Executive Assistant and Program Manager - Wayfair

Executive Assistant to the CFO/CAO, Head of Travel & EA Program

This position is a hybrid in-office role that works out of our Boston HQ. Monday-Thursday will be working in office and Friday is WFH. This is not a virtual / remote position.

Wayfair, the one of the largest omnichannel retailers of home furnishings and housewares in the United States, has an immediate need for a Senior Executive Assistant to manage the day-to-day activities for our Enterprise Leadership members, and lead both the Corporate Travel and EA program for Wayfair. This is a fantastic opportunity for the right individual to support the senior leaders and employees of one of the fastest-growing companies in Boston, MA!

The ideal candidate will bring strong organizational and planning skills, detail orientation, a high sense of urgency, a sense of humor, and problem-solving abilities to the role. This person should be smart, engaging, fun, curious, and unflappable.

Wayfair’s team of Executive Assistants play a crucial role in supporting executives. Their responsibilities include scheduling and coordinating meetings, managing travel arrangements, handling personal tasks (such as errands and appointment scheduling), and serving as the primary point of contact for visiting executives and major corporate investors. In this role, this person will also directly manage multiple senior EAs and shape the ongoing evolution of our EA program.

Wayfair’s travel program sets our global corporate travel strategy focused on ensuring smooth and safe travel at efficient spend. This position offers a unique opportunity for an experienced executive assistant looking to elevate their career.

Key Responsibilities:

• Supporting the Chief Financial Officer, Chief Administrative Officer, and the Chief People Officer. 
• Day-to-day administration and coordination of all areas of executive support.
• Proactively manage calendars with the ability to schedule and prioritize meetings, resolve schedule conflicts, collaborate with other team members, and stay several steps ahead to maintain efficiency.
• Schedule and coordinate numerous weekly and ad hoc meetings, ensuring that all details are managed and communicated effectively with all parties.
• Handle all aspects of travel arrangements, both international and domestic, with the ability to make frequent revisions as necessary.
• Manage business expenses for executives, ensuring timely and accurate processing after each trip.
• Manage and draft communications on behalf of their leaders.
• Provide logistical support for large in-office events, including Investor meetings, All Company Meetings, and employee holiday parties.
• Interact with key internal and external contacts, investors, and other C-level individuals in a professional manner.
• Set Global Corporate travel policy.
• Make business and process efficiency recommendations on travel program and project activities in line with business goals and objectives.
• Manage our travel and travel payments vendors.
• Ensure smooth day-to-day travel booking and traveler support.
• Administer and monitor the travel policies, guidelines and spend to deliver efficient travel.
• Must be able to represent the team in a positive way to people outside the company.
• Act as a point person for visiting executives and large corporate investors.
• Act as a direct manager for 3-5 other senior EA leads.
• Coach and mentor our Executive Assistants in achieving their long term career goals.
• Work closely with the EA Leads and other leaders at Wayfair to expand and enhance our talent development program for our Executive Assistants.
• Thrive in a fast-paced workplace by effectively multitasking and managing competing priorities.

Qualifications:

• Bachelor’s Degree.
• 7+ years of meaningful prior experience as an executive assistant, chief of staff, or other business operations role, including at least 5 years as a manager.
• Experience in working with multiple leaders at once.
• Demonstrable success in talent development and growing direct reports into expanded or new roles.
• Ability to be assertive and give push-back as needed.
• Meticulous attention to detail and strong planning and forward-thinking capabilities.
• Demonstrated ability to anticipate needs and situations before they are fully developed.
• Advanced proficiency in Google Enterprise Suite tools (calendar, mail drive, docs, sheets, slides, meet).
• Excellent written, verbal, and presentation skills.
• Extremely high level of discretion pertaining to confidential information.
• Flexible and able to handle ad hoc issues that may arise outside of core business hours.