Head of Loyalty

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.

Requirements

• Entrepreneurial spirit with a passion for building, iterating, problem-solving, and selling; thrives in ambiguity and fast-paced environments.

• Expertise in growth marketing tactics, A/B testing, rapid experimentation, and scaling customer engagement initiatives.
• Proven ability to design, scale, and optimize customer programs that deliver measurable growth and loyalty.
• 10+ years (preferred) of loyalty program leadership, ideally in retail, hospitality, e-commerce, CPG, travel, or subscription services.
• Proven ability to sell, including evangelizing and gaining buy-in from tenants, executives, and partners.
• Strong analytical ability, translating insights into action across platforms (Google Analytics, marketing automation tools, etc.).
• Familiarity with Salesforce Marketing Cloud or comparable platforms, leveraging automation for personalization and customer engagement.
• Demonstrated success in P&L ownership and ROI-driven decision-making.
• Proven ability to lead and inspire teams and influence senior stakeholders.
• Experience with mobile app development and product management.

About WS Development

Massachusetts-based WS Development is a mixed-use developer with a singular mission: creating places people want to be. With an approach that values art, science, innovation and, above all else, people, WS strives to engage each community it serves with best-in-class experiences, designed with our customers, tenants and partners in mind. Established in 1990, WS is one of few vertically-integrated real estate companies that conceptualizes, owns, operates and leases more than 100 properties that range from cutting-edge urban spaces to lifestyle and community centers. With over 22 million square feet of existing space and an additional nine million square feet under development, it is one of the largest privately-owned development firms in the country.

WS is where great ideas and great people come together to design, build, and operate some of the best loved real estate projects in the country. We live at the intersection of entrepreneurship and establishment. We have the infrastructure of decades supporting a culture of free-thinking excellence.

We expect every WS employee to feel welcomed and valued irrespective of race, color, religion, gender, gender identity or expression, sexual orientation, national origin, disability, age, veteran status, marital status, parental status, cultural background, and life experiences. Or for any other reason.