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Executive Assistant to CEO & Integrator; Offshore

Remote / Online - Candidates ideally in
Kahului, Maui County, Hawaii, 96732, USA
Listing for: Employee Retention Benefits
Remote/Work from Home position
Listed on 2026-06-17
Job specializations:
  • Administrative/Clerical
    Business Administration, Office Administrator/ Coordinator, Virtual Assistant/ Remote Admin
Salary/Wage Range or Industry Benchmark: 60000 - 80000 USD Yearly USD 60000.00 80000.00 YEAR
Job Description & How to Apply Below
Position: Executive Assistant to the CEO & Integrator (Offshore)

Executive Assistant to the CEO & Integrator (Offshore) Job Description

This is a remote position.

1. PURPOSE (Why does this role exist)

The Executive Assistant (EA) to the CEO is a senior execution and leverage role.

The purpose of this role is to:

  • Protect the CEO’s time and focus for strategic thinking, sales, and leadership
  • Ensure CEO priorities translate into action across the organization
  • Reduce friction, chaos, and follow-up gaps in the CEO’s world
2. IMPORTANCE & IMPACT

When this role is working well:

  • The CEO operates in their Unique Ability the majority of the week
  • Leadership initiatives move forward consistently, not sporadically
  • Communication to and from the CEO is organized, filtered, and professional
  • Critical dates (licenses, renewals, key projects) are handled proactively, not reactively

This role directly supports ERB’s ability to scale without burning out the CEO.

3. IDEAL OUTCOME (What success looks like)

Within this role:

  • The CEO’s calendar and commitments are fully owned by the EA
  • Every major project or decision from the CEO has:
    • A clear owner
    • A due date
    • Visible progress
  • The CEO has clean daily briefings and end-of-day summaries and is never surprised by avoidable issues
  • Licenses, registrations, and key deadlines are always current with zero missed renewals
4.

KEY RESPONSIBILITIES 4.1 Executive Calendar & Time Protection

Own and manage the CEO’s calendar strategically, including:

  • Prioritizing high-value activities (sales, strategy, leadership)
  • Filtering and declining low-value or misaligned meeting requests
  • Building in buffer, thinking time, and focus blocks
  • Coordinating internal and external meetings across time zones
4.2 CEO Task & Initiative Execution
  • Track all CEO commitments from meetings, emails, and messages
  • Ensure every commitment has:
    • An owner
    • A due date
    • A follow-up system
  • Provide regular status updates and escalate risks or bottlenecks early
  • Serve as a primary gatekeeper for executive communications
  • Triage email, messages, and inbound requests
  • Draft responses for CEO review where appropriate
  • Maintain confidentiality and discretion at all times
4.4 Meeting Management & Follow-Through

For key leadership and project meetings:

  • Confirm agenda, objectives, and attendees in advance
  • Gather required documents and context
  • Capture notes, decisions, and action items
  • Enter action items into the tracking system and follow up to completion
4.5 Systems, Projects & Process Improvement
  • Maintain and improve structured systems for:
    • Calendar
    • Tasks and projects
    • Documentation and knowledge management
  • Support leadership cadence and planning cycles (weekly, quarterly, annual)
  • Proactively identify workflow inefficiencies and propose solutions
4.6 Licensing, Compliance & Critical Dates
  • Maintain a Licenses & Compliance Tracker for:
    • CEO licenses (insurance, Series 65, etc.)
    • Entity filings and renewals (ERB, ERB Enrollment, ES Aeternum, Guerreros, Terra Aeternum, etc.)
    • Key contracts, domain renewals, and major recurring obligations
  • Work 90 / 60 / 30 days ahead on required CE, filings, or renewals:
    • Register CEO for required courses
    • Schedule CE and renewal time on the calendar
    • Prepare forms and supporting documents in advance
5. COMMUNICATION & TOOLS

Primary communication channels:

  • Microsoft Teams
  • Internal chat tools

Core systems used (subject to change as optimized):

  • High Level (CRM/marketing/telephony)
  • Connec Team
  • Employee Navigator
  • Other CRM or project tools introduced by ERB

Daily updates:

  • Brief check-in via Teams (what’s done, what’s next, blockers)

Weekly summary:

  • Key tasks completed
  • Risks or decisions needed from the CEO
6. WORK SCHEDULE

Standard Schedule (Monday–Friday, Pacific Time):

  • Shift: 8:00 AM–5:00 PM

Flexibility:

  • Occasional extended or shifted hours as required by:
    • CEO meetings
    • Executive travel
    • Urgent leadership initiatives

Availability outside standard hours is expected with reasonable notice.

7. REPORTING STRUCTURE

Direct Reporting:

  • CEO – Employee Retention Benefits, Inc.

Dotted Line / Operational Alignment:

  • Sales Director (for coordination on cross-department initiatives and priorities as needed)
8. PERFORMANCE EXPECTATIONS

Align with ERB’s key performance standards and core values:

  • Driven
  • Adaptable
  • Accountable
  • Humbly Confident

Additional expectations:

  • Maintain a professional, positive tone in all interactions
  • Learn and adapt quickly as systems and processes evolve

High performers may be considered for:

  • Expanded scope
  • Leadership over additional offshore support roles
  • Discretionary performance-based incentives (as mutually agreed)
9. CONFIDENTIALITY & CONDUCT
  • Abide by all internal confidentiality and data protection standards
  • Handle all information (client, employee, financial, legal) with strict discretion
  • Support and embody ERB’s mission and client-first culture in all work
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