Chief of Staff

Come Join Our Fine Fettle Family!

Fine Fettle is a family owned, locally run multi-state cannabis company with operations across Connecticut, Georgia, and Massachusetts. As a leading cannabis retailer, our mission is to create comfort in cannabis while enabling customers and patients to realize cannabis’ full potential to improve their lives. We are dedicated to providing exemplary products and superior customer experiences. We believe that we can truly make a difference in the lives of our patients and customers by utilizing our expertise to educate them about the plant and provide them with the right products to enhance their health and wellbeing.

We help customers incorporate cannabis into their lives in ways that optimally fit their individual needs. To support this mission, we are seeking driven, dedicated, and collaborative individuals who are passionate about contributing to our continued growth within the dynamic cannabis industry.

Fine Fettle is seeking a Chief of Staff to scale the effectiveness and leverage of the CEO. Reporting directly to the CEO, this role serves as the CEO’s top thought partner and execution partner - driving alignment across leadership, managing company priorities, and ensuring the organization is executing effectively against its most important goals.

This is first and foremost a Chief of Staff role. The ideal candidate brings prior experience operating in a Chief of Staff (or similar) capacity and excels at translating strategy into execution. As the business evolves, this individual will also support initiatives related to operations, production, commercial, and retail, helping improve visibility, coordination, and follow-through in these areas.

This role is ideal for someone who has already operated as a Chief of Staff (or in a similar capacity) and is looking to expand their impact into more operationally intensive areas of the business.

• Serve as the CEO’s primary strategic and operational partner.
• Translate high-level vision into clear priorities, execution plans, and measurable outcomes.
• Provide leverage to the CEO by taking ownership of key initiatives and workflows.
• Manage and optimize the CEO’s calendar, meetings, and priorities to maximize focus and impact.

• Own and maintain the company-wide OKR system, ensuring alignment and accountability across teams.
• Drive clarity and consistency in company priorities and progress tracking.
• Ensure cross-functional collaboration happens effectively across the organization.

• Develop and implement systems for data reporting, business analysis, and insight generation.
• Provide clear, actionable insights to support executive decision-making.
• Own preparation and delivery of board materials and governance presentations.

• Support key initiatives across operations, production, and manufacturing as needed.
• Partner with operations leadership to improve visibility into performance, KPIs, and key risks.
• Help drive accountability and follow-through on operational priorities.
• Identify opportunities to improve processes and coordination across teams.
• Act as a connective layer between operations and the broader organization.

• Lead high-priority, cross-functional initiatives from planning through execution.
• Ensure timelines, ownership, and outcomes are clearly defined and delivered.

• Proven experience in a Chief of Staff, strategy, consulting, or similar role supporting senior leadership.
• Highly organized with exceptional attention to detail and follow-through.
• Strong operator mindset - you…