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Harry
Rosoff
Senior Director of Product Marketing
Lumen
Harry is Senior Director of Product Marketing at Lumen Technologies, where he leads positioning and GTM for two of the company's five portfolios: cybersecurity and media solutions. That spans security services built into the network through to Vyvx broadcast, so most of his job is turning deeply technical products into something sales and partner teams can actually take to market. Before Lumen, he spent six years at Microsoft, most recently as Director of GTM Strategy for Cloud Security across the Americas, with earlier stints leading cloud security GTM and compliance, risk and privacy marketing. He picked up a Platinum Club award on the way.
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28 October 2026 11:00 - 11:45
Workshop - Build an AI enablement engine, Not the next deck
Most enablement content dies in a shared drive. Not because it was bad, but because it took six weeks to write, went stale in three, and nobody had the hours to rebuild it. AI does not fix that by writing your battlecards for you. It fixes it by making the rebuild cheap enough to do continuously. This working session walks through how to put AI to work across the enablement stack: turning call recordings and win-loss notes into objection handling that sounds like your actual buyers, generating competitor and persona assets that hold up under scrutiny, and setting up a review loop so what reaches the field is accurate rather than plausible. You will leave with the prompts, the guardrails, and an honest view of where AI still needs a human in the loop. Key learnings: - How to turn raw sales conversations into enablement assets your reps trust, without hand transcribing a single call - A repeatable review process that catches AI confidence before it reaches a customer conversation - Where to draw the line: the enablement work worth automating, and the work that still needs your judgement