Meet the Executive Team

Jessica Brewster
CEO
Jessica is a dynamic cultural leader with a career rooted in creative placemaking and community engagement. Originally from Cheltenham, she studied at Bournside School before pursuing higher education in London, culminating in an MA from the prestigious Royal Academy of Dramatic Art (RADA).
Jessica began her career in television as a Producer / Director, working on acclaimed programmes including The Great British Bake Off. While in TV, she founded Theatre Deli, a pioneering company that transformed vacant buildings into vibrant temporary arts centres in London and Sheffield. Her work there focused on immersive theatre and large-scale community projects that brought people together in unexpected spaces.
With a passion for using culture to shape places and connect communities, Jessica has continued to lead innovative initiatives across the arts. Most recently, she served as Director and CEO of The Roses Theatre, where she combined artistic ambition with strategic business planning and deep-rooted community engagement.

James Baker
Director of Operations
Born and raised in Cheltenham, James has worked in the leisure and culture sector for 17 years and has been part of The Cheltenham Trust since its formation in 2014. He has progressed through a wide range of roles, from hands-on operations to senior leadership.
For the past five years, James has been a member of the executive team, helping to guide the Trust through significant challenges, including the global pandemic, while focusing on community support, operational resilience, and long-term sustainability.
He thrives on the variety and challenge that comes with overseeing a diverse portfolio of venues and is passionate about making a positive social and community impact. A career highlight was preparing the Prince of Wales Stadium to serve as a training base for the Tonga and Argentina teams during the 2015 Rugby World Cup.
James also spent five years as a regional trainer and assessor for the Royal Life Saving Society (RLSS), supporting the Train One, Save Many campaign. In his spare time, he volunteered as a fire marshal at Badminton Horse Trials, a major international event attracting up to 200,000 visitors.
He lives in Cheltenham with his family and is a passionate sports fan, following football, rugby, and Formula 1. He also has a strong appreciation for the town’s historic civic venues and their role in supporting the local economy.

Clare Mathews
Finance Director
Clare is a qualified CIMA accountant with a career spanning several sectors, including aviation, hospitality, banking, and a range of charities. She has also served as a trustee for a local homeless charity.
Originally from Oxford and a graduate of Bristol University, Clare moved to Cheltenham twenty years ago after a decade in London. She enjoys the vibrant cultural life the town has to offer and the surrounding Cotswold countryside.
When not at work, Clare is kept busy with her teenager, foster cats, and garden—though not always in that order.

Lisa Edgar
Head of Culture and Communities
Lisa leads The Wilson Art Gallery and Museum, a thriving cultural space where everyone can discover, enjoy and learn through exhibitions, events and dynamic learning and engagement activities. She also serves as Chair of the Cheltenham Culture Board, which represents 20 cultural organisations working together to develop the town’s rich cultural offer and visitor experience.
Previously Head of Art at National Museum Wales, Lisa focused on making one of Europe’s great national collections accessible to all. She has a deep commitment to learning and engagement, shaped by her experience as Head of Learning at Ffotogallery, Wales’s national agency for film and photography.
Lisa actively supports Cheltenham’s creative community, having established professional development and free studio programmes for local artists and makers. She is a founding member and Chair of g39, an exciting arts space supporting early career artists and the Wales Artist Resource Programme (WARP). She has worked on major international art events including the Venice Biennale and with the British Council in India.
Inclusion, social responsibility, and environmental sustainability are central to Lisa’s values and work at The Cheltenham Trust. Under her leadership, The Wilson is a welcoming and inclusive space where everyone can engage with the arts and Cheltenham’s cultural heritage.

Michael Barlow
Senior Head of Food and Beverage
With over 20 years of experience in the hospitality sector and five years at executive level, Mike brings a broad and dynamic understanding of food and beverage operations to The Cheltenham Trust. His background spans fine dining, contract catering, festivals, hospitals, banqueting, and VIP green rooms—where he has catered for royalty, world leaders, renowned performers and major events.
As Senior Executive Head of Food and Beverage, Mike oversees the Trust’s diverse hospitality portfolio, including café outlets, heritage venues, event bars, banqueting spaces and festival catering. His leadership is focused on innovation, growth and delivering high-quality, memorable guest experiences.
A former chef with a strong appreciation for culinary excellence, Mike combines hands-on operational knowledge with strategic vision. He has driven the development of new revenue streams, introduced contemporary service concepts, and implemented high standards in food quality, service delivery, compliance, stock control and team culture.
Known for his creative thinking and collaborative approach, Mike plays a key role in supporting the Trust’s ambition to deliver outstanding and commercially sustainable hospitality across all its iconic venues.
Away from work, Mike is a proud father of four and remains passionate about the power of food and hospitality to connect people and create lasting memories.

Steve Mitchell
Senior Head of Events, Hires and Partnerships
Steve is a multi-award-winning events professional with over 25 years’ experience in senior leadership roles across the public, private and charity sectors.
Recognised for his energy, creativity and collaborative style, Steve takes pride in delivering events that inspire, engage and consistently exceed expectations. His portfolio spans celebrity celebrations, large-scale weddings, awards ceremonies and fundraising events. During the pandemic, he also qualified as a wedding and funeral celebrant.
Based in Cheltenham, Steve supports several animal welfare charities and recently completed voluntary service as a Special Constable. Outside of work, he enjoys live music, theatre, travel, and looking after an ever-growing collection of houseplants.

Shelley Dobson-Stevens
Head of Leisure
Shelley began her career in leisure in 2008, qualifying as a lifeguard in St Neots, Cambridgeshire. Her passion for sport led her to Hartpury University, where she completed a degree in Sports Business Management.
Over the past 20 years, Shelley has participated in multiple sports at a high level, including football for QPR and rugby for Cheltenham Tigers. She joined Cheltenham Borough Council as a lifeguard in 2011 while still at university and has since worked across almost every area of Leisure at Cheltenham.
In 2023, Shelley became Head of Leisure and joined the executive team. Her vision is to develop Leisure at Cheltenham as a family hub for the town, providing inclusive access to health, fitness and learning opportunities for people of all ages.



