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Jaime
Winslow
Sr Director, Customer Success
Deltek
Jamie Winslow is Senior Director of Customer Success at Deltek, where she leads the GovCon digital segment with a focus on scalable, customer-centric strategies that drive engagement and deliver a seamless experience. With over 14 years at Deltek, she has deep expertise in building success organizations that balance product adoption, retention, and growth, while fostering long-term customer relationships.
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30 October 2025 09:15 - 09:45
The customer marketing pivot: Strategy to drive customer success at scale
As customer bases grow, maintaining meaningful engagement with every account becomes a challenge, especially for Customer Success teams balancing retention goals with limited resources. In this session, Christine Boermeester and Jaime Winslow, Senior Directors of Customer Success at Deltek, will share how they introduced a “customer marketing” style role within Customer Success to extend their reach, improve engagement, and protect renewals. You’ll hear how they: - Identified gaps in the customer journey that were hurting adoption and retention - Used data, automation, and targeted content to reach customers at the right time - Freed CSMs from repeatable tasks so they could focus on strategic conversations - Built alignment across Marketing, Product, and Customer Success Whether you’re a CS leader or an individual contributor, you’ll leave with practical ideas to scale your impact without losing the personal touch that drives customer loyalty.