Quietly Becoming the Differentiator in GTM

Posted on February 2, 2026February 2, 2026 by Kyle James

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 the public face of B2B companies, trust has always been transferred through people. People buy from people they trust. Not workflows. Not sequences. Not platforms. Even as go-to-market becomes more automated, that truth has not changed. If anything, it has become more visible. This tension came up repeatedly in recent conversations, including a GTM Innovators discussion with Joey Lai, where the conversation kept circling back to the same unease: Buyers are seeing more messages than ever, yet trusting fewer of them. The Signal Trust is […]

Monthly Research Recap | January 2026

Posted on February 1, 2026January 30, 2026 by 3Sixty Insights Editorial Team

Recent Research: Market Alert: Four Months In – What’s Really Taking Shape at Clari and Salesloft Four months after announcing their merger, Clari and Salesloft are signaling a disciplined, customer-first approach that prioritizes long-term value over rapid consolidation. Rather than forcing a unified interface or accelerated rebranding, the combined organization is focusing on unifying data and intelligence across platforms while respecting distinct revenue personas and workflows. This data-first, human-in-the-loop AI strategy positions agents and shared intelligence as the connective tissue across the revenue lifecycle, with enterprise governance and adoption at the core. The result is a measured integration that, if executed well, could redefine predictability and execution for modern revenue teams rather than simply delivering a larger revenue technology platform. Solution Spotlight: Verto and the […]

Are GTM Teams Vibe Coding Before They Commit to Platforms Like Gainsight?

Posted on January 29, 2026January 29, 2026 by Kyle James

In many cases, GTM software underdelivers not because it lacks capability, but because teams commit to it before they are operationally ready to absorb it. That observation has been coming up with increasing frequency in recent conversations with customer success leaders, RevOps teams, and GTM executives. Not as a complaint about specific vendors, and not as a rejection of platforms altogether, but as a quieter shift in when buying decisions are made. Instead of moving directly from problem recognition to platform purchase, some teams are inserting a new step in between: building lightweight, AI-assisted internal tools to pressure-test workflows before committing to a full solution. What’s emerging looks less like “build versus buy” and more like “build to get ready.” Let’s Discuss a Recent Example This signal surfaced during a recent episode of the Prompted […]

When Organizational Change Becomes Organizational Damage

Posted on January 28, 2026January 28, 2026 by Nicholas Biron

Over the past several months, I have been sharing a series of posts and videos focused on what I believe is one of the most troubling issues facing organizations today. It is not change itself. Change is necessary. In fact, years ago I wrote extensively about how organizations fail when they cannot keep pace with technology, competition, and shifting market dynamics. That belief has not changed. What has changed is the type of organizational change I am seeing. In many cases, it is so disruptive that it genuinely raises the question of how some businesses manage to stay operational, let alone profitable. One of the earliest themes I raised in this series was the rapidly shrinking tenure of executive leadership. CEOs, CROs, CMOs, and product […]

Community, Purpose, and the Time AI Gives Back

Posted on January 26, 2026January 26, 2026 by Kyle James

If you had ten more hours a week starting tomorrow, what would you do with them? Why not start now? A Hundred-Year-Old Warning About the Future of Work In 1930, right in the middle of the Great Depression, John Maynard Keynes, often described as the father of Keynesian economics, wrote an essay called Economic Possibilities for Our Grandchildren. It was an odd time to be thinking optimistically about the future. Jobs were disappearing, economies were struggling, and uncertainty was everywhere. Instead of focusing on short-term recovery, Keynes stepped back and asked a much bigger question. What happens to society when technological progress reduces the need for human labor? Keynes believed productivity would keep improving and that, over time, humanity would largely solve what he called the […]

AI Onboarding Is Becoming as Important as Employee Onboarding

Posted on January 26, 2026January 26, 2026 by Kyle James

AI is on, but the value is inconsistent. Across GTM teams, AI is everywhere. Copilots draft messages, models prioritize accounts, systems suggest next best actions, and forecasts increasingly rely on machine-driven insight. And yet, a familiar refrain keeps surfacing in conversations with operators and executives alike: sometimes it works, sometimes it doesn’t. This is often framed as an AI maturity problem. In practice, it looks more like an organizational readiness problem. After a year of pilots, labs, and real-world experimentation, the models themselves are no longer the primary constraint. They are improving quickly, shaped by widespread usage and constant iteration. The shift we are now seeing is not about whether AI works. It is about whether organizations are prepared to work with it at scale. […]

The Hidden Cost of Organizational Restructuring: A Caution to Executive Leaders

Posted on January 22, 2026January 22, 2026 by Nicholas Biron

Early in the year, many executive teams confront what feels like an unavoidable reality: organizational restructuring. Budgets reset. Strategies are revisited. New leadership arrives. Pressure mounts to fix what is not working and accelerate progress toward new goals. On the surface, restructuring can feel decisive. It signals action. It creates the impression of transformation. And to be clear, restructuring does have its place. Done thoughtfully, it can unlock efficiencies, clarify accountability, and better align an organization to its market. However, after speaking with hundreds, if not thousands, of businesses across industries, both end users and vendors, I believe there is an uncomfortable truth many executives underestimate. Wide, sweeping organizational restructuring is one of the most disruptive actions a company can take, often with consequences that […]

When Enterprise Social Became the New Press Release Wire

Posted on January 21, 2026January 29, 2026 by Kyle James

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 use social media over the last two decades. A bit of nostalgia if you will. Because enterprise social media did not die. It got professionalized. And in the process, it quietly became something else entirely. Enterprise Social Narrowed Instead of Expanding. It Got Safer. Enterprise social today looks less like a growth channel and more like a modern press release wire: approved messages, distributed at scale, optimized for consistency and safety rather than experimentation. This didn’t happen because social teams forgot how to be creative. It happened because the cost of being […]

When 80% Becomes Good Enough: How Categories Collapse Into Features

Posted on January 20, 2026January 30, 2026 by Kyle James

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 lives and where work happens, it gains the ability to embed capabilities directly into existing workflows, bundle them into existing contracts, and price them at or near zero marginal cost. At that point, even a strong point solution faces a tougher question than feature parity: Is the incremental value worth the incremental cost and complexity? Why This Is Happening Now Several forces are reinforcing each other: Systems of record are consolidating. CRMs and revenue platforms increasingly serve as the canonical source of truth. Distribution has […]

Five AI Signals GTM Leaders Should Be Paying Attention to in 2026

Posted on January 20, 2026January 20, 2026 by Kyle James

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 as a set of predictions. But as I revisited that conversation, what stood out was something more practical. Almost everything we talked about shows up directly in the day-to-day reality of go-to-market teams. Not as abstract future bets, but as signals that are already shaping how GTM leaders think about tooling, trust, productivity, and ROI. These are the same tensions I hear in conversations with CROs, CMOs, RevOps leaders, and heads of customer success who are trying to make sense of AI while still hitting numbers. So rather […]

Market Alert: Four Months In – What’s Really Taking Shape at Clari and Salesloft

Posted on January 16, 2026January 16, 2026 by Kyle James

When Clari and Salesloft announced their merger in early August, the immediate reaction across the market was predictable. Bigger platform. More data. More AI. Another consolidation move in an already crowded revenue technology landscape. Four months later, the more interesting story is not what was announced, but how deliberately the combined organization is choosing to execute. After spending time recently with Cameron Schuette, now Director of Analyst Relations at Clari + Salesloft, it is clear that this merger is being treated less like a branding event and more like a long-term product and data strategy. What is emerging feels disciplined, restrained, and intentionally customer-first. That is still rare in post-merger SaaS stories. The Core Design Choice: Data First, Personas Respected, Humans in Control If you […]

The Hidden Cost of AI in Marketing: When Thinking Gets Outsourced

Posted on January 14, 2026January 14, 2026 by Kyle James

Why critical thinking is becoming marketing’s most valuable skill AI has changed marketing faster than almost any technology before it. In a matter of months, tools like ChatGPT, Copilot, and Claude have made it possible to generate campaigns, content, ads, and messaging variations at a speed that would have been unthinkable just a few years ago. For many teams under pressure to do more with less, that speed feels like a lifeline. But there’s a quieter question emerging beneath the hype: If marketing is getting easier to execute, why does so much of it feel increasingly forgettable? That tension sat at the center of a recent GTM Innovators conversation with Joey Lai, B2B Marketing Director at Mastercard. What followed wasn’t an anti-AI rant, but something […]

Why Conversation Intelligence Is Quietly Becoming a Feature, Not a Category

Posted on January 12, 2026January 8, 2026 by Kyle James

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. Observations pulled from conversations with GTM leaders, patterns we keep seeing in buying decisions, and signals that show up repeatedly as teams try to simplify, consolidate, and justify their go-to-market stacks. One of the clearest signals right now centers on conversation intelligence. Not because it’s failing. But because it’s becoming too successful. What We Mean by “Conversation Intelligence” Before going further, it’s worth defining the term, because it’s still relatively new and often used loosely. Conversation intelligence refers to tools that capture live or recorded conversations, typically sales, customer success, or discovery calls, and […]

GTM Innovators: Why AI Is Making Average Marketing Easier and Great Marketing Rarer

Posted on January 12, 2026January 11, 2026 by Kyle James

AI has made it easier than ever to produce content, launch campaigns, and optimize performance at scale. But has it actually made marketing better? In this episode of GTM Innovators, Kyle James sits down with Joey Lai, B2B Marketing Director at Mastercard, for a candid and deeply thoughtful conversation about what’s being lost as AI tools become embedded in everyday marketing work. Drawing on her experience across fast-growing startups and large enterprise organizations, Joey argues that while AI accelerates output, it often erodes the critical thinking, creativity, and human insight that separate average marketing from great marketing. Together, they explore why optimization has become easier, originality has become rarer, and why the next generation of marketers faces a very real risk of outsourcing their thinking along with their tasks. This conversation goes beyond AI hype to examine: […]

#HRTechChat: The Economics of HR – Speaking the Language of Business with Maria Scarangella

Posted on January 7, 2026January 30, 2026 by Nicole Roberts

In this episode of #HRTechChat, Nicole Roberts is joined by Maria Scarangella to tackle one of the most persistent challenges facing HR today: proving business value in a climate defined by cost pressure, efficiency mandates, and heightened executive scrutiny. Drawing on her 37-year career at GEICO—including leadership of a $2.5B P&L—and her current work building Marstella, Maria explains why HR risks losing its strategic seat when it speaks only in HR metrics instead of business outcomes. Together, they explore how quantifying the true cost of hiring, onboarding, training, and turnover can fundamentally change executive decision-making—from smarter workforce planning to more targeted investments in technology and development. Maria outlines why “a lot” is not a number, how lifecycle cost visibility creates accountability across leaders, and why […]

Monthly Research Recap | December 2025

Posted on January 5, 2026January 5, 2026 by 3Sixty Insights Editorial Team

Recent Research Research Agenda: Changing Workplace Dynamics & The Future of Work in 2026 This 2026 research agenda from Dylan Teggart examines how accelerating AI adoption, shifting labor market dynamics, declining employee engagement, and mounting compliance complexity are fundamentally reshaping the world of work. As employers regain leverage and HR technology enters a period of consolidation and commoditization, the focus of this research is on separating signal from noise—understanding what is truly driving measurable workforce outcomes versus what remains aspirational rhetoric. Through in-depth analysis of real organizational experiences, technology decisions, and execution strategies across the employee lifecycle, this agenda aims to equip HR and business leaders with practical, data-driven insights to turn modern HR, AI, and workforce management investments into tangible results in 2026 and […]

#HRTechChat: Jeff Smith of 15Five on Building Better Managers in the Age of AI

Posted on December 12, 2025January 5, 2026 by Nicole Roberts

In this episode of #HRTechChat, Nicole Roberts sits down with Jeff Smith, COO of 15Five, to unpack what it really takes to build better managers in an era of AI, constant change, and overflowing HR to-do lists. A psychologist by training with deep R&D and product experience, Jeff brings a rare lens on how organizations can redesign systems, expectations, and technology to truly support people leaders—not just measure them. They dig into the mounting pressure on HR and managers, the shift from “HR owns all people issues” to shared accountability, and why management has to be treated as a daily practice, not a one-time promotion. Jeff explains how tools like 15Five and Kona AI can turn everyday one-on-ones into continuous performance data, simplify review cycles, […]

Video: Human in the Loop or Just a Checkbox? Rethinking AI in HR and Support

Posted on December 10, 2025December 10, 2025 by Nicholas Biron

In today’s video, Nicholas Biron break down a growing problem in both customer service and employee experience: AI is being used as a barrier, not an enabler. Vendors love to talk about “human in the loop,” but in reality, that human is usually sitting behind the scenes, not where customers and employees actually interact. The result? Frustration, loss of empathy, and an experience that feels increasingly robotic. He shares real example; from trying to reach a live agent at major providers, to a recent doctor’s visit where AI-driven prompts replaced real human connection, to how AI is affecting performance management. But it’s not all doom and gloom. AI can dramatically improve experience when used correctly. Payroll support is a great example, where AI agents can […]

Video: Are Vendors Losing by Overloading on AI Features?

Posted on December 4, 2025December 4, 2025 by Nicholas Biron

In this video, Nicholas Biron discusses a growing trend in vendor presentations: overloading audiences with AI features instead of focusing on solving real business problems. He shares observations from virtual analyst updates and emphasizes that line-of-business executives often lack advanced AI sophistication. Vendors are urged to differentiate by addressing customer challenges and practical outcomes rather than feature dumps.

Efficiency, Precision, and Discovery: Lessons from Vanillasoft’s Marketing Leaders

Posted on December 4, 2025December 3, 2025 by Kyle James

As part of our ongoing Go-to-Market (GTM) Research, I recently sat down with Jeannie Zaemes, Senior Vice President of Marketing, and James Bishop, Vice President of Marketing at Vanillasoft, for an open conversation about how marketing and GTM strategies and programs are evolving. Vanillasoft is a leader in sales engagement and lead management, giving marketing and sales teams a structured and consistent way to reach prospects, respond quickly, and convert more opportunities. The platform helps organizations streamline outreach, focus on the right accounts, and run GTM programs that are both efficient and precise. By unifying workflows and surfacing actionable signals, Vanillasoft enables customers to turn data into real discovery and momentum in their pipeline. What unfolded was a candid discussion about the state of modern marketing and how efficiency, data precision, and […]

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