Chief of Staff

True Classic is hiring a Chief of Staff to lead the company's most critical, high-impact initiatives across the business. The role requires a highly strategic, analytical, and execution-oriented generalist who thrives in ambiguity and can drive complex initiatives from problem definition through execution and results.

Requirements

• Own and drive the company's highest-priority strategic and operational initiatives
• Translate ambiguous problems into structured workplans
• Drive execution across multiple teams
• Apply a rigorous, first-principles approach to diagnosing opportunities and risks
• Conduct deep-dive analyses on growth opportunities, operational performance, and new initiatives
• Develop clear recommendations grounded in data, customer insight, and financial impact
• Support decision-making with concise, executive-ready materials
• Act as the connective tissue across functions to ensure complex, multi-team initiatives are executed effectively
• Establish operating cadences, decision frameworks, and execution rhythms for priority initiatives and track & measure ongoing impact
• Proactively identify risks, tradeoffs, and dependencies and resolve them before they stall progress
• Support strategy, preparation, and follow-through for leadership meetings, offsites, and company all-hands
• Ensure strategic priorities are clearly communicated and translated into execution
• Identify opportunities to improve how decisions are made and how teams operate

Benefits

• Competitive salary + performance-based bonus
• Unlimited PTO and sick time
• Company-paid medical, dental, and vision insurance
• $100/month Health & Wellness Stipend
• Free Employee Assistance Program (EAP)
• $100/month Personal Workspace/Office Stipend
• $1,000/year True Classic merchandise allowance
• 401(k) plan with 3% company match