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

Eric Robertson: Why CLV Beats Personas for Smarter Marketing Spend - Episode #49

What if the "average customer" your marketing targets doesn't actually exist? In this episode of Connect To Market, host Casey Cheshire sits down with Eric Robertson, Head of Partnerships & Sales at Theta, to explore why building marketing strategies around average customer personas and demographic trivia leads teams to waste budget on the wrong people. Robertson makes the case that customers vary dramatically in value, following Pareto's rule, and that marketers who want to connect to their market need to stop treating spend as a budget line item and start treating it as capital deployed to buy future cash flows from their highest-value relationships. Robertson breaks down customer lifetime value (CLV) as the present value of expected net cash flows from an individual customer relationship, drawing a sharp distinction between CLV and the historical, blended LTV metrics most teams rely on. He walks through Theta's practical approach using behavioral data, specifically RFM (recency, frequency, monetary value), to model retention and value at the individual level, showing how these outputs inform smarter offers like avoiding discounts for full-price buyers and improve allocation across acquisition and retention. Robertson also addresses the role of AI in predictive analytics, noting that it amplifies capability but cannot ignore changing conditions like seasonality or market shocks, and shares his career journey along with advice for marketing leaders: keep learning, partner with finance, and "if you're the smartest person in the room, leave the room." In this episode, we cover: * Why marketing to the "average customer" wastes budget and how Pareto's rule reveals the customers actually worth investing in * How CLV differs from historical LTV and why treating marketing spend as capital deployed to buy future cash flows changes allocation decisions * Using RFM (recency, frequency, monetary value) behavioral data to model individual customer retention and value without relying on demographics * Where AI amplifies predictive analytics and where it falls short when conditions like seasonality or market shocks shift the landscape If you're a B2B marketing leader still building strategy around blended averages and demographic personas, Robertson's CLV-first framework is the wake-up call to start treating your customer base like a portfolio and investing where the returns actually are. 🔔 Don't forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market. Connect with Eric: * LinkedIn: https://www.linkedin.com/in/3ricrob3rtson/ [https://www.linkedin.com/in/3ricrob3rtson/]  * Theta: http://www.thetaclv.com [http://www.thetaclv.com]  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/]

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/]