Jennifer Crawley

The retirement industry runs on platforms that were often built decades ago — and the gap between what those systems do and what plan sponsors, administrators, and participants need today is where Jennifer Crawley does her best work. With over 20 years of experience delivering enterprise technology in financial services and regulated industries, Jennifer specializes in translating the complex business rules of retirement plan administration into scalable, compliant, and modern technology solutions that create lasting operational value.

Jennifer has led technology delivery for leading recordkeeping and trust services providers in the qualified retirement plan space — overseeing the design and deployment of secure, scalable platforms for 401(k) and ESOP administration. Among her most significant achievements is engineering the successful launch of a $200M Health Savings Account recordkeeping platform, integrating real-time payments, debit cards, and banking capabilities that allowed participants to schedule ACH contributions seamlessly. At Convergent, she is currently leading business requirements design for a major enterprise modernization initiative for a retirement plan administrator — defining a multi-module architecture spanning plan document management, client relationship tools, workflow automation, and integration with key industry platforms. Her ability to bridge executive strategy and ground-level delivery, combined with deep expertise in Agile SDLC governance and cross-functional team leadership, makes her a trusted partner for retirement organizations navigating their most complex transformation challenges.