Connect To Market

George Smith: Human Connection Is the Only Marketing AI Can't Fake - Episode #48

If everyone is using AI to create content, what actually makes your brand stand out? In this episode of Connect To Market, host Casey Cheshire sits down with George Smith, Community Engagement Manager at Rewst, to explore how marketers can connect to their market by doubling down on what AI cannot replicate: genuine human connection. Smith argues that as AI-generated content becomes noisier and easier to spot, the competitive advantage shifts to marketers who listen deeply, slow down, and make customers and communities feel heard and valued rather than processed through a funnel. Smith shares practical ways to build those human touchpoints, from picking up the phone for relationship check-ins unrelated to tickets or renewals, to capturing personal details that show customers they matter beyond the transaction. He illustrates the power of plain-language communication with an RFP pitch that was saved by focusing on timelines, budget, risk, and commitment rather than technical jargon. Smith then breaks down what makes community work, explaining that it succeeds when it is genuine, non-transactional, and built around shared interests, citing Rewst's Discord community and the Flow Conference as examples of in-person and digital spaces where real connection drives loyalty and advocacy. In this episode, we cover: * Why AI-generated noise is making human connection the new competitive moat for marketers * How simple, non-transactional touchpoints like phone check-ins and personal detail capture build lasting customer relationships * Translating technical solutions into plain language to win over decision-makers who care about timelines, budget, and risk * What separates thriving communities from dead ones, and why genuine, shared-interest spaces like Rewst's Discord and Flow Conference drive real loyalty If you're a B2B marketing leader watching AI flood every channel with sameness and wondering how to cut through, Smith's playbook for human-first marketing and community building is the differentiation strategy no algorithm can replicate. 🔔 Don't forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market. Connect with George: * LinkedIn: https://www.linkedin.com/in/george-smith-rewst/ [https://www.linkedin.com/in/george-smith-rewst/]  * Rewst: https://rewst.io/ [https://rewst.io/]  Ways to Tune In: * Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa [https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa]  * Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 [https://podcasts.apple.com/podcast/connect-to-market/id1822777920]  * Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d [https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d]  * iHeart Radio: https://iheart.com/podcast/282837141/ [https://iheart.com/podcast/282837141/]  * Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 [https://www.podchaser.com/podcasts/connect-to-market-6138391]  * YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV [https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV]  Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts [https://ringmaster.com/]. Learn more at https://ringmaster.com/ [https://ringmaster.com/]

Brian C. Reed: How Community Storytelling Builds Brands That Stand Out In The AI Era - Episode #47

Does AI make every brand sound exactly the same? In this episode of Connect To Market, host Casey Cheshire sits down with Brian C. Reed, Chief Market Officer at Corsha and veteran B2B tech marketing executive, to explore why marketers who lean on AI for differentiation are actually flattening their messaging into sameness, and how authentic, human storytelling rooted in community is the real engine for memorability and brand preference. Reed makes the case that AI is essential for speed and analytics but cannot replace the kind of stories that come from, flow through, and are amplified by real communities, giving marketers a powerful framework to connect to their market in ways algorithms simply cannot replicate. Reed walks through the sources of strong stories, from founder origin narratives to practitioner communities, drawing on examples ranging from Mad Men-era advertising and Steve Jobs' MacBook Air launch to modern standouts like All Day DevOps, OWASP, and Wiz's memorable RSA presence. He explains how community-led evangelism helped grow NowSecure's credibility, why communities fail when vendor pitching overwhelms peer value, and how organizations like CMO Coffee Talk and the Cybersecurity Marketing Society model authentic community building. Reed also shares his own career journey from engineering to product marketing and offers advice on learning business mechanics beyond building technology. In this episode, we cover: * Why AI "flattens" marketing messaging into sameness and where human storytelling becomes the true competitive advantage * How to source authentic stories from founder origins and practitioner communities that build lasting brand preference * The three paths to community building and what separates vendor-proof communities from ones that collapse under self-promotion * Lessons from Reed's engineering-to-marketer career arc on understanding business mechanics to become a more effective marketing leader If you're a B2B marketing leader wrestling with how to stand out when every competitor has access to the same AI tools, Reed's community-first storytelling framework offers a differentiation playbook that no algorithm can copy. 🔔 Don't forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market. Connect with Brian: * LinkedIn: https://www.linkedin.com/in/briancreed/ [https://www.linkedin.com/in/briancreed/]  * Corsha: https://corsha.com/ [https://corsha.com/]  * Article: https://www.linkedin.com/pulse/ai-flattening-marketing-cue-return-mad-men-brian-c-reed-yfnle [https://www.linkedin.com/pulse/ai-flattening-marketing-cue-return-mad-men-brian-c-reed-yfnle]  * MacBook Air Launch: https://www.youtube.com/watch?v=EJqP8P0dh2o [https://www.youtube.com/watch?v=EJqP8P0dh2o]  Ways to Tune In: * Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa [https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa]  * Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 [https://podcasts.apple.com/podcast/connect-to-market/id1822777920]  * Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d [https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d]  * iHeart Radio: https://iheart.com/podcast/282837141/ [https://iheart.com/podcast/282837141/]  * Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 [https://www.podchaser.com/podcasts/connect-to-market-6138391]  * YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV [https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV]  Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts [https://ringmaster.com/]. Learn more at https://ringmaster.com/ [https://ringmaster.com/]

David Kosloski: Stop Prompting, Start Building AI Systems That Scale - Episode #46

What if the real threat to your marketing isn't falling behind on AI, but not having the systems to use it? In this episode of Connect To Market, host Casey Cheshire sits down with David Kosloski, VP of Marketing at SNUC and host of the Edge Tech Podcast, to explore how marketers connect to their market by building experience, expertise, authority, and trust before chasing tools or tactics. David makes the case that in emerging categories like edge computing, relationships and problem-solution expertise consistently outperform product specs, and that the marketers who win are the ones who start with content and customer insight rather than keyword lists. David walks through his approach to building authority in a new market, from launching podcasts and conducting customer interviews to creating mind maps and repurposing content across formats. He then dives into his perspective on AI, arguing that it won't save teams that lack strong systems, management discipline, and the ability to pressure-test their own work. He shares his framework for agentic workflows, breaking down the difference between skills and agents, the importance of validation loops and structured data (RAG), and how voice-first input is reshaping his personal productivity. He also reflects on his unconventional path from touring music and healthcare into marketing leadership, and shares his take on AI's impact on jobs and the SaaS landscape. In this episode, we cover: * Why E-E-A-T (experience, expertise, authority, trust) matters more than product specs when marketing in emerging categories * How to build market authority from scratch using podcasts, customer interviews, and content repurposing * Why AI amplifies existing systems instead of replacing them, and how to build agentic workflows with validation loops * Using voice-first input and a "second brain" RAG approach to unlock personal productivity with AI If you're a B2B marketing leader navigating a new or technical category and wondering how to layer AI into your workflow without losing the human judgment that makes your marketing credible, David's systems-first framework is the reality check you need. 🔔 Don't forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market. Connect with David: * LinkedIn: https://www.linkedin.com/in/david-kosloski/ [https://www.linkedin.com/in/david-kosloski/]  * SNUC: http://www.snuc.com [http://www.snuc.com/] * Edge Tech Podcast: https://youtube.com/playlist?list=PLFLnc878Df6a2ExKDZEBeJXwHvegv5eUa&si=vGi729ZCr0moeJvQ [https://youtube.com/playlist?list=PLFLnc878Df6a2ExKDZEBeJXwHvegv5eUa&si=vGi729ZCr0moeJvQ]  Ways to Tune In: * Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa [https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa]  * Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 [https://podcasts.apple.com/podcast/connect-to-market/id1822777920]  * Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d [https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d]  * iHeart Radio: https://iheart.com/podcast/282837141/ [https://iheart.com/podcast/282837141/]  * Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 [https://www.podchaser.com/podcasts/connect-to-market-6138391]  * YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV [https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV]  Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts [https://ringmaster.com/]. Learn more at https://ringmaster.com/ [https://ringmaster.com/]

Aaron Bean: Arm Your Buyer Champion to Win CFO Approval - Episode #45

What if your biggest competitor isn't another vendor, but your buyer's fear of making the wrong decision? In this episode of Connect To Market, host Casey Cheshire sits down with Aaron Bean, Co-Founder and Head of Go-to-Market at Supercase.ai, to explore why the most dangerous competitor in B2B isn't a rival product, but buyer indecision. Aaron makes the case that marketers need to connect to their market by focusing on the late-stage buyer journey, equipping champions to win the internal sale in a room the seller will never be in, especially when the CFO starts asking what the problem is costing and why it can't be fixed internally. Aaron shares research showing 61% of deals are lost to indecision and breaks down the three options every buyer weighs: do nothing, build, or buy. He walks through a framework for building decision confidence by quantifying the cost of inaction, creating CFO-credible business cases, and mapping internal advocacy moments into the buyer journey. He also introduces tracking "business case attach rate" as a leading indicator of deal health, and shares lessons from his background in philosophy, entrepreneurship, and global go-to-market work at Lenovo. In this episode, we cover: * Why 61% of B2B deals are lost to buyer indecision, not competitors, and how to fight back * How to arm buyer champions with CFO-credible business cases that quantify the cost of doing nothing * Adding internal advocacy moments to your buyer-journey map so champions aren't left unsupported * Tracking "business case attach rate" as a leading indicator of deal confidence and close rates If you're a B2B marketing leader watching qualified deals stall in committee and losing to "no decision," Aaron's framework for building decision confidence and arming your buyer champions is the playbook you've been missing. 🔔 Don't forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market. Connect with Aaron: * LinkedIn: https://www.linkedin.com/in/aaronbean/ [https://www.linkedin.com/in/aaronbean/]  * Supercase.ai: https://supercase.ai/ [https://supercase.ai/]  Ways to Tune In: * Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa [https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa]  * Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 [https://podcasts.apple.com/podcast/connect-to-market/id1822777920]  * Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d [https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d]  * iHeart Radio: https://iheart.com/podcast/282837141/ [https://iheart.com/podcast/282837141/]  * Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 [https://www.podchaser.com/podcasts/connect-to-market-6138391]  * YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV [https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV]  Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts [https://ringmaster.com/]. Learn more at https://ringmaster.com/ [https://ringmaster.com/]

Brandon Pittser: Drink Your Own Kool-Aid to Build Marketing That Converts - Episode #44

Is your marketing falling flat because you don't actually believe in what you're selling? In this episode of Connect To Market, host Casey Cheshire sits down with Brandon Pittser, VP of Marketing and Funding Development at Filament Games, to explore how marketers can connect to their market by leading with authenticity instead of automation. Brandon makes the case that the most effective marketing starts with genuinely believing in your organization's value, and explains why formulaic, AI-templated outreach is eroding trust with buyers. He shares why humility, honesty, and respecting your audience's intelligence are the real competitive advantages in a landscape flooded with generic messaging. Brandon walks through his playbook for internalizing a company's story, from interviewing discipline leaders to synthesizing perspectives and aligning teams around core value. He then breaks down how Filament Games drives growth through a disciplined inbound content engine, including long-running SEO-driven blogging, a structured editorial calendar, and an expanding video strategy built around repurposing livestreams into short-form clips. He also shares how to build modular content campaigns, maintain editorial flexibility, and lean into your organization's existing strengths to create content that compounds over time. In this episode, we cover: * Why authentic belief in your product is the foundation of marketing that resonates and converts * How to align your team around a unified company story by interviewing internal leaders and synthesizing their perspectives * Building a disciplined inbound content engine with SEO-driven blogging and a flexible editorial calendar * Expanding into short-form video by repurposing livestreams and leaning into organizational strengths If you're a marketing leader tired of watching templated outreach fall flat and looking for a more genuine, sustainable approach to content and demand generation, Brandon's framework for authentic, inbound-first marketing is one worth stealing. 🔔 Don't forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market. Connect with Brandon: * LinkedIn: https://www.linkedin.com/in/brandon-pittser-1b656855/ [https://www.linkedin.com/in/brandon-pittser-1b656855/]   * Filament Games: https://www.filamentgames.com/ [https://www.filamentgames.com/]  * Filament Games Podcast: https://soundcloud.com/filamentgames [https://soundcloud.com/filamentgames]  Ways to Tune In: * Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa [https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa]  * Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 [https://podcasts.apple.com/podcast/connect-to-market/id1822777920]  * Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d [https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d]  * iHeart Radio: https://iheart.com/podcast/282837141/ [https://iheart.com/podcast/282837141/]  * Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 [https://www.podchaser.com/podcasts/connect-to-market-6138391]  * YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV [https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV]  Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts [https://ringmaster.com/]. Learn more at https://ringmaster.com/ [https://ringmaster.com/]