Chief of Staff

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.

Areas of Accountability

Executive Priority Initiatives

• 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

Strategic Analysis & Business Problem-Solving

• 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

PMO Leadership

• 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

Executive Operating Rhythm & Leadership Enablement

• 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

Example Initiatives

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

Cross-Functional Collaboration 

• 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

Qualifications

• 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

Preferred Qualifications

• 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

Workplace Arrangement

• On-site at our office in Calabasas, CA. 

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.