Strategic Executive Assistant to the CEO

Reports to: CEO
Employment Type: Full-Time
Location: Bergen County, NJ (Hybrid or potential remote)

The Opportunity

We are seeking a highly capable Strategic Executive Assistant to help the CEO operate effectively across multiple businesses, investments, and professional responsibilities.

The primary purpose of this role is to protect the CEO’s time, attention, and decision-making capacity. The Executive Assistant will act as a trusted filter, organizer, and closer of open loops, ensuring that routine execution, follow-up, coordination, and verification are handled without unnecessary CEO involvement.

Scheduling and administrative support are part of the position, but they are not the center of the role.

This is a proactive, judgment-oriented position for someone who can anticipate needs, create structure, hold others accountable, and present the CEO with clear, decision-ready information.

Success in this role will result in:

Fewer interruptions and greater focus on high-value priorities
Faster resolution of outstanding issues
Reduced decision fatigue and administrative burden
Stronger accountability from brokers, vendors, partners, and operators
A calendar and inbox aligned with strategic priorities
Problems presented with context, options, and recommended next steps

This role directly supports the growth of multiple businesses by allowing the CEO to remain focused on strategy, relationships, leadership, and important decisions.

What Success Looks Like

The Strategic Executive Assistant will help create an environment in which:

The CEO spends the majority of his time on strategy, relationships, growth, and key decisions
Every meaningful open item has a clear owner, deadline, and next step
Brokers, vendors, bookkeepers, and operating partners move forward without requiring CEO follow-up
The CEO’s inbox, calendar, travel, and follow-ups operate smoothly
Routine issues are resolved at the appropriate level
Important matters reach the CEO with sufficient context and clearly defined options
Deadlines, commitments, and action items do not fall through the cracks

Key Responsibilities

1. Executive Gatekeeping and Information Filtering

This is the highest-priority responsibility of the role.

Serve as the first point of review for inbound emails, requests, documents, and other communications
Determine which matters require CEO attention and which should be resolved, delegated, deferred, or declined
Route issues to the appropriate owner, including business operators, directors, brokers, vendors, bookkeepers, and professional advisors
Protect the CEO from unnecessary “FYI” communications and low-value interruptions
Consolidate fragmented information into clear, concise summaries
Escalate matters involving:
- Material financial impact
- Significant people or personnel decisions
- Strategic direction
- Legal, regulatory, contractual, or reputational risk
- Time-sensitive opportunities or commitments
Present escalated matters with background, options, deadlines, and a recommended next step whenever possible

2. Follow-Up and Open-Loop Management

Maintain a centralized system for tracking commitments, action items, deadlines, and outstanding decisions
Ensure every important item has an owner and next step
Follow up consistently with internal and external stakeholders
Identify stalled items before they become urgent
Close routine loops independently within delegated authority
Provide the CEO with clear visibility into overdue, blocked, or high-risk matters
Ensure verbal commitments and meeting decisions are translated into action

3. Broker, Vendor, and Partner Accountability

Manage follow-up with:
- Commercial real estate brokers
- Investment property brokers
- Vendors and service providers
- Business partners and outside professionals
Establish and enforce clear expectations regarding responsiveness, deliverables, and timelines
Require concise updates, specific next steps, and clearly assigned responsibilities
Ensure brokers provide curated opportunities aligned with established criteria rather than unfiltered listings
Challenge incomplete or unclear responses professionally
Identify underperforming relationships early and escalate them before the CEO is forced to intervene
Help the CEO evaluate whether outside partners should be retained, redirected, or replaced

4. Calendar, Meeting, and Travel Management

Own the CEO’s calendar, scheduling, meeting coordination, and travel arrangements
Protect designated time for:
- Strategic thinking
- Business planning
- Financial and operational reviews
- Board and advisory preparation
- High-value relationship development
Evaluate meeting requests based on priority, purpose, attendees, and expected outcome
Decline, delegate, shorten, or reroute low-value meetings when appropriate
Batch meetings intelligently to reduce fragmentation and unnecessary context switching
Ensure the CEO is properly prepared with agendas, background information, objectives, and decision points
Confirm logistics and resolve scheduling conflicts before they reach the CEO

5. Administrative and Document Management

Manage physical mail, including the company PO Box
Scan, name, organize, route, and securely file documents
Maintain logical and consistent digital filing systems
Coordinate invoices, contracts, forms, and other business paperwork
Ensure documents requiring review, signature, payment, or follow-up are routed promptly
Maintain accurate records across multiple businesses and entities
Create systems that make information easy to retrieve and difficult to lose
Uphold a consistently high standard of organization and confidentiality

6. Financial and Operational Coordination

This position coordinates financial and operational processes but does not replace the CEO, bookkeeper, accountant, or financial advisor.

Coordinate with bookkeepers, payroll providers, CPAs, attorneys, and other professional advisors
Ensure statements, reports, tax documents, payroll information, and requested materials are delivered on time
Organize financial information before CEO review
Prepare concise summaries highlighting deadlines, missing information, unusual items, and decisions required
Monitor recurring administrative and financial obligations
Flag inconsistencies or potential concerns for review
Avoid making financial, legal, or accounting judgments outside the authority of the role

7. Weekly and Monthly Executive Cadence

Prepare a concise weekly executive summary covering:
- Open loops and outstanding commitments
- Decisions required from the CEO
- Upcoming deadlines and meetings
- Blocked or overdue items
- Broker, vendor, and partner updates
- Emerging risks or recurring problems
Maintain a running list of items that require CEO attention
Prepare materials for monthly financial, operational, and strategic reviews
Track prior decisions and confirm that agreed-upon actions are completed
Identify recurring sources of friction and recommend process improvements

Decision-Making Authority

The successful candidate will be given clear authority to operate on the CEO’s behalf within defined boundaries.

Depending on the situation, this may include the authority to:

Decline or redirect inappropriate meeting requests
Request additional information before escalating an issue
Enforce response deadlines
Follow up with brokers, vendors, employees, and professional advisors
Resolve routine administrative matters
Close open items that fall within established guidelines
Protect designated calendar blocks
Return incomplete work and request a decision-ready response

The Executive Assistant is expected to use judgment while recognizing when an issue requires CEO involvement.

What This Role Is Not

This is not:

A traditional personal-assistant or errand-running position
A passive scheduling role
A position that waits for detailed instructions before taking action
A note-taking role without ownership of follow-through
A role for someone uncomfortable holding others accountable
A position requiring constant direction or reassurance

The right person will be comfortable operating independently while maintaining strong communication and appropriate transparency.

Required Qualities

High Ownership

You take responsibility for outcomes, not just assigned tasks. You follow through without repeated reminders and remain accountable until an issue is resolved.

Strong Judgment

You understand the difference between matters that require CEO attention and those that should be handled elsewhere.

Comfort With Ambiguity

You can move work forward even when instructions are not perfectly defined. You ask focused questions when necessary but do not rely on constant direction.

Clear Communication

You communicate in a concise, professional, and decisive manner. You can convert complicated or disorganized information into a clear summary.

Professional Confidence

You are comfortable following up firmly with brokers, vendors, executives, and professional advisors while maintaining positive relationships.

Organizational Discipline

You create reliable systems, maintain accurate records, and prevent commitments from being forgotten.

Pattern Recognition

You identify recurring problems, bottlenecks, and underperformance before they become significant issues.

Discretion

You can be trusted with confidential financial, personnel, business, investment, and personal information.

Calm Execution

You remain composed and effective when priorities shift, information is incomplete, or others are not responding as expected.

Experience and Qualifications

Demonstrated experience managing complex priorities with limited supervision
Strong written and verbal communication skills
Advanced organizational, calendar-management, and follow-up capabilities
Experience supporting multiple businesses, entities, or workstreams
Strong proficiency with modern productivity, communication, document-management, and collaboration tools
Experience working with confidential business and financial information

Experience in one or more of the following areas is strongly preferred:

Entrepreneurial or founder-led businesses
Investment or deal-oriented environments
Professional services
Multi-location businesses
Finance, bookkeeping, or operational coordination

First 90-Day Success Measures

During the first 90 days, the successful candidate will be expected to:

Establish an effective inbox-triage and escalation process
Significantly reduce the volume of routine matters requiring CEO involvement
Assume ownership of recurring administrative responsibilities
Implement a reliable open-loop and follow-up tracking system
Establish weekly reporting and executive-summary routines
Ensure brokers and key vendors provide consistent, structured updates
Create clear escalation criteria for financial, personnel, strategic, legal, and reputational matters
Eliminate unresolved administrative items that lack an owner or next step
Demonstrate sound judgment regarding what should—and should not—reach the CEO
Build sufficient trust to operate independently within established authority

Compensation

Competitive compensation based on experience, qualifications, and demonstrated judgment.

The compensation package may include a performance-based bonus tied to execution quality, reliability, operational improvement, and the level of trust and responsibility earned in the role.

How to Apply

Applicants should submit a current resume

Final Note

This role requires judgment, confidence, discretion, and consistent execution—not perfection.

The ideal candidate enjoys creating structure, taking ownership, solving problems, and being the trusted person who quietly makes everything run better.

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