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

Melissa Beck: AI Is Changing How Buyers Buy, Is Your Marketing Keeping Up? - Episode #54

Are your buyers building shortlists with AI before they ever talk to your sales team? In this episode of Connect To Market, host Casey Cheshire sits down with Melissa Beck, VP of Corporate Marketing at Sumo Logic, to explore how marketers can connect to their market by staying "relentlessly close" to the buyer journey as AI reshapes how prospects discover, research, and decide. Beck makes the case that buyers increasingly use AI tools, communities, peer recommendations, analyst reports, and review sites to form shortlists before engaging any vendor, making AI visibility and presence in the right channels critical for any company that wants to stay in the conversation. Beck walks through how Sumo Logic is responding, from experimenting with tools like Profound to measure AI visibility to investing in organization-wide AI proficiency through an internal AI marketing summit and collaborative sharing of prompts and projects. She shares practical use cases including using AI for analyst report comparisons and building agents like a "brand guardian" workflow, while emphasizing that human connection and storytelling still matter because people buy from people. Beck also reflects on her path from aspiring journalist to comms and marketing leader, shaped by teamwork, curiosity, and continuous learning. In this episode, we cover: * Why buyers are forming shortlists using AI tools, communities, and peer recommendations before ever engaging a vendor, and what that means for marketing's role * How Sumo Logic measures AI visibility with tools like Profound and why tracking your presence in AI-generated answers is now a marketing priority * Building organization-wide AI proficiency through internal summits, collaborative prompt sharing, and practical agent workflows like a "brand guardian" * Why human connection and storytelling remain irreplaceable competitive advantages even as AI transforms every other part of the marketing stack If you're a B2B marketing leader wondering where your buyers are actually spending time and whether your brand is showing up in the AI-driven research channels that matter, Beck's framework for staying relentlessly close to the evolving buyer journey is the strategic reset your team needs. 🔔 Don't forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market. Connect with Melissa: * LinkedIn: https://www.linkedin.com/in/melissambeck/ [https://www.linkedin.com/in/melissambeck/]  * Sumo Logic: https://www.sumologic.com/ [https://www.sumologic.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/]

Anne Murlowski: How to Personalize B2B Marketing Without Being Creepy - Episode #53

What if the key to better marketing isn't more automation but more empathy? In this episode of Connect To Market, host Casey Cheshire welcomes Anne Murlowski, VP of Marketing at Claravine and Host of the SaaSy podcast, to explore how marketers can connect to their market by focusing on individuals, not just companies or personas. Anne makes the case that in an AI-driven "do more with less" environment, the most effective messaging ties directly to a buyer's personal pain points, goals, and career motivators. She explains why account-level assumptions are easier but far less effective, and why narrowing your focus to a small set of high-fit accounts and partnering closely with sales is the real unlock for authentic personalization. Anne walks through practical tactics for researching buying committees without crossing the line, including summarizing a prospect's public LinkedIn activity with private AI tools, active listening for personal details, and thoughtful follow-up that builds trust instead of triggering alarm bells. She also dives into why clean marketing data is essential for reliable reporting and better AI outputs, shares how podcasting can be a powerful relationship-building tool beyond just content, and reveals the learning sources that keep her sharp, from LinkedIn thought leaders to curated Substacks. In this episode, we cover: * Why focusing on individual buyers instead of company-level personas drives stronger engagement and advocacy * How to research prospects authentically using AI tools and active listening without being creepy * The critical role clean marketing data plays in powering reliable reporting and AI-driven personalization * Why narrowing your target account list and partnering with sales unlocks more effective outreach If you're a marketing leader looking to cut through the noise of generic outreach and build real connections with buyers in an increasingly automated landscape, Anne's approach to empathy-driven, data-informed personalization is a playbook worth adopting. 🔔 Don't forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market. Links: * LinkedIn: https://www.linkedin.com/in/annemurlowski/ [https://www.linkedin.com/in/annemurlowski/]  * SaaSy Podcast: https://saasy.podbean.com/ [https://saasy.podbean.com/]  * Claravine: https://www.claravine.com/ [https://www.claravine.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/]

Tim Hillison: The 4S Go-to-Market Framework: State, Scale, System, Signal - Episode #52

What happens when AI can replicate your marketing overnight, and your competitors sound exactly like you? In this episode of Connect To Market, host Casey Cheshire sits down with Tim Hillison, Founder and Chief Marketing Officer of Entry Point 1, to explore how companies can connect to their market by building defensible advantage as AI accelerates output and risks turning every brand into a commodity. Hillison argues that the smartest companies hire storytellers over playbook followers, and poses a powerful guiding question: what would your customers lose if they couldn't do business with you? Hillison introduces his "Four S" framework for building lasting competitive moats. He breaks down State (owning the language around a problem before anyone else, citing Samsara and Gong), Scale (compounding data that improves with every customer interaction, citing Vertiv and Duolingo), System (making your product so embedded in how customers work that leaving means reorganizing everything, citing Rippling and Stripe), and Signal (building data intelligence that explains why customers buy, stay, and expand, citing Harvey and Datadog). He also tackles the ethical implications of "AI-first" layoffs and urges leaders to be intentional about prioritizing human relationships even as they adopt new technology. In this episode, we cover: * Why naming the problem first and owning the category language is the most underrated competitive advantage in B2B * How compounding data and customer interaction loops create scale moats that competitors can't shortcut * Building system stickiness so deep that switching costs protect your business better than any feature ever could * Using signal intelligence to understand not just what customers do, but why they buy, stay, and expand If you're a marketing leader navigating the pressure of AI-driven commoditization and looking for a strategic framework to build real, defensible differentiation, Hillison's Four S model is a recipe worth studying. 🔔 Don't forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market. Connect with Tim: * LinkedIn: https://www.linkedin.com/in/timhillison/ [https://www.linkedin.com/in/timhillison/]  * Entry Point 1: https://www.entrypoint1.com/ [https://www.entrypoint1.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/]

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/]