Kyle James

Director & Principal Analyst

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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.

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 […]

Infographic: Scaling GTM Responsibly – Cohere Health Demonstrates the Power of Maturity-Aligned Platform Choices

Posted on November 5, 2025November 5, 2025 by Kyle James

The New Rules of Discoverability: Michael Cole on GEO, Partnerships, and Authentic Content

Posted on October 29, 2025October 31, 2025 by Kyle James

If 2023 was the year marketers started experimenting with AI, 2025 is the year it starts rewriting the rules of how buyers discover, trust, and choose brands. In this new episode of GTM Innovators, I sat down with Michael Cole, SVP of Marketing at Everflow, to unpack one of the most quietly disruptive shifts happening in go-to-market today: what Michael calls Generative Engine Optimization (GEO). It’s not hyperbole to say we’re watching the end of long-tail SEO as we knew it. What comes next will fundamentally change how companies think about visibility, partnerships, and human-created content. Below are three themes from our conversation that stood out, offering just a glimpse of what we covered in the full episode. 1. The Rise of Generative Engine Optimization […]

GTM Innovators: The GEO Playbook – How Partner Marketing Fuels AI Discoverability with Michael Cole

Posted on October 27, 2025October 27, 2025 by Kyle James

In this episode of GTM Innovators, host Kyle James sits down with Michael Cole, SVP of Marketing at Everflow, to explore how Generative Engine Optimization (GEO) is redefining the rules of search and discoverability. As AI tools like ChatGPT and Gemini become the new front doors to information, long-tail SEO is giving way to a world driven by citations, partnerships, and authentic content. Michael shares how leading brands are adapting—building relationships with publishers, rethinking affiliate strategies, and creating human-led content that fuels visibility across AI-powered ecosystems. If you’ve ever wondered what replaces SEO in the age of AI, this conversation is your new playbook. Subscript to GMT Innovators Series on the following platforms: SoundCloud: https://soundcloud.com/research-859405782 YouTube: https://www.youtube.com/playlist?list=PLsoV6fwX4cpGR2Hg98rc1e1k2-cOqCbhb Spotify: https://open.spotify.com/show/1gvDzcl0jxpPIfu9WYu6U4 iHeartReadio: https://iheart.com/podcast/258127960/ Pandora: https://www.pandora.com/podcast/gtm-innovators/PC:1001097038 iTunes: https://podcasts.apple.com/us/podcast/gtm-innovators/id1790738579 Amazon: https://music.amazon.com/podcasts/1b000615-31cc-49dd-a5d8-f80d5098bf2d/gtm-innovators […]

Anatomy of a Decision: Right-Sized ABM – How Cohere Health Chose the Perfect Platform for Their Team

Posted on October 10, 2025March 31, 2026 by Kyle James

B2B marketing is undergoing a recalibration. The days of chasing MQLs as the north star are giving way to strategies rooted in precision, orchestration, and meaningful engagement across entire accounts. For Brianna Miller, Director of Demand Generation at Cohere Health, this evolution isn’t theoretical. It’s personal, practical, and rooted in years of frontline experience leading ABM initiatives in healthcare technology. As account-based marketing (ABM) continues to gain traction, many GTM leaders face the same challenge: how do you operationalize ABM at scale without overloading your team or overspending on tools? Amid tightening budgets and growing pressure to prove marketing’s revenue impact, ABM must walk a fine line between sophistication and simplicity. When Brianna joined Cohere Health, the company was already exploring account-based marketing platforms. Several […]

GTM Trust Through Analyst Relations with Chris Manfredi

Why Analyst Relations Is the Hidden Trust Engine in Your GTM Strategy

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

In today’s high-stakes world of B2B go-to-market strategy, trust isn’t just a soft skill. It is a strategic advantage. Whether you’re launching a new product, entering a crowded category, or navigating a competitive landscape, the ability to earn and project trust externally and internally can make or break your success. That’s why I sat down with Chris Manfredi, Global Director of Analyst Relations at Sprout Social and co-lead of the Institute of Influencer Analyst Relations, for the latest episode of GTM Innovators. With more than a decade of experience spanning firms like IBM, BlueVoyant, and now Sprout, Chris brings unmatched clarity on the real value of analyst relations. And it goes far beyond Magic Quadrant placement. Here are a few of the key insights we […]

Anatomy of a Decision: How ZRG Partners Turned to Sprout Social to Power Brand Amplification from Within

Posted on August 12, 2025August 12, 2025 by Kyle James

Overview As ZRG Partners expanded from a boutique search firm to a global talent advisory powerhouse with 600+ employees, its rapid growth outpaced brand recognition. Private equity backers challenged leadership with a clear question: What are you doing for marketing? The answer was a complete go-to-market transformation—anchored by employee advocacy through Sprout Social. By empowering its people to tell the ZRG story, the firm turned marketing into a true growth catalyst, driving measurable gains in website traffic, employee engagement, and brand awareness. Key Takeaways From Sales-Driven to Brand-Driven: Transitioned from a purely sales-led growth model to a coordinated GTM engine. People, Process, Platform: Hired strategic marketing leaders, implemented new tech (Salesforce Marketing Cloud, BrightEdge, Jasper AI), and embedded advocacy into culture. Sprout Social Advantage: Chosen […]

GTM Innovators: Building GTM Trust Through Analyst Relations with Chris Manfredi

Posted on August 11, 2025August 12, 2025 by Kyle James

In this episode of GTM Innovators, Kyle James sits down with Chris Manfredi, Global Director of Analyst Relations at Sprout Social, to explore the power of analyst relations as a trust-building force in go-to-market strategy. With over a decade of experience navigating firms like Gartner, Forrester, and IDC, Chris shares how AR serves as a strategic connective tissue across product, marketing, sales, and the C-suite. From managing 1,500+ analyst touchpoints a year to synthesizing insights for executive decisions, Chris offers a behind-the-scenes look at what makes AR truly impactful, especially in today’s AI-driven, insight-saturated landscape. Whether you’re new to AR or looking to take your program to the next level, this conversation is packed with practical wisdom, human-centric perspective, and bold ideas for the future. […]

Solution Spotlight: How SalesScreen Makes Sales Competitions Effortless, Inclusive, and Strategic

Posted on August 5, 2025August 5, 2025 by Kyle James

Reimagine Sales Competitions with Automation, Gamification, and AI-Driven Insights Sales competitions have long been a core motivator in GTM teams—but traditional approaches are often manual, repetitive, and limited in impact. In this Solution Spotlight, we explore how SalesScreen is modernizing the sales competition playbook, offering a powerful platform that turns one of the oldest tactics in sales into one of the smartest. From real-time CRM integration and dynamic competition formats to the launch of Scout, their AI assistant, SalesScreen is helping GTM teams motivate more reps, more often—with less effort. What You’ll Learn: Why traditional contests leave most reps behind—and how to fix it How SalesScreen simplifies competition setup with automation and pre-built templates Ways teams are using gamification to build culture, drive behavior, and […]

OneSource Article: Driving AI Readiness with Unstructured Data – A Look into CalibrAIte’s Impact

Posted on July 29, 2025July 29, 2025 by Kyle James

As organizations race to operationalize AI, a key barrier remains: unstructured data. Emails, chats, voice recordings, and social media are rich in insights—yet difficult to mine without the right tools. That’s where CalibrAIte, a solution by OneSource, enters the equation. 3Sixty Insights recently explored how CalibrAIte empowers organizations to transform this data into structured, actionable intelligence. Our report sheds light on how businesses are using the platform to uncover customer sentiment, reduce manual workflows, and accelerate their journey to AI readiness—without having to overhaul their entire tech stack. OneSource’s approach prioritizes business outcomes first, starting with high-impact use cases that quickly demonstrate value. It’s a strategy that aligns with what we at 3Sixty Insights have identified as a hallmark of successful digital transformation. Read the […]

How to Stop Wasting SMS: Lessons on Trust, Timing, and Texting from Textdrip’s CEO

Posted on July 23, 2025July 23, 2025 by Kyle James

In an era where inboxes are overflowing and attention spans are shrinking, SMS has quietly emerged as one of the most effective yet misunderstood tools in a modern go-to-market (GTM) team’s arsenal. In our latest GTM Innovators episode, I sat down with Phil Portman, founder and CEO of Textdrip, to talk all things business texting. What started as a conversation about automation quickly evolved into a deep dive on trust, transparency, and the subtle art of sending the right message at the right time. 1. The Power and Pitfalls of Business Texting Texting isn’t just a new channel; it’s a different one. The immediacy of SMS is unmatched. According to Phil, “The response rate on texting is 45% compared to 6% in email.” And most […]

GTM Innovators: Texting with Intent – Phil Portman on Smarter SMS for Modern GTM Teams

Posted on July 21, 2025July 20, 2025 by Kyle James

In this episode of GTM Innovators, we sit down with Phil Portman, founder and CEO of Textdrip, to explore how SMS is evolving from a simple communication tool into a powerful, intent-based automation channel for modern go-to-market teams. Phil shares his entrepreneurial journey from flipping houses to building a scalable, compliant SMS platform designed for regulated industries. We dive into how Textdrip leverages AI (without losing the human touch), the dos and don’ts of SMS campaigns, and why deliverability and trust are the new battlegrounds in business texting. If you’re curious about how to integrate SMS into your GTM strategy the right way, this episode is for you. Subscript to GMT Innovators Series on the following platforms: SoundCloud: https://soundcloud.com/research-859405782 YouTube: https://www.youtube.com/playlist?list=PLsoV6fwX4cpGR2Hg98rc1e1k2-cOqCbhb Spotify: https://open.spotify.com/show/1gvDzcl0jxpPIfu9WYu6U4 iHeartReadio: https://iheart.com/podcast/258127960/ […]