OUR PEOPLE
At Kiddiewinks, we believe in lifelong learning and continually enhance our professional methods and practices.
“Sprogs Garden Playschool is not just a school—it’s a truly magical place where children, families, and staff come together to create a nurturing home away from home. I feel so privileged to lead this incredible community and am immensely proud of what we have built together with our dedicated directors and talented team. I am beyond excited to extend this vision with the opening of Kiddiewinks Garden Playschool in September 2025!”
Carrie Chaloner
Director and Owner
Carrie was born and raised in the Cayman Islands and educated in Cayman, Canada and the UK. Although not a teacher, Carrie has three young children and is passionate about early years education as well as protecting the environment. Combining the two felt natural, so she founded our Garden Playschools, a nurturing place where children are encouraged to be children, as well as young ambassadors of our planet.
Jen Stein
Director
Jen is Caymanian and was educated in Cayman, Canada and the UK. She has a Bachelor of Science with Honours in Medical Microbiology and a Postgraduate degree in Law. Jen was a solicitor in London and moved back to the Cayman Islands in 2009 where she worked in law and the financial services industry for 13 years managing large teams and dealing with all aspects of fund and corporate services in Cayman. She left the financial services industry in July 2022 to pursue other interests and has joined the board of directors of Sprogs Garden Playschool alongside her sister Carrie. Jen handles the financial, legal, HR and administrative functions of Sprogs and is an owner and director of Kiddiewinks Garden Playschool in West bay.
Emily Harris
Head of School
Emily is immensely proud to lead the team at our amazing and very special Garden Playschools. She comes to us from the United Kingdom and has a background in both the arts and education, with the theatre being her first true love. Emily’s career to date has been dedicated to developing early years excellence and inclusion, evolving her craft as both an educator and leader as well as expanding her professional pedagogy. She wholeheartedly believes in a child-centered play-based approach to teaching and learning.
Emily studied for her Bachelor of Arts Honours in Drama Applied Theatre and Education at The Royal Central School of Speech and Drama, University of London. During this time, she was involved in numerous educational projects including writing and performing an educational play and the development and facilitation of coinciding workshops that were delivered both across London schools and at the renowned Edinburgh Fringe Festival. Soon after finishing her degree, Emily was delighted to have been chosen to undertake her teacher training with the Ark Network where she trained as a teacher primarily within schools with lower socioeconomics and high levels of special education needs or disabilities. Alongside her teacher training, Emily also completed her Postgraduate at Goldsmiths University alongside her teacher training specialising in the early years field.
Throughout her career in the UK, Emily was part of a select committee of Early Years Educators that worked with the Department of Education to rewrite the British National Early Years Curriculum as well as pilot and review its supporting documentation and her role within this was, not only to advocate for Early Years excellence, but to also consider how this is done in practice with a core focus on personal social and emotional development and communication and language development both pre and post-pandemic within the UK education system. Within her roles as an Early Years Lead, Emily took her settings from ‘Good’ to ‘Outstanding’ in Ofsted Inspections and became a Lead across the network supporting schools and training and coaching teachers within the field both across London and the Midlands.
Emily joined the amazing Sprogs Community in 2022 as Special Educational Needs Coordinator and is extremely passionate and dedicated to providing both excellent and inclusive provision and practice within both Sprogs, Kiddiewinks and the Cayman Islands. Thus far, she has enjoyed working closely with professionals within the field, supporting staff professional development and advocating for inclusion across the Cayman Islands.
Emily is actively involved in community projects and has been a part of the Prospect Playhouse production of The Gruffalo and the island favourite Prospect Playhouse Family Christmas Show. She is currently studying for her Postgraduate Certificate in Leadership at Harvard University, continuing her studies alongside her role as Head of School.
Early Education
Carefully Designed
At Kiddiewinks, we understand that a thoughtfully curated environment for learning and play is essential to every child’s education journey.