Executive Assistant (Job ID: STARIC1EA) in at Inside Out Hiring

🌟 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!

🚨 IMPORTANT - Watch this quick Loom video on how to get hired: 🔗 https://www.loom.com/share/345f776084e642ba99c24aabe40a67a0

🗣️ C1 ENGLISH LEVEL IS REQUIRED. The selected candidate will be speaking strictly in English during their whole shift. 🎙️ PLEASE SUBMIT YOUR RESUME AND AUDIO RECORDING IN ENGLISH.

• 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
  

Our client is a high-capability federal government contracting firm operating in the defense 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 defense and civil leadership.

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. You will be responsible for enforcing accountability across key meetings, tracking compliance, and protecting executive bandwidth so the CEO can focus on scaling capital and strategic growth.

• Meeting Oversight & Task Enforcement: Attend internal and proposal meetings, memorialize 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.
  

⭐ Non-Negotiables (Must-Haves):

• Exceptional Critical Thinking (#1 Requirement): Ability to analyze 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 CEO and 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.
  

• 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).
  

🚀 Submit your application today and take the first step toward your next great opportunity!

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