Phill Keaney-Bolland: How to Be Remembered for Your Brand, Not Just Your Stunt - Episode #51

Phill Keaney-Bolland: How to Be Remembered for Your Brand, Not Just Your Stunt - Episode #51

Is your cybersecurity marketing failing because you're trying to say too much to too many people? In this episode of Connect To Market, host Casey Cheshire sits down with Phill Keaney-Bolland, Co-Founder of Yaya and a brand and design strategist specializing in cybersecurity, to explore how marketers can connect to their market by doing less and getting radically clearer on the fundamentals. Phill argues there is no single hack for better market connection. Instead, leaders need to return to the basics: crisp alignment on target audience, niche, differentiation, and value proposition, something many companies only realize they lack when forced to commit to one message on a website, ad, or trade show booth. Phill walks through why website projects are the ultimate alignment test, revealing that most stall not because of design or development but because teams cannot agree on content and messaging. He shares how effective positioning requires genuine empathy and real customer input, citing Twine Security's practice of speaking with 200 target customers before locking in their messaging. The conversation also dives into why cybersecurity marketing is uniquely noisy and competitive, from the RSA spectacle to the flood of AI-driven startups, and why bold, coherent messaging with a clear through-line is the antidote. Phill also shares his entrepreneurial origin story, early failures, and belief that non-linear learning and embracing mistakes are essential to building something meaningful. In this episode, we cover: * Why "doing less" and returning to fundamentals like audience, niche, and value proposition is the fastest path to marketing clarity * How website projects expose hidden misalignment on messaging, and why content, not design, is what stalls most builds * The power of talking to 200 target customers before locking in positioning, and why empathy beats assumptions every time * What makes cybersecurity marketing uniquely difficult and how bold, coherent messaging cuts through the noise of RSA spectacles and AI startup hype If you're a B2B marketing leader in cybersecurity or any crowded category struggling to differentiate when everyone sounds the same, Phill's "do less, get clearer" framework is the reset your messaging strategy needs. 🔔 Don't forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market. Connect with Phill: * LinkedIn: https://www.linkedin.com/in/phillbolland/ [https://www.linkedin.com/in/phillbolland/]  * Yaya: www.yaya.co [http://www.yaya.co]  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/]

Simon Wilhelm: You've Mastered GEO, But Have You Mastered LLMs & HLLMO? - Episode #50

What if the AI answers your buyers trust are already ignoring your brand? In this episode of Connect To Market, host Casey Cheshire sits down with Simon Wilhelm, Co-Founder of SCAILE Technologies to explore how companies can connect to their market by showing up where buyers are actually looking: inside the answers generated by ChatGPT, Perplexity, and Google AI Overviews. Wilhelm's core thesis is counterintuitive: to win with AI, you need to "be more human and make mistakes," creating unique, valuable content that LLMs want to cite rather than churning out generic AI-generated filler. Wilhelm draws a sharp distinction between AEO (Answer Engine Optimization, focused on appearing in AI-generated summaries and answers) and GEO (Generative Engine Optimization, a broader cross-functional competency that aligns marketing, sales, customer success, and product around a unified value proposition across platforms). He walks through a practical workflow: gather FAQs from sales and support, map buyer intent, pull competitor and community questions into a data lake, generate bottom-of-funnel prompts, test them across multiple LLMs, then publish structured content both on-site and off-site on platforms like Reddit and YouTube. Wilhelm notes that GEO results can appear in as few as 6 to 14 days, warns that mass AI-generated content without real value or EEAT signals can trigger Google spam updates, recommends refreshing existing content before creating new pages, and shares tactical tools including Bing Webmaster Tools for AI query visibility and Google Analytics for tracking AI crawler traffic. In this episode, we cover: * Why "being more human" is the counterintuitive key to getting cited by LLMs, and how unique, imperfect content outperforms polished AI-generated filler * The critical difference between AEO (appearing in AI answers) and GEO (a company-wide competency aligning teams and platforms around a unified value proposition) * A step-by-step workflow for building a "question lake" from sales calls, support tickets, and community forums to generate content LLMs actually pull from * How to measure AI visibility using Bing Webmaster Tools and Google Analytics AI crawler data, and why refreshing existing content beats mass-publishing new pages If you're a B2B marketing leader watching your organic traffic decline as AI answers replace clicks, Wilhelm's GEO framework is the playbook for making sure your brand is the one getting cited, not your competitor. 🔔 Don't forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market. Connect with Simon: * LinkedIn: https://www.linkedin.com/in/simon-leander-wilhelm/ [https://www.linkedin.com/in/simon-leander-wilhelm/]  * Scaile Technologies: https://www.scaile.tech/ [https://www.scaile.tech/]  * GTM Engineer Community: https://gtmengineer.dev/ [https://gtmengineer.dev/]  * TUM Venture Labs: https://www.tum-venture-labs.de/ [https://www.tum-venture-labs.de/]  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/]

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/]