Executive Assistant to the Chief Executive Officer

Executive Assistant To The CEOPenta 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 & ResponsibilitiesExecutive Support & Calendar CommandOwn and manage the CEO's calendar with a strategic lens, proactively resolving conflicts, prioritizing high-value activities, and protecting time for deep workCoordinate complex domestic and international travel, including detailed itineraries, contingency planning, and real-time adjustmentsPrepare the CEO for every meeting and engagement with day-ahead and week-ahead briefings, background research, and materialsManage expense reporting, reimbursements, and budget tracking with complete accuracyServe as the primary gatekeeper for the CEO's time, exercising sound judgment on prioritization and accessProvide scheduling support to other members of the C-suite as needed, coordinating with their assistants and calendars to ensure smooth cross-executive alignmentStrategic & Business SupportAct as a partner to the CEO in streamlining decision-making and daily operationsAssist in the preparation of high-stakes materials, including board presentations, client-facing decks, and executive communicationsSupport business development and client management efforts, including research, meeting prep, and follow-up coordinationManage CRM (Salesforce) needs to ensure data accuracy and timely updatesLiaise with the Board, senior leadership, investors, and external partners with professionalism and discretionAnticipate the CEO's needs and proactively solve problems before they escalateConfidentiality & DiscretionHandle highly sensitive, confidential, and proprietary information with absolute discretionServe as a trusted advisor who can be relied upon in high-pressure, time-sensitive, or sensitive situationsExercise excellent judgment in representing the CEO internally and externallyCross-Functional & Organizational LeadershipPartner with Operations, IT, Marketing, and other teams to ensure seamless execution of CEO prioritiesLead coordination of executive-level events, offsites, and high-profile meetings, managing logistics, vendors, and contracts end-to-endServe as a resource and mentor to other administrative staff, setting the standard for executive support across the firmManage ad-hoc, high-priority projects as directed by the CEOQualifications7+ years of experience supporting C-suite executives, ideally a CEO, Founder, or President, in a fast-paced professional services, consulting, or corporate environmentImpeccable judgment, discretion, and a demonstrated ability to handle confidential information with the utmost integrityExecutive presence and polish, with the ability to represent the CEO credibly in high-stakes settingsExceptional written and verbal communication skillsProven ability to manage complex, competing priorities in a fast-moving environment without dropping detailsA proactive, "no task too big or small" mindset paired with the strategic judgment to know what matters mostStrong 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 automationAvailability and flexibility to accommodate the CEO's schedule, including occasional evenings, weekends, or travel as neededComposure and grace under pressure; unflappable in high-stakes or fast-changing situationsSalary RangeThe 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:Penta Group is committed to providing a comprehensive and competitive benefits package to support the well-being and financial security of our employees. For US employees, our benefits include: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 premiumsRetirement 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 savingsIncome Protection: Employer-paid short-term disability (STD), long-term disability (LTD), and life insurancePaid Parental Leave: 12 weeks of paid parental leave for birthing and non-birthing parentsFlexible Paid Time Off: Flexible Paid Time Off (PTO) policy and a generous holiday scheduleAdditional Perks & Support:A monthly cell phone reimbursementFrequent firm-wide social events and team-building activitiesAccess to Employee Assistance Programs (EAP), including confidential counseling and resources for personal and work-related issuesWellness benefits including a gym membership discount program, mental health resources, and access to virtual health consultationsDiscounted employee-paid pet insurance coverage through NationwideLocationThis 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.