From Oracle and SAP to Founder to Stanford: Holly Roland on Building GTM That Compounds with AI

Send us Fan MailIn 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.Career lessons on moving from IC roles to leadership through collaboration and influence.Why storytelling and positioning are as important as the product itself.The rise of Generative Engine Optimization (GEO) and how it’s reshaping digital presence.A real-world GEO case study that improved readiness from ~30% to nearly 80% in weeks.Why LLM-driven traffic produces higher-intent, higher-conversion buyers than traditional SEO.The importance of reframing your product to match how customers think (not how you describe it).Practical ways to approach AI in GTM; starting with workflows, not tools.Holly’s core message is clear:Great go-to-market isn’t about isolated tactics. It’s about aligning the entire company around how customers discover, buy, and realize value.This episode is a deep dive into modern GTM strategy, combining foundational principles with emerging trends like AI and GEO that are redefining how companies reach and convert buyers.Connect with Vijay Damojipurapu on LinkedInConnect with Holly Roland on LinkedInBrought to you by: stratyve.com