Virtual Assistant

Virtual Assistant (Remote)

Company: Checkmate Holding Group

Position Type: Independent Contractor (1099)

Hours: Approximately 40 Hours Per Week

Compensation: $500-$1500 per week

Location: Remote

About Checkmate Holding Group

Checkmate Holding Group is a diversified holding company managing multiple businesses across a variety of industries, including hospitality, automotive, high-end residential services, home building, construction, marketing, and business development.

We are seeking a highly organized, proactive, and detail-oriented Virtual Assistant to support executive leadership and operations across our portfolio of companies. This position requires strong administrative, communication, marketing, and technology skills, along with the ability to work independently in a fast-paced environment.

Position Overview

The Virtual Assistant will provide executive, administrative, operational, and marketing support across multiple companies under the Checkmate Holding Group umbrella. The ideal candidate is highly organized, resourceful, tech-savvy, and comfortable managing a wide range of responsibilities while supporting ongoing growth initiatives.

This role supports businesses spanning hospitality, automotive, high-end residential services, and home building operations.

Core Responsibilities

Executive & Personal Assistance

• Manage calendars, appointments, and scheduling.
• Coordinate meetings, calls, and vendor appointments.
• Handle various personal assistant tasks as assigned.
• Monitor priorities and ensure important deadlines are met.
• Maintain daily task lists and follow-up schedules.

Meeting Management

• Attend virtual meetings as needed.
• Take detailed meeting notes and meeting minutes.
• Document action items, responsibilities, and deadlines.
• Prepare end-of-day summaries outlining completed tasks and priorities for the following business day.

Administrative Support

• Maintain and update digital calendars daily.
• Coordinate communications with vendors, clients, and business partners.
• Assist with document organization and record keeping.
• Prepare timesheets and track work hours when required.
• Assist with invoice preparation and vendor payment coordination.

Operations & Vendor Coordination

• Support operational tasks across multiple businesses.
• Assist with vendor communication and delegation.
• Track project progress and follow up on outstanding items.
• Ensure tasks are completed efficiently and on schedule.

Legal & Business Administration Support

• Assist with administrative aspects of business formations and entity setup.
• Coordinate business registrations, compliance filings, and corporate documentation.
• Organize legal, licensing, and operational records.
• Conduct administrative follow-up related to company setup and compliance requirements.

Note: This role does not provide legal advice or legal representation.

Marketing, AI & Technology Support Artificial Intelligence & Automation

• Utilize AI tools such as ChatGPT and other productivity platforms to improve efficiency.
• Assist in developing AI-driven workflows and automations.
• Research emerging AI tools and recommend solutions to improve operations.
• Support implementation of AI systems across multiple companies.

Social Media Management

• Assist with content scheduling and publishing.
• Monitor social media platforms and engagement.
• Help coordinate marketing campaigns.
• Support brand consistency across all companies.
• Assist with content creation, captions, and basic graphic coordination.

Website Management

• Review websites for errors, broken links, missing content, and optimization opportunities.
• Assist with website updates and content management.
• Coordinate with developers and marketing teams regarding website improvements.
• Help ensure all company websites remain professional, accurate, and current.

Marketing Support

• Assist with marketing research and competitor analysis.
• Coordinate digital marketing initiatives.
• Support Google Business Profile optimization efforts.
• Assist with lead generation and CRM management.
• Help organize marketing assets and campaign materials.

Additional Responsibilities Research

• Conduct online research on business opportunities, vendors, regulations, competitors, and assigned topics.
• Compile findings into organized reports and summaries.

Special Projects

• Assist with strategic business initiatives.
• Support operational, marketing, and growth-focused projects.
• Manage assigned projects from inception through completion.

Problem Solving

• Proactively identify operational challenges and inefficiencies.
• Recommend solutions and implement approved action plans.
• Help improve workflows, organization, and communication across all businesses.

Qualifications Required

• Excellent written and verbal English communication skills.
• Strong organizational and time-management abilities.
• Ability to work independently with minimal supervision.
• High attention to detail and accuracy.
• Strong internet research skills.
• Proficiency with Google Workspace and Microsoft Office.
• Experience with Zoom and virtual meeting platforms.
• Familiarity with CRM systems and project management software.

Preferred

• Experience as a Virtual Assistant, Executive Assistant, Operations Coordinator, or Administrative Assistant.
• Experience supporting multiple businesses or executives.
• Knowledge of social media management and digital marketing.
• Familiarity with website platforms such as WordPress, Wix, Shopify, or similar systems.
• Experience using AI tools such as ChatGPT and automation platforms.
• Basic understanding of business operations, legal administration, and vendor management.

Success Metrics

The successful candidate will:

• Maintain accurate calendars and scheduling.
• Deliver timely meeting notes and follow-up action items.
• Improve operational efficiency through proactive task management.
• Support marketing and social media initiatives effectively.
• Assist with website maintenance and digital presence management.
• Communicate professionally with clients, vendors, and team members.
• Provide reliable support to executive leadership across multiple companies.

Application Requirements

Please submit:

• Resume
• Relevant experience
• Availability
• Internet speed confirmation
• References (if available)

We are seeking a long-term team member who is dependable, organized, technology-driven, and eager to grow with a dynamic organization operating across hospitality, automotive, high-end residential, home building, and other business sectors.

Our Standard

In this company, we build brands.

And the systems behind them carry the same weight.

We didn’t survive the Manhattan New York ad scene by being polite.

We did it by being right.

We build infrastructure that moves like capital.

Systems that convert, scale, and compound.

Amateurs use AI for convenience.

Professionals use AI to create leverage.

We are not here to maintain tools.

We are here to engineer systems that drive valuation.

No clutter. No drag. No over-explaining.

We don’t patch broken processes forever.

We replace them with systems that don’t break.

We are building infrastructure that scales

without asking for permission.

If this sounds like how you operate —

Join us.

Job Type: Full-time

Work Location: Remote