Rachel Tobac, a hacker and CEO of SocialProof Security, got her start in info-security through the SECTF stage at DEF CON, where she was given a chance to live hack a real company over the phone. She won second place three years in a row and went on to start her own company, training companies on human hacking and security awareness. Despite being underrepresented in the field, Tobac believes that women can succeed in info-security with the right support and community. She emphasizes the importance of having female role models and leaders in positions of power, as well as creating a sense of belonging and support for women in the field. Tobac also highlights the need to educate users about security best practices and set them up with clear technical controls to make smart security choices. For those just starting out in info-security, she advises jumping in and getting feedback, rather than self-selecting out due to perceived inadequacy. Additionally, bug bounty program owners should consider adding social engineering to their scope to evaluate under real-world conditions.