Casey Cheshire

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 fillerThe 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 fromHow to measure AI visibility using Bing Webmaster Tools and Google Analytics AI crawler data, and why refreshing existing content beats mass-publishing new pagesIf 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/ Scaile Technologies: https://www.scaile.tech/ GTM Engineer Community: https://gtmengineer.dev/ TUM Venture Labs: https://www.tum-venture-labs.de/ Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

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 inHow CLV differs from historical LTV and why treating marketing spend as capital deployed to buy future cash flows changes allocation decisionsUsing RFM (recency, frequency, monetary value) behavioral data to model individual customer retention and value without relying on demographicsWhere AI amplifies predictive analytics and where it falls short when conditions like seasonality or market shocks shift the landscapeIf 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/ Theta: http://www.thetaclv.com Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

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 marketersHow simple, non-transactional touchpoints like phone check-ins and personal detail capture build lasting customer relationshipsTranslating technical solutions into plain language to win over decision-makers who care about timelines, budget, and riskWhat separates thriving communities from dead ones, and why genuine, shared-interest spaces like Rewst's Discord and Flow Conference drive real loyaltyIf 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/ Rewst: https://rewst.io/ Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

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 advantageHow to source authentic stories from founder origins and practitioner communities that build lasting brand preferenceThe three paths to community building and what separates vendor-proof communities from ones that collapse under self-promotionLessons from Reed's engineering-to-marketer career arc on understanding business mechanics to become a more effective marketing leaderIf 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/ Corsha: https://corsha.com/ Article: 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 Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

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 categoriesHow to build market authority from scratch using podcasts, customer interviews, and content repurposingWhy AI amplifies existing systems instead of replacing them, and how to build agentic workflows with validation loopsUsing voice-first input and a "second brain" RAG approach to unlock personal productivity with AIIf 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/ SNUC: http://www.snuc.comEdge Tech Podcast: https://youtube.com/playlist?list=PLFLnc878Df6a2ExKDZEBeJXwHvegv5eUa&si=vGi729ZCr0moeJvQ Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

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 backHow to arm buyer champions with CFO-credible business cases that quantify the cost of doing nothingAdding internal advocacy moments to your buyer-journey map so champions aren't left unsupportedTracking "business case attach rate" as a leading indicator of deal confidence and close ratesIf 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/ Supercase.ai: https://supercase.ai/ Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

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 convertsHow to align your team around a unified company story by interviewing internal leaders and synthesizing their perspectivesBuilding a disciplined inbound content engine with SEO-driven blogging and a flexible editorial calendarExpanding into short-form video by repurposing livestreams and leaning into organizational strengthsIf 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/  Filament Games: https://www.filamentgames.com/ Filament Games Podcast: https://soundcloud.com/filamentgames Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

How can marketers stay adaptable, leverage AI effectively, and earn a true seat at the table?In this episode of Connect To Market, host Casey Cheshire welcomes Max Maurier, VP of Marketing at Absolute Security, to explore why adaptability is the most critical skill for modern marketing teams. Max shares how marketing is uniquely positioned to pivot faster than other functions, and why leaders must continuously evolve their strategy, channel mix, and team capabilities in response to shifting buyer behavior, company priorities, and emerging technology.He dives into the importance of aligning deeply with company-wide goals (not just reacting to sales requests), and how strong analytics and system fundamentals can help marketers build credibility and trust at the executive level. From rethinking event-heavy strategies to creating a more balanced, targeted digital approach, Max outlines what it takes to operate as a truly strategic marketing function. He also unpacks practical AI use cases, like account research and planning, while emphasizing the need to keep humans in the loop to avoid low-quality, “AI slop” outputs.In this episode, we cover:Why adaptability, not rigid planning, is the key to modern marketing successHow to align marketing with broader business objectives to increase impact and influencePractical ways to apply AI across marketing teams without over-relying on itHow to use data, analytics, and systems to earn trust and a seat at the executive tableIf you're a marketing leader looking to stay ahead of constant change, better integrate AI, and elevate your role within the organization, Max’s insights will challenge how you think about strategy, execution, and leadership.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Max:LinkedIn: https://www.linkedin.com/in/maxmaurier/ Absolute Security: absolute.com Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

What if the fastest way to improve your marketing performance isn’t better messaging but better data?In this episode of Connect To Market, host Casey Cheshire welcomes Alex Schutte, Senior Vice President of Marketing at Hubstaff, to explore how marketers can connect to their market by prioritizing data clarity before refining messaging. Alex explains why many B2B teams struggle with alignment and trust due to inconsistent definitions and fragmented reporting, and how fixing these foundational issues can unlock stronger decision making and revenue impact. He shares why marketers who lead with data, not just campaigns, are better positioned to earn executive trust and drive meaningful growth.He breaks down how leaders can move from disconnected metrics to a unified, revenue driven strategy by standardizing key definitions across the funnel, building a centralized executive dashboard, and adopting a bow tie growth model that captures the full customer lifecycle. From analyzing top customers and segmenting effectively to operationalizing LTV and aligning spend accordingly, Alex outlines practical ways to turn data into a strategic advantage. He also touches on forecasting, attribution realities, and how to lead teams with clear expectations and unbiased insights.In this episode, we cover:Why data clarity is the foundation for effective go to market strategyHow to standardize definitions and build a single source of truthUsing a bow tie model to understand growth across the full customer lifecycleAligning marketing efforts to revenue and using LTV to guide smarter decisionsIf you’re a marketing leader looking to improve performance, strengthen alignment, and build credibility with executives, Alex’s approach offers a clear roadmap for turning better data into better business outcomes.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Alex:LinkedIn: https://www.linkedin.com/in/alexschutte/  Hubstaff: https://hubstaff.com/   Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

What if your most powerful growth strategy isn’t reaching more people, but starting with the ones closest to you?In this episode of Connect To Market, host Casey Cheshire welcomes Melissa Moody, Founder of Wednesday Women and Host of the Joy of Connecting podcast, to explore how brands can drive growth by returning to authentic human relationships. Melissa introduces her “concentric circles of influence” framework, a practical approach to prioritizing the people closest to your business first, employees, leaders, and internal advocates, before expanding outward to investors, partners, customers, and ultimately the broader market. She explains why starting from the inside out creates stronger alignment, clearer storytelling, and more effective market engagement.She breaks down how organizations can activate employees as brand storytellers, align incentives with investors and advisors to unlock opportunities, and build strategic partnerships as a scalable growth lever. Melissa also highlights the importance of customer success as a marketing function, emphasizing customer-driven content over feature-heavy messaging. From prioritizing inner circles in small teams to maintaining brand consistency at scale, she outlines a more human, relationship-first approach to modern go-to-market strategy.In this episode, we cover:Why human connection outperforms automation in today’s noisy marketing landscapeUnderstanding and applying the concentric circles of influence frameworkEnabling employees and internal stakeholders as authentic brand advocatesLeveraging partnerships and customer success as powerful growth driversIf you’re a marketing leader looking to build stronger relationships, create more authentic engagement, and scale your impact from the inside out, Melissa’s framework offers a clear and actionable path to connecting with your market in a more meaningful way.🔔 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/melissammoody/  Wednesday Women: wednesdaywomen.org Joy of Connecting Podcast: https://www.joyofconnect.ing/ Sign up for Alaska Salt Company's email list: https://alaskasaltco.com/ Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

How can B2B SaaS companies build a strong go-to-market foundation and turn their website into a true driver of pipeline?In this episode of Connect To Market, host Casey Cheshire welcomes Ian Dowe, Senior Vice President Marketing at HealthAxis, to explore how marketers can connect to their market through a deeply data-driven foundation. Ian explains why understanding your total addressable market, identifying active buyers, defining ICPs and personas, and mapping solutions to real pain points must come before any campaign execution. He shares how gaps in this foundation often stem from organizational maturity and why early success can create false confidence as markets inevitably shift.He breaks down how leaders can build from the ground up by aligning product to buyer needs using frameworks like the KANO model, then layering in narrative, brand, and go-to-market strategy. From structuring MarTech stacks and internal processes to defining product marketing roadmaps and revenue metrics, Ian outlines a practical, step-by-step approach to building a scalable marketing engine. He also reframes creativity as strategic problem-solving and challenges teams to rethink websites as buyer enablement platforms that educate and qualify prospects deeper in the funnel.In this episode, we cover:Why a strong data-driven foundation is critical before executing marketing campaignsAligning product, messaging, and GTM strategy using buyer needs and the KANO modelReframing websites as buyer enablement platforms that drive deeper funnel engagementBuilding scalable marketing systems across MarTech, processes, and revenue metricsIf you’re a marketing leader looking to strengthen your GTM foundation while turning your website into a true growth engine, Ian’s approach offers a clear roadmap for building, scaling, and adapting in an ever-changing B2B landscape.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Ian Dowe:LinkedIn: https://www.linkedin.com/in/ian-dowe/  Health Axis Group: healthaxis.com  Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

How can booth design and messaging transform your trade show results?In this special episode of Connect To Market, I sat down with Bill Kenney, Founder & Client Advocate of MEET. Bill brings his wealth of knowledge on booth strategy and lead generation, offering practical insights that help businesses turn trade show floors into high-performing sales opportunities.Bill breaks down why traditional booth setups often fall short and how a customer-centric approach makes all the difference. He shares how focusing on pain-point-driven messaging, like asking direct, relatable questions, can immediately attract qualified prospects. Bill also emphasizes the importance of keeping booth designs clean and simple, ditching cluttered text and irrelevant graphics for bold headlines that speak to real customer needs. Plus, he explains how to train your team for short, high-impact conversations and collect the right data for post-show follow-up.In this episode, we cover:Why customer-focused booth messaging outperforms company-centric designsThe power of short, strategic conversations over lengthy sales pitchesWhy cluttered booths and generic giveaways can hurt your brand presenceBill’s framework for turning trade shows into high-performing lead gen channelsIf you’re ready to transform your trade show booth into a lead-generating powerhouse, this episode is packed with actionable insights you won’t want to miss!🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Bill:LinkedIn: https://www.linkedin.com/in/bkenney/  MEET Company website: https://meetroi.com/ Blog: https://meetroi.com/blogs/  Belly 2 Belly Podcast: http://meetroi.com/podcast/  Softland Partners Company website: https://softlandpartners.com/ Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

How can marketers better connect with their market when customer insights are often filtered, polished, or stuck in silos?In this episode of Connect To Market, host Casey Cheshire welcomes B2B GTM Leader Angela Earl to explore how organizations can strengthen their connection to customers by listening more closely- not just to feedback, but to the real conversations happening across their teams. Angela explains why the most valuable insights often emerge when things aren’t going well, and why leaders must create an environment where honesty and vulnerability are encouraged so teams feel comfortable sharing what they’re truly hearing from customers.She shares why building a shared understanding of the customer across go-to-market teams is critical, and how marketers can capture real signals such as objections, friction points, and recurring questions through tools like call transcripts and systems like Salesforce or HubSpot. Angela also emphasizes the importance of establishing a regular cadence to review feedback and ensure insights move across teams rather than getting lost in isolated systems. From using AI to accelerate research to validating insights through real conversations, she outlines practical ways leaders can stay close to the voice of the customer.In this episode, we cover:Why real conversations often reveal more than polished customer feedbackBuilding a shared understanding of the customer across go-to-market teamsCapturing and sharing real customer signals through tools and systemsCreating a regular feedback cadence to prevent insights from getting stuck in silosIf you’re a marketing leader looking to strengthen alignment across teams while staying closer to the voice of the customer, Angela’s approach offers practical ways to turn everyday conversations into meaningful market insight.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Angela:LinkedIn: https://www.linkedin.com/in/angelanearl/  Book: https://a.co/d/1oth0TT Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

How can B2B brands win discovery, trust, and positioning when most cybersecurity messaging blends together?In this episode of Connect To Market, host Casey Cheshire welcomes Valerie Zargarpur, Head of Marketing at Monad, to explore how marketers can connect to their market through brand story rather than just visual identity. Valerie explains why B2B, especially cybersecurity, often relies on jargon and executive-focused messaging, even though day-to-day users champion products. She shares why focusing on real customer insights and validated use cases can help brands stand out and build trust in a crowded market.She breaks down how leaders can move from generic messaging to earning understanding by listening to customers, reviewing sales conversations for themes, challenging assumptions about the ideal customer profile, and positioning around use cases that resonate. From creating cohesive go-to-market narratives to leveraging origin stories for brand personality, Valerie outlines practical ways to differentiate and connect with audiences. She also reflects on iterative testing of messaging and applying B2C lessons in niche B2B contexts.In this episode, we cover:Why B2B and cybersecurity brands often blend in and how storytelling can differentiate themBuilding a cohesive narrative from customer insights and validated use casesLeveraging origin stories to create brand personality and emotional connectionIterative testing of messaging to ensure clarity, simplicity, and resonanceIf you’re a marketing leader looking to break through the noise while building deeper market trust, Valerie’s approach offers a clear roadmap for sharpening positioning, increasing credibility, and connecting with real users through authentic brand story.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Valerie:LinkedIn: https://www.linkedin.com/in/valerie-zargarpur/  Monad: https://www.monad.com/ Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

How can marketers escape the tactics trap and build category strategy that actually connects to the market?In this episode of Connect To Market, host Casey Cheshire welcomes John Rougeux, Founder of Flag & Frontier, to unpack why marketers are often set up for failure when they’re handed KPIs without influence over strategy. John argues that real market connection starts with understanding the category, buyer environment, and problem maturity - not chasing isolated tactics. Using a race car analogy, he explains why fundamentals matter more than surface-level optimization and how marketing becomes powerful when it shapes direction, not just execution.John outlines three core pillars: first, aligning on the real problem and who it’s for by talking directly to customers; second, assessing the maturity of that problem to determine whether to create a category, carve out a niche in a mature market, or reinforce leadership like Salesforce; and third, distilling strategy into a clear narrative that aligns internal teams and guides external messaging. Drawing a parallel to a trial lawyer’s structured argument, he explains how strong strategy blends logic and emotion to move markets. He also shares lessons from his path from finance to performance marketing to advising companies at strategic inflection points, including examples like how Zoom reinvigorated a crowded space.In this episode, we cover:Why marketers get trapped in tactics without strategic influenceHow to define the right problem through customer conversationsHow category maturity shapes whether you evangelize, niche down, or leadWhy strategy must be distilled into a narrative that aligns teams and drives growthIf you’re a marketing leader navigating crowded markets, executive misalignment, or a major inflection point, John’s framework offers a practical roadmap for moving from activity to alignment and from tactics to true category strategy.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with John:LinkedIn: https://www.linkedin.com/in/johnbrougeux/  Flag and Frontier: flagandfrontier.com  Substack: https://substack.com/@johnrougeux Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

How can challenger brands win discovery, trust, and positioning as generative AI reshapes how buyers find and evaluate solutions?In this episode of Connect To Market, host Casey Cheshire welcomes Valerie Riley, Vice President of Marketing & Strategy at Unbounce and Co-Host of the Closing Time podcast, to explore how generative engine optimization (GEO) is transforming modern marketing. Valerie explains why GEO is emerging as a defining 2026 trend and how it shifts discovery from traditional search rankings to AI-generated recommendations. She shares why this shift can favor focused challenger brands over large incumbents that have historically dominated through budget and content scale.She breaks down how marketers can move from buying attention to earning understanding by sharpening positioning, embracing specificity, and creating content that educates rather than shouts. From building credibility through transparent comparisons to activating authentic B2B influencer relationships, Valerie outlines practical ways to increase trust and relevance in AI-driven discovery. She also reflects on internal AI adoption, top-down leadership support, and the discipline required to focus strategy when resources are limited. In this episode, we cover:Why GEO is reshaping discovery and favoring challenger brandsHow specificity and niche positioning improve AI visibilityPractical strategies for trust-building through education and comparisonsThe role of influencer marketing and internal AI adoption in accelerating growth If you’re a marketing leader looking to compete in an AI-powered landscape while building deeper market trust, Valerie’s approach offers a clear roadmap for sharpening positioning, increasing credibility, and winning in generative search.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Valerie:LinkedIn: https://www.linkedin.com/in/valerie-riley-marketer/  Unbounce: https://unbounce.com/  Closing Time Podcast: https://www.insightly.com/closing-time/ Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

How can mastering MarTech unlock customer connection and marketing success in the age of AI?In this episode of Connect To Market, host Casey Cheshire welcomes Scott Brinker, Martech Analyst and Advisor at ChiefMartec, to explore how marketing is evolving in a technology-driven world. Scott shares how prioritizing direct customer engagement, maintaining brand integrity, and delivering exceptional experiences provides a foundation for more effective, human-centered marketing.He explores how AI is reshaping consumer behavior, why traditional marketing principles remain important, and how marketing leaders can balance technology with human connection. From leveraging customer advocacy to ethical considerations in algorithmic pricing, Scott breaks down actionable strategies for creating loyal audiences, building trust, and driving meaningful impact. He also reflects on his journey in MarTech and how it informs his approach to marketing leadership.In this episode, we cover:Why customer interaction is essential for modern marketingHow AI is transforming marketing strategies and consumer expectationsPractical strategies for fostering customer loyalty and advocacyEthical considerations in AI-driven marketing and algorithmic pricingIf you’re a marketing leader looking to thrive in a fast-paced digital landscape while keeping human connection at the center, Scott’s approach offers a clear roadmap for building more strategic, customer-focused, and impactful marketing.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Scott:LinkedIn: https://www.linkedin.com/in/sjbrinker/Chief Martec: chiefmartec.comWays to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

How can marketers build stronger connections by truly listening to their customers?In this episode of Connect To Market, host Casey Cheshire sits down with Emily Ward, Vice President of Marketing at Maxwell, to explore why direct customer conversations are still one of the most powerful tools in a marketer’s toolkit. Emily shares how common obstacles like egocentric thinking, fear of honest feedback, and internal gatekeeping can prevent teams from deeply understanding their audience and how to break through them.She unpacks practical ways to get closer to customers, from partnering with customer success teams to leveraging events, outreach, and qualitative feedback to uncover real pain points. Emily also reflects on her marketing origin story, the importance of differentiating yourself in a crowded market, and how emerging technologies like AI are reshaping SEO, inbound tracking, and the future of marketing. Throughout the conversation, she offers grounded advice for leaders who want to adapt, learn faster, and continuously refine their strategies based on what customers actually need.In this episode, we cover:Why talking directly to customers is essential for effective marketingHow to overcome internal gatekeeping and fear of customer feedbackPractical methods for uncovering deeper customer pain pointsHow AI and emerging technologies are influencing modern marketing strategiesIf you’re a marketing leader looking to build more authentic connections and create strategies rooted in real customer insight, Emily’s perspective offers clear, actionable guidance for staying relevant and effective in an evolving landscape.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Emily:LinkedIn: https://www.linkedin.com/in/emily-ward-marketing-vp/ Maxwell: https://himaxwell.com/ TikTok: https://tiktok.com/@emilyward011  Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

How can strategic storytelling help marketers stand out in an AI-driven world?In this episode of Connect To Market, host Casey Cheshire sits down with Tim Lozier, Owner of Big Breakthrough Marketing, to explore how shifting the focus from company-centric messaging to the buyer’s story creates clearer, more effective marketing. Tim shares why the most impactful content starts with understanding the real questions buyers are asking- and how AI can be used as a tool to surface those insights, not replace human judgment.He breaks down the role of long-form, evergreen content in building trust and authority, alongside the importance of short, digestible formats that meet audiences where they are. From prioritizing clarity over jargon and frameworks over features to encouraging a culture of smart experimentation, Tim offers practical guidance for modern marketing leaders navigating an increasingly noisy landscape. He also reflects on his own path into marketing and the lessons that shaped his leadership philosophy.In this episode, we cover:Why telling the buyer’s story is more powerful than promoting the companyHow AI can help uncover the questions buyers are truly askingThe role of long-form, evergreen content alongside short, digestible formatsWhy clarity, frameworks, and authentic helpfulness drive standout marketingIf you’re a marketing leader looking to create content that cuts through the noise and truly serves your audience, Tim’s insights provide a thoughtful framework for building trust, relevance, and impact in today’s AI-driven discovery world.🔔 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/timlozier/  Big Breakthrough: https://big-breakthrough.com/  TOTData: https://www.totdata.com/  Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/ 

How can mastering market messaging   unlock founder-led growth in B2B SaaS?In this episode of Connect To Market, host Casey Cheshire welcomes Chris Silvestri, Founder & Chief Conversion Copywriter at Conversion Alchemy, to unpack how achieving message-market fit can transform B2B marketing effectiveness. Chris shares how deeply understanding your market through research, internal team alignment, and competitive analysis creates a strong foundation for smarter strategy and more impactful messaging.  He explores why many marketing challenges stem from unclear positioning, and how asking the right questions, analyzing competitors, and understanding customer psychology brings clarity, focus, and stronger collaboration across teams. From balancing AI-assisted copywriting with human-driven creativity to refining messaging strategies based on market insights, Chris breaks down practical approaches for building differentiated, resonant market communication. He also discusses how his journey into copywriting and everyday experiences shaped his approach to marketing and leadership.In this episode, we cover:Why understanding your market is essential for effective messagingHow internal alignment and competitive analysis drive team successThe role of AI personas and human-driven copywriting in crafting messagingPractical steps to differentiate your offerings and refine your value propositionIf you’re a marketing leader or founder looking to connect more deeply with your market and customers, Chris’s approach offers a clear roadmap to building a more strategic, human-centered, and effective messaging strategy.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Chris:LinkedIn: https://www.linkedin.com/in/christophersilvestri/  Conversional Alchemy: https://conversionalchemy.net/ Message-Market Fit Podcast: https://christophersilvestri.com/podcast/ Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: 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. Learn more at https://ringmaster.com/