True Classic · 1 week ago
Chief of Staff
Calabasas, CA
Full-time
Onsite
Mid, Senior Level
4+ years expTrue Classic is a fast-growing apparel brand seeking a Chief of Staff to lead critical initiatives across the business. This role requires a strategic and analytical generalist who will work closely with the President of Growth and CEO to execute high-priority opportunities and drive complex initiatives from problem definition to measurable results.
Consumer GoodsE-CommerceFashion
Responsibilities
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
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
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
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
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
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
Qualification
Required
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
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
Benefits
Unlimited PTO and sick time
Company-paid medical, dental, and vision insurance
100% employee premium coverage
65% dependent premium coverage
$75/month Wellness Stipend
Free Employee Assistance Program (EAP)
$75/month Work From Home Stipend
$75/month Learning & Development Stipend
$1,000/year True Classic merchandise allowance
401(k) plan with 3% company match
Company
True Classic
True Classic is an e-commerce platform that offers a wide range of tees for men.
51-200 employees
Funding
Current Stage
Growth StageTotal Funding
unknownKey Investors
1686 Partners
2025-05-01Series Unknown
Leadership Team
Matthew Winnick
Co-Founder
Recent News
EIN Presswire
2025-11-20
San Diego Union-Tribune
2025-11-14
2025-10-30
Company data provided by crunchbase