Head Learning Development Jobs in Massachusetts (NOW HIRING)

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.

Key Position Attributes and Responsibilities:

• 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.

AI & Innovation

• Proactively identify opportunities where AI tools can reduce manual effort, improve accuracy, or accelerate workflows across your team's day-to-day work.
• Test and pilot AI-powered solutions relevant to your role; document findings and share learnings with colleagues to build team-wide capability.
• Partner with cross-functional teammates to develop and refine AI-assisted processes that are practical, scalable, and aligned with WS standards.

Requirements

• Entrepreneurial spirit with a passion for building, iterating, problem-solving, and scaling; thrives in ambiguity and fast-paced environments; a tenacious builder.
• Familiarity with or experience using AI tools; curiosity about how emerging technology can improve workflows and team efficiency is strongly preferred.
• 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.

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.