Senior EA / Executive Support Lead

Chief of Staff / Executive Assistant

Work Arrangement: Primarily Work From Home, with Hybrid Requirements When Needed

Employment Type: Full-Time

Salary: Fixed, Competitive Package (To Be Disclosed During Recruitment)

About the Role

We are looking for an exceptional Chief of Staff / Executive Assistant to work closely with a high-performing, fast-paced senior executive.

This is not a traditional Executive Assistant position. We need someone who can think strategically, make independent decisions, take control of situations, and confidently challenge the executive when necessary.

The ideal candidate is highly capable, emotionally intelligent, assertive, and exceptionally organized. They should be comfortable working alongside a strong personality and have the confidence to push back, establish boundaries, and make sound decisions in the executive's best interests.

We are looking for someone who does not simply follow instructions but anticipates needs, solves problems, and ensures that priorities are executed effectively.

This role requires a high level of trust, professional compatibility, discretion, and accountability.

Key Responsibilities

Executive Partnership and Strategic Support

• Serve as a trusted right-hand partner to the executive, providing both strategic and operational support.
• Actively manage the executive's priorities, commitments, and competing demands.
• Exercise independent judgment and make decisions without requiring constant approval.
• Confidently challenge ideas, provide honest feedback, and recommend alternative approaches when necessary.
• Help the executive stay focused on high-impact activities by managing distractions and unnecessary commitments.
• Anticipate potential issues and proactively implement solutions.

Executive Management and Decision-Making

• Take ownership of the executive's calendar, meetings, schedules, and daily priorities.
• Confidently decline, redirect, or reschedule requests that do not align with business priorities.
• Act as a professional gatekeeper, protecting the executive's time and attention.
• Make informed decisions on behalf of the executive within clearly established authority.
• Manage sensitive conversations and competing stakeholder expectations with professionalism and tact.
• Bring structure, accountability, and follow-through to a fast-moving executive environment.

Operational Coordination and Execution

• Oversee important projects, deliverables, and executive-level initiatives.
• Coordinate with internal teams, external partners, clients, and key stakeholders.
• Monitor action items and ensure commitments are completed on time.
• Identify operational inefficiencies and recommend improvements.
• Prepare executive briefings, reports, presentations, and correspondence as needed.
• Handle confidential business matters with exceptional discretion.

Relationship and Stakeholder Management

• Develop a strong, trust-based professional working relationship with the executive.
• Communicate confidently with senior leaders and influential stakeholders.
• Maintain composure and sound judgment during high-pressure situations.
• Navigate challenging personalities and sensitive discussions with maturity and professionalism.
• Represent the executive professionally in meetings and communications when authorized.

Qualifications and Experience

Required Qualifications

• Significant experience as a Senior Executive Assistant, Chief of Staff, Executive Business Partner, or in a similar senior executive support role.
• Proven experience working directly with C-suite executives, founders, business owners, or other senior decision-makers.
• Demonstrated ability to independently manage executive priorities and make sound business decisions.
• Strong communication, negotiation, stakeholder management, and problem-solving skills.
• Exceptional organizational abilities and attention to detail.
• High emotional intelligence, professional maturity, and resilience.
• Ability to remain composed and decisive in high-pressure environments.
• Strong proficiency in executive productivity tools, scheduling platforms, and business communication systems.
• Ability to maintain strict confidentiality and exercise excellent professional judgment.

Highly Preferred

• Experience supporting a high-profile, entrepreneurial, or particularly fast-paced executive.
• Experience in a Chief of Staff or strategic Executive Business Partner capacity.
• Proven ability to challenge senior leaders constructively and professionally.
• Experience coordinating multiple projects and managing complex stakeholder relationships.
• Demonstrated ability to operate with minimal supervision and take full ownership of responsibilities.

The Ideal Candidate

We are looking for someone who:

• Is confident, not submissive. Can respectfully disagree with an executive and explain why a different approach is better.
• Is a decision-maker, not just a task-taker. Can evaluate situations, exercise judgment, and take action independently.
• Has a strong personality and professional presence. Is comfortable engaging with influential, demanding, and high-performing individuals.
• Is emotionally mature. Understands how to manage difficult conversations, maintain boundaries, and remain composed.
• Is naturally proactive. Anticipates what needs to happen before being asked.
• Can take control. Brings structure to ambiguity, manages competing demands, and ensures things get done.
• Understands professional boundaries. Can build a close, trusted working partnership while maintaining appropriate professionalism.
• Is exceptionally dependable. Takes accountability seriously and consistently delivers high-quality work.

Work Arrangement

This position is primarily work from home, offering flexibility while requiring a high level of availability, responsiveness, and accountability during agreed working hours.

A hybrid arrangement may be required when the executive or client is physically present, particularly for important meetings, business engagements, and other executive support needs.

The successful candidate must be comfortable adapting to changing business priorities and occasional in-person requirements.

Why Join Us

This is an opportunity to work closely with a high-performing executive in a position that offers significant responsibility, autonomy, and exposure to senior-level business decisions.

You will be trusted to take ownership, influence outcomes, and contribute meaningfully to the executive's effectiveness and the organization's success.

We are not simply looking for someone who can manage a calendar. We are looking for someone who can manage priorities, challenge decisions, bring order to complexity, and become an indispensable professional partner.