Chief of Staff

About True Classic and the Role

True Classic is seeking a Chief of Staff to spearhead the company’s key transformative projects across all facets of the business. This position demands a highly strategic, analytical, and proactive generalist who excels in ambiguity, embraces full ownership, and can efficiently guide complex initiatives from inception to completion, delivering measurable outcomes.

Working closely with the President, CEO, and Chief Transformation Officer, the Chief of Staff will pinpoint, organize, and implement the company's top business priorities. Offering broad autonomy and cross-departmental exposure, this role provides significant influence over how True Classic operates at its highest level across all product categories, global markets, and sales and marketing channels.

Core Responsibilities

• Lead and manage the company’s critical strategic and operational projects end-to-end, maintaining clarity, momentum, and successful outcomes.
• Transform vague challenges into structured action plans with defined success metrics.
• Drive cross-functional execution by coordinating multiple teams and ensuring accountability for timelines and results.
• Translate strategies into actionable steps and measurable business impact.
• Leverage rigorous analytical methods to identify opportunities and risks within the business.
• Conduct comprehensive analyses on growth potentials, operational performance, and new initiatives.
• Develop concise, data-supported recommendations for informed decision-making.
• Create executive-level materials to support leadership discussions.
• Serve as the central coordinator aligning cross-departmental efforts, including Marketing, Product, Merchandising, Operations, and Finance.
• Establish and maintain operating rhythms, decision frameworks, and ongoing impact tracking for priority projects.
• Identify and mitigate risks and dependencies to prevent progress delays.
• Facilitate leadership meetings, offsites, and company-wide assemblies by preparing strategic content and follow-ups.
• Enhance decision-making processes and team operations continuously.

Example Strategic Initiatives

• Expand and professionalize the wholesale commercial channel, including pipeline management and go-to-market activities.
• Enhance end-to-end operational efficiency covering supply chain, warehousing, logistics, and fulfillment.
• Manage the integrated marketing and go-to-market calendar, coordinating product launches, campaigns, and promotions.
• Optimize omnichannel pricing and promotion strategies.
• Identify and lead new initiatives driving growth, margin improvement, or operational speed.

Cross-Department Collaboration

• Align and coordinate with executive leadership for strategic planning and decision-making.
• Partner with Marketing to refine channel strategies and performance testing.
• Work with Merchandising and Product teams on product strategy and lifecycle management.
• Collaborate with Operations to ensure scalable and timely execution.
• Engage Finance for business case development and performance tracking.

Qualifications and Experience

• Must hold a Bachelor’s degree.
• Between 4 and 8+ years of experience in top consulting firms (e.g., Bain, BCG, McKinsey), investment banking, or senior operating roles.
• Proven track record managing complex projects from start to finish in dynamic environments.
• Strong analytical and problem-solving capabilities with the ability to interpret data into actionable business insights.
• Excellent communication and interpersonal skills enabling influence with senior executives.
• Exceptional project management and organizational expertise, capable of taking concepts through to execution.
• Demonstrated ability to lead cross-functional initiatives and influence without direct authority.
• Proactive, hands-on approach with an entrepreneurial spirit and willingness to engage directly in tasks.
• Comfortable navigating fast-paced, ambiguous settings and driving transformative change.

Preferred Attributes

• Experience working in consumer goods, eCommerce, retail, or marketplace environments.
• Previous roles as Chief of Staff, in Strategy & Operations, or Special Projects management.
• Ease operating within ambiguous, founder-led organizational cultures.

Workplace and Compensation

• This is an onsite position requiring attendance at the Calabasas office at least three days per week.
• Competitive base salary with an additional performance-based bonus, dependent on your experience.
• Unlimited paid time off and sick leave.
• Company-funded medical, dental, and vision insurance benefits.
• A $100 monthly stipend dedicated to health and wellness expenses.
• Access to a free Employee Assistance Program (EAP).
• A $100 monthly stipend for personal workspace or office expenses.
• An annual $1,000 merchandise allowance for True Classic products.
• Participation in a 401(k) retirement plan including a 3% company match.

Equal Opportunity and Company Culture

True Classic proudly embraces diversity and inclusivity across race, religion, color, national origin, gender identity, sexual orientation, age, veteran status, and abilities. Assistance for disabilities is available through Human Resources.

Founded in 2019, True Classic focuses on delivering premium apparel with an emphasis on fit, quality, and meaningful impact. The company highlights a performance-driven culture based on clear principles known as the True Classic Operating System, which promotes decisive action, continuous improvement, and empathetic leadership.

If you thrive in dynamic environments, value ownership, and desire to make significant contributions that drive company growth, we encourage you to join and help shape the future at True Classic.