Women often take leadership positions with a high risk of failure, a phenomenon known as the Glass Cliff. While existing literature has focused on demand-side motivations for nominating women for precarious positions, limited attention has been paid to the supply-side and workers' willingness to apply for such positions. In this study, we investigate gender differences in the willingness to lead financially successful versus financially struggling organisations under two different leadership selection institutions. Under the Opt-in institution, candidates must actively express interest in the leadership position. Under the Opt-out institution, all candidates are automatically considered for the leadership position unless they actively choose to decline. We find that under the Opt-in institution, men are less likely to apply for leadership in struggling versus successful organisations, driven by shifting empirical norms and a residual preference for "winner-seeking." In contrast, women's willingness to lead is not affected by financial status. As a result, a gender gap emerges in leadership for successful organisations but not for struggling organisations. This gap disappears under the Opt-out institution, suggesting that institutional design offers a policy tool for promoting gender-balanced applicant pools.