Second Executive Assistant to the President & Chief Operating Officer

What We Need We are seeking a highly organized, proactive, and trusted Second Executive Assistant to support the President & Chief Operating Officer in a fast-paced media and entertainment environment. Reporting directly to and working in close partnership with the Primary Executive Assistant, this role is responsible for taking ownership of defined operational, business, and personal responsibilities to ensure seamless day-to-day execution. This position is ideal for an ambitious, highly capable assistant who is excited to learn, jump in wherever needed, and grow within a C‑suite support function. You will act as an extension of the Primary EA in anticipating needs, maintaining constant communication, and ensuring nothing slips through the cracks in a high‑trust, high‑volume office. What You’ll Do Calendar & Schedule Support Partner with the Primary EA to manage the President & COO’s complex, high-volume calendar, ensuring smooth transitions and proper preparation across all commitments Coordinate internal leadership meetings, cross functional check-ins, production calls, studio briefings, and external partner meetings Monitor recurring meetings and ensure invites, agendas, meeting materials, and dial in details are correct and distributed; flag upcoming deadlines, priorities, and scheduling risks early Maintain deep familiarity with the President & COO’s preferences, relationships, and working style Travel & Logistics Coordinate business and personal travel arrangements, including flight schedules, ground transportation, hotel accommodations, catering, and itineraries Prepare detailed itineraries and provide on-the-ground support for trips, events, and offsites Support on-site meetings while traveling, including catering coordination and printed materials Manage logistics with privacy, discretion, and accuracy Business & Office Operations Manage and reconcile business expenses Maintain organized filing systems, contact lists, and documentation Support special projects and ad hoc initiatives as assigned Coordinate onsite meetings, including catering and materials Availability & Flexibility Must be available after hours, on weekends, and on short notice as needed Expected to travel regularly with the President & COO Flexibility and responsiveness are critical to success in this role What You’ll Need Excited about the media and entertainment industry Ambitious and eager to jump in wherever needed Strong drive and growth mindset Exceptionally organized and detail oriented Calm, adaptable, and resilient in high-pressure environments Comfortable with ambiguity and learning as they go Interested in being a long-term assistant and trusted partner Serving as a trusted point of contact for sensitive matters Working Style & Team Dynamic High transparency and frequent communication Clear expectations and constant alignment A collaborative, team-first mentality What You’ll Bring Respect for others and a strong belief that others should do this in return Ability to perform work and resolve straightforward problems within established procedures with moderate supervision Understanding of when to seek guidance for unforeseen problems Close attention to detail, following up until issues are resolved Solid written and verbal communication skills Compensation Salary to be determined by multiple factors including but not limited to relevant experience, knowledge, skills, other job-related qualifications, and alignment with market data. $28.84 - $36.05 Location New York, NY: 125 West 55th Street, 10019 Position Type Regular Time Type Full time Pay Type Hourly Benefits iHeartMedia’s benefits offering is flexible and offers a variety of choices to meet the diverse needs of our changing workforce, including the following: Employer sponsored medical, dental and vision with a variety of coverage options Company provided and supplemental life insurance Paid vacation and sick time Paid company holidays A Spirit day to encourage and allow our employees to more easily volunteer in their community A 401K plan Employee Assistance Program (EAP) at no cost - services include telephonic counseling sessions, consultation on legal and financial matters, emotional well-being, family and caregiving A range of additional voluntary programs, such as spending accounts, student loan refinancing, accident insurance and more! We are accepting applications for this role on an ongoing basis. The Company is an equal opportunity employer and will not tolerate discrimination in employment on the basis of race, color, age, sex, sexual orientation, gender identity or expression, religion, disability, ethnicity, national origin, marital status, protected veteran status, genetic information, or any other legally protected classification or status. Non-Compete will be required for certain positions and as allowed by law. Our organization participates in E-Verify. Click here to learn about E-Verify. #J-18808-Ljbffr NAB Leadership Foundation