After spending more than two decades in enterprise software and sitting through hundreds of product demonstrations as both a sales executive and now an industry analyst, I’ve become convinced that one of the most overlooked reasons vendors lose competitive deals […]
The Product Is Not the Raw Material One of the more useful ways to understand AI in B2B software is to stop thinking about it as a feature for a moment. AI is starting to behave more like a productive […]
Pricing Gets Pulled Into The Workflow The first two articles in this thread focused on AI execution and the GTM interface layer. But once AI systems move from assistance to action, another question becomes harder to avoid: how does the business meter, price, package, govern, bill, […]
The Signal People buy from people they trust. That’s not new. What is changing is when that trust gets built, and who is responsible for creating it. In a growing number of go-to-market teams, that responsibility is shifting earlier in the process. Not to sales, but to marketing. The SDR […]
From Alignment to Elimination For years, B2B companies have tried to solve the same problem: how to get sales and marketing aligned. Fifteen years ago, when I was at HubSpot, we called it smarketing. Weekly meetings, shared definitions, handoff agreements. […]
A Simple Example That Isn’t So Simple Pulling on another thread from Conga Connect 2026, one of the more interesting conversations I had during the week was with Geoff Webb, VP Product and Portfolio Marketing at Conga. While much of […]
I was at Conga Connect 2026 last week and had the chance to witness something you don’t see very often in B2B technology. A brand redesign revealed live to customers. Not teased on social media. Not rolled out quietly through […]
I spent this past week at Conga Connect 2026, speaking with customers, executives, and operators across the revenue ecosystem. The brand reveal will likely be the moment most attendees remember from the event. I covered that story separately. But […]
This 3Sixty Insights infographic examines how one organization rebuilt a fragile SDR engine after realizing that its outbound motion had become overly dependent on email and weighed down by a costly “Franken-stack” of tools such as ZoomInfo, Groove, and Gong. […]
This infographic, based on analysis from Kyle James, examines the hidden cost of the typical “Franken-stack” sales environment where multiple disconnected tools handle data, engagement, calling, and analytics. This fragmentation creates a significant productivity drain as teams spend hours each […]
A Quiet Migration Play Reshaping GTM For more than two decades, CRM has functioned as both the filing cabinet where structured customer data lives and the desk where go-to-market work gets done. If you wanted visibility, you logged into CRM. […]
Kyle James and I recently had a conversation with Zuora, one of the early pioneers and leading platforms in subscription-based billing. They have spent more than a decade helping organizations operationalize recurring revenue models. What stood out in our discussion […]
For most B2B SaaS companies, the SDR function is the daily engine of pipeline creation. For one Apollo.io customer, that engine had become fragile: over-reliant on email, constrained by tool sprawl, and misaligned with how modern buyers actually want to […]
Over the last year, one of the strongest signals emerging from ongoing GTM research has been a clear shift toward efficiency. Not incremental efficiency, but structural efficiency. GTM teams are under pressure to do more with fewer tools, fewer handoffs, […]
For years, Apollo.io was seen primarily as a data vendor. Most people who knew the name placed it next to ZoomInfo and Clearbit, assuming it was another place to find company and contact records. That framing made sense at the […]
There is a reason sales reps still exist. There’s also a reason brands continue to rely on founders, executives, employees, and even public figures to carry their message. From celebrities lending credibility to consumer brands, to founders and operators becoming […]
Remember when social media felt creative? When brands experimented in public. When posts sounded human. When the goal was to learn what resonated, not just to avoid what might blow up. Maybe that’s just showing my age, or maybe it’s just having experienced a change in the way brands […]
We are seeing more GTM categories compress into platform features, not because point solutions stopped innovating, but because platforms already own two advantages that are hard to overcome: the system of record and distribution. Once a platform owns where data […]
In December, I had a conversation with Matthew Stein on the Agent.ai podcast about AI predictions for 2026. The discussion ranged across models, platforms, media, economics, and some fairly bold ideas about where things might break or consolidate next. On the surface, it was framed […]
A New Year, a New Set of Field Notes As we head into 2026, we’re kicking off a new weekly series we’re calling GTM Field Notes. These posts are not meant to be definitive market maps or polished frameworks. They are closer to working notes. […]