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.

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Solutions Spotlight: Rethinking What Enterprise eCommerce Really Means

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

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. […]

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

Posted on May 8, 2025May 7, 2025 by Kyle James

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

Posted on May 7, 2025May 7, 2025 by Kyle James

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 […]

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

Posted on May 7, 2025May 7, 2025 by Kyle James

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 […]

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

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

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

Posted on May 5, 2025May 7, 2025 by Kyle James

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

Posted on April 30, 2025May 21, 2025 by Kyle James

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 […]

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

Posted on April 28, 2025May 21, 2025 by Kyle James

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

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

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

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

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

Posted on April 17, 2025April 17, 2025 by Kyle James

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: […]

GTM Innovators: AI, Babelfish & the Future of Translation: A GTM Deep Dive with Sara Rosso

Posted on April 14, 2025April 14, 2025 by Kyle James

In this episode of GTM Innovators, host Kyle James sits down with Sara Rosso, Senior Director of Product Marketing at Smartcat, for a wide-ranging conversation on the evolving role of AI in global go-to-market strategies. From her roots in engineering to her marketing leadership across companies like HubSpot, Automattic, and now Smartcat, Sara shares how AI is transforming content localization, translation workflows, and the very nature of cross-border collaboration. Tune in as we explore why AI might just be the new Babelfish—and what that means for product marketers, enterprise teams, and the future of global communication. 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, hello, hello. Hello, […]

Turning the Competitive Tide: How AI Empowers GTM Teams to Win

Posted on April 9, 2025April 9, 2025 by Kyle James

In today’s hyper-competitive B2B landscape, knowing your competition isn’t a nice-to-have—it’s a matter of survival. But ask any go-to-market leader and they’ll tell you: enabling your sales team to confidently compete is an uphill battle. The traditional approach to competitive intelligence (CI) is time-consuming, inconsistent, and often fails to keep up with the pace of change. In a recent episode of the GTM Innovators podcast, I sat down with Jon White, SVP of Product at Crayon, to dig into how AI is flipping this dynamic—and empowering sales, product, and marketing teams to operate with a new level of speed and confidence. Here are three major areas where AI is becoming a game-changer in competitive intelligence: 1. Arming Sales Teams in Real-Time with AI-Powered Enablement Sales […]

GTM Innovators: AI + Competitive Intelligence – A Smarter Way to Compete, with Jon White from Crayon

Posted on April 7, 2025April 7, 2025 by Kyle James

In this episode of GTM Innovators, host Kyle James sits down with Jon White, SVP of Product at Crayon, to explore how AI is reshaping the world of competitive intelligence. Jon shares how Crayon is helping go-to-market teams move beyond manual research and outdated battle cards by harnessing AI to surface real-time insights, identify emerging competitors, and enable sales teams with smarter, more strategic content. From parsing call transcripts to tracking digital footprints, Jon walks us through the evolving tech stack for modern competitive enablement—and what’s coming next. Whether you’re in sales, product, or marketing, this is a conversation you won’t want to miss. Jon’s Recent LinkedIn Post Referenced in the Show Referenced GTM in the AI ERA Webinar Subscript to GMT Innovators Series on […]

Analyst Insight: Empowering the Frontline Workforce – Inspiring Change Through Intelligent Communication and Insights

Posted on April 4, 2025April 4, 2025 by Kyle James

In an era where digital transformation is reshaping industries, frontline workers—who make up nearly 80% of the global workforce—often remain underserved by enterprise technology. Beekeeper addresses this gap by leveraging AI-driven solutions to enhance communication, engagement, and operational efficiency. By prioritizing a mobile-first approach, Beekeeper ensures that frontline employees—who almost always have a mobile phone on them—can seamlessly access the tools they need without the barriers of traditional workplace technology. Through our exploration of Beekeeper’s AI-powered approach, three key takeaways emerged in the transformation of frontline work: AI-Driven Translation & Inclusive Communications – Breaking down language barriers to foster seamless, real-time workplace communication that can improve team cohesion, increase workplace safety and compliance, and harness skills. Manager Enablement to Boost Frontline Engagement – Equipping frontline […]

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Why Playing It Safe Is Hurting Your GTM Strategy

Posted on April 3, 2025April 30, 2025 by Kyle James

There’s a quiet revolution happening in B2B go-to-market strategy, and it doesn’t involve flashy tools or cold outreach hacks. It’s founder-led growth—driven by real people with strong points of view who are willing to step into the spotlight. In our latest GTM Innovators episode, I sat down with Finn Thormeier, founder of Project 33, to unpack how B2B SaaS companies can turn their internal expertise into a high-performing demand engine. Finn has helped dozens of B2B leaders go from silent operators to visible, credible thought leaders—and the results speak for themselves. One of the biggest takeaways? Your content strategy doesn’t need more polish—it needs more point of view. The GTM Power of Founder-Led Growth When your buyers are skeptical and drowning in noise, what cuts […]

Analyst Insight: The Power of Data Freedom – How Act-On is Redefining Marketing Automation

Posted on April 2, 2025May 21, 2025 by Kyle James

In today’s fast-moving digital landscape, businesses need marketing automation solutions that enhance—not restrict—their ability to innovate. Too often, organizations find themselves trapped in rigid marketing ecosystems, where switching costs, limited integrations, and outdated architectures prevent agility. Act-On has taken a radically different approach, championing “Data Freedom” as a core principle. By enabling seamless integrations, multi-instance support, and an intuitive user experience, Act-On ensures that marketers are in full control of their data and engagement strategies. More than just a philosophy, this approach empowers organizations to scale efficiently while maintaining the flexibility to work with any tool they choose. Seamless Integrations: Enabling True Data Freedom For marketing teams, data is only as powerful as their ability to access, analyze, and act on it. Traditional marketing automation […]

GTM Innovators: Why Thought Leaders Win – Finn Thormeier on Content, Clarity, and Controversy

Posted on March 31, 2025March 31, 2025 by Kyle James

In this episode of GTM Innovators, Kyle James chats with Finn Thormeier, founder of Project 33, about how B2B founders and execs can unlock growth by building authentic, strategic personal brands. Finn breaks down what separates real thought leaders from content noise, how to turn subject-matter expertise into consistent demand, and why controversial takes (when done right) drive results. If you’re leading a GTM motion and want your voice to cut through, this episode is your playbook. Finn’s Top 100 Target Accounts 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 Transcript: Kyle James 00:00 Kyle, welcome to another episode of GTM Innovators by 3Sixty Insights. I’m your host, Kyle James, and […]

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Why B2B Partnerships Are the Hidden Growth Engine in GTM Strategies

Posted on March 26, 2025March 26, 2025 by Kyle James

B2B partnerships have long been an underutilized lever in go-to-market (GTM) strategies. While traditional partner marketing has existed for decades, many companies have struggled to make it a repeatable, scalable growth engine. In our latest episode of GTM Innovators, we sat down with Jenn Steele, CEO of SoundGTM, to explore how businesses can unlock the true power of B2B partnerships. From her early days in IT leadership to marketing leadership at HubSpot, Amazon, and more, Jenn has seen firsthand why many companies fail at partnerships—and how a fresh approach can turn them into a high-impact GTM channel. In this blog, we’ll dive into three of the key themes covered in our conversation: How B2B partnerships have evolved and why traditional approaches fall short The […]

GTM Innovators: Rethinking B2B Partnerships: Jenn Steele’s Approach to Modern GTM

Posted on March 24, 2025March 24, 2025 by Kyle James

In this episode of GTM Innovators, we sit down with Jenn Steele, founder and CEO of SoundGTM, to explore how B2B partnerships are evolving as a powerful growth strategy. Jenn shares her journey from IT leadership to marketing powerhouse—spanning roles at HubSpot, Amazon, and beyond—and why she believes traditional partner marketing is broken. We dive deep into the challenges of scaling B2B partnerships, the role of AI in optimizing demand generation, and how companies can leverage their ecosystems for smarter growth. Whether you’re a GTM leader, startup founder, or marketing strategist, this conversation is packed with insights on modernizing your partnership approach and driving real revenue impact. 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: […]