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Head of Loyalty

Head of Loyalty

WS DevelopmentChestnut Hill, MA, US
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Insider Program Head

Overview : We are building a best-in-class, first-of-its-kind, loyalty program that redefines how retailers engage customers and attract new ones. The Insider program will not only support the WS Development portfolio, but also serve as a scalable, innovative business line in its own right. With strong tenant and consumer buy-in already established, we are seeking a dynamic, strategic, scrappy, entrepreneurial leader to own, run, and grow this business into a transformative force in customer engagement.

The Head of Loyalty will set the vision, strategy, and execution of Insider, ensuring it delivers meaningful connections with shoppers and tenants while driving measurable business outcomes (tenant sales, customer engagement, program revenue). Working closely with WS Development's executive team, this person will scale Insider through strategic leadership, best-in-class technology development, and disciplined operational execution. With tens of thousands of current members and several new properties launching soon, Insider is at a key inflection point. We believe that Insider is poised to be a powerful, differentiated tool that sets us apart in the retail landscape.

Key Position Attributes and Responsibilities :

  • Lead the strategy, development, and ongoing evolution of Insider.
  • Own revenue, budget, and ROI targets for Insider, ensuring financial sustainability and growth.
  • Champion Insider as a tenant value driver, educating partners on how to leverage the program for sales growth.
  • Deliver a seamless, differentiated, and delightful experience for members across digital and physical touchpoints.
  • Define product requirements, customer segments, goals, benefits, and rewards.
  • Make fast, data-driven decisions and foster a culture of experimentation, learning, and iteration to accelerate program performance.
  • Foster a test-and-learn culture with a start-up mindset, ensuring marketing campaigns and program features are optimized for ROI.
  • Execute the long-term business plan, balancing near-term wins with sustained growth.
  • Collaborate with leasing, marketing, and property teams to position Insider as a key differentiator that creates significant value for tenants and drives customer loyalty.
  • Partner with the Head of Digital Engagement and VP of Marketing on budget planning and KPIs, ensuring clear reporting to executive leadership.
  • Drive acquisition and engagement through growth marketing campaigns and integrated communications (media, signage, email, app engagement).
  • Analyze customer data and insights to refine the program, improve retention, and maximize lifetime value.
  • Identify and evaluate new opportunities for Insider, including strategic partnerships, collaborations, and cross-property initiatives.
  • Manage and grow a small, high-performing team.
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Head Of • Chestnut Hill, MA, US

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