As the digital recruitment market in Indonesia becomes increasingly competitive, it is crucial for Chatterhire, a job portal tech startup, to retain a strong user base for sustainability and growth. Retention is vital for demonstrating product-market fit, monetization potential, and attracting future investments. To achieve this, Chatterhire aims to shift its focus from aggressive user acquisition to retention, by optimizing its platform for regular use. This research combined quantitative data on user in-app activities with qualitative feedback from in-depth interviews. The quantitative analysis utilized Customer Lifecycle Management (CLM) techniques, including cohort analysis, behavioral cohort analysis, and funnel analysis, to identify critical experiences that encourage users to return, reasons for user churn, and features that need enhancement for better retention. The study found that retaining users is challenging for an episodic-use app like a job portal, where engagement is sporadic and infrequent. Once users secure a job, their need for the app diminishes, leading to significant drops in engagement and even app uninstalls. Therefore, the company needs to expand the platform’s features to provide additional reasons for users to return. Additionally, ensuring users perceive the app’s value through repeated interactions is essential. The research revealed that users who apply for at least four jobs within the first seven days are likely to have higher retention. This research highlights the importance of integrating intrinsic value into the product to foster a sustained user journey. The Hooked Model’s core elements—Trigger, Action, Variable Reward, and Investment—can encourage habitual use and sustained engagement, crucial for maintaining a competitive edge in the digital recruitment industry.