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. About the Role: 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. Primary Responsibilities Include, but Are Not Limited To: CEO Partnership & Strategic Execution: 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. Company Alignment & OKRs: 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. Data, Reporting & Decision Support: 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. Operations & Cross-Functional Support: 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. Project Management: Lead high-priority, cross-functional initiatives from planning through execution. Ensure timelines, ownership, and outcomes are clearly defined and delivered. Skills and Qualifications: 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 understand how businesses run and can engage effectively in operational topics. Data-driven and analytical, with the ability to turn complexity into clear insights. Strategic thinker who is equally comfortable executing. Comfortable with ambiguity and fast-paced, evolving environments. Strong communicator with the ability to build alignment and influence across teams. Systems-oriented, with the ability to design and improve workflows and processes. Ability to pass a Federal Background Check with no felony convictions Critical Competencies: 5 to 10+ years of experience in Chief of Staff, consulting, strategy, business operations, or similar roles. Demonstrated experience working closely with senior executives. Experience in cannabis, CPG, manufacturing, or other operationally complex environments is highly advantageous. Exceptional analytical, problem-solving, and project management skills. Excellent written and verbal communication skills. Proven ability to manage multiple priorities and projects simultaneously. Highly self-motivated, proactive, and results-oriented. Strong interpersonal skills and ability to build consensus across teams. Benefits: Competitive pay with opportunities for growth, development, and advancement. Comprehensive benefit packages that offer medical, dental, vision, and life insurance. Paid time off, including holidays and vacation days. 401(k) Retirement Savings Plan with Employer Matching Contributions. Generous Employee Discount. A collaborative and supportive work environment at a growing company. Americans With Disabilities Statement: Must be able to perform all essential functions of this position with reasonable accommodation. If you need accommodation during the application and/or hiring process, please reach out to our HR Department. EEO Statement: We are an Equal Opportunity Employer. Our goal is to be a diverse workforce that is representative, at all job levels, of the communities we serve. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, gender expression, national origin, protected veterans’ status, and will not be discriminated against on the basis of disability or any other applicable legally protected characteristic. #J-18808-Ljbffr