Head of Site Merchandising, Content & Commerce Strategy

About The Role

The Real Real is seeking an experienced Director to lead Site Merchandising, Fashion Editorial Content, and Commercial Planning across our digital ecosystem. This leader will own the integrated commercial calendar and drive the strategy, execution, and optimization of all on‑site experiences—homepage, category pages, and key content placements that bring brand, trend, and promotion to life. This role sits at the intersection of merchandising, trend storytelling, and content marketing—combining analytical rigor with creative excellence to deliver experiences that inspire buyers, attract consignors, and maximize GMV.

• Own the annual commercial plan — build, align, and execute the master campaign calendar including key events (e.g., Black Friday, Cyber Monday, 4th of July, seasonal drops, and TRR‑exclusive moments).
• Lead site merchandising strategy — define the site structure / taxonomy, category storytelling, and content hierarchy to ensure seamless navigation, optimized conversion, and elevated brand presentation.
• Oversee merchandising fashion editorial and trend content – partner with brand and merchandising to develop trend stories, editorial features, and category spotlights that inspire discovery and reinforce TRR’s authority in luxury resale.
• Drive performance through storytelling — integrate trend, promotion, and assortment data into cohesive narratives that drive demand, consignor engagement, and lifetime value.
• Collaborate cross‑functionally with marketing, planning, merchandising, and digital analytics to ensure campaigns are merchandised for impact, measured for performance, and continuously optimized.
• Lead and develop a high‑performing team across Site Merchandising, Fashion Merchandising Editorial, and Commercial Planning—fostering creativity, accountability, and cross‑functional excellence.
• Own reporting and insights on campaign and site merchandising performance, providing actionable recommendations to inform content, pricing, and assortment decisions.
• Define how The Real Real brings product, promotion, and storytelling together across the site—owning the commercial heartbeat that drives performance and deepens our connection with buyers and sellers alike.

• 5+ years in a leadership role
• 10+ years of experience in digital merchandising, site experience, and commercial planning at a leading retailer or digital‑first brand.
• Proven success driving GMV and engagement through integrated content, storytelling, and data‑driven merchandising.
• Deep understanding of e‑commerce site experience, customer journeys, and merchandising systems (Salesforce Commerce Cloud or similar).
• Expert collaborator—adept at partnering with Brand, Marketing, Planning, and Merchandising to build unified, high‑impact campaigns.
• Strategic and operational—able to set vision and execute with precision across complex cross‑functional timelines.
• Passionate about luxury, fashion, and sustainability with an instinct for trend and customer insight.
• Skilled people leader with experience developing creative and analytical talent across content and merchandising disciplines.
• Ability to travel 10%

• Employee Stock Purchase Plan
• 401K with Company Match
• Medical, Dental & Vision Insurance
• Paid Parental Leave
• 9 Paid Company Holidays
• Flexible Time Off (With Manager Approval)
• Find out more about our Benefits here.

The expected salary range for this role is $170,000-$185,000. To determine starting pay we carefully consider a variety of factors, including primary work location and an evaluation of a candidate’s skills, experience, market demands, and internal parity. Additionally, salary is just one component of TRR’s total rewards package. Depending on role, employees may also be eligible for a bonus program, incentive pay and benefits.

The Real Real is the world’s largest online marketplace for authenticated, resale luxury goods, with 37 million members. With a rigorous authentication process overseen by experts, The Real Real provides a safe and reliable platform for consumers to buy and sell their luxury items. We have hundreds of…