Every meaningful career is built one decision at a time. But what separates the good from the great, and how do companies consistently attract and nurture exceptional talent? In a recent episode of the DexFactor Podcast, I had the pleasure of sitting down with Charlie O'Driscoll, a seasoned expert in technology hiring who currently leads tech recruitment at Monzo. Previously, Charlie guided software engineering hiring at Deliveroo through their high-profile IPO and was instrumental in talent acquisition efforts at Improbable. Our conversation dove deeply into the essence of great hiring practices, transformative talent programs, and the human-centric approach that truly drives organisational success.
Charlie’s career has always been focused on building teams capable of extraordinary things. When asked about his most memorable hire, Charlie didn't simply point to a big name or a high-profile position—though he's hired plenty of impressive leaders throughout his career. Instead, he shared a profound insight about the power of transformative hiring at a grassroots level. At Monzo, Charlie led the creation of an innovative internship program designed explicitly for employees from their customer operations team who wanted to transition into software engineering. This program has become one of the cornerstones of Monzo's talent strategy, not only because it develops technical skills but also because it fundamentally reshapes lives and careers.
The best hires we've ever made are about giving people a chance to fundamentally change their careers—and their lives
That time when…
"The best hires we've ever made are about giving people a chance to fundamentally change their careers—and their lives," Charlie emphasized. It’s a sentiment deeply aligned with Dex’s mission to empower people to find and thrive in careers they genuinely love. Monzo's internship initiative, now in its third successful year, illustrates perfectly what happens when companies prioritize human potential over credentials alone. With 18 individuals already having completed or participating in the program, Charlie’s goal is even more ambitious: envisioning a day when one of these homegrown talents rises to a senior leadership role.
Charlie's reflections underscored the fact that great hiring isn’t just about spotting existing talent—it’s about creating the right environment for that talent to flourish. He emphasised onboarding as a critical differentiator between good hires and great hires. Companies often overlook this phase, assuming that once someone is hired, the hardest part is over. In reality, the onboarding experience is pivotal. It’s the bridge between a candidate’s potential and their actual impact on the organisation.
Best onboarding practices
"Fundamentally, I do think onboarding is one of the key things from separating good from great," Charlie noted, highlighting that even the most capable people can struggle without proper integration into company culture and systems. He pinpointed two vital elements of effective onboarding: providing ample space and time for new hires to adjust, and clearly setting expectations about their early-stage contributions. Success isn’t immediately measured by rapid outputs or quick wins, but by how well newcomers can observe, learn, and begin navigating internal dynamics.
The conversation also touched on common pitfalls that occur when new hires don't land as expected. According to Charlie, failures typically result not from technical deficiencies but from subtle behavioural misalignments. Skills can be taught; behaviours and cultural fit are far more nuanced and significantly harder to shift. "Technical brilliance can sometimes hide these behavioural flags," Charlie explained. Companies often see technical skills and past achievements as predictors of future success, overlooking that the methods and style of achieving those results matter equally—sometimes even more.
Fundamentally, I do think onboarding is one of the key things from separating good from great
Best practices
Charlie illustrated this point clearly with a challenging hire from his time at Improbable, recruiting field engineers or developer evangelists. This role required a unique blend of passion and pragmatism: finding skilled engineers who were passionate about game development but willing to sacrifice building their own games to instead create demos to showcase Improbable’s platform to others. Such roles inherently conflict with the intrinsic motivations of many candidates, making alignment on values and motivation critical. Charlie’s perseverance paid off after a year-long recruitment effort, successfully hiring a candidate from Singapore who stayed three years and made substantial contributions.
His advice to candidates applying for roles at Monzo was refreshingly direct and deeply aligned with Dex’s values. Charlie urged candidates to thoughtfully consider whether Monzo’s mission—to make banking and finance accessible to everyone—truly resonates with them. Alignment on mission and values isn’t a luxury; it’s essential. Candidates who genuinely connect with a company’s purpose don’t just perform better—they thrive, contributing to a culture of authenticity and sustained growth.
When it comes to receiving job offers, Charlie provided valuable guidance rooted in personal fulfilment and long-term satisfaction rather than purely financial considerations. He advised candidates to weigh offers not just by salary, but by factors that significantly impact overall happiness: work-life balance, meaningful progression opportunities, the strength and values of the team, and personal alignment with the company's mission. He noted that the best career moves are those that enrich personal lives, not merely bank accounts.
In closing, Charlie candidly addressed common misconceptions in the recruitment world—particularly the widespread belief among candidates that artificial intelligence screens their CVs. "We don't have AI CV screening," he clarified emphatically. Human recruiters are still at the heart of the process, making human decisions. This simple but powerful statement reinforces a core Dex value: that the hiring process is fundamentally about connecting with individuals on a personal level, understanding their unique potential, and matching them thoughtfully with opportunities that allow them to shine.
Technical brilliance can sometimes hide these behavioural flags
In conclusion
My conversation with Charlie reinforced a key theme central to Dex's approach: exceptional talent acquisition isn’t merely about filling vacancies—it's about genuinely understanding, nurturing, and empowering people. Great hiring practices aren’t transactional; they’re transformational. They change lives, shape careers, and drive organisations to new heights. Charlie’s insights serve as a timely reminder that at the core of every successful hire is a profoundly human story—a narrative of potential realised, challenges overcome, and opportunities embraced.
At Dex, we believe passionately in this narrative. As we continue to build platforms and strategies aimed at connecting talent with purposeful work, Charlie’s reflections provide powerful guidance. Effective recruitment and onboarding aren’t just administrative tasks—they’re strategic imperatives that shape the future of companies and the lives of individuals within them. We remain committed to championing a vision of work where passion aligns seamlessly with purpose, where each hiring decision echoes Charlie's own belief: careers should fundamentally transform lives for the better.
