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 of Growth and CEO 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.

All of True Classic’s roles are global and omni-channel, leading designated areas of accountability across all product categories, countries, and sales and marketing channels. This role will have impact across DTC, retail, wholesale, marketplaces, and emerging channels, ensuring strategic alignment and executional rigor across the enterprise.

Areas of Accountability

CEO / President 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, coordinating efforts across Marketing, Product, Merchandising, Operations, and Finance
• 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

Executive Operating Rhythm & Leadership Enablement

• 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

Example Initiatives

The specific focus areas will evolve based on business priorities and the Chief of Staff is also expected to initiate and own new projects based on observed opportunities and leadership priorities, but examples include:

• International expansion deep-dive: Identify priority markets, define winning playbooks, and drive execution to accelerate international growth
• Emerging channel acceleration (e.g., TikTok Shop): Partner with internal and external teams to optimize product strategy, content, affiliates, and marketing
• Cross-channel commercial optimization: Lead enterprise-wide initiatives to improve how product flows across channels and how priority initiatives are executed at scale
• New strategic opportunities: Proactively identify and propose initiatives that move the needle on growth, margin, or speed

Cross-Functional Collaboration 

• Executive leadership: Strategic alignment, decision-making, and operating cadence
• Marketing: Channel strategy, performance optimization, and experimentation
• Merchandising & Product: Product strategy, assortment decisions, and lifecycle management
• Operations: Execution feasibility, speed, and scalability
• Finance: Business case development, ROI tracking, and performance measurement

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
• Excellent project management and organizational skills, with the ability to drive ideas from concept to execution
• Strong executive communication skills and interpersonal skills, with the ability to influence senior stakeholders
• Demonstrated ability to influence without authority and work cross-functionally
• Hands-on operator with an entrepreneurial mindset; willing to roll up sleeves and do what it takes to win
• Ability to thrive in a fast-paced, ambiguous environment and drive change effectively

Preferred Qualifications

• Experience in consumer, eCommerce, retail, or marketplace businesses
• Prior Chief of Staff, Strategy & Operations, or Special Projects experience
• High comfort level operating in ambiguity and founder-led environments

Workplace Arrangement

• 5x/week in-office in Calabasas

Compensation and Benefits

Compensation

• Competitive salary + performance-based bonus, dependent on experience

Time Off

• Unlimited PTO and sick time

Health & Wellness

• Company-paid medical, dental, and vision insurance

  • 100% employee premium coverage

  • 65% dependent premium coverage

• $75/month Wellness Stipend

• Free Employee Assistance Program (EAP)

Work & Growth Support

• $75/month Work From Home Stipend

• $75/month Learning & Development Stipend

Perks

• $1,000/year True Classic merchandise allowance

• 401(k) plan with 3% company match

True Classic is proud to be an equal opportunity employer. We celebrate and support differences in race, religion, color, national origin, gender, sexual orientation, gender identity, age, veteran status, and abilities. If you need assistance or accommodation due to a disability, please contact Human Resources.