Signal Driven Territory Planning
by Rye Overly Territory planning has traditionally been a periodic exercise. Sales teams divide up accounts, assign priorities, establish coverage, and revisit the plan at the next quarterly review. The problem is that markets do not operate on a quarterly schedule, and neither do buying opportunities. An account that looks unremarkable today may become a […]
The AI SDR Problem
By Rye AI has made it possible to automate much of the SDR workflow. Account research, contact discovery, personalization, sequencing, follow-up, and CRM work can increasingly happen with little human involvement. That sounds like a productivity breakthrough. But there is a question the industry isn’t asking enough: what if we’re optimizing the wrong constraint? For […]
The GTM Motion Is Becoming the Product
By Rye Overly One of the more interesting dynamics in enterprise software is what happens when a category becomes mature enough that the underlying products begin to converge. The convergence is rarely absolute. There are still meaningful differences in architecture, performance, integrations, pricing, support and product philosophy. But the differences become less decisive as competitors […]
Weekly Territory Planning
By Rye Overly One of the hardest parts of working in tech sales is not finding things to do. It is deciding what actually deserves your attention. Every week there are more accounts, more requests, more ideas, and more potential opportunities than anyone can realistically execute well. The difference between being busy and being productive […]
AI Half Way into 2026
by Rye Overly The first half of 2026 has made one thing clear: AI is no longer a side project. It is becoming part of how every technology company operates. The layoffs we have seen across the industry have been difficult and, in many cases, painful to watch. It is understandable that many people view […]
GTM Skills AI Won’t Replace
By Rye Overly Artificial intelligence is changing almost every part of go to market. Prospecting is faster. Research takes minutes instead of hours. Emails can be written in seconds. Call summaries, CRM updates, meeting notes, forecasting, and account planning are all becoming easier. That can feel threatening if your job revolves around completing those tasks. […]
Helping Shape AI Education
I’m excited to share that I’ve accepted a board position with the University of Colorado Colorado Springs (UCCS) to help advise on the development of its strategic AI program. Artificial intelligence is reshaping every industry, but the real opportunity is not just understanding the technology. It is helping students and professionals learn how to apply […]
Startup Funding Stages
By Rye Overly If you spend enough time around startups, you will eventually hear founders casually say things like “we are raising a Seed round” or “they just closed a Series B.” To outsiders, those labels can sound like financial jargon. To founders, operators, and investors, they represent entirely different realities. Each stage of a […]
How AI Helps Sales Teams Find High-Intent GTM Buying Signals Faster
By Rye Overly Modern GTM outreach is no longer about sending mass cold emails. The highest-performing outbound teams win by reaching prospects at the exact moment something important changes inside their business. These moments are called compelling events. Examples include: funding rounds executive hires product launches hiring surges expansion into new markets technology migrations mergers […]
Personalization at Scale
My name is Rye Overly and I write about what really works in the day-to-day of a GTM motion. Hyper-personalization has quickly become a central theme in modern go-to-market strategy. With the rise of AI tools, teams now have the ability to tailor messaging at a level that wasn’t possible before. On the surface, that […]