Executive Assistant to the Chief Executive Officer

Penta is a leading corporate affairs advisory firm that helps organizations predict what matters and shape outcomes. By combining proprietary intelligence, stakeholder insights, and strategic counsel, we help CEOs and leadership teams navigate the increasingly complex intersection of business, policy, culture, and reputation. Our clients turn to us when the stakes are high, the signals are difficult to interpret, and the consequences of getting it wrong are significant. We are building a new model for corporate affairs advisory and are seeking leaders who want to help define the future of the industry.

Penta’s global team brings decades of experience in business, government, communications, research, data science, and media. Our clients include many of the world’s most influential organizations across technology, financial services, energy, healthcare, and other sectors, including over 25% of the Fortune 100. Penta has offices in New York, Washington DC, San Francisco, London, Brussels, Dublin, and Singapore.

Summary Of Position Penta Group is seeking an exceptional Executive Assistant to serve as a strategic partner and force multiplier for our CEO. This is not a traditional administrative role. We’re looking for someone who can operate at the speed and altitude of a high-performing executive, anticipate needs before they’re voiced, and manage the CEO’s time, information, and priorities with total discretion and precision.

The right candidate will be a highly polished, sharp, and resourceful professional with a track record of supporting C-suite executives in fast-paced, high-stakes environments. You will be a gatekeeper, a sounding board, a fixer, and a trusted extension of the CEO — equally comfortable managing a complex international travel itinerary, synthesizing a board deck, or navigating a sensitive stakeholder conversation. This role demands exceptional judgment, unflappable composure under pressure, and the ability to represent the CEO’s interests and voice with credibility across the firm and with external partners, clients, and board members.

We’re especially interested in candidates who are fluent with AI tools and know how to use them to work faster and smarter, whether that’s drafting and refining communications, synthesizing research and briefing materials, or streamlining scheduling and administrative workflows. This is a role for someone who sees AI as a lever for higher-value work, not a replacement for judgment.

The CEO is supported by a Chief of Staff for strategic initiatives and cross-functional priorities. This role is focused on calendar management, logistics, and operational execution for the CEO, along with scheduling support for other members of the C-suite as needed.

Duties & Responsibilities Executive Support & Calendar Command

• Own and manage the CEO’s calendar with a strategic lens, proactively resolving conflicts, prioritizing high-value activities, and protecting time for deep work
• Coordinate complex domestic and international travel, including detailed itineraries, contingency planning, and real-time adjustments
• Prepare the CEO for every meeting and engagement with day-ahead and week-ahead briefings, background research, and materials
• Manage expense reporting, reimbursements, and budget tracking with complete accuracy
• Serve as the primary gatekeeper for the CEO’s time, exercising sound judgment on prioritization and access
• Provide scheduling support to other members of the C-suite as needed, coordinating with their assistants and calendars to ensure smooth cross-executive alignment

Strategic & Business Support

• Act as a partner to the CEO in streamlining decision-making and daily operations
• Assist in the preparation of high-stakes materials, including board presentations, client-facing decks, and executive communications
• Support business development and client management efforts, including research, meeting prep, and follow-up coordination
• Manage CRM (Salesforce) needs to ensure data accuracy and timely updates
• Liaise with the Board, senior leadership, investors, and external partners with professionalism and discretion
• Anticipate the CEO’s needs and proactively solve problems before they escalate

Confidentiality & Discretion

• Handle highly sensitive, confidential, and proprietary information with absolute discretion
• Serve as a trusted advisor who can be relied upon in high-pressure, time-sensit…