We investigate the gender imbalance in the financial advising industry by analysing 32 in-depth qualitative interviews of female and male financial advisers in Australia and New Zealand. Using the framework of organisational structures, advisers’ preferences and stereotypical discrimination, we identify barriers for women and the adaptive strategies they employ to overcome them. Findings show that sales-based structures, servicing client needs, difficulties networking, a dominant masculine management culture and the gendered nature of flexible work inhibit women’s careers in financial advice. Strategies to overcome these barriers are finding the ‘right’ manager, receiving mentoring, selective networking and establishing a partnership arrangement with another adviser.