Introduction: The Saudi Arabian healthcare divisions that recruit and hire pharmacists include hospital pharmacy, community pharmacies, universities, and research centres. Local studies showed that hospital pharmacy is the most preferred sector, while community pharmacy is the least preferred. However, jobs in hospital pharmacy are limited compared to community pharmacy. Hence, to accommodate the increasing numbers of pharmacy graduates and to facilitate the implementation of Saudi Vision 2030, which promotes primary healthcare and the participation of both private and non-governmental organisations in healthcare delivery, community pharmacy ought to be Saudised. This study was conducted to assess the career choices made by Saudi pharmacy students and the enablers that influence their career choice, especially in community pharmacy. Methods: A prospective cross-sectional approach was used. A total of 437 final year pharmacy students were recruited from 15 pharmacy schools around the country. Results: Salary and advancement opportunities as well as geographical location, benefits, and work environment were found to be “very important” enablers when making career decisions. Hospital pharmacy was selected as the most preferred sector by 242 (55.4%) of the participants, while community pharmacy was the least favoured pharmacy sector (17% or 6.2%). The enablers that might influence the consideration of a job in community pharmacy included career aspiration and social accountability. On the other hand, the barriers were personal beliefs about the sector and the nature of the work. Conclusions: The community pharmacy sector was found to be the least preferred sector to work in. The study revealed a list of enablers that the participants found to be relevant or of high relevance when choosing community pharmacy as a career pathway. Some of the enablers contribute to the role of the pharmacist towards the local community, social accountability, and towards the country’s Vision, such as interaction with the general public and educating them. Other enablers are related to the pharmacists’ career aspirations, such as owning a business. Some of the barriers that were found relevant include high workload, inflexible working hours, and limited opportunities for professional development. Localisation of community pharmacies would help to create more jobs for national pharmacists, increase the participation of female pharmacists in the workforce and support the achievement of Vision 2030. The barriers should be tackled on several levels: undergraduate curriculum, regulatory, and actual practice. Undergraduate education needs to include primary pharmaceutical care services in its curriculum. Regulatory changes include enforcing the renationalisation of the community pharmacy sector and permitting females to work in community pharmacies without location restrictions.