Our Team
Meet the team at Childcare Bookings
Management Team
Dan McCaffrey – Managing Director
Dan is the owner and Managing Director of Childcare Bookings, and has extensive experience across education and childcare. He is a founding member of the DfE steering group tasked with planning for the future of wraparound childcare. Dan is also an experienced primary school governor, giving him clear insight into the financial and organisational pressures on schools today.
Dan’s passion is helping schools maximise their impact on every child in their care. He understands that with shrinking budgets, schools are being forced to act and think more commercially and is proud to run a business that help schools achieve that, whilst enabling them to retain their primary focus on providing pupils with a great education.
Dan lives in Sussex with his family, their indifferent cat and badly behaved dog.
Ali Eagle – Operations Director
Ali has worked in the wraparound childcare sector for over 15 years, starting out with hands-on roles in clubs, through to being the Commercial Director of the 5th largest school-age childcare provider in the UK. He was responsible for the creation of our market-leading Online Booking System, and is an expert in payment and administration services for childcare.
Ali has supported a huge variety of Schools & MATs with the successful operation of their own childcare, from single schools to the largest MATs in England. He is passionate about finding innovating ways in which software & technology can help improve the quality & accessibility of wraparound care in the UK.
Outside of work, Ali enjoys watching sports and spending time with his young family.
Chris Riley – Development Director
Chris has a passion for solving complex business problems by creating bespoke software solutions. Over the last 20 years, he has supported businesses in improving their processes and efficiency in a number of sectors, including; printing & media, medical and health insurance, mental health and wellbeing and of course wraparound childcare.
From a family of teachers, the move to join Childcare Bookings has been a natural transition. Having built the booking system from the ground up, Chris is now an expert in the field of childcare administration technology.
In his spare time Chris enjoys spending time with his family and is a keen outdoor enthusiast. He enjoys long walks, paddle boarding and his most recent passion is running; having completed his first marathon in April 2024. He also feeds his inner nerd by playing some rather long and technical board games with friends and family.
School and Parent Support Team
Behind the scenes, our dedicated support team plays a vital role in keeping your wraparound childcare running smoothly every day.
They are the first point of contact for parents, handling bookings, payments, changes and queries with care, clarity and efficiency.
By managing day-to-day enquiries centrally, our team protects school and Trust staff from unnecessary interruptions, ensuring clear boundaries and consistent communication. Parents know exactly where to go for support, and schools can be confident that queries are handled promptly and professionally.
With experience across school-run childcare and a strong understanding of the challenges schools and Trusts face, our support team provides reliable, calm and knowledgeable assistance — helping create a better experience for families while reducing workload for the people delivering care.
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Find out how we remove your childcare admin whilst increasing your income.