Senior Executive Assistant

Senior Executive Assistant to Executive Chair & CEOsLocation: Aurora, IllinoisWork Arrangement: On-siteBase Salary Range: $80,000–$90,000 annually About the RoleSimplify Recruiting is hiring on behalf of a group of healthcare technology businesses seeking a Senior Executive Assistant to support the Executive Chair and three CEOs.We’re looking for an experienced executive assistant who anticipates needs, exercises sound judgment, and keeps competing priorities moving with accuracy and composure. You will manage complex calendars, executive communications, global travel, and customer engagements, while responding effectively to last-minute changes.Success in this role requires initiative, clear communication, discretion, and dependable follow-through. Key ResponsibilitiesManage complex calendars across four senior leaders and multiple time zones, proactively resolving scheduling conflicts and prioritizing executive time.Independently coordinate executive requests within delegated authority, clarify requirements when needed, and escalate issues appropriately.Organize executive and customer visits, including meeting schedules, transportation, catering, conference-room preparation, and audiovisual readiness.Handle last-minute scheduling, travel, and logistical changes while communicating tradeoffs and keeping stakeholders informed.Plan domestic and international travel, prepare detailed itineraries, coordinate required documentation, and reconcile expenses.Draft and review executive correspondence, prepare meeting summaries, track action items, and follow through to completion.Prepare board materials, presentations, executive briefings, and other leadership communications.Coordinate with clients, partners, their Executive Assistants and Chiefs of Staff, and internal HR, IT, and Finance teams.Work across global time zones, including close coordination with India-based teams.Maintain confidential documents and handle sensitive executive and business information with discretion.Improve administrative workflows using Microsoft 365 and approved AI tools, with careful attention to accuracy and confidentiality. Key Requirements7+ years of experience supporting C-suite or senior executive leadership.Demonstrated experience directly supporting multiple senior executives simultaneously and resolving competing calendar and priority requests.Strong independent judgment, with the ability to anticipate needs, take initiative, and determine when clarification or escalation is necessary.Ability to distinguish urgent from important requests, communicate tradeoffs, and execute accurately under pressure.Strong listening skills and clear, concise written and verbal communication.Adaptability and composure during executive visits, customer meetings, and sudden increases in activity.Exceptional attention to detail, including reliable checks for scheduling, travel arrangements, and meeting logistics.Strong domestic and international travel coordination experience.Advanced proficiency in Microsoft 365, including Outlook, Teams, PowerPoint, and Excel.Ability to use modern technology and AI tools effectively and responsibly.Proven discretion, professionalism, and dependable follow-through.Ability to work on-site in Aurora, Illinois, with schedule flexibility during executive visits, customer meetings, and peak activity periods. Preferred QualificationsExperience in healthcare, healthcare technology, SaaS, or professional services.Experience supporting executives in global organizations, particularly across U.S.–India operations.Experience supervising administrative or office-support staff. Please submit your résumé highlighting your experience supporting multiple senior executives, coordinating complex logistics, and managing competing priorities.