Executive Assistant

About The Role

Total Wine & More is seeking an Executive Assistant to join our team in our Bethesda, MD office. This role will need to provide high‑quality, proactive administrative support to multiple executive leaders across. You will manage a wide range of executive administrative operations, including phone and inbox support, digital file and document management, coordinating complex calendars and meetings, and arranging domestic and international travel.

You will also contribute to special projects by organizing workflows, tracking milestones, and supporting the execution of project plans. This position partners closely with other EAs and cross‑functional stakeholders to maintain smooth, professional operations across the three functions.

• Coordinate the daily calendar, travel, and meeting logistics for multiple executive leaders, including scheduling, prioritization, and proactive conflict resolution.
• Support department operations by preparing agendas, meeting materials, and food arrangements, and assist in tracking meeting outcomes and next steps as well managing Town Hall content and deadlines, organizing team engagement events, and assisting with seasonal décor and special projects.
• Manage administrative tasks such as organize and maintain current files, expense reconciliation, report printing, mail handling, travel itineraries, reservation documents, and subscription records and note transcription to ensure smooth day‑to‑day execution.
• Assist with onboarding and offboarding processes, internal communications, and resource coordination for HR programs and team support needs.
• Maintain office organization and supplies, including floor‑level responsibilities like replenishing materials, coordinating clean‑up efforts, and troubleshooting basic tech issues.

• Bachelor’s degree with 1-4 years of administrative assistant experience for SVP or above, retail experience a plus.
• Exceptional organization and prioritization skills, with the ability to keep projects and programs on track, anticipate next steps, and confidently guide others to meet deadlines.
• Proactive problem‑solving and clear, effective communication, with the judgment to pivot quickly and stay productive in fast‑changing environments.
• Positive energy and team‑oriented mindset, contributing to a strong, engaging, and purpose‑driven team culture.
• Strong cross‑functional collaboration skills, partnering effectively with other EAs, IT, Facilities, and broader business teams.
• Advanced proficiency in Microsoft Office and collaboration tools, including Outlook and PowerPoint (animations), intermediate Excel and Word, and Microsoft Teams or Zoom.
• Ability to anticipate needs and proactively surface relevant information, risks, deadlines, or emerging issues before they escape.
• High level of discretion and confidentiality, especially when handling sensitive talent, organizational, legal, or commercial information.
• Comfort navigating ambiguity, multi‑tasking, and maintaining productivity under tight deadlines.
• Understanding of People and Supply Chain operating cycles and peak periods, with the ability to adjust priorities during critical time frames.
• Strong attention to detail and accuracy, including advanced proofreading skills.
• Working knowledge of legal documentation, compliance, writing, and legal support services.

• Paid Time Off (PTO)
• Generous store discounts
• Health care plans (medical, prescription, dental, vision)
• 401(k), HSA, FSA, Pre‑tax commuter benefits
• Disability & life insurance coverage
• Paid parental leave
• Pet insurance
• Critical illness and accident insurance
• Discounted home and auto insurance
• College tuition assistance
• Career development & product training
• Consumer classes
• + More!

Total Wine & More is the country's largest independent retailer of fine wine, beer and spirits, and we continue to grow our footprint year over year. Total Wine offers exciting and unique career opportunities across the country and in our corporate office. Our strength is our people. We have a commitment to training and career growth, all in an environment that values new ideas and teamwork.

If you share our entrepreneurial spirit and a…