The RealReal · 1 week ago
Head of Site Merchandising, Content & Commerce Strategy
The RealReal is the world’s largest online marketplace for authenticated, resale luxury goods, and they are seeking an experienced Director to lead Site Merchandising, Fashion Editorial Content, and Commercial Planning across their digital ecosystem. This role involves owning the integrated commercial calendar and driving the strategy, execution, and optimization of all on-site experiences to enhance buyer engagement and maximize GMV.
E-CommerceFashionLifestyleMarketplace
Responsibilities
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 RealReal 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
Qualification
Required
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%
Benefits
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)
Company
The RealReal
The RealReal is an online marketplace for authenticated and consigned luxury goods.
H1B Sponsorship
The RealReal has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (5)
2024 (10)
2023 (10)
2022 (14)
2021 (8)
2020 (6)
Funding
Current Stage
Public CompanyTotal Funding
$356.87MKey Investors
GreyLion CapitalGreat Hill PartnersGreenspring Associates
2019-06-28IPO
2019-03-01Series H· $70M
2018-07-25Series G· $115M
Recent News
2026-01-23
WSJ.com: US Business
2026-01-22
2026-01-14
Company data provided by crunchbase