Head of Loyalty

Overview

We are seeking a tenacious entrepreneur who is dynamic and strategic and wants to build and scale Insider, a best-in-class, first-of-its-kind loyalty program that redefines how retailers engage customers and attract new ones. The Insider program is not only a critical driver for the WS Development portfolio, but is also positioned to become a scalable, standalone business well outside of the WS portfolio.

With strong tenants and consumer adoption already in place, Insider is at a pivotal inflection point.

The Head of Loyalty will lead Insider’s evolution through strategic leadership, best-in-class technology development, and disciplined operational execution, driving measurable outcomes such as retailer sales, customer engagement and delight, and program profitability. With rapid membership growth and a number of new properties poised to launch soon, Insider is uniquely positioned to become a differentiated solution and transformative force in the retail landscape and beyond.

Insider is a high-priority initiative within WS Development’s Strategic Initiatives team and will work closely with the executive leadership to continue to build the vision, set the roadmap, and execute a go-to-market strategy that turns Insider into a significant revenue-generating platform well beyond our properties.

• Lead the overall strategy, growth, and ongoing evolution and scaling of Insider.
• Identify and evaluate new opportunities for Insider, including strategic partnerships, collaborations, and cross-property initiatives.
• Own revenue, budget, and ROI targets for Insider, ensuring financial sustainability and 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.
• Analyze customer data and insights to refine the program, improve retention, and maximize lifetime value.
• Manage and grow a small, high-performing team.

• Entrepreneurial spirit with a passion for building, iterating, problem-solving, and scaling; thrives in ambiguity and fast-paced environments; a tenacious builder.
• Past experience will include developing and executing one or more comprehensive go-to-market (GTM) strategies, scaling digital products or platforms into standalone business offerings, including pricing, positioning, and partnership models.
• Demonstrated success in P&L ownership and ROI-driven decision-making.
• Proven ability to lead and inspire teams and influence senior stakeholders.
• Preferred familiarity with loyalty programs, ideally in retail, hospitality, e-commerce, CPG, travel, or subscription services.
• Proven ability to design, scale, and optimize customer programs that deliver measurable growth and loyalty.
• Proven ability to sell, including evangelizing and gaining buy-in from partners, executives, investors, etc.
• Expertise in growth marketing tactics, A/B testing, rapid experimentation, and scaling customer engagement initiatives. Strong analytical ability, translating insights into action across platforms (Google Analytics, marketing automation tools, etc.).
• Experience with mobile app development and product management.

The expected salary range for this position is $175,000-$225,000 per year. Actual compensation will be based on factors such as skills, qualifications, experience, and location. This role is also eligible to participate in our annual bonus program.

Massachusetts-based WS…