Director, Digital Merchandising & Strategy

About The Role

As the Leader of Digital Merchandising & Strategy, you own revenue, conversion, and engagement across all digital platforms. This role leads the end-to-end product discovery experience, ensuring customers can seamlessly find the right products while maximizing conversion, GMV, and long-term customer value.

The Digital Merchandising & Strategy team ensures:

• Search, browse, and navigation work seamlessly
• The right products surface at the right time
• Site experience and recommendations drive engagement and sales
• Traffic translates into revenue by optimizing how customers discover products
• We are assessing and optimizing site funnel health

This is a hybrid execution + analytics + strategy function. The team sets direction, uses data to identify opportunities, and directly implements changes on-site. A strong test-and-learn mindset is critical, as continuous experimentation is core to improving performance.

The Leader of Digital Merchandising & Strategy at a high level is responsible for setting strategic direction and determining what to build or optimize to drive business impact.

• Own digital revenue performance, driving conversion, engagement, and end-to-end funnel health
• Define and execute product discovery strategy across search, browse, navigation, and recommendations
• Lead personalization strategy to ensure the right products surface for the right customer at the right time
• Translate business goals into a clear, prioritized digital roadmap, balancing quick wins with long-term investments
• Identify and prioritize the highest-impact opportunities across the customer funnel
• Partner cross-functionally with Product, Engineering, Marketing, and Creative; act as the voice of the business and customer in product development
• Use data to diagnose performance, inform strategy, and define a robust testing roadmap; lead A/B experimentation and scale learnings
• Monitor key performance metrics and deliver actionable insights on a weekly, monthly, and quarterly basis
• Lead and develop a team responsible for day-to-day digital execution and continuous experience improvement
• Proactively identifies opportunities and challenges the status quo

• Bachelor's degree required, advanced degree a plus.
• 5-10+ years in digital merchandising, e-commerce, or product-led growth
• Strong experience with marketplace or high-SKU environments
• Deep understanding of search, browse, and recommendation systems to Focuses on highest-impact work that drives business outcomes
• Proven track record of driving conversion and revenue growth
• Experience optimizing search + browse
• Comfort using AI tools to increase productivity, streamline day-to-day work, and accelerate learning, with an understanding of responsible use
• Experience partnering closely with Product and Engineering teams
• Highly data-driven with strong analytical toolkit (ie Google Sheets, Looker, Amplitude)
• Thrives in fast-changing environments; able to pivot quickly and lead through uncertainty
• Uses data to form insights, shape strategy, and drive execution
• Embraces experimentation, iterates quickly, and learns from results
• Uses data and logic to solve complex problems and influence cross-functional partners
• Builds, develops, and motivates high-performing teams

• 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 $-$. 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…