Retail Tech Insights | Optimizing Digital Retail Through Insight, Innovation and Agility

A featured contribution from Leadership Perspectives: a curated forum reserved for leaders nominated by our subscribers and vetted by the Retail Tech Insights Advisory Board.

Macy’s [NYSE: M]

Optimizing Digital Retail Through Insight, Innovation and Agility

Tilia Wong

Tilia Wong

Omnichannel Analytics Architect

Tilia Wong is VP of Digital Strategy and Analytics for Macy’s Digital, leading digital operations and analytics to drive data-informed growth and enhance the customer experience. Before joining Macy’s, she spent several years at Amazon, where she gained valuable P&L experience running multiple retail functions spanning operations, merchandising and technology, while championing data-driven growth. Her career began in construction after earning a civil engineering degree, where she developed strong leadership skills. She later moved into consulting at McKinsey & Co focusing on analytics for the semiconductor industry in areas such as R&D, manufacturing and product strategy. Across her journey, she has championed the use of data to drive efficiency, innovation, and strategic decision-making in complex environments.

This feature explores Wong’s approach to building analytic and operational systems that deliver measurable impact and shares practical insights on how strategic thinking and cross-functional collaboration drive lasting business success.

Building Systems of Insight across Industries

In my current role, I ensure that Macy’s Digital teams have the analytic and operational frameworks necessary to optimize performance and customer experience, focusing on the core drivers of digital success: traffic, conversion and average order value. Transitioning across industries, from construction to consulting to e-commerce, I have leveraged my experience to establish clear baselines for operational efficiency and data-driven strategy. In every role, my priority has been strengthening analytics capabilities to ensure all decisions are driven by actionable insights and measurable outcomes.

Over the past decade, the evolution of data and technology has been remarkable. Early discussions focused on machine learning, followed by interest in blockchain and more advanced analytical models, before the rise of artificial intelligence (AI). Each phase expanded what could be achieved with structured data, though one truth remains constant. The quality of outcomes depends on disciplined data structures and human interpretation that provides context. Without that foundation, even the most advanced systems rest on fragile ground. To reach the peak of prescriptive analytics and AI, organizations must first master the lower levels of the Analytics Hierarchy of Needs; starting with reliable Data Collection and robust Descriptive Analytics.

AI holds tremendous promise to enhance efficiency and accelerate decision-making. Innovation in the field moves rapidly, with new applications and emerging companies introducing creative solutions every few months. Retail provides an especially rich environment for experimentation. Its deep data ecosystem and quick customer feedback cycles create strong conditions to refine experiences and optimize performance with agility.

“Effective digital growth pivots away from short-term Conversion Rate gains, centering instead on maximizing Customer Lifetime Value, with analytics informing every design choice to nurture that goal.”

For organizations, the key challenge lies in deciding where automation ends and human oversight continues. Machines process vast volumes of information, while judgment and context remain essential to guide their direction. Building confidence in AI outputs requires thoughtful governance, clear standards and a balanced approach that keeps insight and integrity at the center of progress.

Personalization that Elevates the Shopping Experience

The team has focused on enhancing personalization to create a more curated and elevated shopping experience for Macy’s customers. The vision is to deliver a curated and elevated shopping experience that embodies value through inspiration, discovery and ease rather than price alone. This vision reinforces Macy’s dedication to meaningful customer engagement across every interaction.

A recent redesign of the website reflects this evolution, with a refreshed look and feel that better aligns with the brand’s vision. Every detail of the digital experience is guided by data-driven insight. Decisions around homepage design, navigation, visuals and personalized recommendations are thoughtfully shaped to make each interaction intuitive and engaging. Across the website and app, personalization informs product suggestions, promotions and curated experiences that make customers feel recognized and valued.

These initiatives are showing measurable success. Through the use of data and AI, Macy’s has seen stronger engagement, higher conversion rates and growing enthusiasm for premium merchandise. Critically, while many teams focus heavily on optimizing short-term Conversion Rate, our strategic lens prioritizes long-term Customer Lifetime Value. Cohort analysis and propensity modeling informs how we nurture high-value customer segments. The ability to excite customers about elevated products demonstrates the impact of thoughtful innovation grounded in data and human understanding.

Collaboration between Data and Business

Collaboration remains at the core of analytics. Building effective tools depends on human interpretation in understanding what data to collect, what it represents and how machines should apply it. This process requires close partnership among business teams where collective judgment shapes the structure of information and ensures insights that truly matter. For instance, it is essential to govern the data and strategic framework for personalization, ensuring short-term transactional pressures don’t compromise the long-term design choices that build customer equity.

In a curated retail setting, human perspective continues to guide forecasting and creativity. Machines excel at pattern recognition but still struggle to anticipate future trends or consumer preferences several seasons ahead. Envisioning the ideal Category Mix, determining required Inventory Depth, and ensuring optimal Margin Dollars requires intuition and market knowledge that strengthen the analytical process. Data provides the visibility, but it is the team’s human judgment that executes how we draw the shopper’s attention to the right new product at the right time.

That same collaboration extends to communication with customers. Analytics can refine timing and delivery, while the core message and story remain driven by business insight. When data and human creativity work together, they build a thoughtful approach that deepens customer connection and sustains brand strength.

Leading with Agility and Foresight

Growth in analytics begins with agility and foresight. In a rapidly changing environment, staying adaptable is essential. What appears to be the right solution or partner may evolve within a few years, especially in large organizations where switching costs are high. Building systems that allow flexibility helps teams respond to shifts without disruption and ensures long-term stability.

Strong data architecture forms the foundation of that flexibility. It may not be the most exciting aspect of the work, but it is essential. Taking the time to organize, clean and strengthen the underlying data structures ensures everything built on top remains stable and reliable. It requires patience, steady investment and a long-term mindset that prioritizes sustainable systems over quick gains.

Talent development completes this cycle of growth. The nature of analytical work continues to evolve, requiring teams to stay familiar with new tools and approaches. Encouraging experimentation and continuous skill upgrades ensures readiness for future demands. As automation takes on routine tasks, leaders must consciously redirect their teams toward higher-value opportunities. This includes moving the team away from routine CVR optimization toward complex LTV modeling and design partnerships. This approach not only sustains productivity but also keeps people engaged in meaningful, forward-looking work.

Together, flexibility, strong data foundations and adaptive talent form the core of enduring excellence in analytics. Each reinforces the other, creating an ecosystem prepared for transformation and sustained success.

The articles from these contributors are based on their personal expertise and viewpoints, and do not necessarily reflect the opinions of their employers or affiliated organizations.