True Classic is hiring a Chief of Staff to serve as the right hand to the CEO and lead the company’s most critical, high-impact initiatives across the business. This role is designed for a highly strategic, financially rigorous, AI-first, and execution-oriented generalist who thrives in ambiguity, operates with extreme ownership, and runs toward the company’s biggest and most complex challenges.
This is not a strategy-only role. The Chief of Staff will personally drive initiatives from problem definition and prioritization through implementation and measurable results. The right person will combine the ability to see the full strategic picture with the willingness and capacity to operate deeply in the details.
The Chief of Staff will work directly with the CEO and partner closely with the executive leadership team to translate the CEO’s vision and the company’s strategy into a prioritized, owned, and sequenced operating plan. This person will identify the opportunities that matter most, direct resources toward them, remove blockers, and ensure the work gets finished. Given True Classic’s scale and growth trajectory, this role offers significant autonomy, company-wide exposure, and the opportunity to help shape the next chapter of the business at the highest level.
Own and drive the company’s highest-priority strategic and operational initiatives, serving as the person responsible for clarity, momentum, and results from start to finish
Translate the CEO’s vision and company strategy into prioritized, sequenced operating plans with clear owners, deadlines, and success metrics
Identify and rank the strategic priorities that will have the greatest impact on company performance
Drive execution across multiple teams, holding stakeholders accountable to commitments and outcomes
Remove blockers, resolve competing priorities, and ensure initiatives move from ideas and recommendations to completed results
Maintain a highly hands-on role in daily execution, carrying whatever the business needs the role to own
Apply a rigorous, first-principles approach to diagnosing opportunities and risks across the business
Evaluate performance across the full P&L, including revenue, product margin, gross margin, contribution margin, EBITDA, and net income
Partner with Finance on zero-based budgeting, cost discipline, financial modeling, and performance management
Conduct deep-dive analyses on new markets, channels, products, customer segments, operational performance, and strategic investments
Build customer lifetime value segmentation and cohort models, including analysis by acquisition channel, first-order value, repeat behavior, and contribution
Establish guardrails for profitable customer acquisition and new-customer contribution profit
Evaluate growth opportunities using a contribution-first lens, including channel economics, pricing architecture, and gross-to-net impact
Develop clear, executive-ready recommendations grounded in data, customer insight, operational feasibility, and financial impact
Act as the connective tissue across functions to ensure complex, multi-team initiatives are executed effectively
Coordinate efforts across Marketing, Product, Merchandising, Operations, Supply Chain, Finance, Technology, and Commercial Partnerships
Establish operating cadences, decision frameworks, dashboards, and execution rhythms for the company’s highest-priority initiatives
Create clarity around owners, deadlines, dependencies, decisions, and expected outcomes
Proactively identify risks, tradeoffs, and cross-functional dependencies and resolve them before they stall progress
Step directly into areas that are under-resourced, underperforming, or facing a new business need; diagnose the issue, direct resources toward it, and drive the solution
Lead operational turnarounds across systems, supply chain, processes, and ways of working
Build repeatable processes and operating systems so improvements remain in place after responsibility transitions back to the functional team
Use AI to build dashboards, agents, analyses, and workflows that increase organizational speed, visibility, and output
Serve as a strategic and execution partner to the CEO, helping translate vision into priorities, decisions, and action
Support the strategy, preparation, and follow-through for leadership meetings, offsites, company all-hands, and other executive operating forums
Ensure strategic priorities are communicated clearly and translated into accountable execution throughout the organization
Maintain visibility into the company’s most important initiatives and ensure leadership has the information needed to make timely decisions
Identify opportunities to improve how decisions are made, how resources are allocated, and how teams operate together
Help strengthen the company’s daily execution and accountability by creating clarity around priorities, owners, deadlines, and decisions
Support the CEO and executive leadership team in managing True Classic’s most important external partnerships and vendor relationships
Set a high standard for AI-first operating practices and help raise the company’s overall technical and analytical capabilities
The specific focus areas will evolve based on business priorities. The Chief of Staff is also expected to proactively identify, propose, and own new initiatives based on observed opportunities. Examples include:
P&L expansion and financial discipline: Drive top-line growth and bottom-line expansion in lockstep, improving margins across the full financial stack while partnering with Finance on zero-based budgeting and cost control
Omni-channel and global growth: Identify and execute opportunities across direct-to-consumer, marketplaces, retail and wholesale partners, owned retail stores, and new or underpenetrated global markets
New product and assortment opportunities: Partner with Product and Merchandising to evaluate new categories, assortment expansion, product opportunities, pricing architecture, and channel-specific strategies
Customer and lifetime value intelligence: Build robust customer segmentation and cohort models to identify the customers worth acquiring and retaining, establish profitable acquisition guardrails, and improve repeat behavior and retention
Pricing and channel economics: Establish clear channel roles, pricing architecture, gross-to-net discipline, and contribution expectations by channel rather than relying on blended averages
Strategic partnership development: Build and strengthen relationships with major retail, wholesale, marketplace, platform, technology, supply chain, logistics, and capital partners while protecting both the relationship and the underlying economics
Cross-functional operational turnarounds: Step into critical areas of the business, including Marketing, Operations, Product, Finance, Supply Chain, or Technology, to diagnose issues, mobilize resources, and build sustainable solutions
AI-first operating systems: Build dashboards, agents, analytical tools, and automated workflows that improve decision-making, increase team capacity, and accelerate execution
New strategic opportunities: Proactively identify and propose initiatives that meaningfully improve growth, margin, customer value, organizational capacity, or speed
Executive Leadership: Strategic alignment, decision-making, resource allocation, operating cadence, and company-wide accountability
Marketing: Customer acquisition, retention, channel strategy, performance optimization, customer segmentation, and experimentation
Merchandising & Product: Product strategy, assortment decisions, pricing architecture, category expansion, and lifecycle management
Operations & Supply Chain: Execution feasibility, operational turnarounds, systems, warehousing, logistics, fulfillment, speed, and scalability
Finance: P&L management, zero-based budgeting, business case development, unit economics, ROI tracking, and performance measurement
Commercial Partnerships: Retail, wholesale, marketplace, platform, technology, logistics, and other strategic partner relationships
Technology & Data: AI-enabled workflows, dashboards, agents, modeling, automation, and the systems required to improve company-wide execution
Bachelor’s degree required
Significant experience in strategy, operations, finance, consulting, investment banking, general management, or another role requiring ownership of complex business outcomes
Exceptional financial literacy, with the ability to quickly understand a P&L and independently build financial models, business cases, and unit-economic analyses
Proven ability to drive both top-line growth and bottom-line improvement, with a strong understanding of contribution margin and channel economics
Demonstrated experience owning complex, cross-functional initiatives from initial problem definition through implementation and measurable results
Broad business judgment and the ability to add value across Marketing, Operations, Product, Merchandising, Finance, Supply Chain, and Technology
Experience operating across multiple channels, including direct-to-consumer, marketplaces, retailers or wholesale partners, and owned retail
Strong analytical and problem-solving skills, with the ability to translate data into clear business decisions
Deep fluency with AI and the technical capability to build or directly develop dashboards, models, agents, workflows, and other practical tools
Exceptional executive communication and interpersonal skills, with the ability to influence senior stakeholders and create alignment across teams
Excellent project management and organizational skills, with the ability to establish clear priorities, owners, deadlines, and operating rhythms
Demonstrated ability to influence without authority and hold cross-functional stakeholders accountable
Hands-on operator with an entrepreneurial mindset who is willing to work deeply in the details and personally drive execution
Ability to thrive in a fast-paced, ambiguous environment and run toward the company’s hardest and most complex problems
High capacity, high ownership, low ego, and a track record of raising the standard of execution for those around them
Experience in a global consumer, eCommerce, retail, wholesale, or marketplace business
Prior experience as a Chief of Staff, General Manager, Strategy & Operations leader, Transformation leader, or Special Projects leader
Experience scaling an omni-channel business across direct-to-consumer, marketplaces, retail partners, and owned retail stores
Experience managing or negotiating significant commercial, retail, technology, supply chain, logistics, or capital partnerships
Background in top-tier consulting or investment banking combined with demonstrated hands-on operating experience
Experience building AI-enabled operating tools, workflows, dashboards, or internal systems
High comfort level operating in ambiguity, high-growth environments, and founder-led organizations
On-site at our office in Calabasas, CA.
Company-paid medical, dental, and vision insurance
$100/month Health & Wellness Stipend
Free Employee Assistance Program (EAP)
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.
