Kyle James
Director & Principal Analyst
kjames@3sixtyinsights.com

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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.
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Solutions Spotlight: Redesigning CRM with Creatio – The Rise of No-Code, Unified AI, and Agentic Automation

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In the fast-changing world of business software, few areas are transforming as quickly as Customer Relationship Management (CRM). Once just a digital contact list, CRM is now expected to be a central hub for sales, marketing, and customer success, helping teams work smarter, faster, and more effectively. But with these growing expectations comes new complexity. Creatio is tackling this challenge by rethinking CRM from the ground up, making it AI-powered, no-code, and agent-driven. “Our goal is to put AI and automation into the hands of non-technical users, not just IT,” said Burley Kawasaki, Global VP of Product Marketing and Strategy at Creatio. This approach doesn’t just support agility, it sparks innovation. Teams can quickly build and improve their tools without needing to write code or […]

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Solutions Spotlight: Appian’s Secret to Reliable and Scalable AI – The Appian Data Fabric

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Introduction In the rapidly evolving world of enterprise automation, where organizations are racing to leverage artificial intelligence (AI) for competitive advantage, one challenge persists: ensuring AI is not just intelligent, but also reliable, secure, and scalable. For highly regulated industries such as finance, healthcare, and government, the stakes are even higher. AI solutions must deliver results without compromising security or compliance. Yet for many enterprises, the AI journey is fraught with complexity. Legacy systems, siloed data, and the need for stringent compliance often slow down progress or create barriers to deployment. Even with the rise of powerful generative models, the challenge of integrating AI into real-world business processes in a secure, ethical, and efficient way remains unsolved for many. What enterprises need is not just […]

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What Mark Kilens Wants Every GTM Leader to Know: Craft, Collaborate, Educate

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The latest episode of GTM Innovators features a candid, insightful conversation with Mark Kilens—VP of Marketing at EasyLlama and Founder of TACK. If you know Mark, you know he doesn’t pull punches. In this episode, he shares what he believes are some of the most foundational (yet often overlooked) truths about modern go-to-market (GTM) success. While the tools and tactics available to marketing, sales, and product teams have evolved rapidly, Mark’s perspective reminds us that GTM excellence doesn’t come from chasing shiny objects. It comes from mastering the basics, creating alignment, and building systems that scale through value. Below, we explore three key takeaways from our discussion that any GTM leader, especially those in early-stage or scaling companies, should pay attention to. Cross-Functional Alignment Isn’t […]

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GTM Innovators: Creating Demand Through Community – A GTM Chat with Mark Kilens

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In this episode of GTM Innovators, we sit down with Mark Kilens for a conversation that brings us back to the GTM fundamentals. Mark is the VP of Marketing at EasyLlama and Founder of TACK. Mark shares how the most effective go-to-market strategies today are rooted in community, education, and trust. From building scalable programs to fostering authentic engagement, Mark’s insights may sound simple—but they’re powerfully foundational. Whether you’re refining your GTM motion or starting from scratch, this episode is packed with timeless advice on creating real demand through human connection. 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 Audacy: https://www.audacy.com/podcast/gtm-innovators-cf67e Transcript: Kyle James 00:00 Kyle, welcome to another episode of GTM […]

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Solutions Spotlight: Redefining Partner Marketing – Attribution, Advocacy, and Acceleration with Everflow

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As organizations navigate increasingly complex go-to-market strategies in 2025, the spotlight continues to shine on partner marketing as a scalable and cost-effective growth lever. However, for many companies, affiliate, referral, and strategic partnership programs remain underutilized, siloed, or underserved by legacy technologies. During a recent conversation with Michael Cole, SVP of Marketing at Everflow, we uncovered key insights into how the company is helping to redefine partner marketing for the modern era. Their approach centers on three essential pillars: Attribution clarity Innovative referral structures Accelerated time to value Attribution Clarity Across the Full Funnel One of the most pervasive challenges in partner and performance marketing is attribution. Legacy systems—particularly those anchored in last-click models—fail to recognize the value of early-funnel engagement. Influencers, content creators, and […]

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Solutions Spotlight: Rethinking What Enterprise eCommerce Really Means

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How OroCommerce is helping B2B organizations modernize workflows, consolidate tech stacks, and redefine what it means to sell online “So if I’m engaged in a CPQ process via email or a quick chat, and I send over a quote, is that eCommerce? I don’t know. Does it matter? Not really.” — Aaron Sheehan, Head of Product Marketing & Strategic Partnerships, OroCommerce This deceptively simple question gets right to the heart of what’s changing in enterprise commerce today. In B2B, eCommerce isn’t just about clicking “Add to Cart” on a website. It’s about enabling commerce wherever it happens, whether that’s a rep typing into a quote tool, a buyer sending a purchase order by email, or a distributor logging into a branded portal from their phone. […]

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Crayon Blog: A Smarter Way to Compete – How AI Is Reinventing Competitive Intelligence

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In a world where two thirds of sales opportunities are competitive—and those opportunities close at 5x the rate of non-competitive ones—competitive intelligence (CI) is a necessity. Yet most companies aren’t just underperforming—they’re flying blind. That’s why Crayon’s Jon White, SVP of Product, joined 3Sixty Insights’ GTM Innovators podcast to talk with Kyle James about how AI is changing the CI game forever. This post breaks down Jon’s key takeaways and what your team can do to compete smarter, faster, and with more impact. Why Competitive Enablement Is Broken (And How AI Can Help Fix It) Competitive intelligence used to be a manual grind: scanning websites, collecting review site quotes, reading press releases, and trying to translate all that noise into something useful for your reps. This is the […]

The Hidden Risks of AI: John Baldino on Bias, Empathy, and Smarter Adoption

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In the latest episode of GTM Innovators, I had the pleasure of hosting John Baldino, President of Humareso and co-host of the But First Coffee Podcast. Our conversation tackled some of the most critical topics organizations must consider as they rush to embrace AI in their go-to-market and talent strategies. While the promise of AI is exhilarating, John provides a grounded and necessary perspective on the challenges we must confront before blindly integrating these technologies. Let’s dive into a few of the major themes from our conversation and share why every business leader should be thinking critically about how they vet the AI tools shaping their future. The Danger of Entrenchment: Bias in AI One of the most striking points John raised was the hidden […]

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Solutions Spotlight: Gainsight and the Future of the Customer Operating System

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Introduction: Rethinking the Post-Sale Customer Experience In the B2B SaaS world, retention is the new acquisition. As organizations look to scale more efficiently and deliver lasting value to customers, the post-sale journey has emerged as the most critical, and often under-orchestrated, part of the go-to-market equation. Gainsight is meeting this moment with a clear, bold vision: the Customer Operating System (Customer OS). With an expanding platform that integrates customer success, product experience, education, community, and AI, Gainsight is positioning itself as the central nervous system for customer-led growth. Today, successful companies recognize that customer success isn’t just a department; it’s a company-wide motion. Gainsight is capitalizing on this shift by delivering a platform that creates alignment across teams, ensures data consistency, and prioritizes outcomes over […]

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Solutions Spotlight: The Great Awakening in GTM – How 6sense’s Decade of Data Pioneering Set the Stage for AI-Driven Revenue Growth

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B2B buyers today are nearly 70% through their purchase journey before engaging a seller, and more than 80% of the time, they’ve already chosen their preferred vendor when they do. This is not a fluke; it’s a global pattern validated across regions and industries. According to 6sense’s 2024 Buyer Experience Study, buyers initiate contact in 83% of cases, and the majority of those conversations begin with the vendor they ultimately choose. In this environment, traditional lead-generation and sales tactics struggle to keep pace. Revenue teams need earlier insight, better prioritization, and tools that can meet buyers where they already are in their journey. We’re witnessing what could be described as a “great awakening” in revenue technology. After a decade of collecting and categorizing trillions of […]

GTM Innovators: Vetting the Future with John Baldino – Trust, AI, and the Human Touch

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In this episode of GTM Innovators, host Kyle James sits down with John Baldino, President of Humareso and co-host of the But First Coffee Podcast, for a candid conversation on the future of AI in the workplace. This discussion explores how organizations must balance innovation with responsibility when adopting AI technologies. John shares his insights on building trust, maintaining ethical standards, and preserving the human element as AI continues to reshape the way we work. From recruitment to performance management, this episode offers practical advice for leaders navigating the rapidly evolving landscape of technology and talent. 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 Transcript: Kyle James 00:00 Kyle, welcome everybody to […]

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Reinventing Coaching, GTM Outcomes & AI Design for the Frontlines – A Conversation with Scott Newman

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When you think about how AI is transforming the world of go-to-market, your mind probably jumps to sales tools, marketing automations, or maybe even predictive analytics. But in the latest episode of GTM Innovators, I had the chance to sit down with Scott Newman, Chief Strategy Officer at OneSource, and what we uncovered goes much deeper — especially for anyone thinking about the future of frontline employees, customer experience, and real AI enablement. In short, Scott and his team aren’t just layering AI on top of legacy processes — they’re reimagining entire systems from the ground up. The result? A radically different approach to agent onboarding, performance coaching, and real-time support that’s not only effective, but surprisingly human. Here are three big themes we explored […]

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GTM Innovators: Reimagining BPO with AI – Innovation and Insights from OneSource CSO Scott Newman

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In this episode of GTM Innovators, we sit down with Scott Newman, Chief Strategy Officer at OneSource, to explore how AI is fundamentally transforming the BPO industry. Scott shares how OneSource is leveraging its platform, CalibrAIte, to move beyond traditional contact center operations—empowering frontline agents, automating coaching and QA processes, and generating the structured data companies need to truly adopt AI. From real-time feedback loops to global scalability, Scott offers actionable insights and hard-won lessons on what it really takes to innovate in one of the most human-centric corners of the business world. OneSource Report: Analyst Insight: The Hidden AI Adoption Barrier – Why 80% of Companies Aren’t Ready 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: […]

Empathy at Scale: Why Customer Success Must Be the Heart of Your GTM Strategy

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Featuring insights from GTM Innovators guest Mike Lemire In today’s fast-paced, tech-powered go-to-market landscape, it’s easy to forget that behind every KPI and automation flow is a real person trying to solve a real problem. But for Mike Lemire—CEO & Lead Coach at Harmonic Leadership and a seasoned customer success leader with a background as unique as it is powerful—empathy isn’t just a “nice to have.” It’s a strategic imperative. In our latest GTM Innovators episode, I sat down with Mike to explore how customer success can drive real, lasting value when it’s rooted in empathy, guided by persona-driven engagement, and connected deeply across the GTM organization. Here are just a few themes we unpacked that I think every modern GTM leader should reflect on. […]

GTM Innovators: Empathy at Scale – Mike Lemire on Customer Success in a Digital World

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In this episode of GTM Innovators, Kyle James sits down with Mike Lemire of Harmonic Leadership—musician turned customer success executive—for a wide-ranging conversation on the evolving role of CS in go-to-market strategy. From his early days at Blue Note Records and Yahoo to leadership roles at HubSpot, Toast, and Overjet, Mike shares his unique journey and what it taught him about empathy, value delivery, and scalable success. Tune in as we explore how AI, automation, and persona-driven engagement are shaping modern CS teams—and why human connection still reigns supreme in a digital-first world. 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 Transcript: Kyle James 00:00 Kyle, welcome to another episode of GTM […]

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From Afterthought to Strategic Superpower: AI’s Expanding Role in Translation and GTM

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For decades, translation has been treated like a checkbox—an afterthought at the tail end of a marketing campaign or product rollout. But thanks to the rise of AI-powered platforms like Smartcat, that mindset is shifting dramatically. In a recent episode of GTM Innovators, we sat down with Sara Rosso, Senior Director of Product Marketing at Smartcat, to explore how AI is transforming not just the how of translation, but the when, where, and why. Here are a few of the most eye-opening themes from our conversation: Translation as a Core Go-to-Market Strategy (Not a Final Step) Traditionally, companies launched a campaign or product in English, then outsourced translations to local agencies—waiting days or weeks for the final version. But Smartcat is enabling a new playbook: […]