Kyle James

Director & Principal Analyst

Sort Research

Kyle is a seasoned technology problem solver and product management leader with over two decades of experience. He has founded two successful startups, nuCloud and .eduGuru, both of which exited, and was among the earliest team members at HubSpot (NASDAQ:HUBS) and OneScreen.ai. Throughout his career, Kyle has been instrumental in building and scaling innovative solutions across various industries, driving both product and business growth. His contributions have helped organizations navigate complex challenges, launching products that resonate with users and generate meaningful value. While he’s a self-professed tech geek, Kyle’s true passion lies in helping people solve problems through technology. His approach is grounded in a belief that there’s always a better way to do things, and he thrives on challenging the status quo. Whether leading product development or mentoring teams, Kyle is deeply focused on simplifying workflows and creating solutions that deliver measurable impact. His hands-on leadership style fosters collaboration, empowering teams to push boundaries and achieve successful outcomes. Obsessed with knowledge and driven to share what he learns, Kyle enjoys troubleshooting, problem-solving, and improving processes to create lasting impact. His relentless curiosity and commitment to continuous learning ensure that he is always evolving, finding new ways to drive innovation and inspire those around him. He is dedicated to the idea that technology, when applied thoughtfully, can transform how we work and live.

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

Posted on February 19, 2026February 19, 2026 by 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 […]

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 […]

Anatomy of a Decision: How One Customer Rebuilt Its Entire SDR Motion with Apollo.io

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

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 engage. What started as a narrow search for a fix to email deliverability became a full-scale rebuild of the customer’s sales development motion on Apollo. A Legacy SDR Engine Starts to Strain Apollo’s customer helps organizations deliver personalized, data-driven video experiences at scale, thereby increasing engagement, conversion, and long-term customer value. After nearly two decades in market and a long-established SDR organization, the customer had a mature outbound motion that had been refined over many years. But by early 2024, the cracks were hard to […]

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? […]

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 […]

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 […]

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. […]

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 […]

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Solution Spotlight: Verto and the AI Thought Partner — Empowering the Accidental Project Manager in a Do-More-With-Less Era

Posted on January 15, 2026January 15, 2026 by Kyle James

Across the UK public sector, local councils, and the NHS, organizations are facing increasing pressure to deliver more complex programs under tighter budgets. Transformation initiatives are expanding, transparency requirements are growing, and expectations for measurable outcomes have never been higher. Yet many of the individuals responsible for driving this work are not formally trained project managers. They are policy leaders, clinicians, service owners, and operations specialists who were chosen because they understand the work better than anyone. The team at Verto has begun to commonly refer to these individuals as accidental project managers. The term does not imply a lack of capability; they are often the most knowledgeable and trusted people available. What they typically lack are the structured frameworks, repeatable workflows, and strategic lenses […]

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: […]

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 […]

Research Agenda: 2026 Go-to-Market B2B

Posted on November 18, 2025November 20, 2025 by Kyle James

Introduction Building on the insights and conversations from the 2025 GTM Research Agenda, this year’s focus deepens our understanding of how efficiency, authenticity, and AI collaboration are shaping modern go-to-market strategies. Through discussions with industry leaders and operators, we’ve identified emerging intersections between human creativity, data-driven precision, and automation. The 2026 agenda continues this exploration, emphasizing community-driven learning and practical application across the GTM ecosystem. These topics remain working hypotheses but have matured through initial discovery and community conversations. They are shared here to invite continued exploration and deeper dialogue with practitioners, vendors, and operators. Rather than presenting final positions, our intent is to surface the most relevant and timely GTM questions for 2026. We will continue to solicit input, opinions, and insights from practitioners […]

Zero Trust in the Age of AI: Why Enterprise Security Principles Are Becoming the Blueprint for Digital Trust

Posted on November 13, 2025November 13, 2025 by Kyle James

As enterprises wrestle with how to adopt AI responsibly, they’re rediscovering the same lesson cybersecurity mastered years ago: trust must be earned, verified, and continuously monitored. The Trust Recession in Technology I recently had the opportunity to sit down with John Armstrong, Senior Product Marketing Manager for Application & Network Security at Ivanti. Our conversation started with Ivanti’s approach to cybersecurity and the growing importance of Zero Trust. But as these conversations often do, it quickly expanded. We found ourselves talking not only about the challenges of securing networks but also about the growing challenge of trusting artificial intelligence. That connection between cybersecurity and AI is not accidental. Both domains are struggling with the same fundamental problem: trust. Cybersecurity spent decades building systems to verify […]