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Index/RevOps/B2B Go-To-Market Leaders
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From Oracle and SAP to Founder to Stanford: Holly Roland on Building GTM That Compounds with AI

B2B Go-To-Market Leaders · 2026-04-23 · 48 min

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Episode notes

Send us Fan Mail In this episode of the B2B Go-To-Market Leaders Podcast, Vijay Damojipurapu sits down with Holly Roland , former executive at SAP and Oracle and founder of Rebel GTM, to break down what go-to-market really means in today’s AI-driven world. Holly introduces a simple but powerful framework: go-to-market is an infinity loop of discovery and value, where buyers move from awareness to purchase, and then into expansion, cross-sell, and advocacy. Yet most B2B companies still over-index on acquisition while underinvesting in the value loop. Drawing from decades of experience across enterprise tech and startups, Holly shares how she evolved from product management into go-to-market leadership, and why she ultimately built Rebel GTM to help companies align product, marketing, sales, and customer success into one unified system. They dive into: Why go-to-market should be viewed as a discovery loop + value loop, not just a funnel. The common mistake B2B companies make by prioritizing new logos over expansion. How marketing alone can’t fix growth if upstream and downstream functions are misaligned.

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