Associate Director, Site Experience

About the role

Chewy is seeking an Associate Director, Healthcare Merchandising to lead the merchandising vision, strategy, and execution for Pharmacy (Rx).

Responsibilities

• Own the customer journey for Pharmacy (Rx) ensuring experiences are customer-first, data-driven, and strategically aligned to enterprise goals.
• Act as the primary advocate for the Chewy customer, ensuring site enhancements reflect customer needs, preferences, and feedback.
• Develop and execute 2+ year site content and merchandising strategies that boost awareness, engagement, and conversion.
• Translate customer insights and market trends into prioritized roadmaps and opportunities that balance innovation with operational execution.
• Educate customers on Site Experience strategies and prioritization that maintains focus on what we should and shouldn’t do based on customer insights and delivering an optimal customer experience.
• Deliver onsite campaign strategies for time-bound and evergreen customer-facing messages that effectively address customer problems, align with objectives, and target key audiences with optimized messaging, creative and onsite flow.
• Partner with Category, Product, Marketing, Tech, and CRM to deliver unified, personalized site experiences across Pharmacy (Rx) offerings.
• Manage prioritization and trade-offs across multiple high-impact initiatives in collaboration with cross-functional partners, while also fostering relationships with Senior level leaders.
• Oversee complex, cross-functional programs from concept to launch, ensuring customer alignment and timely delivery.
• Lead communication to Senior Stakeholders (including CEO, President- Healthcare, President- Retail) and Senior Leaders on progress against strategic initiatives, pillars and opportunities in Monthly Business Reviews and SLT updates.
• Partner with the Site Analytics team, ensuring Pharmacy (Rx) full funnel, campaign and ad-hoc reporting that results in fast, data-driven decisions and impactful narratives.
• Utilize AI powered tools to complete analysis and build stories that accurately and quickly contextualize and visualize insights.
• Directly lead a team of merchandising professionals, providing coaching, feedback, and growth opportunities tailored to individual strengths and career goals.
• Foster a collaborative, inclusive culture with a focus on continuous improvement, operational rigor, and shared success.
• Ensure the team is equipped with the resources, processes, and support needed to deliver transformational initiatives at scale.

Requirements

• 8+ years in e-commerce merchandising, site experience, or product marketing, with at least 3+ years in a leadership role managing cross-functional teams and enterprise-level initiatives.
• Proven track record of driving site strategy and execution in complex, high-growth businesses — ideally in healthcare, content, or services.
• Experience leading teams of 3–5+ direct reports, including hiring, coaching, and performance management.
• Deep understanding of Customer Experience Excellence, CX Data & Insights, Site Merchandising Strategy & Planning, Program & Initiative Delivery, and Cross-Functional Partnership at a strategic leadership level.
• Strength in Data Analysis & Storytelling, A/B Testing & Experimentation, and Business Acumen to influence senior partners.
• Track record of using data as a persuasive tool to advocate for change and drive customer-first decisions.
• High judgment for customer facing creative execution, ensuring customer-facing experiences inspire trust, delight, and conversion.
• Exceptional relationship-building and communication abilities, including comfort presenting to executive leadership.

Qualifications

• Strong analytical skills and ability to interpret data to make informed decisions.
• Excellent problem-solving and decision-making skills.
• Ability to manage multiple projects simultaneously and prioritize tasks effectively.
• Strong interpersonal and communication skills, with the ability to collaborate with cross-functional teams.
• Experience working in a fast-paced, dynamic environment.

Skills

• Data analysis and storytelling skills.
• A/B testing and experimentation.
• Business acumen and persuasive communication.
• Customer experience excellence.
• Leadership and team management.

Benefits

• Base salary range: $149,000 - $245,000.00.
• Eligible for 401k and a new hire and annual equity grant.
• C08+ positions may also be eligible for annual bonus.
• Comprehensive benefits package including medical/Rx, vision, dental, life, disability, hospital indemnity, critical illness, and accident.
• Paid holidays, PTO, parental leave, family services benefits, backup dependent care, flexible spending accounts, telemedicine, pet adoption reimbursement, employee assistance program, and discounts.

Pay

• Base salary range: $149,000 - $245,000.00.

Schedule

• Exempt salary team members have unlimited PTO, subject to manager approval.
• Team members may be eligible for paid sick and family leave in compliance with applicable state and local regulations.