In the city of Ibadan, Nigeria’s largest urban center, Olufela Osideko began her journey into cybersecurity. However, her story does not begin with childhood computers or a typical techie influence. Instead, she had to battle depression and uncertainty. Her unconventional path from being a struggling 19-year-old to a successful penetration tester offers valuable insights for the hacker community, particularly around representation, persistence, and the transformative power of opportunity.
“I have always considered myself an outlier because of the way I approach and see life,” she shares. In 2020, at 19 years old and while dealing with severe depression during the COVID pandemic, she found herself at a crossroads after failing to meet university entrance requirements for pharmacy school.
The turning point came in April 2021 when a friend shared a cybersecurity training link (not a phishing link, she jokes). “I had no idea what cybersecurity was about but I was not really doing anything valuable with my time, so I just figured if I got into the cohort, I will find out what it’s about,” she recalls. That single click would fundamentally alter her life trajectory.
Accepted into the CyberGirls 1.0 cohort founded by Confidence Staveley—”the first women-only cybersecurity program for women in Africa”—Osideko began her journey on May 31st, the day after her birthday. “For me, it felt like I was starting a new phase,” she reflects.
Within months of starting the program, Osideko had gravitated toward offensive security. “I had been spending a lot of time on TryHackMe at the time and capturing-the-flag competitions, and I found it really interesting, which made me come to the conclusion that I wanted to be on the offensive side of security,” she says. Today, she specializes in finding vulnerabilities in web applications and APIs as a penetration tester for Digital Encode, a cybersecurity consulting firm in Lagos.
Her first taste of bug bounty success came unexpectedly in 2022 while conducting a penetration test for a client. “They were using a third-party payment gateway, and I reported it to the company. They awarded me a bounty of $900,” she explains. “I was still new to the space and it was an eureka moment for me.”
For Osideko, cybersecurity represents more than just a career—it’s a calling. “It gives me a sense of purpose. There are a couple of things I have tried in my life, but nothing comes close to hacking. I am obsessed with it; if I had all the time in the world, I would continue learning about it as much as I can,” she states emphatically.
The practical impact has been equally profound. “I was able to land my first job without a degree or certifications, which over the years has improved the quality of my life. I can manage to take care of myself and not have to call home for help,” she notes. The field has also connected her with “friends, who are now family—my support system who keep me grounded.”
One particularly memorable moment came in 2024 when she traveled internationally for a client penetration test. “I had never flown in a plane, but in 2024, I traveled out of my country to conduct a pen test for a client. It was a surreal moment for me,” she shares.
When discussing underappreciated vulnerabilities, Osideko highlights race condition vulnerabilities as particularly concerning. “I don’t think I have seen anyone talk about [race condition vulnerabilities], and to even discover that they have been around for years is quite shocking to me,” she observes. “I think they’re not talked about enough, and they’re dangerous because of the different ways this vulnerability could play out in real life.”
Her tool of choice remains Burp Suite: “Burp Suite has to be top of my list for web hacking, I love it!”
Regarding AI’s impact on cybersecurity, she maintains an optimistic outlook. “I think I have heard some people say that AI will take away a lot of jobs, but I don’t agree. I think AI will help to make processes faster,” she argues. “I believe it will also open up more job opportunities for cybersecurity professionals pen testing AI, assessing the risks they pose, and lots more.”
Osideko describes her current role as both collaborative and demanding. “I work independently at times, and there are projects that I don’t handle alone. I also work with a team to get the job done,” she explains. “It can be intense; everything is time-bound, and clients want results. Then there is the constant need to learn a lot of things on the go; if there is no proper structure, it can get overwhelming very fast.”
A key motivator for Osideko’s involvement with Bugcrowd’s HackHers network stems from the stark gender disparity she witnesses in the field. “I was at a bug bounty meetup hosted by a friend of mine, and only five women were present; the rest were men. By percentage, I would say 90% were men and 10% were women,” she recalls. “Women are still underrepresented in cybersecurity…. What Bugcrowd is doing by starting the HackHers network is a great initiative.”
Reflecting on her journey, Osideko identified crucial lessons about self-advocacy and confidence that have spurred her forward. “I wish I had prioritized myself more. I also wish that I had ignored the people who discouraged me from doing some of the things I wanted to do in the beginning,” she admits.
Her advice for aspiring hackers is direct and encouraging: “Never doubt yourself. You can do this. The world is waiting for you, and we need you. Start hacking, and draw inspiration from other people who have done it before you. Just do it!”
To maintain her mental health in this demanding field, Osideko emphasizes the importance of balance. “I watch movies, listen to music, and most importantly, I take a break from my screen to recharge and relax,” she shares.
For 2025, her goals include reporting valid bugs to Bugcrowd programs and sharpening her skills, recognizing that “pen testing is different from bug hunting; while the skills are the same, the approach is different.”
Highlighting the determination that has carried her from low points in her life to discovering and excelling in the world of cybersecurity, Osideko’s story serves as a powerful reminder that cybersecurity careers can emerge from unexpected circumstances and that diversity of background strengthens the entire field. “I have read a couple of Hacker Spotlight stories on Bugcrowd, and I muttered to myself that someday I will be featured too,” she concludes.