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The Web Is Forking Again

Last week I wrote that SaaS isn’t dying. It’s being sorted. Thin workflow tools are under pressure, systems of record are becoming infrastructure, and the era of easy multiple expansion is behind us. That conversation was about repricing.  This one is about rewiring.  Underneath the market volatility, the internet itself is quietly adapting to a new kind of client. And if you zoom out far enough, the pattern looks familiar.  When mobile arrived, the web did not disappear. It evolved. The same underlying systems and content still existed, but they were redesigned to render differently depending on the device. Responsive design and mobile-first frameworks did not replace the desktop web; they standardized it for a second client. Companies that recognized that shift early rebuilt their interfaces accordingly and captured the next wave of growth. We […]

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SaaS Isn’t Dead. It’s Growing Up.

I was super early at HubSpot, a first one hundred employee.  I watched the company go public. I used some of the gains from that IPO to put a down payment on my house. It was one of those rare moments where a long bet actually paid off in a tangible way.  A year ago, HubSpot was trading above $800 a share. Today it sits in the low $200s. That is a decline of more than 70 percent in roughly twelve months.  And it is not alone.  Across B2B SaaS, billions in market cap have evaporated. Multiples have compressed. Growth stocks have been punished. The easiest narrative is that SaaS is dead and AI finished the job.  I do not think that is what is happening.  What we are seeing feels much more like SaaS growing up.    The Easy Era […]

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

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

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

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. […]

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

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

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 […]

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

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

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: […]

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

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

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, […]

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

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 […]

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

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 […]

GTM Innovators: Ditching Buyer Personas – Mastering Hyper-Personalization in Modern GTM

In this episode of “Ditching Buyer Personas: Mastering Hyper-Personalization in Modern GTM,” host Kyle James sits down with serial entrepreneur and content aficionado Nick Zeckets the CEO at Air Traffic Control to explore the evolving landscape of AI-driven marketing. From delivering the right content at precisely the right time to automating relevance at scale, Nick shares why traditional buyer personas are losing their power—and how organizations can embrace hyper-personalization for more meaningful engagement. Tune in for a deep dive on leveraging real-time data, refining your content strategy, and empowering teams across sales, marketing, and customer success to create truly individualized experiences. 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 […]

GTM Innovators: Unlocking GTM Success – AI, Behavioral Science & Demand Gen with Sheri Otto

In this episode of GTM Innovators, host Kyle James sits down with Sheri Otto, founder and CEO of Growth Lane Strategies, to explore the evolving role of AI, behavioral science, and demand generation in modern go-to-market (GTM) strategies. As businesses struggle to connect content to revenue, Sheri shares her expert insights on how AI can go beyond just content creation to drive real engagement, improve segmentation, and optimize the customer journey. From identifying high-intent buyers to leveraging AI for strategic decision-making, this conversation is packed with actionable takeaways for marketers, sales teams, and product leaders looking to elevate their GTM motions. Tune in to discover how AI is reshaping demand generation and why the best-performing companies are embracing it as a strategic growth partner—not just […]

GTM Innovators: Building Smarter with AI – Tim Macchi on Automation, Research & Product Strategy

In this episode of GTM Innovators, we sit down with Tim Macchi, Growth Product Manager at TeamGantt, to explore how AI is reshaping the way we build and optimize products. From using AI agents for QA testing to accelerating market research and streamlining product analytics, Tim shares his hands-on experience with automation and AI-powered workflows. We dive into how product managers can leverage AI to work smarter, reduce inefficiencies, and unlock new growth opportunities. Whether you’re a product leader, marketer, or innovator looking to stay ahead of the AI revolution, this conversation is packed with insights you won’t want to miss! 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 […]

GTM Innovators: The Future of Demand Gen – AI, Data, and Personalization with Prashant Kaw

Demand generation is undergoing a major transformation, and AI is at the center of it all. In this episode of GTM Innovators, host Kyle James sits down with Prashant Kaw to explore how AI is reshaping demand gen workflows, disrupting traditional attribution models, and redefining go-to-market strategies. From hyper-personalization to the rise of dark social, we dive deep into the biggest challenges and opportunities for marketers in an AI-driven world. Tune in for insights that will help you stay ahead in the evolving landscape of B2B marketing. 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 Welcome to another episode of GTM Innovators by 3Sixty Insights. I’m your host. […]