Executive Assistant to the Chief Executive Officer

About Penta Group

Penta is a premier corporate affairs advisory company guiding organizations through complex intersections of business, policy, culture, and reputation via proprietary intelligence, insights, and strategic advice. Serving many top-tier companies worldwide, including over a quarter of the Fortune 100, Penta operates globally with offices in New York, Washington DC, San Francisco, London, Brussels, Dublin, and Singapore.

Role Overview

The Executive Assistant position at Penta is a strategic partnership role supporting the CEO, requiring anticipatory management of the CEO’s schedule, priorities, and communications with utmost discretion and precision. This role involves sophisticated calendar management, international travel logistics, and preparation of critical briefing materials, functioning as a trusted advisor and representative of the CEO across internal teams and external stakeholders.

Key Responsibilities

• Strategically own and manage the CEO’s calendar, resolving conflicts and safeguarding time for focused work.
• Organize intricate domestic and international travel plans with contingency readiness and real-time adjustments.
• Prepare detailed meeting briefings and background research to equip the CEO for engagements.
• Handle expense reporting and budget tracking accurately.
• Act as the primary gatekeeper of the CEO’s time, making informed decisions on priorities and access.
• Support scheduling for other C-suite executives, ensuring alignment and coordination.
• Partner with the CEO to streamline daily operations and decision-making processes.
• Assist in creating high-impact materials like board presentations and client decks.
• Support business development activities including research, meeting preparation, and follow-up correspondence.
• Maintain CRM data accuracy and timely updates using Salesforce.
• Engage professionally with the Board, investors, senior leadership, and external partners.
• Proactively identify and resolve potential issues before escalation.
• Protect sensitive information with strict confidentiality and exercise sound judgment in representing the CEO.
• Collaborate cross-functionally with operations, IT, marketing, and other teams to execute priorities smoothly.
• Organize executive-level events, offsite meetings, and manage vendor relationships and contracts end-to-end.
• Mentor and support other administrative staff, setting high standards for executive assistance across the firm.
• Take on special high-priority projects as assigned by the CEO.

Required Qualifications

• Minimum 7 years’ experience supporting senior executives, preferably a CEO or equivalent, in fast-paced professional services or corporate settings.
• Excellent judgment, discretion, and ability to manage confidential information with integrity.
• Polished executive presence able to represent the CEO credibly in critical situations.
• Strong written and verbal communication skills.
• Proven track record of managing multiple complex priorities efficiently.
• Proactive approach to tasks, combining attention to detail with strategic discernment.
• High proficiency with Microsoft Office, Google Workspace, and Salesforce or similar CRM platforms.
• Experienced and fluent in using AI tools (e.g., Claude, ChatGPT, Copilot) to enhance productivity and workflow automation.
• Willingness to accommodate flexible hours, including some evenings, weekends, or travel as required.
• Remain calm and composed in pressure situations, exhibiting professionalism at all times.

Compensation and Benefits

The annual salary ranges from $90,000 to $120,000, based on experience and relevance to the role.

• Comprehensive medical, vision, and dental insurance largely covered by the company for employees and partially for dependents.
• 401(k) retirement plan with a generous employer match structure.
• Employer-paid disability and life insurance coverage.
• Paid parental leave of 12 weeks for all parents.
• Flexible paid time off policy and substantial holiday allowance.
• Monthly cell phone reimbursement.
• Frequent social and team-building events.
• Access to Employee Assistance Programs offering confidential support services.
• Wellness programs including gym discounts and mental health resources.
• Discounted employee-paid pet insurance.

Location and Diversity Commitment

This role is open to candidates anywhere in the United States with remote work flexibility. Although not mandatory, proximity to Chicago (CEO's location) is welcomed. Occasional travel or in-office presence may be necessary.

Penta Group upholds equal employment opportunities and complies with anti-discrimination laws, supporting diverse candidate backgrounds and providing reasonable accommodations for individuals with disabilities throughout the hiring process.