In our first #FinnemoreFireside of the Autumn term we’re joined by Stephen Bilboe, CEO of Esenda – the payments platform that’s quietly transforming how independent schools manage fees, finance, and family experience. With a background in MIS and education software, Steve brings a sharp eye for solving complex problems with simple, intuitive tech. We talk about the journey from idea to £2 billion+ in processed payments, the real challenges schools face around finance and compliance, and what’s next for Esenda as they expand their reach across the UK and beyond.

It’s a fascinating chat where Nick and Steve discuss, amongst other things:

• What happens when someone moves from MIS and finance software into the world of payments? Steve’s journey from WCBS to CEO of Esenda reveals how shifting focus to a niche problem can unlock big impacts for schools.

• We explore what it’s really like stepping into a CEO role: what you plan for, what actually happens, and how to stay adaptable when the strategy you walked in with doesn’t survive the first month.

• With a payments platform now processing over £2 billion, the conversation touches on what rapid scaling really looks like and how to stay personal and people-focused even while growing fast.

• From independent schools to the maintained sector, we chat about the changing nature of fee collection, the need for modern infrastructure, and what smarter payments could look like in future.

• There’s a look at how AI and automation are supporting speed, efficiency, and smarter decision-making, and where it’s still vital to keep a human touch in customer comms.

• We get into the challenge of serving schools as enterprise-grade clients—balancing long buying cycles, tight budgets, and the need for tech that just works.

• As the conversation unfolds, there’s insight into how schools (and edtech providers) might rethink the payment process entirely, moving away from off-the-shelf solutions to ones that are integrated, intelligent, and bespoke.

• And finally, we talk about the future of Esenda, of edtech, and of a sector where AI, personalisation, and user experience could finally start to close the gap between consumer expectations and school reality.