Legal Executive Assistant (Job ID: DLCBEN1EA)

Insideoutva; Northern (KY); Hybrid; USD 22,000 - 25,000; Full time

Job summary

Insideoutva is seeking a Senior Legal Executive Assistant / Paralegal for a fully remote role to support the business owner in a prominent commercial real estate group. You will manage complex legal documents, coordinate with external counsel, and oversee contract administration while supporting executive scheduling and strategic administration.

The ideal candidate has 10–15 years of experience, exceptional English, high integrity, advanced Excel skills, and the ability to work autonomously in a

Qualifications

• 10–15 years of paralegal/legal executive assistant experience, preferably in commercial real estate or corporate law.
• Deep familiarity with legal terminology, contract structures, and document drafting.
• Advanced Excel proficiency with complex workbooks.
• Excellent written and spoken English.
• High integrity and discretion.

Responsibilities

• Prepare, review, organize, and manage complex legal documents, commercial real estate contracts, leases, demand letters, settlement agreements, and sensitive corporate files.
• Establish strict document-management protocols to guarantee accuracy, compliance, and absolute confidentiality.
• Proactively manage and follow up with external attorneys to secure outstanding contract reviews, legal filings, background screenings, and critical deliverables on schedule—removing the operational mental load from the business owner.
• Coordinate seamlessly with lenders, title companies, appraisers, surveyors, insurance providers, and third-party consultants to support transaction closings and due diligence processes.
• Organize exhibits, litigation support documents, correspondence logs, witness files, demand letters, small claims documentation, and evidentiary materials.
• Serve as a trusted operational right hand to the owner, taking charge of executive communications, complex scheduling, high-priority business initiatives, and daily workflow oversight.
• Input and track operational action items within project management platforms (e.g., Hubstaff, Cadence) to maintain full transparency, complete oversight, and daily accountability across all active initiatives.
• Collaborate with operations, shared-services teams, and external consultants to keep real estate development projects moving forward smoothly.

Skills

Paralegal / Legal EA

Contract management

Advanced Excel

English fluency

Autonomy

Problem solving

Tools

Hubstaff

Cadence

Microsoft Office

Job description

Exciting Remote Opportunity! We're Hiring a Legal Executive Assistant!

Are you a highly experienced and autonomous legal professional looking for long-term stability and growth? We are seeking an exceptional Senior Legal Executive Assistant / Paralegal to serve as a critical operational pillar for the business owner of a prominent commercial real estate group!

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 Details at a Glance

• Job Title: Legal Executive Assistant
• Job ID: DLCRIC1EA
• Industry: Commercial Real Estate & Property Development
• Location: South Africa / LATAM / PH
• Job Status: Full Time
• Work Schedule: Monday to Friday, 7:00 AM to 4:00 PM (CST)
• Salary: $2000 to $2200 per month
• Target Start Date: ASAP

About the Client

Our client is a highly dynamic developer and owner of a prominent commercial real estate group. Headquartered in the US, the business is supported by an established, high-performing operations team composed of specialized industry professionals, including architects, civil engineers, general contractors, and consultants. As the owner scales operations and integrates modern technology—including AI and content leverage—they require a dedicated, high-level professional to support executive and legal functions directly.

About the Role

We are seeking a highly autonomous Senior Legal Executive Assistant / Paralegal with 10 to 15 years of experience to serve as a critical operational pillar for the business owner. We are looking for a long-term team member seeking stability and professional growth rather than a short-term contract opportunity.

This is not an entry-level virtual assistant position—it requires sharp critical thinking, rigorous document management, advanced technical capability, and the ability to hit the ground running without hand-holding. You will act as a direct liaison and driver for legal and operational deliverables, managing external attorneys, keeping commercial real estate contracts on track, coordinating with lenders and title companies, and maintaining structure across our broader development and shared-services teams.

Key Responsibilities

Legal & Contract Administration

• Prepare, review, organize, and manage complex legal documents, commercial real estate contracts, leases, demand letters, settlement agreements, and sensitive corporate files.
• Establish strict document-management protocols to guarantee accuracy, compliance, and absolute confidentiality.

Rigorous Version Control & Records Management

• Maintain strict document version control, audit trails, standardized naming conventions, document indexing, and electronic records systems for all contracts, lender markups, attorney revisions, and title commitment updates.

Attorney & Deliverable Management

• Proactively manage and follow up with external attorneys to secure outstanding contract reviews, legal filings, background screenings, and critical deliverables on schedule—removing the operational mental load from the business owner.

Lender & Third-Party Coordination

• Coordinate seamlessly with lenders, title companies, appraisers, surveyors, insurance providers, and third-party consultants to support transaction closings and due diligence processes.

Litigation Support & Organization

• Organize exhibits, litigation support documents, correspondence logs, witness files, demand letters, small claims documentation, and evidentiary materials.

Executive Support & Strategic Administration

• Serve as a trusted operational right hand to the owner, taking charge of executive communications, complex scheduling, high-priority business initiatives, and daily workflow oversight.

Task Tracking & Workflow Optimization

• Input and track operational action items within project management platforms (e.g., Hubstaff, Cadence) to maintain full transparency, complete oversight, and daily accountability across all active initiatives.

Cross-Functional Team Synergy

• Collaborate seamlessly with existing operations, shared-services teams, floor managers, civil engineers, and external consultants to keep real estate development projects moving forward smoothly.

Qualifications & Skills

Core Requirements (Non-Negotiable):

• Proven Experience:10to 15 years of significant, verifiable background as a Paralegal, Legal Executive Assistant, or Legal Secretary—ideally within commercial real estate, corporate law, or property development. (Candidates with under 10years of experience or call-center-only backgrounds will not be considered.)
• Legal & Technical Skillset: Deep familiarity with legal terminology, contract structures, complex document drafting, demand letters, background screenings, title commitment revisions, and meticulous record-keeping.
• Advanced Microsoft Excel Proficiency: Strong command of Excel, including filtering, formulas, tracking schedules, status reporting, and maintaining complex project workbooks.
• High English Fluency & Comprehension: Exceptional spoken, written, and reading English comprehension, with the ability to understand complex U.S. business culture and commercial real estate nomenclature.
• Unquestionable Integrity & Discretion: Absolute honesty, strong moral principles, and total discretion when handling high-level financial, operational, confidential, and proprietary business details.

Soft Skills & Competencies:

• Proactive Critical Thinking & Autonomy: High emotional intelligence, sharp critical thinking, and a demonstrated ability to operate independently and troubleshoot complex issues.
• Substance Over Style & Team Synergy: Proven practical competence and ability to deliver tangible output beyond strong interview skills, alongside strong interpersonal skills to integrate seamlessly into an established team structure.

Tech & Remote Work Infrastructure:

• Tech-Savvy & System Familiarity: High digital literacy with proficiency or fast adaptation to productivity platforms, project tracking systems (e.g., Hubstaff, Cadence), Microsoft Office Suite (Word, Excel, Outlook, Calendar), and modern AI/automation tools.
• Remote Reliability: Dedicated, quiet home-office setup with a reliable, high-speed internet connection.
• Power/Internet Backups: Robust power and internet backup solutions (e.g., UPS/inverter/secondary connection) are required to ensure uninterrupted daily connectivity.