Executive Assistant Winemaker Jobs in Reston, VA

Total Wine & More is seeking an Executive Assistant to join our team in our Bethesda, MD office. This role will support the Chief Financial Officer. This role will provide high-quality, proactive administrative and operational support across a broad range of executive priorities and business activities. You will manage complex calendars, travel, executive meetings, communications, and confidential materials while helping leaders stay organized, informed, and focused on key priorities.

This position partners closely with executive leadership, other Executive Assistants, and cross-functional stakeholders to maintain strong coordination, communication, and day-to-day operations across the Finance department.

• Coordinate calendars, travel arrangements, and meeting logistics for the CFO, including prioritization and proactive conflict management
• Prepare agendas, presentations, executive materials, and support documentation for leadership and board-related meetings
• Support department operations by coordinating meetings, tracking action items and deadlines, and helping manage follow-up across multiple stakeholders
• Assist with Town Hall coordination, leadership communication, team engagement activities, and special projects
• Manage administrative operations including expense reporting, document management, travel itineraries, reservation coordination across the organization
• Support onboarding/offboarding activities, internal communications, and team operational needs as needed
• Handle highly sensitive financial, legal, and organizational information with professionalism and discretion

• Bachelor’s degree with 5+ years of experience supporting senior executives, preferably within Finance, Legal, or other corporate leadership functions
• Exceptional organizational and prioritization skills, with the ability to anticipate needs, manage competing priorities, and maintain strong attention to detail
• Strong judgement, follow-through, and problem-solving skills in dynamic and evolving environments
• Excellent written and verbal communication skills
• Advanced proficiency in Microsoft Office Suite and collaboration tools, including Outlook, PowerPoint, Teams, Word, and Excel
• Experience supporting executive meetings, leadership communications, and board-related materials preferred
• High level of discretion and confidentiality when handling sensitive information
• Ability to operate independently while maintaining strong collaboration across teams and stakeholders

• 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!

We recognize our team members are our biggest asset, and we value the critical role each play in contributing to the company’s success. It is our commitment to support and provide access to the resources needed to take care of their health and wellbeing. That is why we offer a variety of benefits, tools, and resources to support through our Total Rewards program.

Total Wine & More considers several factors when establishing compensation. Compensation may vary based on a number of factors including, but not limited to, market location, job-related knowledge, skills and/or experience. The actual hourly rate will equal or exceed the required minimum wage applicable to the job location. Estimated salaries determined by third parties have not been validated by Total Wine & More.

Total Wine & More is an equal opportunity employer and all qualified applicants will receive consideration for employment without discrimination based on race, color, religion, national origin, sex, sexual orientation, age, marital status, veteran status, disability, or any other characteristic protected by applicable law. Total Wine & More makes reasonable accommodations during all aspects of the employment process, including during the interview process. Total Wine & More is a Drug Free Workplace.

The information provided above indicates the general nature and level of work required of the position and is not a comprehensive list of all responsibilities or qualifications. Benefits list is only a highlight of some of the benefits offered to team members; eligibility for certain benefits apply.The anticipated close date of this posting is 120 days from the posted date indicated above.