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