Leadership and cybersecurity play a critical nexus in the quickly changing digital landscape of today. Organizations must keep ahead of innovation and risk since as technology develops, so do the threats that come with it. Discover the world of Chief Identity Hacker and CEO Sallyann Della Casa, a dynamic character that has led her career by saying the unsaid.
In this exclusive article, we dig into the perspectives and experiences of these two crucial positions, examining how they work together to protect GLEAC (an on-demand platform with a network of over 2,500 of the world’s leading experts, mentors, and coaches) from new cyberthreats and lead it in the direction of expansion. Learn how the strategic vision of a CEO and the in-depth knowledge of digital vulnerabilities held by a Chief Identity Hacker combine to create innovative, resilient solutions that protect assets and drive accomplishments.
What are the main factors that guided you to where you are now?
It took several wrong turns to become who I am today. I started as a young corporate lawyer at 21 in the U.S., a path I found myself on because of my confidence and tendency to speak up. But I hated every moment of it. The legal profession in the U.S. is steeped in rigor and tradition, which conflicted with my deeply creative and innovative nature. After a decade of practicing law, I finally had the courage to leave it behind and embark on a journey to discover who I am and why I’m here after my dad passed away.
Since stepping away from that profession, my life has taken fascinating turns. With my five-plus degrees, Igave myself permission to start my own NGO, the Growing Leaders Foundation across the Caribbean, which focuses on equipping at-risk youth and adults with soft and transferable skills to make them job-ready. This initiative led to a partnership with the UN to teach financial literacy across the school systems. That experience directly connects to an opportunity just two weeks ago in the Kingdom with QOL and the UN, where I was invited to join the advisory team to innovate a groundbreaking Quality of Life Index for 100 cities. This chance wouldn’t have arisen without my NGO work a decade ago.
During this NGO period, Careem also came knocking. I was undecided for six months before finally saying YES. That decision, along with proximity to data scientists, technology, and experiments around what motivates people to perform, along with witnessing rapid growth with systems, opened my eyes to the possibilities that led to building GLEAC and filing my first patent on training agents and AI in soft/transferable skills.
I think the key factors that brought me to where I am today are my willingness to say YES and my refusal to cling to a fixed notion of who I can become (which, by the way, is the title of my 2016 book: *Who Will I Become*).
When I eventually exit GLEAC, I have no idea who the next version of me will be, but I’m excited to find out and meet her.
Given your 20+ years of experience and accomplishments, what would you say was your biggest achievement?
I have many symbols of success, but my greatest achievement is who I am during failure and challenging times. It’s in these moments that true character is revealed. I always show up with calmness, focus, resilience, and kindness. I take the lead on difficult conversations, make tough decisions, and remain consistent. I’m far from perfect, but I hope my reputation and accomplishments reflect who I am—and continue to be—especially when things aren’t going my way.
What is the quote that inspires you the most?
“Intelligent people solve problems. Wise people avoid them.” In a world where many are eager to prove and be paid for their intelligence, I strive to bring wisdom to the table.
How would you balance the pursuit of wealth and success with personal fulfillment and happiness?
I believe that true balance is elusive when you’re excelling at something, and I’m not a multi-tasker—I’m a uni-tasker.
Right now, all my focus is on GLEAC until I find the right strategic global partner to work with me to take what I’ve built from 1-10 to 10-100. I want to set an example in the region of what women without a tech background can achieve in the tech and AI space, and it’s not about ego. Proximity is key; we’re more likely to emulate what we can see. It’s the entire ethos of why GLEAC exists. If I can get you close to those who think differently or similar from you, just maybe you can change your mind or become the best version of yourself all due to proximity to a role-model.
There are few, if any, female-led tech and AI startups in the region that have achieved massive scale or a successful exit.
Once I’ve accomplished what I need to with GLEAC, I plan to take three months to reconnect with nature—rolling around in the grass and hugging trees—before diving into my next venture. There are still so many things I want to build. I’ve definitely caught the startup bug, and I believe I have 2-3 more in me. It’s supposed to get easier after the second one, or so I’ve heard from all my guy friends who have successfully exited 3+ startups.
What personality traits contributed to you being the CEO of GLEAC?
I’m not a brilliant CEO, and that’s not imposter syndrome talking (which by the way is some ridiculous term invented in a lab by scientists) —I’m simply not great at it. My goal is to hire a CEO or bring on a Co-CEO very soon. I don’t enjoy operations; I handle them because I must. What I naturally excel at is product development, UX, business development, and community engagement. My leadership style is laissez faire meaning I give folks a lot of bandwidth to figure things out with their own skills and talents which only works with very highly competent motivated people. Culturally that does not work everywhere.
Many founders aren’t great CEOs, which is one reason so many startups fail. I’m keenly aware of my shortcomings, which can be both a blessing and a curse—for now I’m incredibly hard on myself and tend to also overperform to make up for it.
I recently had the pleasure of having my experts share knowledge with the Transformation team at PIF on leadership succession academies for the portfolio companies, where we emphasized that in today’s complex world, being a great CEO might no longer be a one-person job. We anticipate more organizations will adopt the Co-CEO model, as the diverse skills needed to drive performance, stay relevant, innovate,and operate efficiently particularly b/c like Nvidia, organizations are becoming flatter.
How do you foresee the mentorship community/industry evolving over the next ten years, and what strategies are you implementing to stay ahead?
If you asked anyone whether they’d prefer taking an online course or speaking directly with someone who’s already done it to guide them, what do you think they’d choose? The future of learning lies in mentorship, on-demand experts, coaches, and learning communities.
My platform offers this through a community of over 2,500 experts available on-demand, or you can use your own network to mentor each other on our platform. We’re even on the brink of seeing AI-powered mentors.Already, we’re utilizing GPTs to deliver Individual Development Plans to employees.
To stay ahead in people development and knowledge transfer, embracing technology and AI is essential.
By mining questions, conversations, and insights, and by listening to the organic, unstructured learning that occurs in mentor communities—whether through video calls or GPT-driven interactions—you’ll gain crucial insights into what your teams need, what products to offer your customers next, and much more.
In light of your journey and experiences, what message would you like to convey to aspiring entrepreneurs?
It’s the hardest thing I’ve ever done being a sole Founder and entrepreneur, and everyday is a mix of fear and courage. I am not sure if this ever stops. There’s a reason why about 90% of those who attempt it fail—it’s not for everyone, and you need to understand your risk tolerance before diving in.
That said, with an experimental mindset, I encourage everyone to give it a try—as long as your sense of self and identity isn’t tied to the outcome or success of it.
What is your personal leadership philosophy, and how does it shape the approach and methodologies used by GLEAC?
Leadership is about how you act where you stand; it has nothing to do with titles, education, pedigree, or the size of your bank account.
Viewing leadership through this lens, I give everyone with potential a fair shot. Sometimes it backfires, but other times I see remarkable individuals who blossomed under my guidance. Today, they’re leading teams at some of the biggest unicorns in the region, and they’re not even 30 yet. I deeply care who others, particularly young people, become under my watch and that can be a blessing or a huge problem if you are coasting along.
What is the most valuable lesson learned from your professional journey?
For me, it’s all about setting boundaries and learning to let go. You’re not entitled to be on anyone else’s journey, nor are they on yours. Compassion, kindness, and focus require strong boundaries to protect your energy. Don’t hesitate to ask for and create the space and environment you need to thrive if you plan on showing up at your 200% in life.
It’s a bit of a secret, but I’m a deep introvert. Most people don’t notice because I’m so passionate about my work and confident in public. What they don’t realize is that after those public appearances, I often retreat for days to recharge.
Tell us more about what distinguishes GLEAC from others providing similar services?
Let me clarify what our community of 2,500 of the world’s leading experts, mentors, and coaches, combined with our technology, is *not*, by contrasting it with some familiar names:
We are not just a coaching platform. Instead, we offer or can complement coaches, with mentors, and experts together on one platform, on demand for anything from a quick 10-minute conversation, which C-suites appreciate having at their disposal, to a full 90-minute session or team fireside chat tailored to your needs. Every employee or team has different requirements. Many coaches lack operational experience; often, a mentor or expert with hands-on knowledge is what’s needed to compliment them. We bridge all these gaps at every level in one platform.
We are not consultants who we recognize respectfully as having a place in the ecosystem. Our experts,mentors, and coaches bring deep operational experience. Their knowledge transfer comes from having been there, done that, or actively doing it now in emerging fields. This practical insight makes a huge difference in your ability to act on the conversation. Often, the vendor or partner you need to build, solve, or finance your challenge is right there in the room in our sessions across every domain.
We are not an asynchronous on-line learning platform. We compliment this type of learning and often help drive engagement and completion. Our approach is dynamic, community based and interactive. You can launch your own, white-labeled academy with our technology overnight, offering courses led by our experts, mentors, and coaches in sprints over 4-6 weeks or several months, with personalized GPT-driven learning plans for each learner. Because our experts form a true community, what they teach is tailored to the outcomes you want to see on the job immediately.
Our technology platform is trusted by clients in the Kingdom, including the Financial Academy of Saudi,PIF, QOL, and Transform for SIDF, among others. Globally, since
Our inception five years ago, we’ve had the privilege of working with renowned names like PWC, Prada,Richemont Group, Indian Oil, Valaris, ONGC, and Expo 2020’s Skills of the Future Pavilion (which became the 2nd most visited pavilion), among many others.
How did Covid impact GLEAC? And how did you overcome this period?
We had to pivot. At the time, we were 1.5 years in, offering only an online micro-practice learning system focused on soft skills in the flow of work. We still have that system today, which functions like an apprenticeship, immersing you in 5-minute daily scenarios through our app or WhatsApp, where you practice applying skills in the workplace.
During COVID, Prada USA approached us, asking for real humans to lead learning stand-ups with their managers every Monday. In response, we welcomed our first 50 mentors into the community in September2020, marking the beginning of the GLEAC you see today. Now, our micro-practices are enhanced with expert insights—immediately after completing a practice, you can see how five experts would have handled the same situation.
Are there any upcoming projects or initiatives you’re particularly excited about, and how do they align with GLEAC’s strategic goals?
We’re truly excited about our work in the Kingdom. With fewer legacy systems in place, the speed at which we can deploy our technology has been remarkable, and the need and appreciation for the type of knowledge transfer we provide have been incredible. We’re considering setting up an entity in Saudi Arabia before the end of the year and are actively seeking the right strategic partner.
On a personal note, I’m particularly excited about AI agents. By the end of the year, this technology is set to revolutionize every LMS as we know it. We’ll be launching an entirely new version of our micro-practices, integrated with AI agents, before the year’s end. I’m eager to see Individual Development Plans (IDPs) and GPT-powered learning plans become commonplace in the Kingdom, transforming how knowledge is transferred and delivered across organizations.
It’s an exciting time to be alive!
