Executive Assistant and Office Manager

Wingate Living

Schedule: Full-Time

Monday – Friday

Salary: $90,000-100,000

Benefits: 401K, Health, Dental, Vision insurance

Your Career. Your Calling. Our Commitment to Exceptional Care.

At Wingate Living, we're more than just senior living--we're builders of lifestyles, friendships, and communities you'll be proud to be part of. As a family-owned company with over 30 years of experience throughout Massachusetts and Rhode Island, we offer a unique blend of healthcare and hospitality through a full continuum of premier services.

Position Summary

The Executive Assistant & Office Manager serves as a trusted partner to the President, CEO, COO, and SVP of Development at Wingate Living, providing high-level administrative support while ensuring the smooth day-to-day operation of the corporate home office. This is a highly visible role requiring exceptional organizational skills, professional discretion, strong communication, and the ability to work independently across multiple priorities.

Essential Duties And Responsibilities

Executive & Administrative Support

• Provide dedicated executive support to the President, CEO, COO, and SVP of Development
• Manage and monitor the President and COO’s calendars weekly; proactively identify and resolve scheduling conflicts, including last-minute changes and adjustments
• Prepare and distribute meeting agendas; send prep communications to all stakeholders ahead of key meetings
• Manage the bi-weekly Operations Review, monthly investor and/or partner meeting series end-to-end
• Coordinate logistics for annual company-wide meetings including the Community Business Plan Presentations and Senior Managers' Strategic Planning Meeting
• Arrange all travel for the President —flights, ground transportation, and accommodations; prepare detailed itineraries
• Support the COO with all administrative tasks, including memo drafting and document proofreading
• Support the SVP of Development with tracking system updates and document organization as needed
• Liaise with Mass-ALA on behalf of the President; manage membership portal, training registrations, and annual awards ceremony participation
• Coordinate gift ordering for special occasions and recognition as directed
• Prepare and submit monthly expense reports for the CEO, President and COO
  
  

Office Management

• Greet and welcome all office visitors in a professional and friendly manner
• Screen and manage incoming calls and correspondence; respond where appropriate or route to the relevant team member
• Maintain a clean, organized, and fully stocked office environment; perform daily routines
• Manage all office supply ordering through WB Mason and Amazon; maintain inventory levels across the kitchen and supply room
• Manage facilities needs through the Taurus Management portal; maintain vendor relationships with Culligan, Shred-IT, Cintas, Xerox, and Quadient
• Sort and distribute incoming mail; maintain and update the office directory monthly
• Reconcile corporate card charges monthly; process and route invoices to appropriate finance contacts
  
  

Communications and Events

• Serve as the primary internal communicator for all home office operational matters
• Draft and distribute email announcements to the correct audience — Home Office List or Wingate ALL
• Manage the annual holiday schedule; coordinate early dismissal plans and send all holiday communications with President approval
• Manage the monthly birthday recognition program via Snappy for home office and community leaders
• Coordinate monthly birthday card production and mailing for all community employees
• Plan and execution of office and company-wide events and celebrations
• Perform other tasks or duties as needed or directed.
  
  

Position Requirements

• Bachelor's degree preferred; 5 years of executive administrative experience required
• Proficiency in Microsoft Office Suite (Word, Excel, PowerPoint, Outlook) and Microsoft Teams
• Strong written and verbal communication skills across all levels of the organization
• Highly organized with the ability to manage multiple priorities, changing needs, and competing deadlines
• Proactive and self-directed; comfortable working independently with minimal supervision
• Exercises sound judgment and maintains strict confidentiality at all times
• Willingness to learn platforms including ADP, Yardi, SharePoint, and Snappy