AI Monetization Is Becoming A GTM Systems Problem

Posted on May 21, 2026May 21, 2026 by Kyle James

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, and reconcile the work those systems perform? That may sound like a finance question at first. In practice, it quickly becomes a GTM systems problem. The reason is straightforward. If AI agents generate research, enrich records, resolve support issues, recommend pricing, trigger workflows, consume credits, or make purchases on behalf of users, monetization has to keep up with behavior that is more dynamic than traditional seat-based software. Seats Stop Explaining The Value Traditional SaaS pricing worked well when value could be approximated by human access. A user had a seat. A team bought […]

Mitratech Article: Your 2026 Human Resource Compliance Checklist – What to Prioritize First

Posted on May 20, 2026May 20, 2026 by 3Sixty Insights Editorial Team and Dylan Teggart

Insights from the 2026 State of HR Compliance Report to help you prioritize what actually matters. We all know the saying: if everything is a priority, nothing is. And right now, that tension is very real for HR team leaders who are balancing talent goals with rising expectations around process consistency and proof. Compliance work has expanded in ways that are easy to feel and hard to neatly quantify. New compliance requirements keep showing up. Enforcement patterns shift. Everyday decisions generate more questions that require proof, consistency, and documentation. In the 2026 State of HR Compliance Report, 75% of respondents said their compliance needs have changed, and more than half (54%) said those needs have increased over the past two years. Those shifts appear in […]

The Interface Layer Is Becoming The New GTM Battleground

Posted on May 12, 2026May 6, 2026 by Kyle James

The Desk Is Moving The MCP story is useful because it gives us a concrete signal to look at. But after sitting with the broader market scan, I do not think the bigger story is really about a protocol. The bigger story is that vendors are competing to become the layer where AI understands business context, retrieves the right information, and triggers action across workflows. Some of that competition is happening through MCP. Some of it is happening through agent studios, context graphs, embedded copilots, AI connectors, and conversational workspaces. The control point may be moving upward. The system of record still matters because it holds structured customer memory. But the place where operators ask questions, interpret signals, and move work forward may become just as important. […]

The Uncomfortable Truth About Modern Analyst Coverage

Posted on May 11, 2026May 11, 2026 by Nicholas Biron

Why Modern Research Requires More Than Press Releases and Earnings Calls Over the last few months, I’ve found myself in a familiar conversation with vendors across multiple technology markets, and it usually starts in a straightforward way. One of our analysts reaches out to learn more about a platform, and we ask for a briefing so we can understand the company’s direction, recent product changes, customer adoption trends, and overall go-to-market strategy. We also try to speak directly with customers so we can understand how the solution performs in real environments rather than just in theory. The responses we get vary widely. Some vendors are open, collaborative, and willing to engage in meaningful discussion. Others are far more constrained in their ability or willingness to […]

Video: The Hidden Reason No One Is Winning in B2B Tech Right Now

Posted on May 8, 2026May 8, 2026 by Nicholas Biron

Most software and technology providers are not losing because of market conditions. They are losing momentum because they are stuck in a cycle of constant planning, reorganization, and strategic resets. In this video, Nicholas break down what we are seeing across the market: organizations that continuously redefine their go-to-market strategy but never fully commit to execution. Leadership turnover, shifting priorities, and repeated restructuring are creating internal misalignment and externally, messaging that feels flat, generic, and indistinguishable. The result is a market filled with capable providers, but very few that are truly pulling ahead. He walks through a real-world pattern that is becoming increasingly common, why it is happening, and the impact it is having on growth, positioning, and competitive differentiation. More importantly, he outlines what […]

Model Context Protocol Is Becoming The New Interface Between Revenue Data And AI Execution

Posted on May 6, 2026May 5, 2026 by Kyle James

For the last year, much of the AI conversation in GTM has focused on assistants. Sellers get writing help. Marketers get content suggestions. Customer teams get summaries. Those use cases matter, but a different pattern is emerging across revenue technology. AI systems are moving closer to execution, and that creates a practical problem. They need access to business context before they can do useful work. That is where MCP is starting to matter. MCP, or Model Context Protocol, is a way for AI tools to connect with business systems so they can retrieve relevant information and, in some cases, take action without every vendor building an integration. In plain terms, it gives AI a more standardized way to ask trusted systems what is happening and what it is allowed to do […]

Workforce Management in the Age of Unknowns

Posted on May 5, 2026May 4, 2026 by Dylan Teggart

Most workforce management strategies are built for predictability. Maybe that’s the problem. In 2026, that thinking may now be a liability as the defining WFM challenges instead seem to be managing what dashboards can’t show you, AI workforce transformation is reshaping headcount decisions, data trust, and risk, as the modern workplace slowly becomes a human-AI hybrid—part judgment, part automation, part AI assistant. These changes will permanently alter the workforce, as a slow, sequenced cut moves through organizations from function to function, quarter by quarter, until organizations look fundamentally different from the way they did 10 years ago. So far, US job losses tied to AI have hit approximately 100,000 in the last 6–12 months, with companies like Amazon shedding 30,000 employees since October 2025, not […]

The 30-Minute Rule: Why GTM Buyers Are Rewriting How Software Gets Selected

Posted on May 5, 2026May 5, 2026 by Kyle James

Here is a great little story on how one GTM team made a software purchase decision. It’s something I believe is a good reminder if you’re still thinking in terms of feature comparisons and vendor evaluations. Most teams are no longer trying to find the best tool, they’re trying to find something that works quickly enough to justify moving forward. Good enough is winning as long as it returns value quickly and is easy for the team to use. A Different Starting Point In a recent conversation with Tom Weiss, the Chief Product and Technology Officer at MX8 Labs, that shift showed up in a way that felt almost casual. His team needed a CRM. They had tried stretching tools like ClickUp into that role, moved through a couple of alternatives, and ended up in a familiar place. Inconsistent usage, incomplete data, and very little confidence in what the […]

The Risks of Overconfidence in Compliance Management

Posted on May 4, 2026May 4, 2026 by Dylan Teggart

Leadership often assumes a lot of “known knowns” when managing a business. Obstacles, challenges, and surprises are just part of being at the helm of an organization, but there are more unknowns out there than most would care to admit. A balance of caution and confidence is important for navigating these challenges. You don’t want to run a business scared. But there has to be a balance between these two to avoid the grinding halts of being overly cautious and the blind spots that overconfidence can miss. This combination of rising complexity and high self-reported confidence suggests a known knowns vs. unknown unknowns scenario: Known knowns are known things, such as existing or longstanding compliance problems, documented requirements, or tested controls. Known unknowns are acknowledged […]

Monthly Research Recap | April 2026

Posted on May 1, 2026May 1, 2026 by 3Sixty Insights Editorial Team

Upcoming Events: PrismHR Live 2026 | June 14 – 16th, 2026 PrismHR LIVE brings together HR service providers, PEOs, payroll organizations, and HCM technology leaders for a focused exchange on workforce management, compliance, benefits administration, and platform innovation. Representing 3Sixty Insights, Dylan Teggart will be on site engaging with industry leaders, participating in key discussions, and capturing insights that reflect where the market is heading, making this a valuable opportunity for both learning and meaningful connection across the HR services ecosystem. Recent Research: Benchmark Report: State of HR Compliance 2026 – Benchmark Findings on Confidence, Complexity, and the AI Effect The State of HR Compliance 2026 Benchmark Report examines how organizations are navigating an increasingly complex compliance landscape shaped by regulatory change, workforce evolution, and […]

The Quiet Death of the SDR: Why Some GTM Teams Are Letting Marketing Reclaim the Pipeline

Posted on April 27, 2026April 27, 2026 by Kyle James

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 function is not disappearing overnight. In many organizations, it remains a critical part of the revenue engine. But in a specific and increasing subset of companies, we are seeing something more subtle unfold. The work SDRs used to do is being absorbed. Not eliminated, not replaced, but absorbed into marketing. And in that shift, ownership of the early pipeline begins to move with it. Why This Is Happening Now This shift does not come from a single decision. It is the result of several pressures converging at […]

The Hamster Wheel of Reorganization: Why Solution Providers Are Struggling to Win

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

In today’s software and technology landscape, one question continues to surface in our conversations with vendors and service providers: who is truly winning? Historically, this was a relatively straightforward question to answer. There were always clear market leaders, organizations that consistently differentiated themselves through sharp strategy, compelling messaging, and disciplined execution. Over the past 12 to 24 months, however, that answer has become increasingly difficult. Outside of a handful of pure-play AI organizations, infrastructure leaders and a small handful of solution providers, the market is no longer defined by clear breakout winners. Instead, many providers appear to be locked in a competitive stalemate, winning their share of business but failing to establish sustained momentum. At 3Sixty Insights, we believe one of the most significant contributors […]

The Growing Gap Between Vendor Messaging and Organizational Reality

Posted on April 21, 2026April 21, 2026 by Nicholas Biron

At 3Sixty Insights, we have a dedicated practice focused on HR, Benefits, and Payroll. Over the past several years, we have seen a clear shift in how organizations in this space position themselves in the market. The messaging has evolved beyond helping companies become more effective and efficient, expanding into themes centered on improving employee experience and building stronger workplace cultures. Conceptually, this evolution makes sense. There is no shortage of research supporting the idea that engaged and satisfied employees are more productive and contribute more meaningfully to organizational success. It is a logical progression in messaging, and one that resonates with buyers. However, over time, I have found myself increasingly questioning whether some of these organizations are truly operating in alignment with what they […]

How Social Media and Behavioral Insights Are Helping Employers Detect Misconduct Before Day One

Posted on April 7, 2026April 8, 2026 by Dylan Teggart

All business leaders have been there: a candidate looks great on paper, so you invest in hiring them, but once on board, they fail to meet expectations. 50% of today’s workers are digital natives, and with this number expected to increase to 75% over the next five years, most organizations still rely on outdated screening methods—résumés, interviews, and post-offer background checks—that are ill-equipped to capture behavioral red flags that often appear online but not on paper. From disclosing company information to violating safety protocols to harassing others, new hires with less visible issues, such as intolerance, tardiness, or substance abuse problems, can misalign with company policies or culture, jeopardizing your team’s productivity or your brand image. In-person interviews can fall short when you need to […]

Why Some Restaurants Win and Others Struggle

Posted on April 2, 2026April 2, 2026 by Nicholas Biron

For the better part of the last decade, Wednesdays have followed a simple pattern in my household. Somewhere between the workday winding down and the week feeling just long enough, my family and I head out to dinner. It is not a special occasion, not a celebration, just a routine. And over time, that routine has turned into something more valuable than I expected. It has become a lens into the restaurant industry at its most honest point. Wednesday is not a peak night. There are no built-in excuses. No surge of weekend traffic to mask operational issues. What you see on a Wednesday evening is, more often than not, the reality of a restaurant’s performance. What stands out is how stark the contrast has […]

Monthly Research Recap | March 2026

Posted on April 1, 2026March 31, 2026 by 3Sixty Insights Editorial Team

Recent Research: Research Agenda: Bridging Leadership and Labor – 3Sixty Insights’ 2026 Combined Workforce Agenda This Combined Workforce Agenda outlines the key research priorities for 2026 from 3Sixty Insights, focusing on how organizations can bridge leadership strategy and employee experience in the modern workplace. The agenda integrates perspectives from two analysts — Nicole Roberts and Dylan Teggart — each with complementary emphases on organizational leadership capability, workforce strategy, labor market dynamics, and technology-enabled work execution. Analyst Insight: California Labor Laws and Compliance: Burden, Benchmark, or Competitive Advantage? This Analyst Insight examines the widely held perception that California’s labor laws make the state unusually difficult for businesses to operate in. While the analysis finds that California does impose more complex compliance requirements than most U.S. states, […]

Why AI Governance Requires Narrative Alignment

Posted on March 30, 2026March 30, 2026 by Kyle James

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 the event focused on pricing, workflows, and AI embedded into revenue systems, our discussion kept circling a deceptively simple example that revealed a much larger issue. We started talking about NDAs. Not complex contracts or pricing strategy. Just NDAs. As Geoff pointed out, these are among the most common documents in any deal process, and yet they regularly slow things down. A rep sends one over, legal reviews it, questions come back, revisions happen, and what should be routine turns into delay. This is exactly […]

Three Signals About the Future of Revenue Execution from Conga Connect 2026

Posted on March 16, 2026March 23, 2026 by Kyle James

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 in conversations with operators and revenue leaders throughout the week, a different set of signals stood out. They all pointed to the same underlying challenge: revenue teams are still struggling with friction inside the deal process. During the opening session, Conga CMO Celia Fleischaker shared several statistics that framed the scale of the problem. Only 8% of organizations report strong confidence in their pricing decisions. 45% say they lose deals due to slow quote approvals. 72% report that slow contracting increases risk and compliance exposure. […]

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 […]

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