Marketer Top AI List

Ben Rubenstein

Top AI Marketer in Boston Honoree

Senior Manager, Digital Marketing & AI

About Ben:

As Senior Manager of Digital Marketing at Flywire, Ben has established himself as a forward-thinking architect of agentic growth, moving AI from one-off tasks into interconnected, production-ready workflows. Ben pioneered the transition from basic text-generation prompts to engineering sophisticated, custom Claude agents that handle end-to-end digital advertising automation. By connecting these intelligent agents directly to live ad-platform data, he created a continuous feedback loop. This structural “digital memory” allows the system to autonomously analyze historical performance data, apply optimizations to active campaigns in real time, and measure absolute performance.

Ben’s systematic approach has driven major compounding wins across campaign velocity and modern search visibility. His automation frameworks have compressed digital campaign operations time by 25% by entirely eliminating manual cross-platform reporting, copy variants, and repetitive ad builds. Crucially, Ben has positioned Flywire at the forefront of the Generative Experience Optimization (GEO) landscape by building custom LLM visibility monitoring tools. These automated scanners track how the brand surfaces across engines like ChatGPT, Perplexity, Gemini, and Claude on non-branded search queries, resulting in a 21% surge in brand mentions and a 13% increase in source citations to consistently out-pace major legacy fintech and education competitors.

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