Turning Technology into Business Results
Buying software is easy; implementing it successfully is the challenge. That is where Charlene Gillespie steps in. As the Director of Professional Services at Windward Software, Charlene is the bridge between the technical product and the people who use it.
She oversees the critical "Day One" operations—managing the implementation specialists, trainers, and data migration teams that bring new clients onto the Windward System Five platform. Her work ensures that complex ERP deployments are executed smoothly, minimizing downtime and maximizing user adoption.
A Veteran of Client Success
Charlene is a true veteran of the Windward ecosystem. Having been with the company for over two decades, she possesses an encyclopedic knowledge of the software's capabilities. She has moved through the ranks from direct support to leadership, giving her a unique empathy for the end-user experience.
Her expertise lies in Change Management and Operational Workflow. She understands that moving to a new point-of-sale or inventory system is stressful for business owners, and she builds processes designed to alleviate that anxiety through structured training and precise project management.
Leadership & Philosophy
Operating out of Windward’s hometown in Penticton, British Columbia, Charlene fosters a culture of accountability and education within her team. She believes that excellent software is useless without excellent training. Her leadership ensures that Windward clients aren't just "users," but empowered experts in their own systems.
