Executive Operations & Systems Assistant

Executive Operations & Systems Assistant

Long-Term, Full-Time Role Supporting Multiple Businesses

We are looking for an unusually capable, resourceful, and trustworthy person to become deeply involved in the day-to-day operations of several growing businesses.

This is not a traditional virtual assistant position.

You may be organizing email s and schedules one day, building an automation or workflow the next, and then helping us launch a ---------- community, document a construction process, research a new software tool, or create a small internal program.

Our businesses operate in very different industries, including:

• Construction, excavation, hauling, and project management
• Business consulting and operational improvement
• Technology, automation, media, and software development
• Personal branding and content creation

Some of these businesses overlap, but each has different customers, terminology, priorities, and operating systems. The right person must be able to move between them without becoming overwhelmed.

What You May Work On

Your responsibilities may include:

• Managing and organizing executive email accounts
• Identifying messages that require immediate attention
• Drafting replies and following up on outstanding conversations
• Managing calendars, meetings, deadlines, and reminders
• Organizing files, documents, contacts, and business information
• Creating standard operating procedures, checklists, and workflows
• Turning informal instructions into clear, repeatable systems
• Building automations using tools such as Zapier, Make, ChatGPT, Google Workspace, and similar platforms
• Creating and managing ---------- servers, channels, roles, and workflows
• Helping manage social media accounts and content schedules
• Researching topics, tools, vendors, regulations, and business opportunities
• Creating reports, summaries, spreadsheets, presentations, and project documents
• Updating CRM, task-management, or project-management systems
• Writing or modifying small scripts and internal programs
• Using AI tools to improve efficiency and reduce repetitive work
• Coordinating with employees, contractors, clients, vendors, and collaborators
• Tracking open projects and making sure important tasks do not disappear
• Learning how each business operates and helping us improve it

You will not necessarily be expected to know how to do every one of these things on your first day. However, you must be comfortable learning unfamiliar tools, researching solutions, testing ideas, and figuring things out without needing step-by-step instructions for every task.

Who We Are Looking For

The ideal person is:

• Extremely organized
• Highly trustworthy and discreet
• Comfortable handling confidential business and personal information
• Technically capable and interested in automation
• A strong written communicator
• Able to understand complicated instructions
• Able to turn conversations and rough ideas into organized action plans
• Comfortable asking intelligent questions when necessary
• Proactive rather than constantly waiting for assignments
• Capable of recognizing priorities and potential problems
• Detail-oriented without losing sight of the larger objective
• Calm when several projects are happening at once
• Willing to take ownership of outcomes
• Honest when they do not understand something
• Able to receive direct feedback without becoming defensive
• Interested in building a long-term role rather than completing occasional freelance tasks

We value good judgment more than blind obedience. We need someone who can understand the purpose behind a task, notice when something does not make sense, and suggest a better approach.

Required Skills

You should have strong experience with several of the following:

• Google Workspace
• Gmail and calendar management
• Google Docs and Google Sheets
• Project-management platforms
• ChatGPT and other AI tools
• Online research
• Process documentation
• SOP and workflow creation
• Social media management
• Written English
• Basic graphic or presentation creation
• Automation platforms
• Basic coding, scripting, or no-code development

You do not need to be an expert in every category. We are primarily looking for someone with strong foundational skills, excellent judgment, and the ability to learn quickly.

Important Expectations

This role will require a high level of trust.

Over time, the person we hire may have access to sensitive communications, internal business information, financial documents, social media accounts, operational systems, and private schedules.

For that reason, honesty, confidentiality, reliability, and good judgment are non-negotiable.

You must also be comfortable working with business owners who move quickly, think out loud, and regularly develop new ideas. Part of your job will be helping convert those ideas into organized projects, assigned responsibilities, and completed work.

We are not looking for someone who says “yes” to everything and then quietly misses deadlines. We prefer early communication, realistic expectations, and honest progress updates.

What Success Looks Like

A successful person in this position will gradually become someone who:

• Understands how each business operates
• Knows where important information is located
• Keeps projects and conversations organized
• Identifies tasks before they become emergencies
• Reduces the number of small decisions the owners must personally handle
• Creates systems that make the entire organization more efficient
• Protects the owners’ time and attention
• Helps transform ideas into completed projects
• Becomes a trusted and valuable part of the organization

We are looking for someone who wants to grow with the businesses. As your capabilities, responsibilities, and impact increase, there will be opportunities for the role to expand.

How to Apply

Please do not send a generic application.

Begin your application with the words:

“Systems create freedom.”

Then include the following:

1. A brief introduction explaining why this unusual role interests you.
2. Examples of the most complicated administrative, technical, or operational work you have handled.
3. A list of the software, automation, AI, coding, and project-management tools you have used.
4. An example of a process, SOP, workflow, or automation you created.
5. A description of a time you were given an unfamiliar task and had to figure it out independently.
6. Your preferred monthly compensation.
7. Your availability and working hours.
8. A link to a short video introduction of approximately two to three minutes.

In your video, explain:

• What makes you different from a typical virtual assistant
• How you approach tasks you have never completed before
• How you manage confidential information
• Why you believe you could become a trusted long-ter ---------- mber of our team

Applications that do not follow these instructions will not be considered.

Final Note

We recognize that this job description covers a broad range of responsibilities. We are not looking for someone who has already mastered every possible task.

We are looking for a sharp, dependable, technically curious person who can learn, organize, solve problems, protect confidential information, and steadily become more valuable to the organization.

If you enjoy bringing order to complexity, building systems, learning new technology, and helping ambitious people turn ideas into reality, this may be an excellent position for you.