What does it really mean to lead with heart in a world driven by targets, technology, and transformation?
That’s the central question in a recent episode of the Brave Bold Brilliant podcast, where host Jeannette Linfoot sat down with Jesper With-Fogstrup, Group CEO of Moneypenny. What followed was a wide-ranging, refreshingly candid conversation about leadership, culture, innovation – and the human values that bind them together.
Whether you’re a business leader, entrepreneur, or someone interested in where values meet vision at the highest levels, this episode offers a rare glimpse into what modern leadership truly looks like.
One of Jesper’s most striking reflections came early in the discussion: “You can’t scale without soul. Tech enables it, but people drive it.”
It’s a deceptively simple idea, but one that underscores his approach to leadership across a career that spans travel, finance, proptech, and now communications.
Jesper argued that genuine business success isn’t just about hitting milestones—it’s about building teams with purpose. “You need different perspectives in the room,” he explained. “Different backgrounds, different lived experiences. That’s how you solve problems creatively.”
He also contrasted empathetic leadership with what he calls the “clinical” scaling mentality, hyper-focused on metrics, but often detached from the people behind the numbers. The best results, he believes, come from leaders who care: about their teams, their customers, and the impact they’re making.
Another recurring theme was trust – both inside teams and with clients.
Jesper challenged the common business language of “outsourcing,” preferring to think in terms of partnership. He described trust as something earned every day, especially when handling something as valuable as another business’s brand or customer experience.
“You’re not just fulfilling a contract,” he said. “You’re taking responsibility for how someone else shows up in the world. That’s a big deal.”
Jesper has led digital transformation efforts across multiple industries, so it’s no surprise the conversation turned to innovation. But unlike the usual hype cycle, he brought a thoughtful, grounded view to the role of AI and automation.
At the core of his thinking is this: technology should never replace people – it should elevate them.
He gave an example of building AI voice agents that can answer calls and handle common tasks – but crucially, they’re designed to escalate seamlessly to a human when needed. And when that handoff happens, the human picks up with full context.
“None of that ‘please start from the beginning’ stuff,” he quipped. “That’s a terrible experience. And it’s avoidable.”
Jesper sees technology as a tool to free people up to do what they’re best at – bringing empathy, nuance, and problem-solving into conversations. His approach is less about chasing the latest trend, and more about creating meaningful, useful systems that make work better for everyone involved.
When asked about how he makes decisions in a fast-moving tech landscape, Jesper offered a simple principle: “I don’t know everything. That’s the point.”
He described deliberately building teams where disagreement is encouraged. “I tell everyone who works with me that 10% of their job is to disagree with me,” he said. “You don’t want people who just nod along.”
That humility, paired with curiosity, seems to be a key part of his leadership style. Jesper admitted to running at “110 miles per hour” but said he’s learned to slow down enough to test, reflect, and challenge assumptions. Mistakes, he argued, aren’t the enemy, they’re the source of growth.
In one of the episode’s more personal moments, Jesper opened up about being an openly LGBTQ+ leader – and how he balances visibility with not wanting to be defined by labels.
“I happen to be gay,” he said, “but I don’t think anyone should have to lead with that. What matters is who you are and what you bring.”
He spoke about the power of inclusion, not just as a social good, but as a way to build stronger, more resilient businesses. The best teams, he argued, are composed of people who think differently, feel differently, and bring different things to the table.
Every day at 5:20 PM, Jesper’s calendar pings with a simple reminder: “Was it a good or bad day, and what did you change today?”
That question, he says, keeps him grounded. It reminds him that leadership isn’t about managing the status quo – it’s about moving things forward, however incrementally.
“If I didn’t try to make something better today, then what was the point?”
It’s a habit that encapsulates Jesper’s mindset: change-oriented, people-focused, and relentlessly curious.
Jeannette asked Jesper about negative experiences in leadership, and he didn’t shy away. He described moments of imposter syndrome, unexpected setbacks, and a particularly difficult situation with a former boss who made an inappropriate comment.
Instead of retaliating, Jesper chose to treat it as a learning opportunity. “I respected them, and I thought maybe we could turn it into a moment of growth,” he explained.
It was a powerful example of leading with compassion and purpose, even when it would have been easier not to.
Toward the end of the episode, the conversation turned to social impact and investment. Jesper is a vocal advocate for impact investing, particularly around homelessness – a cause close to his heart.
He shared a personal story about sitting down with a man outside Old Street station, learning about the cascade of life events that led to him sleeping rough.
“It reminded me how close any of us could be to that line,” he said. “We need systems that give people a second chance.”
There are podcast episodes that feel like content – and there are episodes that stay with you. This was one of the latter. Jesper’s conversation with Jeannette was filled with thoughtful reflections on leadership, technology, inclusion, and kindness. It wasn’t about hype or headlines. It was about the values that guide people at the top – and what it means to lead with soul.
You can listen to the full episode at brave-bold-brilliant.com or on your favourite podcast platform.
At Moneypenny, this isn’t just a conversation – it’s our culture.
Jesper’s leadership philosophy is already shaping how we blend people and technology to help businesses of all sizes deliver brilliant service. From intelligent call handling to live chat and AI voice solutions, everything we offer is designed to put people first.
Get in touch today to discover how we help businesses like yours.
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