Executive Administrative Assistant

Job DetailsJob Location: Cornerstone Corporate Office - Indianapolis, IN 46260Position Type: Full TimeJob Shift: DayJob Category: Admin - ClericalAt Cornerstone Companies, we don’t just build medical facilities — we create environments where healthcare thrives. For more than 35 years, Cornerstone has been a national leader in healthcare real estate development, construction, leasing, and management. With over $1 billion in completed developments and 10 million square feet managed across 22 states, we are proud to shape some of the nation’s most advanced medical spaces. Behind every successful organization is strong leadership — and strong executive support. We are seeking a highly experienced Executive Administrative Assistant to provide trusted, high-level support to the Chief Executive Officer who leads both Cornerstone Companies and Birge and Held. This role is ideal for a seasoned professional who thrives in a fast-paced environment, anticipates needs before they arise, and takes pride in enabling leadership to perform at their best. If you are organized, discreet, proactive, and thrive on solving complex logistical challenges — this is an exceptional opportunity to work at the center of two dynamic organizations. Why Cornerstone? Our culture is built on the three core values we live every day: Caring - We build lasting relationships with clients, partners, and teammates. In this role, you will serve as a trusted partner who supports the CEO and executive leadership team with professionalism and reliability. Creative - We develop thoughtful, innovative solutions that drive long-term success. Our Executive Assistant plays a key role in solving complex scheduling, travel, and logistical challenges with creativity and foresight. Character - We lead with integrity — always. This position requires the highest level of confidentiality, trust, and sound judgment when handling sensitive executive matters. When you join Cornerstone, you become part of a team that values professionalism, accountability, and collaboration — while supporting projects that directly impact healthcare delivery across the country. What You’ll Do As the Executive Administrative Assistant to the CEO, you will serve as a trusted partner responsible for coordinating the many moving pieces that support executive leadership across multiple organizations. Key responsibilities include: Managing the CEO’s complex calendar across multiple companies, including meetings, travel, and key events Anticipating scheduling conflicts and proactively prioritizing requests to maximize executive effectiveness Coordinating domestic and international travel logistics, including commercial and charter transportation Managing administrative and financial coordination for executive-related matters, including tracking invoices and approved transactions Supporting vendor coordination and administrative oversight for executive-owned properties Planning and coordinating executive events, company gatherings, and special initiatives Preparing weekly calendar summaries and schedule updates for the executive leadership team Maintaining executive memberships, subscriptions, and professional affiliations Supporting the CEO and external advisors with organization of tax-related documentation Serving as a trusted gatekeeper who helps prioritize requests and manage access to executive time Handling confidential information with professionalism, discretion, and sound judgment QualificationsWhat You Bring 10+ years of executive administrative support experience, preferably supporting C-suite leadership Demonstrated success managing complex calendars, travel coordination, and executive logistics Exceptional organizational skills and ability to manage competing priorities High level of discretion and professionalism when handling sensitive information Strong written and verbal communication skills Ability to anticipate needs, solve problems independently, and operate with minimal supervision Proficiency with Microsoft Office and executive scheduling tools Preferred: Experience supporting a CEO or executive leading multiple organizations Experience coordinating complex travel itineraries including charter travel Familiarity with basic accounting, invoicing, and expense tracking Experience supporting executive events and multi-stakeholder functions Notary public certification or willingness to obtain after hire Work Environment This role operates primarily in a professional office environment and works closely with executive leadership. Occasional schedule flexibility may be required to support executive travel, events, or time-sensitive matters. Join Our Team This is a unique opportunity to play a trusted and highly visible role supporting leadership across two growing organizations. If you are a seasoned executive assistant who thrives on organization, discretion, and making things run smoothly behind the scenes, we would love to hear from you. Cornerstone Companies is an equal opportunity employer and values diversity in the workplace.