In a recent LinkedIn post, Kieran Flanagan argues that most people misunderstand the core value proposition of HubSpot, asserting it’s far more than a mere contact database. Instead, Flanagan positions HubSpot as the central repository for “Go-To-Market (GTM) context,” a critical element he believes is often missing for sales agents.
Flanagan elaborates on this distinction by contrasting the capabilities of AI models like ChatGPT and Claude with the unique value of accumulated business intelligence. He points out that while AI can analyze data and identify basic metrics, such as deals that haven’t moved in 30 days, it lacks the nuanced understanding of industry-specific timelines or the historical context of why certain objectives might hinder or advance a deal.
“Today, you can plug Claude or ChatGPT into a pipeline export and ask what’s at risk. The model can do the math. It can tell you which deals haven’t moved in 30 days.”
However, Flanagan stresses that this is where AI’s limitations become apparent. The true challenge, according to Flanagan, lies not in the models themselves, but in the data context they operate with.
The Contextual Gap in AI-Driven Sales
Flanagan highlights that AI models struggle with industry-specific benchmarks and historical performance data. “It can’t tell you whether 30 days is fast or slow for your industry. It can’t tell you whether the objective that just landed is the same one that killed a similar deal last month, or provide intelligence on how companies in your space overcome that objective,” he writes.
This gap, Flanagan explains, stems from the nature of context itself. He posits that context isn’t something that can be engineered or built into an AI model from scratch; it must be accumulated over time through real-world application and experience.
“It’s because they are context problems, not model problems. Context isn’t something you can build; you have to accumulate it.”
HubSpot’s Accumulated GTM Intelligence
Flanagan then turns to HubSpot’s long-standing presence in the market as a key differentiator. With over two decades of operation and serving more than 280,000 businesses, HubSpot has, in his view, amassed an unparalleled depth of GTM context.
This extensive dataset, Flanagan argues, provides invaluable intelligence, patterns, and insights into what constitutes successful GTM strategies across a wide spectrum of business journeys. “HubSpot has been accumulating GTM context for two decades across 280,000+ businesses running their actual GTM on our platform,” he states.
The Earned Intelligence Layer
He emphasizes that this isn’t a feature that can be easily replicated or shipped as a standalone product. Instead, it’s “earned context by delivering value across such a large customer set.” Flanagan points to HubSpot’s long-standing commitment to open data layers, including contacts, deals, and conversations, supported by robust APIs and connectors for various AI models. He notes the significant growth observed in the usage of their LLM connectors.
“What I’m really excited by is the intelligence layer being opened up next. A GTM context layer that any agent can call. Yours, ours, or whatever you build next.”
Looking ahead, Flanagan expresses enthusiasm for the future of GTM operations. He anticipates that by opening up this intelligence layer, modern GTM professionals will be empowered to iterate and refine their strategies at an unprecedented speed, leveraging this deep, accumulated context.
📝 About This Content
This article is based on insights shared by Kieran Flanagan on LinkedIn.
📅 Originally posted on May 5, 2026 | View original post on LinkedIn →