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Executive Assistant
Job ID:DEADJ1EA Industry: Construction & Development Location: LATAM / South Africa Employment Type: Full-Time Schedule: Monday–Friday, 7:00 AM–4:00 PM Central Time (Flexibility Required) Compensation: $2,000–$2,500 per month Target Start Date: Within 30 Days
Build Systems. Drive Execution. Become the Right Hand to a Veteran Entrepreneur.
Are you a highly proactive Executive Assistant who thrives on turning chaos into structure?
Do you enjoy taking a rough idea, voice note, or quick instruction and transforming it into an organized plan that actually gets executed?
Our client is looking for more than a traditional administrative assistant. This is an opportunity to become the operational right-hand to an experienced entrepreneur, helping modernize workflows, manage priorities, leverage AI, and build systems that support a growing construction and development business.
If you are resourceful, highly organized, tech-savvy, and comfortable taking ownership in a fast-moving environment, this could be an exceptional long-term opportunity.
About the Client
Our client is an established construction, site work, and development entrepreneur operating across Wisconsin, USA.
With more than 45 years of industry experience, he has built a highly efficient business generating approximately $3M–$5M in annual revenue with a lean team of approximately 5–15 field crew members and a focused back-office operation.
The business manages active construction and development projects while the owner remains deeply involved in:
Managing job sites and field operations
Pursuing new projects across the state
Coordinating vendors and contractors
Overseeing business operations
Developing patented products and new business opportunities
This is the company's first dedicated remote Executive Assistant hire, making this a unique opportunity to help shape how the business operates as it transitions toward more modern, technology-enabled systems.
About the Role
This is a high-impact Executive Assistant and Operations Support role for someone who wants to be deeply involved in helping a business owner execute.
The founder regularly works 14–16-hour days during peak construction season and needs a highly capable partner who can bring structure to a fast-moving environment, manage competing priorities, and independently drive tasks forward.
You will serve as the owner's central execution hub—helping transform manual processes, handwritten notes, and scattered priorities into organized digital systems and actionable workflows.
You will also leverage modern AI tools, particularly Claude, to conduct research, synthesize information, draft communications, solve operational problems, and improve efficiency.
This is not a role for someone who waits for detailed instructions for every task. The ideal candidate can listen, think critically, ask the right questions, and take ownership of execution.
What You'll Do
Executive Workflow & Priority Management
Help the owner transition from handwritten notes, paper lists, and fragmented reminders into structured digital workflows.
Maintain organized task lists, priorities, deadlines, and follow-up systems.
Ensure important action items do not get lost in a fast-moving work environment.
Help the owner stay focused on high-priority business and operational decisions.
Proactively identify upcoming needs, risks, and unfinished tasks.
Operational Coordination & Follow-Ups
Manage and drive follow-ups with vendors, contractors, partners, and other stakeholders.
Assist with sourcing project quotes and gathering relevant information.
Track operational tasks and ensure next steps are clearly documented.
Help coordinate communication between the owner and the local back-office team.
Maintain visibility across multiple moving projects and responsibilities.
Research & AI-Powered Execution
Use AI tools, particularly Claude, to conduct research and synthesize complex information.
Transform large amounts of information into concise, actionable summaries.
Assist with drafting communications, documents, workflows, and internal materials.
Explore practical ways to use AI and automation to improve daily operations.
Apply strong judgment when researching opportunities, vendors, business ideas, and operational solutions.
Personal & Life Administration
Help reduce the owner's mental load by managing personal administrative responsibilities.
Coordinate appointments, bookings, reservations, and scheduling.
Assist with family logistics and personal planning as needed.
Proactively organize personal tasks so the owner can remain focused during demanding work periods.
Internal Coordination
Work closely with the owner and local administrative team to maintain alignment.
Help organize communication across executive, operational, and administrative priorities.
Ensure important information is documented and shared with the appropriate stakeholders.
Support a smoother connection between field operations and back-office administration.
Systems, SOPs & Business Improvement
As you become more familiar with the business, you will have the opportunity to:
Document Standard Operating Procedures (SOPs).
Build repeatable workflows and process documentation.
Develop dashboards and tracking systems.
Identify inefficiencies and recommend practical improvements.
Help the business gradually transition from manual processes into scalable digital systems.
This role has significant potential to grow as you become a trusted operational partner.
What We're Looking For
Required Qualifications
3+ years of experience as an Executive Assistant, Operations Coordinator, or similar high-level support role.
Proven experience supporting a founder, business owner, senior executive, or C-suite leader.
Excellent written and spoken English communication skills.
Strong organizational, prioritization, and time-management abilities.
Ability to manage multiple workflows without losing attention to detail.
Comfortable working independently and making sound decisions with limited direction.
Strong critical thinking and problem-solving skills.
Ability to adapt quickly when priorities change.
AI & Technology Skills
Strong proficiency or demonstrated capability with AI tools.
Experience using Claude is highly preferred.
Comfortable using AI for:
Research and information gathering
Research synthesis
Drafting communications
Problem-solving
Process improvement
Workflow development
Strong understanding of how technology and automation can improve business operations.
Key Traits for Success
Highly Proactive
You do not wait to be told about every next step. You anticipate needs, follow through, and bring solutions forward.
A Strong Critical Thinker
You can take incomplete information, identify what matters, and determine the best path forward.
Resourceful
When you encounter a problem, your first instinct is to investigate, find options, and propose solutions.
Organized and Structured
You naturally create order, systems, and clarity—even when the environment around you is fast-moving.
Comfortable With Ambiguity
Construction and development projects can change quickly. You can adapt without becoming overwhelmed.
Patient and Tech-Savvy
The owner is accustomed to traditional pen-and-paper workflows but is motivated to modernize. You should be comfortable helping guide and onboard someone into digital systems with patience and structure.
Ownership-Oriented
You treat responsibilities as something to own—not simply tasks to complete.
Preferred Experience
The following are highly valued but not mandatory:
Experience supporting construction, development, real estate, field operations, or project-based businesses.
Experience building SOPs and process documentation.
Experience with task management and operational tracking systems.
Familiarity with automation tools and AI-supported workflows.
Experience supporting entrepreneurs who manage multiple businesses or projects.
Experience working in a fast-paced, high-growth environment.
Why Join This Opportunity?
This is an opportunity to work directly with an experienced entrepreneur and play a meaningful role in modernizing and scaling his business operations.
You will have the chance to:
Become a trusted right-hand partner to a highly experienced business owner.
Take ownership of meaningful operational responsibilities.
Help transform a traditional business into a more modern, technology-enabled operation.
Work directly with AI and emerging productivity tools.
Build systems and workflows that create a lasting impact.
Gain exposure to construction, development, entrepreneurship, and business operations.
Grow into a broader strategic operations role over time.
If you are looking for a role where your ideas, initiative, organizational skills, and ability to execute truly matter, we encourage you to apply.
Apply today and take the next step toward becoming an essential operational partner to a growing U.S.-based construction and development business.
InsideOutVAS is a staffing and recruitment firm that connects businesses with remote talent from LATAM and other regions for various operational and client-facing roles. The company works across multiple industries including business coaching, property management, and advertising agencies, placing skilled professionals in positions ranging from lead generation and appointment setting to property management and marketing operations. They focus on building high-performing teams for growing companies, emphasizing results-oriented hiring, accountability, and operational excellence. InsideOutVAS serves as a bridge between businesses needing quality talent and professionals seeking remote work opportunities with competitive compensation structures.
