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

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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 […]

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

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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 […]

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

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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 […]

GTM Trust Through Analyst Relations with Chris Manfredi

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

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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 […]

GTM Trust Through Analyst Relations with Chris Manfredi

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

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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. […]

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

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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 […]

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

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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 […]

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

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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/ […]

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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 […]