Executive Assistant (Job ID: STARIC1EA)

Inside Out Hiring; United States; Remote; USD 28,000 - 33,000; Full time

Job summary

Inside Out Hiring is seeking an experienced Executive Assistant to act as a high-level proxy for the CEO in a fast-growing federal government contracting firm. This role emphasizes governance, process enforcement, and action-item accountability across global teams.

The candidate must demonstrate exceptional critical thinking, proactive problem solving, and strong English fluency to engage with executive leadership and offshore contractors in a compliant, results-driven environment.

Qualifications

• Exceptional Critical Thinking to analyze complex documents and extract strategy.
• Executive alignment and respect for hierarchy in a high-stakes environment.
• Proactive problem solving with actionable options for the CEO.
• Rigorous process and audit mindset with strict deadline discipline.
• Fluent English communication for executive-level interactions.

Responsibilities

• Meeting Oversight & Task Enforcement: attend meetings, capture actions, and ensure accountability.
• Process & SOP Policing: monitor workflows against SOPs and enforce deadlines.
• Document Extraction & Quality Audit: review dense documents and extract core priorities.
• Team & Time Tracking Audit: verify daily hours and deliverables for compliance.
• Executive Proxy & SOP Maintenance: keep momentum whenCEO is in investor meetings.

Skills

Exceptional Critical Thinking

Executive Alignment & Respect for Hier

Proactive Problem Solver

Process & Audit Mindset

Fluent English Communication

Tools

Clockify

Slack

Google Workspace

Job description

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

Are you an exceptionally sharp, disciplined professional with a knack for critical thinking and process enforcement? We are looking for an elite Executive Assistant to serve as a high-level force multiplier and operational proxy for the CEO of a fast-growing federal government contracting firm!

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: STARIC1EA

• Industry: Federal Government Contracting

• Location: LATAM / South Africa

• Job Status: Full Time

• Work Schedule: Monday to Friday, 6:00 AM to 3:00 PM (Eastern Time)

• Salary: $2500 to $3000 per month

• Target Start Date: ASAP

About the Client

Our client is a high-capability federal government contracting firm operating in the defence and civil sectors. Built on a lean, high-leverage operational model, the company holds 8 prime federal contract vehicles with a combined ceiling of $30M–$100M+. The organization relies on rigorous processes, clear accountability frameworks, and data‑driven systems to deliver high‑impact strategic results for top‑level defence and civil leadership.

About the Role

The Chief Executive Officer is seeking a grounded, disciplined, and exceptionally sharp Executive Assistant to serve as a high‑level force multiplier.

This is not a traditional administrative or task‑oriented VA role. You will act as the CEO’s operational proxy—maintaining control, keeping the executive engine running, auditing internal processes, and ensuring project managers and proposal teams execute critical strategy without dropping the ball or relying on superficial answers.

Key Responsibilities

• Meeting Oversight & Task Enforcement: Attend internal and proposal meetings, memorialise action items, and follow up relentlessly to hold team members accountable to deliverables.

• Process & SOP Policing: Monitor daily workflows against established SOPs and RACI frameworks. Act as a firm, respectful enforcer of company standards and deadlines.

• Document Extraction & Quality Audit: Review dense technical documents, policies, and RFPs to extract core priorities, catch glossed‑over compliance steps, and ensure teams do not submit superficial or filler content.

• Team & Time Tracking Audit: Ensure global team members accurately log daily hours and deliverables in Clockify to meet federal compliance standards.

• Executive Proxy & SOP Maintenance: Maintain operational momentum when the CEO is engaged in investor meetings, while keeping Standard Operating Procedures up to date as the company scales.

Qualifications & Skills

Non‑Negotiables (Must‑Haves):

• Exceptional Critical Thinking (#1 Requirement): Ability to analyse and synthesize complex technical/RFP documents, quickly separating high‑value strategic details from surface‑level commentary or filler.

• Executive Alignment & Respect for Hierarchy: High EQ—assertive and firm when policing project teams and offshore contractors, while remaining grounded, respectful, and fully aligned with executive leadership (no insubordination or ego).

• Proactive Problem Solver: Takes initiative to bring actionable options and solutions to the table rather than passing open‑ended problems back to the CEO.

• Process & Audit Mindset: Uncompromising attention to detail with zero tolerance for missed deadlines, unlogged hours, or glossed‑over requirements.

• Fluent English Communication: Flawless written and verbal English suitable for direct CEOand executive‑level interactions.

Nice-to-Haves:

• Federal Contracting & RFP Familiarity: Basic understanding of government bid/proposal workflows (RFPs, task orders, compliance matrices, or working with Subject Matter Experts).

• AI & Automation Tools: Hands‑on experience using generative AI tools (Claude, ChatGPT) for workflow creation, drafting, or operational support.

• Systems & Workflow Tracking: Familiarity with process frameworks (e.g., RACI/ROSI), performance metrics, or task‑based tracking systems.

• Tool Proficiency: Prior experience using Clockify (tied to task‑based time tracking) or Slack/Google Workspace in a fast‑paced remote environment.

Tech Stack & Tools

• AI & LLM Tools: Claude, ChatGPT (used for operational workflow building and custom tools).

• Time & Expense Tracking: Clockify (tied to gate‑step‑task tracking and federal audit/DCAA compliance).

• Communication & Workflow: Google Meet / Zoom, Slack, persona‑based workflow tools, and Cadence (daily start‑of‑day / end‑of‑day check‑ins).