Chief of Staff

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

The Chief of Staff will work directly with the President, CEO, and Chief Transformation Officer to identify, structure, and execute the highest-priority opportunities facing the business at any given moment. Given our scale and growth trajectory, this role offers significant autonomy, cross-functional exposure, and the opportunity to shape how the company operates 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 quarterback responsible for clarity, momentum, and outcomes from start to finish
• Translate ambiguous problems into structured workplans with clear success metrics
• Drive execution across multiple teams, holding stakeholders accountable to timelines and results
• Ensure initiatives move from strategy to action to measurable impact

Strategic Analysis & Business Problem-Solving

• Apply a rigorous, first-principles approach to diagnosing opportunities and risks across the business
• 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

PMO Leadership

• 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
• Proactively identify risks, tradeoffs, and dependencies and resolve them before they stall progress

Qualifications

• Bachelor's degree required
• 4–8+ years of experience in top-tier consulting (e.g., Bain, BCG, McKinsey), investment banking, or operating roles
• Proven ability to own complex initiatives end-to-end in fast-paced environments
• Exceptional analytical and problem-solving skills, with the ability to translate data into clear business decisions
• Strong executive communication skills and interpersonal skills
• Excellent project management and organizational skills
• Demonstrated ability to influence without authority and work cross-functionally

Benefits

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

Workplace Arrangement

3x/week in-office in Calabasas