This graduation project focused on redesigning the onboarding experience for learners enrolled in Vani.Coach’s Communication Fitness (CF) program, a B2B app-based coaching intervention aimed at improving workplace communication skills. The existing onboarding process relied heavily on manual interventions by Learning Success Managers (LSMs), leading to inconsistent learner experiences, delayed engagement, and high operational load. Using the Double Diamond framework, the project began with qualitative and quantitative research, including LSM interviews, stakeholder discussions, Mixpanel behavior analysis, and onboarding call observations. Insights revealed learner confusion around app access, practice initiation, and expectations, alongside LSM fatigue from repetitive tasks and limited progress visibility. The onboarding journey was redesigned into two phases: Phase 1 focused on standardisation and automation through structured communication, instructional assets, and tracking systems; Phase 2 addressed learner motivation and habit formation. The redesign enabled learners to begin practice confidently from Day 1 while reducing LSM effort and improving scalability.