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. 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 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, 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 Wholesale commercial channel acceleration: Accelerate and professionalize the wholesale channel end-to-end, inclusive of pipeline management, sales support, and go-to-market mobilization. Drive execution, operationalize the wholesale selling dashboard and pipeline tracker, and evaluate strategic partnerships to expand our wholesale footprint End-to-end operations efficiency & effectiveness: Drive operational efficiency and effectiveness across the operations organization, spanning supply chain, warehousing, logistics, and fulfillment Integrated marketing & GTM calendar ownership: Own the integrated marketing effort to drive strategy and execution across our consolidated marketing calendar, including new product and category launches, major promotions and campaigns, and channel-specific activations Pricing & promotion strategy optimization: Own the development of a unified, omnichannel pricing and promotion architecture 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 Strong executive communication skills and interpersonal skills, with the ability to influence senior stakeholders Excellent project management and organizational skills, with the ability to drive ideas from concept to execution 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 3x/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/month Health & Wellness Stipend Free Employee Assistance Program (EAP) Work & Growth Support $100/month Personal Workspace/Office 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. #J-18808-Ljbffr