Despite recent advancements for women in leadership roles, women remain underrepresented in sport coaching contexts. Mentorship has been advocated as a potential avenue for advancing and sustaining the careers of women coaches. In line with this, national sporting bodies have implemented mentorship programs to pair new and aspiring women coaches with senior women leaders. While recent program evaluations show promising results, more research is needed to understand how these programs are implemented and experienced by program participants. The purpose of this study was to qualitatively explore women's experiences of two national women in coaching mentorship programs. Perspectives were gathered from 21 Canadian sport stakeholders that included program mentees, mentors, and staff. Data were analyzed using a reflexive thematic approach. Four themes were identified related to how mentorship programs can lead to sustained advancement of women in coaching: (a) purposefully recruit mentorship participants, (b) prioritize women in coaching at an organizational level, (c) advance women through proactive sponsorship, and (d) engage in long-term planning for sustaining women in coaching. Findings add to the ongoing work in Canada to support women in coaching throughout their careers and may inform future formalized mentorship opportunities for women coaches. Practical contributions will be discussed, including the importance of understanding how women perceive mentorship opportunities and how ongoing challenges can continue to be identified and addressed (e.g., lack of financial support available).