Executive Assistant to CEO

Senior Executive Assistant to the CEO

Location: Natick, MA

Schedule: Full-Time | On-Site

Compensation: $90,000–$100,000

 

Our client is a highly successful and established professional services organization seeking an exceptional Senior Executive Assistant to support its Founder and Chief Executive Officer.

This is not a traditional administrative support position. The Senior Executive Assistant will serve as a trusted strategic partner and right hand to an extremely busy executive, helping create structure, maintain momentum, and ensure that competing priorities are managed effectively.

 

The ideal candidate is highly proactive, exceptionally organized, and able to anticipate needs before they arise. This person must be comfortable operating in a fast-moving environment, managing up when necessary, and providing the reminders, follow-through, and accountability needed to keep a senior executive focused and on track.

 

Key Responsibilities

• Serve as the primary gatekeeper, strategic partner, and trusted resource to the CEO.
• Manage a highly complex and constantly changing calendar with urgency, accuracy, and sound judgment.
• Proactively identify scheduling conflicts, competing priorities, and potential issues before they disrupt the CEO’s schedule.
• Prioritize meeting requests, communications, deadlines, and commitments based on importance and business impact.
• Provide direct reminders and follow-up to ensure the CEO remains on schedule and key commitments are completed.
• Coordinate complex domestic travel, including flights, accommodations, ground transportation, detailed itineraries, dining reservations, speaking engagements, and contingency plans.
• Anticipate travel disruptions and make real-time adjustments when plans change.
• Coordinate internal and external meetings, speaking engagements, conferences, and public appearances.
• Prepare the CEO for meetings by organizing schedules, materials, background information, and key follow-up items.
• Monitor deadlines, commitments, and action items to ensure accountability and execution.
• Manage sensitive communications and confidential information with complete discretion.
• Build strong relationships with employees, clients, business partners, and other external stakeholders.
• Assist with personal executive logistics and lifestyle management as needed.
• Identify opportunities to improve efficiency, organization, communication, and overall executive productivity.
• Handle special projects and evolving priorities with limited direction.

Qualifications

• Bachelor’s degree required.
• 7+ years of experience supporting a CEO, Founder, President, or other C-level executive.
• Experience supporting senior executives within a large organization, high-growth business, or similarly demanding environment.
• Demonstrated success managing complex calendars, competing priorities, frequent travel, and rapidly changing schedules.
• Extensive experience coordinating detailed domestic travel arrangements and executive itineraries.
• Experience supporting an executive with frequent speaking engagements, public appearances, or external commitments is strongly preferred.
• Exceptional organizational, time-management, and follow-through skills.
• Strong judgment and the ability to make independent decisions with limited oversight.
• Confidence and executive presence to manage up, communicate directly, and keep a senior executive accountable.
• Ability to anticipate challenges and implement solutions before problems occur.
• High emotional intelligence and the ability to interact effectively with a wide range of personalities.
• Excellent written and verbal communication skills.
• Absolute professionalism, discretion, and respect for confidentiality.
• Ability to remain calm, adaptable, and solutions-focused when priorities change unexpectedly.
• Advanced proficiency with Microsoft Outlook, Word, Excel, PowerPoint, and calendar management tools.

 

The Ideal Candidate

The successful candidate will be someone who naturally thinks several steps ahead. They will not wait to be told what needs to happen and will take ownership of the CEO’s schedule, commitments, and priorities.

This individual must be comfortable creating order in an environment with constant movement and change. They will be resourceful, direct, polished, and confident enough to respectfully push back when necessary while maintaining a strong and trusted relationship with the CEO.

 

Why Consider This Opportunity?

• Direct partnership with a highly accomplished Founder and CEO.
• Opportunity to have a meaningful and immediate impact on executive productivity.
• Highly visible role with significant responsibility and autonomy.
• Stable and successful organization with a strong professional reputation.
• Competitive starting compensation of $90,000–$100,000, with flexibility for a truly exceptional candidate.
• Comprehensive benefits package