Executive Assistant to the Chief Executive Officer

Penta is a leading corporate affairs advisory firm that helps organizations predict what matters and shape outcomes through proprietary intelligence, stakeholder insights, and strategic counsel. Penta serves CEOs and leadership teams across business, policy, culture, and reputation, with offices in New York, Washington, D.C., San Francisco, London, Brussels, Dublin, and Singapore.

Penta Group is seeking an exceptional Executive Assistant to serve as a strategic partner and force multiplier for the CEO. This is a high-impact role focused on managing the CEO's time, information, priorities, calendar, travel, logistics, and operational execution with discretion and precision.

The ideal candidate will be a polished, resourceful professional who can support a C-suite executive in fast-paced, high-stakes environments. The role involves acting as a gatekeeper, sounding board, fixer, and trusted extension of the CEO while representing the CEO credibly with employees, clients, board members, investors, and external partners.

Penta is especially interested in candidates who are fluent with AI tools and can use them to improve communications, research, briefing materials, scheduling, and administrative workflows. The position is location-agnostic within the United States and may be performed fully remote, with occasional travel or in-person availability as needed. Candidates near Penta's offices, including Chicago, are welcome.

The base salary range is $90,000 to $120,000 per year, depending on experience and qualifications. Benefits include healthcare, retirement benefits with a 401(k) match, disability and life insurance, paid parental leave, flexible paid time off, cell phone reimbursement, employee assistance programs, wellness benefits, social events, and discounted pet insurance.

• 7+ years of experience supporting C-suite executives, ideally a CEO, Founder, or President, in a fast-paced professional services, consulting, or corporate environment.
• Impeccable judgment, discretion, and demonstrated ability to handle confidential information with the utmost integrity.
• Executive presence and polish, with the ability to represent the CEO credibly in high-stakes settings.
• Exceptional written and verbal communication skills.
• Proven ability to manage complex, competing priorities in a fast-moving environment without dropping details.
• A proactive, no-task-too-big-or-small mindset paired with the strategic judgment to know what matters most.
• Strong technology fluency, including Microsoft Office Suite, Google Workspace, and Salesforce or a comparable CRM.
• Demonstrated fluency with AI tools such as Claude, ChatGPT, or Copilot and a track record of using them to improve the speed and quality of work.
• Availability and flexibility to accommodate the CEO's schedule, including occasional evenings, weekends, or travel as needed.
• Composure and grace under pressure, remaining unflappable in high-stakes or fast-changing situations.

• Own and manage the CEO's calendar strategically, 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 meetings and engagements 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 regarding prioritization and access.
• Provide scheduling support to other C-suite members and coordinate cross-executive calendar alignment.
• Partner with the CEO to streamline decision-making and daily operations.
• Assist with high-stakes materials, including board presentations, client-facing decks, and executive communications.
• Support business development and client management through research, meeting preparation, and follow-up coordination.
• Manage Salesforce or comparable CRM needs to ensure data accuracy and timely updates.
• Liaise professionally and discreetly with the Board, senior leadership, investors, and external partners.
• Anticipate the CEO's needs and proactively solve problems before they escalate.
• Handle highly sensitive, confidential, and proprietary information with absolute discretion.
• Serve as a trusted advisor in high-pressure, time-sensitive, or sensitive situations.
• Exercise excellent judgment when representing the CEO internally and externally.
• Partner with Operations, IT, Marketing, and other teams to execute CEO priorities seamlessly.
• Coordinate executive-level events, offsites, and high-profile meetings, managing logistics, vendors, and contracts end-to-end.
• Serve as a resource and mentor to other administrative staff and help set the standard for executive support across the firm.
• Manage ad hoc, high-priority projects as directed by the CEO.