Executive Assistant / Chief of Staff (Job ID: KENSAM1EA)

Insideoutva; Idaho; Hybrid; USD 22,000 - 28,000; Full time

Job summary

Insideoutva is seeking an Executive Assistant / Chief of Staff to act as the executive's operational proxy, managing complex scheduling, cross‑department coordination, and proactive governance across multiple growth lines. You will build Excel playbooks, implement AI workflows, and enforce priorities to enable strategic focus.

The role requires sharp, proactive execution, strong English communication, and the ability to operate across international time zones with occasional travel support.

Qualifications

• Experience supporting a founder/CEO in operations, projects, or chief-of-staff roles.
• Advanced Excel proficiency with multi-sheet models and quoting/calculation logic.
• Entrepreneurial, proactive drive; able to manage up and focus on priorities.
• Practical experience using AI platforms (Claude/ChatGPT/Copilot) for workflow automation.
• Excellent written and spoken English suitable for high-level professional communication.
• C1 level English; able to communicate strictly in English during shift.
• Strong attention to logistics and sequencing to prevent downstream failures.

Responsibilities

• Manage complex scheduling and travel across multiple programs and time zones.
• Coordinate cross-department tasks and ensure proper handoffs in sequence.
• Gatekeep executive calendar, triage issues, and enforce deadlines.
• Prepare and review customer-facing documents, contracts, and proposals.
• Develop and maintain AI-driven tracking tools and dashboards to streamline admin tasks.
• Document and own SOPs across Cruise, Military, and Commercial verticals.
• Onboard via shadowing before taking independent ownership.

Skills

Executive support

Advanced Excel

Entrepreneurial drive

AI fluency

Flawless English

C1 English level

High-attention logistics

Tools

Claude

ChatGPT

Microsoft Copilot

Deel

Teams

Google Meet

Slack

Job description

Exciting Remote Opportunity! We're Hiring an Executive Assistant / Chief of Staff!

Job Details at a Glance

• Job Title: Executive Assistant / Chief of Staff
• Job ID: KENSAM1EA
• Industry: Beverage Equipment & Logistics Services
• Location: LATAM / South Africa
• Job Status: Full Time
• Work Schedule: Monday to Friday, 8:00 AM to 5:00 PM Eastern Time Flexibility required when the owner travels, with possible weekend requirements on rare occasions.
• Salary: $2000 to $2500 per month
• Target Start Date: Within 2 Weeks

About the Client

The company is a niche global provider of beverage equipment and services, managing programs for a major beverage brand across multiple international cruise lines. Its operations span cruise ship servicing, an expanding footprint in U.S. military contracts, and a growing presence in the juice category alongside its core soda business. The organization operates globally, with projects spanning Australia, New Zealand, the United Kingdom, and other regions, supported by an in-office team along with a small number of remote staff.

About the Role

This role exists because the founder's time is increasingly consumed by complex day-to-day operational coordination across multiple growing business lines - specifically cruise line service programs, military contract expansions, and new juice product initiatives. The organization requires a sharp, forward-focused operational partner to act as an extension of the executive.

This is not a passive task-taking role. You will serve as the executive's operational proxy - managing complex scheduling, cross-department coordination, tracking "domino-effect" logistics, and helping the executive "work himself out of a job" regarding daily execution. You will bring immediate structure, build simple Excel playbooks, integrate AI workflows, and proactively enforce priorities so the executive can stay focused on strategic growth.

Key Responsibilities

Complex Scheduling & Travel Support

• Maintain full-time availability during US business hours without major constraints over the next 12 months.
• Manage complex scheduling across concurrent programs (cruise line servicing, military contracts, and juice line expansion).
• Act as a flexible support anchor when the executive travels across international time zones (UK/Belfast/US), maintaining light availability (~6 times per year) during travel days.

Cross-Department Liaison & Sequencing

• Serve as the connective hub among departments. Ensure interdependent tasks and handoffs are tracked and executed in strict sequence, understanding that a missed step creates a domino effect downstream.

Proactive Executive Gatekeeping & Priority Management

• Manage access to executive bandwidth. Act as a constructive "boss" over the executive's calendar, triaging inbound issues, keeping the executive aligned on key priorities, and enforcing deadlines.

Playbook & Customer-Facing Deliverables

• Prepare and review all customer-facing documents, contracts, and proposals.
• Maintain and update the company’s multi-tab Excel Playbook (incorporating complex formulas, labor/parts calculations, and paste links) to generate accurate estimates and project totals.

AI & Workflow Automation

• Utilize AI engines (Claude, ChatGPT, Microsoft Copilot) to think through operational challenges, build automated tracking tools, create dashboards, and streamline routine administrative workflows.

Process Documentation & SOP Ownership

• Maintain simple, repeatable systems and Standard Operating Procedures (SOPs) across all business verticals (Cruise, Military, Commercial) to ensure operational consistency and calm execution.

Operational Shadowing & Onboarding

• Complete an initial onboarding period shadowing internal planning functions to learn the interconnected sequencing of the business before assuming independent ownership.

Qualifications & Skills

• Executive Support Experience: Prior experience supporting a founder, CEO, or senior executive in an operations, project management, or chief-of-staff capacity within a logistics-heavy or multi-department business.
• Advanced Excel Proficiency: Advanced expertise in Microsoft Excel (formulas, multi-sheet paste links, financial/quoting models, dynamic totals). Willingness to complete a practical skills assessment is required.
• Entrepreneurial Drive & Assertive Mindset: Forward-focused and proactive. Takes initiative to manage up, keep the executive on track, and solve problems independently rather than waiting for step-by-step instructions.
• AI Fluency & Automation Aptitude: Practical experience using AI platforms (Claude, ChatGPT, Copilot) for prompting, process creation, building tracking tools, and optimizing administrative tasks.
• Flawless English Communication: Exceptional written and verbal English skills suitable for professional correspondence with high-level military representatives, corporate cruise executives, and vendors.
• C1 English Level is required. The selected candidate will be speaking strictly in English during their whole shift.
• High-Attention Logistics & Sequencing: Strong operational intuition for complex systems where task misplacement creates downstream failures.

Tech Stack

• Microsoft Office (Excel, Word, Outlook)
• AI Tools (Claude, ChatGPT, Microsoft Copilot)
• Deel (Employer of record / payroll)
• Video conferencing tools (Teams, Google Meet)
• Messaging platforms (Slack, WhatsApp)
• Scheduling and project tracking tools