Executive Assistant

Company Description Good Trouble Small Batch Kentucky Bourbon exists to remind us that great things begin with a conversation.

We believe bourbon has always been about more than what is in the glass. It is about the people around it. The stories shared. The friendships formed. The ideas sparked. The communities strengthened.

Inspired by the call to make “good trouble,” we create award-winning bourbon and experiences that bring people together around a shared purpose: connection. Through culture, conversation, music, entrepreneurship, and community engagement, we celebrate those who dare to dream, build, lead, and leave the world better than they found it.

We don’t just make bourbon.

We create moments that inspire connection, conversation, and change.. Good Trouble is equally dedicated to social impact, donating a portion of every bottle sold to the Shine Your Light Foundation. This commitment reflects a core belief in giving back to communities as an essential part of doing business.

Role Description The Executive Assistant is a full-time, remote or hybrid role based in Chicago, IL. This role will provide high-level executive support, including managing calendars, coordinating meetings, arranging travel, and preparing internal and external communications. The Executive Assistant will handle expense reports, track reimbursements, and support budgeting-related administrative tasks. Day-to-day responsibilities include organizing documents, maintaining files, preparing presentations, and assisting with meeting agendas, notes, and follow-ups. The role also involves serving as a primary point of contact for internal and external stakeholders, ensuring timely, clear communication and supporting special projects as needed in a fast-paced, growing organization.

Qualifications

• Candidates should possess strong Executive Administrative Assistance and Administrative Assistance skills, including calendar management, travel coordination, and document organization.
• Candidates should possess solid Executive Support and Expense Reports experience, including preparing, tracking, and reconciling expenses for senior leaders.
• Candidates should possess excellent Communication skills, both written and verbal, with the ability to interact professionally with diverse stakeholders.
• Proficiency with productivity tools (e.g., Microsoft Office or Google Workspace) and familiarity with basic project coordination or task management software.
• Strong attention to detail, organization, and time-management skills, with the ability to handle confidential information with discretion.
• Prior experience supporting executives or senior leadership, preferably in a small business, consumer goods, or hospitality/spirits environment, is beneficial.
• High school diploma or equivalent required; an associate or bachelor’s degree in Business Administration, Communications, or a related field is preferred.