While the fields of work-integrated learning (WIL) and career development share common goals, WIL literature tends to focus on student employability more than students' ability to manage their careers. The Leading Edge program at a Canadian institution, the University of Victoria, brings together these two disciplines as it draws from theory and methodology in WIL and career development to strengthen student experiential learning and prepare students for meaningful careers. Four reflective questions form the core of the program, and support students to become pro-active experiential learners, embrace diversity and become career-ready during their academic journey. The authors present the theoretical underpinnings in career development, WIL and experiential learning that inform the program development, and analyse its strengths and challenges. The paper concludes with an exploration of how the Leading Edge, an online program, can support learners to navigate the challenges of the current labour market conditions created by COVID-19.