The Web Is Forking Again

Posted on March 9, 2026March 9, 2026 by Kyle James

Last week I wrote that SaaS isn’t dying. It’s being sorted. Thin workflow tools are under pressure, systems of record are becoming infrastructure, and the era of easy multiple expansion is behind us. That conversation was about repricing. This one is about rewiring. Underneath the market volatility, the internet itself is quietly adapting to a new kind of client. And if you zoom out far enough, the pattern looks familiar. When mobile arrived, the web did not disappear. It evolved. The same underlying systems and content still existed, but they were redesigned to render differently depending on the device. Responsive design and mobile-first frameworks did not replace the desktop web; they standardized it for a second client. Companies that recognized that shift early rebuilt their interfaces accordingly and captured the next wave of growth. We […]

Monthly Research Recap | February 2026

Posted on March 2, 2026February 26, 2026 by 3Sixty Insights Editorial Team

Recent Research: Research Agenda: Workforce Strategy, HR Enablement & HR Technology in an AI-Augmented World Nicole Roberts’ research agenda examines how workforce strategy, HR enablement, and HR technology are evolving as AI and automation reshape how work is performed and managed. The research focuses on enabling managers to lead effectively at scale, connecting skills and leadership capability to measurable business outcomes, designing HR–IT technology ecosystems that support AI-augmented work, navigating workforce transitions such as M&A and restructuring, and improving how organizations measure workforce performance to inform executive decision making. Grounded in practitioner experience and real-world case examples, the agenda emphasizes translating workforce data, technology investments, and workflow design into clearer decisions, stronger execution, and sustainable organizational capacity. Analyst Insight: Beyond Contact Data – How Apollo.io […]

SaaS Isn’t Dead. It’s Growing Up.

Posted on March 2, 2026March 9, 2026 by Kyle James

I was super early at HubSpot, a first one hundred employee. I watched the company go public. I used some of the gains from that IPO to put a down payment on my house. It was one of those rare moments where a long bet actually paid off in a tangible way. A year ago, HubSpot was trading above $800 a share. Today it sits in the low $200s. That is a decline of more than 70 percent in roughly twelve months. And it is not alone. Across B2B SaaS, billions in market cap have evaporated. Multiples have compressed. Growth stocks have been punished. The easiest narrative is that SaaS is dead and AI finished the job. I do not think that is what is happening. What we are seeing feels much more like SaaS growing up. The Easy Era […]

Is CRM Becoming Infrastructure?

Posted on February 23, 2026February 27, 2026 by Kyle James

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. If you wanted to move a deal forward, you logged into CRM. If leadership wanted forecast accuracy, you logged into CRM. That coupling may be loosening. In a recent conversation with Burley Kawasaki at Creatio, a trend surfaced that I have begun to hear in multiple vendor discussions. Platforms like Creatio are being layered on top of existing CRM systems, including Salesforce. The CRM continues to store data and enforce workflow. But users increasingly operate elsewhere. Teams. Outlook. Mobile interfaces. Agent-driven environments. The system of […]

Rethinking Recurring Revenue: Why Customer Retention Is the Real Growth Strategy

Posted on February 19, 2026February 19, 2026 by Nicholas Biron and Kyle James

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 was a simple but critical distinction. Subscription billing technology enables recurring revenue. It does not guarantee recurring success. Across the B2B software market and other subscription-driven industries, companies have adopted recurring billing infrastructure at scale. Platforms like Zuora provide the mechanics. They allow organizations to invoice accurately, manage subscription terms, automate renewals, and support complex pricing models. That enablement layer is foundational. However, many organizations mistakenly believe that implementing subscription billing is synonymous with building a sustainable recurring revenue engine. The financial model tells a […]

Nicole Roberts Contributes Analyst Perspective to HR Voices 2026 Compliance Report

Posted on February 18, 2026February 18, 2026 by 3Sixty Insights Editorial Team and Nicole Roberts

As HR compliance grows more complex in 2026, Nicole Roberts, Principal HR Industry Analyst at 3Sixty Insights, emphasizes a critical reality: compliance technology is only as effective as the expertise guiding it. In the HR Voices: 2026 Regulatory Transformations and Disruptions in HR Compliance report, developed with OutSolve, Nicole highlights the widening gap between tool adoption and practitioner judgment. As organizations deploy more automation across HR and compliance workflows, validating outputs with experienced human oversight becomes essential. Nicole’s contribution centers on the operational risks emerging from overreliance on systems alone. “Tools can’t replace expertise,” she explains, noting that compliance teams must still interpret signals, validate decisions, and understand regulatory nuance beyond what dashboards and alerts can provide. This perspective reflects what many HR leaders are […]

From Data Abundance to Decision Scarcity in Sales Intelligence

Posted on February 17, 2026February 12, 2026 by Kyle James

Sales teams have more data and more recommendations than ever. What they have less of is confidence in what to do next. Across GTM organizations, a consistent pattern is emerging: sales intelligence systems are excellent at surfacing signals, but far less effective at reducing decisions. The result is not ignorance, but hesitation. Not a lack of insight, but analysis paralysis. Sales intelligence has largely solved for visibility. It has not yet solved for conviction. Why this is happening now Over the past decade, sales intelligence vendors have steadily filled in every layer of the data stack. Conversation intelligence platforms like Gong introduced a powerful form of judgment scaffolding. They surface deal risk, coaching gaps, and behavioral signals that were previously invisible. For many teams, Gong […]

Revenue Orchestration Is Replacing Point Solutions as the Unit of Value

Posted on February 9, 2026February 9, 2026 by Kyle James

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, and less operational drag. That pressure is reshaping buying behavior, stack design, and increasingly, the M&A landscape across B2B SaaS. Consolidation has become one of the clearest expressions of that shift. Not consolidation for scale alone, but consolidation in service of simpler workflows and clearer accountability. Buyers are showing less appetite for assembling best-in-class stacks and more interest in reducing complexity across how revenue is actually planned, executed, and measured. That context is what made the recent completion of Conga’s acquisition of the B2B business […]

Analyst Insight: Beyond Contact Data – How Apollo.io Is Rewiring the Sales Stack for the Efficiency Era

Posted on February 6, 2026February 11, 2026 by Kyle James

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 time, but it no longer fits the reality of what Apollo has become. What started as a large dataset of business contacts has quietly evolved into a single workspace for managing prospecting, outreach, and inbound sales workflows. The change reflects something larger happening across go-to-market teams everywhere. With budgets tightening and leaders under pressure to prove ROI on every line item, the modern stack is shrinking. Companies are asking one simple question: Why does this process need six tools when it could run in one? […]

LinkdedLive: HR Bytes Workbreak | February 12th @ 12pm Eastern

Posted on February 4, 2026February 4, 2026 by 3Sixty Insights Editorial Team and Nicole Roberts

Join 3Sixty Insights’ Nicole Roberts for an upcoming LinkedLive as they bring brief, digestible bytes on the 𝗛𝗥 𝗕𝘆𝘁𝗲𝘀 𝗪𝗼𝗿𝗸 𝗕𝗿𝗲𝗮𝗸. They will dive into the latest trends and innovations shaping the now and next of HR. They will also be discussing AI-Powered HR: From Hype to Implementation. BIG question on everyone’s mind, “How do we and our people build trust with these systems?” Learn more and register for the event here: HR Bytes Workbreak

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 […]

HR Must Speak the Language of the Business or Be Excluded from the Decisions That Matter

Posted on January 29, 2026January 29, 2026 by Nicole Roberts

HR leaders are not lacking insight, empathy, or strategic intent. What often limits their influence is not the absence of data, but the absence of shared language with the executives making organizational decisions. Even when HR has the right information, its impact can fall flat if those insights are not framed in terms that connect directly to how leaders think about performance, risk, and value creation. In a recent episode of HRTechChat, I spoke with Maria Scarangella, founder of Marstella and former Vice President of Talent and Enterprise Learning at GEICO. Our conversation explored a challenge many HR leaders intuitively understand but often struggle to address directly: HR is not sidelined because it lacks value. It is sidelined when its insights are framed in HR […]

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 […]

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