Chief of Staff in Des Plaines, Illinois

Chief Of Staff

Good Trouble 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. Be Good, Do Good to Shine Your Light foundation supports the company's belief in giving back to communities. Team members join a growing spirits company that blends craftsmanship with purpose.

The Chief of Staff is a full-time, hybrid role based in Chicago, IL, with flexibility for partial work from home. This role will act as a strategic advisor and operational partner to the CEO, helping translate vision into actionable plans and ensuring alignment across priorities. Day-to-day responsibilities include organizing and leading cross-functional initiatives, managing executive calendars and key meetings, preparing briefing materials, and tracking follow-ups and deliverables.

The Chief of Staff will coordinate business planning, support budgeting and performance reviews, and develop dashboards or reports to monitor progress toward company goals. This role will also support stakeholder communications, assist with investor and partner relations, and help shape internal processes as the company scales. The ideal candidate is comfortable working in a growing, entrepreneurial environment in the spirits or consumer goods space.

• Strategic planning and execution skills, including experience turning high-level goals into detailed project plans and measurable outcomes.
• Strong organizational and project management skills, with the ability to prioritize multiple initiatives, manage timelines, and ensure follow-through.
• Excellent written and verbal communication skills, including experience preparing executive presentations, board materials, and concise summaries.
• Stakeholder management and relationship-building skills, with the ability to collaborate effectively across functions and levels, and represent leadership in meetings.
• Financial and business acumen, such as comfort with budgets, KPIs, and operational metrics, and the ability to synthesize data for decision-making.
• Experience in an entrepreneurial, high-growth, or startup environment; exposure to consumer packaged goods, beverage alcohol, or hospitality is a plus.
• High level of discretion and integrity when handling sensitive information, with sound judgment and a solution-oriented mindset.
• Bachelor's degree in Business, Communications, Public Policy, or a related field; advanced degree (MBA or similar) is a plus but not required.
• Comfort working in a hybrid environment in Chicago, IL, with occasional evening or weekend availability for events, tastings, or partner meetings.