This Master’s thesis investigates strategies for Yonderland, Europe's largest premium outdoor retailer, to attract and retain Generation Z, a demographic not previously targeted by the company. Through extensive research, including qualitative and quantitative methods, a literature review, interviews with stakeholders, and multiple creative sessions, a comprehensive strategy was formulated for Yonderland and the focus subsidiaries — Bever, A.S Adventure, and Cotswold Outdoor — to appeal to Generation Z's unique preferences and behaviors. Key findings reveals Generation Z, born between 1995 and 2010, as digital natives who value social consciousness, authenticity, and transparency in their brand interactions. This demographic heavily relies on social commerce and peer recommendations, incorporating digital seamlessly into their lifestyles, which influences their loyalty and purchasing decisions. Despite an interest in premium outdoor products, Yonderland initially overlooked the potential of engaging with this demographic, missing significant sale opportunities. The research suggests a strategic pivot towards building authentic connections with Generation Z by emphasizing environmental and social values, and utilizing digital platforms like TikTok for effective engagement. Highlighting the role of over a million Gen Z creators on social media, the strategy focuses on leveraging these influencers to foster genuine interactions and product discovery, emphasizing the importance of authenticity and relatability in marketing efforts. The research critiques Yonderland's existing loyalty programs for their transactional focus, which fails to resonate with Generation Z's values of self-expression, inclusivity, and personalization. It further identifies issues such as a one-size-fitsall approach, lack of meaningful customer journey integration, and underutilization of customer data for personalized experiences. This misalignment underscores the need for a strategic overhaul of Yonderland’s loyalty programs to resonate with Generation Z’s values of self-expression, inclusivity, and personalization. To address these challenges, the thesis suggests an overhaul of these programs to better align with Generation Z's expectations, needs and values. It proposes a shift towards a premium paid membership propositions that emphasizes customer engagement, community building, and personalization through the introduction of a Customer Data Platform, Atelier Café, and Membership App. The new strategy aims to enhance customer engagement, loyalty, and community building, positioning Yonderland to better meet Generation Z’s sophisticated needs while redefining retail customer experiences through connectivity and a focus on sustainability. The Customer Data Platform is designed to enable Yonderland to play a more relevant role in their customers’ digital lives, transitioning from fragmented customer insights to a comprehensive understanding of customer needs and behaviors. This marks a shift towards more relevant digital engagement. The Atelier Café is introduced as a community hub for member events, circularity, and craftsmanship, serving as a focal point for community engagement, workshops, and events that resonate with Generation Z’s values focused on sustainability and craftsmanship. Meanwhile, the Membership App enhances discovery, community, and personalized experiences across its Discovery, Shop, Service, and Community Pages, revolutionizing Yonderland’s engagement and diverging from conventional retail practices towards embracing sustainability and community. This integrated approach signifies a move away from traditional retail models, fostering a more connected and personalized customer experience. This approach, along with leveraging TikTok as the primary marketing channel and launching the Member Days, aligns closely with Generation Z’s preferences, aiming to boost brand visibility, loyalty, and growth by fostering authentic connections. To seamlessly integrate this new paid membership proposition into Yonderland’s offerings, a futurestate service blueprint has been developed alongside a strategic roadmap. The thesis concludes that Yonderland can successfully attract and retain Generation Z by aligning its strategies with the demographic's preferences for authenticity, community-building, and environmental and societal values.