Executive Assistant to the Chief Executive Officer

Role Description

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-sensitive, or sensitive situations.
  • Exercise excellent judgment in representing the CEO internally and externally.
• Cross-Functional & Organizational Leadership
  • Partner with Operations, IT, Marketing, and other teams to ensure seamless execution of CEO priorities.
  • Lead coordination of 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, setting the standard for executive support across the firm.
  • Manage ad-hoc, high-priority projects as directed by the CEO.

Qualifications

• 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 a 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 comparable CRM).
• Demonstrated fluency with AI tools (e.g., Claude, ChatGPT, Copilot) and a track record of using them to improve speed and quality of work, from drafting and research to scheduling and workflow automation.
• Availability and flexibility to accommodate the CEO's schedule, including occasional evenings, weekends, or travel as needed.
• Composure and grace under pressure; unflappable in high-stakes or fast-changing situations.

Salary Range

The base salary range for this position is $90,000 to $120,000 per year, depending on a candidate's experience and qualifications as they relate to the position.

Benefits

• Healthcare Coverage:
  • Excellent medical, vision, and dental insurance through Cigna and UNUM, with the company covering the majority of individual employee premiums and 50% of dependent premiums.
• Retirement Benefits:
  • A 401(k) plan with a generous employer match, contributing 100% on the first 3% of salary deferred and 50% on the next 2%, helping employees maximize their retirement savings.
• Income Protection:
  • Employer-paid short-term disability (STD), long-term disability (LTD), and life insurance.
• Paid Parental Leave:
  • 12 weeks of paid parental leave for birthing and non-birthing parents.
• Flexible Paid Time Off:
  • Flexible Paid Time Off (PTO) policy and a generous holiday schedule.
• Additional Perks & Support:
  • A monthly cell phone reimbursement.
  • Frequent firm-wide social events and team-building activities.
  • Access to Employee Assistance Programs (EAP), including confidential counseling and resources for personal and work-related issues.
  • Wellness benefits including a gym membership discount program, mental health resources, and access to virtual health consultations.
  • Discounted employee-paid pet insurance coverage through Nationwide.

Location

This position is location-agnostic within the United States. Candidates may be based near one of Penta's US offices or work fully remote. The CEO is based in Chicago, so candidates in or near Chicago are welcome, though it is not a requirement. Given the nature of the role, some flexibility for occasional travel or in-person availability may be required.