Andrea Berkshire
Andrea Berkshire
As vice president of new business sales for the Contingent Workforce Strategies (CWS) Council at Staffing Industry Analysts (SIA), Andrea Berkshire is responsible for creating a global market-driven sales strategy and sales execution plan to achieve membership growth in a newly developed role. She is focused on building infrastructure for the CWS Council enterprise sales team by enabling technology and demonstrating the SIA CWS Council value proposition.
Berkshire brings over 25 years of diverse experience in the contingent workforce industry. Initially, she owned a successful executive search recruiting firm before transitioning into enterprise software sales, focusing on technologies supporting the contingent workforce sector. Berkshire’s journey led her to excel, achieving membership in the prestigious Winner’s Circle President’s Club at SAP Fieldglass. Subsequently, she joined VNDLY, a small vendor management system (VMS) startup, as its 22nd employee and the first in sales prior to its Series B funding round. There, she played a pivotal role in driving grassroots sales efforts, contributing significantly to VNDLY’s successful acquisition by Workday.
Moreover, Berkshire is deeply committed to advancing women in the workforce and advocating for work-life balance. During her career, she established a Women in Business group, to align with a global movement for women’s economic empowerment, both online and offline. Berkshire’s dedication extends to championing the cause of working mothers through her blog, where she shares insights and personal experiences. In 2021, her viral post on setting boundaries as a working mom garnered worldwide attention, accumulating over 4 million views and amplifying her voice as an advocate for positive change.
A true native of Richmond, Virginia, Berkshire has always harbored a deep love for the Virginia Blue Ridge Mountains, where she spent many weekends throughout her life. In 2022, she and her husband fulfilled their lifelong dream by purchasing an 80-acre property – a 1913 farmhouse – in the mountains, embarking on an extensive renovation journey. Beyond her professional endeavors, Berkshire finds joy in spending time with her family, engaging in the restoration of their land and home.
An ardent gardener, Berkshire is determined to cultivate enough vegetables and fruits to sustain her family as well as contribute to the local community and for those in need. “It’s a small contribution that can directly change a life,” she said. Berkshire has two children, two bonus children – Australian Shepherds – and a cat. They are all devoted animal lovers. When not tending to her garden or home, Andrea indulges her passion for the outdoors, often exploring the beauty of the Blue Ridge Mountains and traveling to new destinations.
