Finding Your Voice in FinTech Leadership

FinTech Recruitment and Inclusion

In the latest episode of FinTech’s DEI Discussions, hosted by Nadia, Jenny Hadlow, Chief Operating Officer at Checkout.com, shares how she’s helping shape a more inclusive financial technology industry. With a clear passion for operational excellence and cultural impact, Jenny provides a refreshingly practical perspective on how FinTech firms can embed diversity, equity, inclusion, and belonging (DEIB) into the very core of their business models.

Throughout the conversation, Jenny discusses her career journey, her role as a DEIB sponsor, the development of Checkout.com’s employee communities, and how she played a central role in helping the company achieve 47% female hiring last year. The themes of purpose, action, and accountability run throughout this compelling episode, offering essential insights for those in the FinTech recruitment ecosystem—from HR leaders and hiring managers to executive teams and individual contributors.

A FinTech Career Rooted in Purpose and Global Perspective

Jenny’s journey into FinTech reflects many of the trends we see in FinTech recruitment today: dynamic career pivots, international experience, and the search for roles that offer real-world impact. After spending over a decade in the SaaS sector—including helping to take a company through IPO—Jenny transitioned to FinTech through a venture capital connection who introduced her to Checkout.com.

She describes the move as not only professional but deeply purposeful. Payments, as she points out, are essential infrastructure for the digital economy. From household brands like Dyson and Sainsbury's to fast-scaling digital businesses, Checkout.com’s services touch every layer of commerce. For Jenny, this tangibility is what made FinTech such a compelling sector to join. It offered the scale of impact she was seeking and the opportunity to build products that make a real difference to both businesses and consumers around the world.

This perspective is particularly relevant to the FinTech recruitment sector, where we continue to see a rise in purpose-driven candidates looking for more than just a job—they want to contribute to something meaningful. At Harrington Starr, we’re seeing a clear shift in what talent wants: mission, inclusivity, and impact.

The Real Meaning of Belonging in FinTech Workplaces

In addition to her role as COO, Jenny is a DEIB sponsor at Checkout.com—a responsibility she takes seriously. Her focus is on belonging, which she believes is the truest outcome of any DEI effort. It’s not about box-ticking or one-off campaigns. Belonging, as Jenny puts it, is what employees feel every single day when they show up to work.

Her approach is refreshingly candid. She acknowledges the persistent presence of unconscious bias and systemic barriers but balances this with a proactive mindset. She emphasises the need to focus not just on merit, but on potential—a distinction that holds particular value for recruitment professionals. What someone is capable of doing should weigh just as heavily as what they’ve done in the past. This mindset shift opens the door for more inclusive hiring, diverse leadership, and upward mobility within organisations.

Jenny also reflects on her own background, including growing up in a female-empowered environment at an all-girls school and within her family. It wasn’t until she entered the global business world that she realised the culture she had taken for granted was not universal. This awakening prompted her to take ownership of creating more inclusive environments, especially as she moved into more senior roles.

Building FinTech Culture Through Internal Communities

A major part of Checkout.com’s DEI success stems from its internal communities—nine in total—that cover a broad range of identities and interests, including women’s groups, LGBTQ+ initiatives, and disability inclusion. These communities were already in existence but lacked the leadership and structure to thrive. That’s when Jenny stepped in.

She personally recruited every community leader across the nine groups and implemented a three-tier leadership model. Each community has a direct leader, a leadership team sponsor, and an executive sponsor. This structure ensures that the communities are not tokenistic but are instead empowered with authority, visibility, and resources.

Jenny worked closely with each group to help them understand their charters, plan their engagement activities, and develop their rhythm. What emerged from this was a robust network of employee-led communities that contribute meaningfully to Checkout.com’s culture. These groups now advise on policy, participate in company communications, and support the wider business during challenging times.

This level of intentionality demonstrates how inclusive cultures aren’t just created from the top down or from external consultants. They are cultivated internally, through consistent effort and genuine engagement. For those involved in FinTech recruitment, this offers a key takeaway: diverse talent thrives not just on entry but when there are sustained cultural mechanisms that support belonging and visibility.

Gender Diversity in FinTech Hiring: 47% Female Representation

One of the most notable achievements shared in the episode is Checkout.com’s success in achieving 47% female representation in its hiring efforts. This statistic is impressive not just for its size but for the coordination and commitment it represents. Jenny is quick to credit the wider team, especially the People and Talent Acquisition (TA) functions, for their role in this accomplishment.

She outlines the various stages of the recruitment pipeline where intentional decisions were made. First was the employer brand—ensuring that the public image of Checkout.com reflected its inclusive internal culture. Then came the focus on diverse candidate slates. TA teams were empowered and expected to ensure hiring managers saw a broad spectrum of applicants before final decisions were made.

Interview panels themselves were scrutinised for diversity. Jenny recalls a moment where a senior female candidate remarked that Jenny was the only woman she had spoken to in the process. That comment was a reminder of the power of representation—not just among applicants, but within the decision-making process itself.

Additionally, Checkout.com placed a heavy focus on internal mobility. Many of the women hired were in junior roles, and the question then became how to nurture and promote them into leadership. Jenny’s own department has achieved gender parity, but her sights are now set on increasing the number of women in senior positions—a goal that echoes across the wider FinTech landscape.

Why FinTech Businesses Must Act Now on Inclusion

The conversation also addresses the shifting global attitudes towards DEIB, particularly in the US. Jenny expresses concern about companies pulling back from inclusion initiatives, citing political and social pressures. In contrast, she says Checkout.com is doubling down on its DEIB commitments—a stance that has been positively received by employees.

Her advice to businesses is clear: now is not the time to retreat. The industry should be accelerating action, not pausing it. She encourages companies to stay loyal to their DEIB commitments and to resist the urge to wait for perfect conditions or big budgets.

Jenny also challenges the idea that impactful DEI work requires grand gestures. Small, consistent actions—like hosting monthly community lunches or inviting internal voices to speak on key topics—can accumulate into major cultural shifts. She believes that every individual, regardless of role or seniority, can contribute to creating a more inclusive FinTech workplace.

A Blueprint for Inclusive FinTech Hiring and Leadership

Jenny’s story, and Checkout.com’s progress, offer a blueprint for how to do DEIB right in the FinTech space. It’s about structure, intention, and the long game. The lessons shared in this episode of FinTech’s DEI Discussions are particularly useful for hiring managers, recruiters, and business leaders who are actively shaping the future of FinTech talent.

The emphasis on belonging, the proactive recruitment of community leaders, and the tangible improvements in gender representation all point to a single truth: culture doesn’t just happen. It is built—brick by brick—through deliberate, thoughtful action. And when that culture is inclusive, it doesn’t just benefit underrepresented groups; it strengthens the organisation as a whole.

At Harrington Starr, we work with FinTech companies across the UK, Europe, and the US to help them build these types of teams. We believe that inclusive recruitment is smart recruitment. It’s not only about meeting diversity metrics—it’s about unlocking the potential that lies within a truly representative workforce.