaborations — including large-scale event production and new concept development.

The company culture is dynamic, fast-paced, and excellence-driven, combining the precision of corporate execution with the creativity of luxury brand development. This role is ideal for someone who thrives in high-performance environments, enjoys variety, and takes pride in being the organizational force behind an entrepreneurial executive leading several thriving businesses.

Benefits

Comprehensive Medical, Dental, and Vision Insurance 

Voluntary Short-Term Disability Insurance 

Voluntary Accident & Critical Illness Insurance

Voluntary Life Insurance 

Health Savings Account (HSA) 

ZayZoon (Early Access to Earned Wages) 

Employee recognition program 

SparkPlug Vendor recognition incentives

Employee & Industry Discounts

Equal opportunity employer

GOLDLEAF and Affiliates are an Equal Opportunity Employer.