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Chesney Windsor has a diverse work experience spanning multiple industries. Starting in 2010, Chesney worked as a Consultant at ITS Specialist Construction Personnel for a few months before moving on to become a Consultant & Relationship Manager at Sanderson Recruitment plc. In 2011, Chesney took a break and engaged in traveling. Upon returning in 2012, Chesney joined Friends Life Group as a Contingent Workforce Manager. Later that year, in 2015, Chesney transitioned to Royal London Asset Management as a Recruitment Business Partner. In 2018, Chesney joined Sanderson as the Head of Relationship Management, Managed Services, and later held the role of Lead Business Partner. Currently, Chesney is working as the Client Services Director, Solutions at Sanderson.

Chesney Windsor attended the University of the West of England from 2007 to 2010, where they obtained a Bachelor of Science (BSc Hons) degree in Building Surveying. Prior to that, they attended Colston's School from 2000 to 2007, although no specific degree or field of study is mentioned for this period. Additionally, Chesney obtained several certifications, including CCWP - SOW Management from Staffing Industry Analysts in June 2019, AGILE Project Management Practitioner from APMG International in April 2019, and a professional development certificate on The Business of Retail Investment Fund Management Companies from The Investment Association in 2015.