Chicago Office & Admin Specialist; Contractor Chicago, IL - Hybrid

Chicago Office & Admin Specialist (Contractor)

Chicago, IL - Hybrid

Transcarent's Chicago Office & Admin Specialist (Contractor)
is a part-time, contract position
, responsible for the day-to-day operations, experience, and functionality of the Chicago office. This role serves as the single-threaded owner for office operations, workplace experience, and executive visit coordination - ensuring the office runs smoothly, employees feel supported, and leadership visits are seamless. This role also provides overflow and backup support to the Executive Assistants (EA) for executive leadership, assisting with administrative coordination, logistics, and preparation related to executive priorities and leadership activities.

The individual in this role will work closely with the EA to ensure seamless executive support, particularly during periods of high volume, travel, or executive presence in the Chicago office.

This is a highly cross-functional role requiring strong organization, ownership, and proactive communication.

• Own all building management requests, vendor coordination, and facilities-related issues.
• Oversee office supplies, snacks, and water replenishment, ensuring consistent availability within budget.
• Oversee office necessities (kitchen, common areas, meeting rooms) and maintain high-quality workplace experience for a positive employee experience.
• Maintain and update office security access lists in partnership with IT and People Operations. Primary point of contact for contracted facilities vendors and monitoring PHI compliance.
• High level calendar management skills, with conference room scheduling as needed.
• Provides information to stakeholders (employees and senior leadership) by answering questions and requests in a timely fashion.
• Assist with onboarding of new employees by providing tours and procedural training.
• Handle sensitive and confidential information with discretion and sound judgment when supporting executive priorities.
• Provide administrative and logistical assistance to the EAs, including calendar coordination, meeting preparation, travel logistics support, and follow‑up tracking as needed.
• Act as a backup resource for EAs during periods of high demand, executive travel, or planned time away.
• Support preparation for senior leadership visits to the Chicago office, including space readiness, agendas, materials, and on‑site coordination.
• Partner with the EAs to ensure consistent, high‑touch executive and visitor experiences.

• Own and execute Moments That Matter (one day a month) and other office-based social programming, including end-to-end planning and logistics for Chicago-based Town Halls and in‑office gatherings, to foster connection, engagement, and alignment among employees. Manage communications for the Chicago Slack channel, including office updates, events, and announcements.
• Partner with Marketing on ad hoc swag orders, office branding needs, and special requests.

• Manage and coordinate senior leadership requests related to Chicago office visits.
• Partner closely with EAs on senior leadership travel, office logistics, and visit coordination.
• Manage visitor room bookings, ensuring spaces are prepared and a high‑touch experience is delivered.
• Assist with security list updates related to executive and visitor access.

• Act as a connector between People Ops, IT, EAs, Marketing, and Facilities.
• Ensure clear ownership, timely follow‑through, and proactive, forward‑looking communication across stakeholders.

• 3–5+ years of experience in Office Management, Workplace Operations, Executive Operations, Administrative Assistant support.
• Strong organizational skills with the ability to manage multiple work streams simultaneously.
• Excellent written and verbal communication skills.
• Comfort working cross‑functionally and handling confidential information.
• Proactive, detail‑oriented, attention to detail, and solutions‑focused mindset.
• Experience supporting executive visits or leadership teams is a plus.
• Ability to lift and move heavy items as needed to support office…