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Explore alternative career paths in technology beyond the traditional engineer-to-manager trajectory in this 21-minute conference talk from The Diana Initiative 2025. Discover how roles in technical writing, developer advocacy, and curriculum development offer opportunities to remain deeply technical while leveraging communication, education, and storytelling skills. Learn about the critical impact these less visible but highly technical professionals have on product success, from creating documentation that accelerates adoption to developing learning content that upskills users and sharing research findings. Gain insights into how these career paths serve as bridges between security teams and communities, presented by Kennedy Toomey, an Application Security Researcher & Advocate at Datadog with extensive experience as an Application Security Engineer working with developers on vulnerability remediation and secure coding practices.