Executive Assistant (Job ID: PROKYL1EA)

Inside Out Hiring; United States; Remote; USD 22,000 - 28,000; Full time

Job summary

Inside Out Hiring is seeking a proactive Executive Assistant to serve as the operational right-hand partner for a veteran entrepreneur. This remote role supports a Wisconsin-based leader from LATAM or South Africa, handling digital transformation, research, and communications.

You will leverage Claude and other AI tools to turn handwritten notes into structured workflows, draft collateral, and enable projects to move smoothly. Fluency in English and 3+ years of executive support are required.

Qualifications

• 3+ years as an Executive Assistant or similar supporting founders or C-suite.
• Flawless written and spoken English with strong prioritization and time-management.
• Strong proficiency with AI tools, especially Claude, for research and workflow development.
• Highly proactive, self-directed, organized, and capable of guiding a traditional business into digital workflows.

Responsibilities

• Manage executive workflow and priorities; maintain task lists and follow-up systems.
• Coordinate operations and follow-ups with vendors, contractors, and partners; assist with project quotes.
• Conduct AI-assisted research and draft communications, SOPs, and dashboards.
• Coordinate personal appointments and family logistics to reduce mental load for the owner.
• Document SOPs, build repeatable processes, and identify operational efficiencies.

Skills

Executive support

AI tools Claude

English proficiency

Prioritization

Time management

Tools

Claude AI

Job description

Exciting Remote Opportunity! We're Hiring an Executive Assistant!

Are you a highly proactive Executive Assistant who thrives on turning chaos into structure and leveraging modern AI tools? We are seeking an exceptional Executive Assistant based in LATAM or South Africa to serve as the operational right-hand partner to a veteran construction and development entrepreneur operating across Wisconsin, USA!

C1 ENGLISH LEVEL IS REQUIRED. The selected candidate will be speaking strictly in English during their whole shift.

Job Details at a Glance

• Job Title: Executive Assistant

• Job ID: PROKYL1EA

• 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

About the Client

Our client is an established construction, site work, and development entrepreneur with over 45 years of industry experience. Generating $3M–$5M in annual revenue with a lean field team of 5–15 crew members, the business manages active construction and site work while developing new business opportunities and patented products. As the company's first dedicated remote Executive Assistant, you will help modernize workflows and transition traditional, pen-and-paper processes into scalable digital systems.

About the Role

This is a high-impact Executive Assistant and Operations Support role. The founder regularly works 14–16-hour days during peak construction season and needs a central execution hub—someone who can take rough ideas, handwritten notes, or voice messages and transform them into organized digital workflows. You will leverage modern AI tools (particularly Claude) to conduct research, synthesize information, draft communications, build SOPs, and keep multi-faceted projects moving seamlessly.

Key Responsibilities

• Executive Workflow & Priority Management: Transition the owner from paper lists into structured digital workflows; maintain task lists, priorities, follow-up systems, and proactively manage risk.

• Operational Coordination & Follow-Ups: Drive follow-ups with vendors, contractors, and partners; assist with project quotes; maintain visibility across moving field/office projects.

• Research & AI-Powered Execution: Use AI tools (Claude) to research opportunities, synthesize complex information into actionable summaries, draft collateral, and optimize daily operations.

• Personal & Life Administration: Coordinate personal appointments, bookings, reservations, family logistics, and administrative tasks to reduce the owner's mental load.

• Systems, SOPs & Business Improvement: Document Standard Operating Procedures (SOPs), build repeatable process documentation, create dashboards, and identify practical operational efficiencies.

Qualifications & Skills

Core Requirements:

• Experience: 3+ years as an Executive Assistant, Operations Coordinator, or high-level support role directly supporting founders, business owners, or C-suite executives.

• Communication & Judgment: Flawless written and spoken English with exceptional prioritization, time-management, critical thinking, and problem-solving abilities.

• AI & Tech Fluency: Strong proficiency with AI tools (specifically Claude) for research synthesis, drafting communications, problem-solving, and workflow development.

• Mindset: Highly proactive, self-directed, resourceful, organized, and patient in helping guide a traditional business owner into modern digital workflows.

Preferred Experience:

• Background in construction, development, real estate, field operations, or project-based businesses.

• Experience building SOPs, process documentation, task tracking systems, or AI-supported automation workflows.