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Rachel Headings began their work experience in 2000 as a Marketing Coordinator at Fanning Howey, where they provided support for proposal generation, interview coaching, and general administrative duties. Rachel then joined Woolpert in 2004 as a Senior Marketing Manager, overseeing the marketing plan for design and infrastructure management service lines and coordinating firm-wide initiatives. In 2012, they joined Burgess & Niple as a Corporate Marketing Manager, responsible for enhancing the client experience and implementing the marketing strategy. Rachel was later promoted to the role of Director, Marketing Communications, where they developed and executed the long-range marketing strategy, supported mergers and acquisitions, and led staff development.

Rachel Headings, CPSM, completed their education at Cedarville University from 1996 to 2000, earning a Bachelor of Arts degree in Marketing. In addition to their degree, they have obtained certifications including the Certified Professional Services Marketer (CPSM) from the Society for Marketing Professional Services (SMPS) in February 2008. Rachel also completed the "Inclusive Mindset for Committed Allies" certification from LinkedIn in June 2022.