Meet Jenny

A career shaped by opportunity

Jenny’s own career is a powerful example of the opportunity Checkout.com can create. She joined as Head of Revenue Operations in the Commercial team, coming from SaaS and learning the complexity of payments quickly. Four years later, she is COO and CHRO, leading Operations and People.

“I lead with the fact that I started as the Head of RevOps here in the Commercial team and am now the COO and CHRO over Operations and People. I didn’t join as an executive, but found my way there with so much support and coaching from the leaders here today. And I’m not an old guard or a payments native.”

Her progression reflects a broader belief in potential. People grow here by bringing curiosity, judgement and ambition to meaningful work, in an environment that recognises what they can contribute now and creates space for what they can become.

“We are a company that believes in and promotes potential, not based on someone’s CV. We take bets on high potential individuals and their ability to stretch and learn, even if they have not done that work or role before.”

High performance starts with clarity

Jenny has a clear view of the culture we are building here, where high standards are explicit, ownership is real and people understand the outcomes they are accountable for.

High performance can be easy to misread as pressure, constant urgency or a culture where effort matters more than impact. At Checkout.com performance starts with knowing what matters, understanding what good looks like and being honest about whether the work is moving the business forward.

“We remain outcome focused as a company. That is why goal setting is core to everything we do here, at every level. It is the outcome that matters, not the milestone or the activity it takes to get there.”

Effort matters, but effort is not the end measure. In a fast-moving environment, the real value comes from focus and the ability to produce work that creates impact.

“Hard work is tightly correlated with the right end outcome, but a lot of time spent on something does not always guarantee the quality of the outcome. Working smarter is far more valuable than simply working harder.”

AI is changing the way great work gets done. The strongest performers are using new tools to create more space for the critical thinking, judgement, communication and storytelling that raise the quality of the work.

“Those embracing AI can reduce the time spent on core tasks and use that time to improve the critical thinking and storytelling that goes on top of it. That improves the quality of what we are producing and diversifies the skills of our employees.”

Checkout.com is a place for people who care about outcomes, not optics, and who are energised by the accountability that comes with meaningful work.

The energy behind high performance

Jenny is open about the intensity of the work here. Payments is a demanding industry, where reliability, speed and execution matter every day because our merchants depend on us to help them move money around the world with confidence. But she does not see that energy as something to apologise for. With the right clarity, team and purpose, it can be motivating.

“People often speak about intensity as a bad thing. We don’t see it that way here. Intense can be fun and challenging. It can bring people together to play as a team and collaborate.”

The point is not to keep people busy. It is to bring talented people together around meaningful problems and create the conditions for them to do some of the best work of their careers.

“Your days can be incredibly rewarding and satisfying when something is full on. We want people who agree with that.”

This environment will not be for everyone. But for people who are motivated by challenge, momentum and ownership, it can be deeply energising.

Building with the best 

Building with the best is not about rewarding the loudest voice in the room or valuing individual brilliance over the team. It is about humility, expertise and the standard people help create around them.

“We want people who are humble, eager to learn and believe in building expertise. It takes a lot of time and effort to become an expert and we believe in all being payments experts here.”

Payments is complex, and the people who thrive here stay curious. They build depth in their own area, learn from the people around them and care more about getting to the right answer than being seen to have every answer themselves.

“If you relish being the smartest person in the room and hearing your own voice, Checkout.com is not for you.”The strongest people here make those around them better. 

Autonomy to make an impact

Ownership here goes beyond responsibility for a task. Jenny describes it as understanding the outcome, making decisions, taking accountability and staying close to the impact of your work.

“There is a lot of room to make and own decisions here, to take bets and to meaningfully impact the outcomes of the business in every role and team.”

This can be one of the most rewarding parts of working here. People are trusted to contribute beyond a narrow job description, think commercially, collaborate across teams and understand how their work ladders up to our company goals. That autonomy can be deeply motivating, but it only works when people are willing to take accountability for what happens next.

“It means taking accountability for the challenges of getting there sometimes. We want people who are excited by that autonomy and authority, and who do not shy away from owning the outcome, good or bad.”

In practice, that means bringing solutions, not just surfacing problems. It means making decisions with imperfect information, being honest when something is not working and staying proactive about changing course. Ownership is not a slogan, it is how work moves, how decisions are made and how people build trust.

Pace paired with judgement

“We run at a very fast pace here, and that makes every day exciting and energising. You can go from idea to action in the span of a day.”

Pace is one of the reasons Jenny finds the environment exciting, but speed only becomes a strength when people understand what the moment requires. Some work needs depth, some needs a decision and some simply needs to be clear enough to move the business forward.

“I fundamentally don’t believe that speed and quality are contradictory to each other, but sometimes speed and depth can be.”

The challenge is knowing what the outcome really requires, because speed is not the risk in itself. The risk comes from adding complexity that does not serve the decision, slowing the work down and pulling time away from other priorities.

“The risk is not whether we favour speed over quality, but whether we misjudge how much of each is required for the right end output.”

Building a feedback culture 

Feedback is not treated as a formal moment that happens once or twice a year. Through Fabric, our home-grown performance tool, it is built more continuously into how people work, connect to goals and reflect on their impact.

Jenny points to two qualities that make feedback work in practice. People need the self-awareness to hear feedback properly and act on it, as well as the curiosity to understand how teams, decisions and customer needs connect. Together, those qualities help people plan better, collaborate more effectively and deliver against the outcome.

“Feedback is easy to give and get here, but it’s most meaningful and most impactful when people are self-aware. Self-aware individuals genuinely listen and understand how feedback resonates with their own lived experience. Because they are already reflecting on their work, the feedback feels like a collaborative next step rather than a surprise.”

That mindset is what makes feedback valuable in a fast-moving environment. It encourages people to stay close to their own performance, understand how their work lands with others and keep improving, rather than waiting for direction or relying only on formal review cycles.

“People who are naturally curious will learn how things come together across all of the teams and departments to create the end outcome.”

The aim is clearer expectations, better conversations and stronger alignment between individual work and business outcomes.

Finding the right fit

Jenny’s emphasis on transparency is rooted in helping people understand whether this is the right environment for them. A high-performance culture will not suit everyone, and candidates should know what is expected, what is valued and how the business operates before they choose to join.

“Choosing a company is like choosing a university or a friend group. Everyone should make sure they understand the culture and that it is a fit for them today.”

Today, ‘fit’ means the way we work already feels natural to someone, rather than being something they hope to grow into later.

“It shouldn’t be aspirational to how you believe you should work or behave, but completely natural to how you operate already.”

The interview process and Operating Principles are designed to make expectations visible, from high standards and ownership to pace, curiosity, feedback and accountability. For candidates, that clarity helps them make a more informed choice. For the business, it helps build stronger alignment with people who are genuinely energised by this way of working.

Place for people who want to build

At Checkout.com, high performance is measured by outcomes, expertise, curiosity, ownership, pace and the willingness to keep learning as the work gets more complex.

For the right people, that combination can be career-defining. It means working with exceptional colleagues on meaningful problems, being trusted with decisions that matter and growing through feedback, exposure and responsibility. It means joining an environment where high standards are not abstract. They show up every day in how people think, collaborate and deliver.

“The potential is unlimited here at Checkout.com, and I can say that honestly from my own career journey here.”

For people who are energised by that, Checkout.com can be a deeply rewarding place to build. Explore careers at Checkout.com and find a role where you can grow, contribute and help shape what comes next.