Twenty-first-century doctoral candidates face a consistently evolving employment landscape. This paper explores how gender and age influence doctoral students' perceptions of employability preparedness provided by their higher education institution for future career pathways. A survey-based study (n = 222) was undertaken at a large regional Australian university to assess what employment pathways graduates intend to pursue, how prepared they feel for these pathways, and what strategies could be utilised to increase the effectiveness of doctoral training with a view to employability. Transition pedagogy is used as a lens to unpack and explore participants' perceptions about systems designed to support success. Key findings include (1) a surplus of candidates seeking academic careers; (2) candidates reporting doctoral training inadequately prepares them for their preferred career path; and (3) young males feeling most prepared by their doctoral programme and older females feeling the least prepared. We discuss how preparedness is not experienced equally, and how the conditions of higher education are constructed with assumptions of who a doctoral candidate is, with implications for who is most likely to benefit from it.