Chief of Staff

True Classic is hiring a Chief of Staff to serve as the right hand to the CEO and lead the company’s most critical, high-impact initiatives across the business. This role is designed for a highly strategic, financially rigorous, AI-first, and execution-oriented generalist who thrives in ambiguity, operates with extreme ownership, and runs toward the company’s biggest and most complex challenges. This is not a strategy-only role. The Chief of Staff will personally drive initiatives from problem definition and prioritization through implementation and measurable results. The right person will combine the ability to see the full strategic picture with the willingness and capacity to operate deeply in the details. The Chief of Staff will work directly with the CEO and partner closely with the executive leadership team to translate the CEO’s vision and the company’s strategy into a prioritized, owned, and sequenced operating plan. This person will identify the opportunities that matter most, direct resources toward them, remove blockers, and ensure the work gets finished. Given True Classic’s scale and growth trajectory, this role offers significant autonomy, company-wide exposure, and the opportunity to help shape the next chapter of the business at the highest level. Areas of Accountability Executive Priority Initiatives Own and drive the company’s highest-priority strategic and operational initiatives, serving as the person responsible for clarity, momentum, and results from start to finish Translate the CEO’s vision and company strategy into prioritized, sequenced operating plans with clear owners, deadlines, and success metrics Identify and rank the strategic priorities that will have the greatest impact on company performance Drive execution across multiple teams, holding stakeholders accountable to commitments and outcomes Remove blockers, resolve competing priorities, and ensure initiatives move from ideas and recommendations to completed results Maintain a highly hands-on role in daily execution, carrying whatever the business needs the role to own Strategic Analysis & Business Problem-Solving Apply a rigorous, first-principles approach to diagnosing opportunities and risks across the business Evaluate performance across the full P&L, including revenue, product margin, gross margin, contribution margin, EBITDA, and net income Partner with Finance on zero-based budgeting, cost discipline, financial modeling, and performance management Conduct deep-dive analyses on new markets, channels, products, customer segments, operational performance, and strategic investments Build customer lifetime value segmentation and cohort models, including analysis by acquisition channel, first-order value, repeat behavior, and contribution Establish guardrails for profitable customer acquisition and new-customer contribution profit Evaluate growth opportunities using a contribution-first lens, including channel economics, pricing architecture, and gros...