<![CDATA[The Connect to Market (CTM) Community: Podcast]]>https://www.connecttomarket.com/s/podcasthttps://substackcdn.com/image/fetch/$s_!0Zku!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd48bd9b1-b54c-4280-9bca-52d4ee8836e4_1280x1280.pngThe Connect to Market (CTM) Community: Podcasthttps://www.connecttomarket.com/s/podcastSubstackFri, 10 Jul 2026 10:16:07 GMT<![CDATA[Melanie Brancaleone: Human Conversations That Drive Event Marketing ROI - Episode #55]]>https://www.connecttomarket.com/p/human-conversations-that-driving-event-marketing-roihttps://www.connecttomarket.com/p/human-conversations-that-driving-event-marketing-roiThu, 09 Jul 2026 09:00:51 GMTAre your trade show leads filling your CRM but starving your pipeline?

In this episode of Connect To Market, host Casey Cheshire sits down with Melanie Brancaleone, Vice President of Marketing at Testkube, to explore how marketers can connect to their market by getting in-person at events, where direct conversations reveal real language, context, and problems that forms and digital channels simply cannot capture. Brancaleone makes the case that the trade show floor is one of the most underrated sources of buyer intelligence, and that the marketers who treat events as listening posts rather than lead-collection stations are the ones who actually move pipeline.

Brancaleone walks through her tactical playbook for working a booth: start with a human warm-up to build rapport, act as a buffer to route true prospects to technical teammates, and listen in on demos, especially when multiple prospects or even customers join, to capture the exact vocabulary buyers use for future campaigns. She draws a sharp distinction between event goals, separating net-new lead generation from advancing in-flight opportunities, and recommends meeting rooms for late-stage deals and founder or executive meetings to accelerate pipeline. She also tackles common event mistakes, advising against parties at large conferences and recommending differentiated plays like breakfasts in Vegas. On swag, she urges teams to prioritize lead quality over volume by tagging “swag only” badge scans and being intentional about giveaways. Post-event, she recommends a fast thank-you email with clear CTAs, immediate BDR follow-up, and long-tail tracking. She closes with a leadership philosophy rooted in measurement, testing, and building a culture that allows failure as a path to learning and improvement.

In this episode, we cover:

  • Why in-person event conversations reveal buyer language, context, and pain points that digital channels and forms cannot capture

  • How to work a booth strategically by warming up prospects, buffering for technical teammates, and listening in on demos to harvest campaign vocabulary

  • Separating event goals between net-new lead generation and advancing in-flight deals, and using meeting rooms and exec meetings to move pipeline

  • Post-event follow-up that works: fast thank-you emails with clear CTAs, immediate BDR outreach, long-tail tracking, and tagging “swag only” scans to protect lead quality

If you are a B2B marketing leader pouring budget into events but struggling to prove ROI or convert badge scans into real pipeline, Brancaleone’s quality-over-volume framework is the tactical reset your event strategy needs.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

]]><![CDATA[Melissa Beck: AI Is Changing How Buyers Buy, Is Your Marketing Keeping Up? - Episode #54]]>https://www.connecttomarket.com/p/ai-is-changing-how-buyers-buyhttps://www.connecttomarket.com/p/ai-is-changing-how-buyers-buyThu, 02 Jul 2026 09:00:45 GMTAre 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.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

]]><![CDATA[Anne Murlowski: How to Personalize B2B Marketing Without Being Creepy - Episode #53]]>https://www.connecttomarket.com/p/how-to-personalize-b2b-marketing-without-being-creepyhttps://www.connecttomarket.com/p/how-to-personalize-b2b-marketing-without-being-creepyThu, 25 Jun 2026 09:01:23 GMTWhat 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.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

]]><![CDATA[Tim Hillison: The 4S Go-to-Market Framework: State, Scale, System, Signal - Episode #52]]>https://www.connecttomarket.com/p/the-4s-go-to-market-frameworkhttps://www.connecttomarket.com/p/the-4s-go-to-market-frameworkThu, 18 Jun 2026 09:02:23 GMTWhat 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.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

]]><![CDATA[Phill Keaney-Bolland: How to Be Remembered for Your Brand, Not Just Your Stunt - Episode #51]]>https://www.connecttomarket.com/p/how-to-be-remembered-for-your-brand-not-just-your-stunthttps://www.connecttomarket.com/p/how-to-be-remembered-for-your-brand-not-just-your-stuntThu, 11 Jun 2026 09:01:55 GMTIs 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 an example of a company’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.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

]]><![CDATA[Simon Wilhelm: You've Mastered GEO, But Have You Mastered LLMs & HLLMO? - Episode #50]]>https://www.connecttomarket.com/p/youve-mastered-geo-but-have-you-mastered-llms-and-hllmohttps://www.connecttomarket.com/p/youve-mastered-geo-but-have-you-mastered-llms-and-hllmoThu, 04 Jun 2026 09:02:06 GMTWhat 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.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

]]><![CDATA[Eric Robertson: Why CLV Beats Personas for Smarter Marketing Spend - Episode #49]]>https://www.connecttomarket.com/p/why-clv-beats-personas-for-smarter-marketing-spendhttps://www.connecttomarket.com/p/why-clv-beats-personas-for-smarter-marketing-spendThu, 28 May 2026 09:02:03 GMTWhat 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.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

]]><![CDATA[George Smith: Human Connection Is the Only Marketing AI Can't Fake - Episode #48]]>https://www.connecttomarket.com/p/human-connection-is-the-only-marketing-ai-cant-fakehttps://www.connecttomarket.com/p/human-connection-is-the-only-marketing-ai-cant-fakeThu, 21 May 2026 09:02:20 GMTIf 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.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

]]><![CDATA[Brian C. Reed: How Community Storytelling Builds Brands That Stand Out In The AI Era - Episode #47]]>https://www.connecttomarket.com/p/how-community-storytelling-builds-brands-in-the-ai-erahttps://www.connecttomarket.com/p/how-community-storytelling-builds-brands-in-the-ai-eraThu, 14 May 2026 09:01:47 GMTDoes 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 helps grow 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.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

]]><![CDATA[David Kosloski: Stop Prompting, Start Building AI Systems That Scale - Episode #46]]>https://www.connecttomarket.com/p/stop-prompting-start-building-ai-systemshttps://www.connecttomarket.com/p/stop-prompting-start-building-ai-systemsThu, 07 May 2026 09:00:44 GMTWhat if the real threat to your marketing isn’t falling behind on AI, but not having the systems to use it?

In this episode of Connect To Market, host Casey Cheshire sits down with David Kosloski, VP of Marketing at SNUC and host of the Edge Tech Podcast, to explore how marketers connect to their market by building experience, expertise, authority, and trust before chasing tools or tactics. David makes the case that in emerging categories like edge computing, relationships and problem-solution expertise consistently outperform product specs, and that the marketers who win are the ones who start with content and customer insight rather than keyword lists.

David walks through his approach to building authority in a new market, from launching podcasts and conducting customer interviews to creating mind maps and repurposing content across formats. He then dives into his perspective on AI, arguing that it won’t save teams that lack strong systems, management discipline, and the ability to pressure-test their own work. He shares his framework for agentic workflows, breaking down the difference between skills and agents, the importance of validation loops and structured data (RAG), and how voice-first input is reshaping his personal productivity. He also reflects on his unconventional path from touring music and healthcare into marketing leadership, and shares his take on AI’s impact on jobs and the SaaS landscape.

In this episode, we cover:

  • Why E-E-A-T (experience, expertise, authority, trust) matters more than product specs when marketing in emerging categories

  • How to build market authority from scratch using podcasts, customer interviews, and content repurposing

  • Why AI amplifies existing systems instead of replacing them, and how to build agentic workflows with validation loops

  • Using voice-first input and a “second brain” RAG approach to unlock personal productivity with AI

If you’re a B2B marketing leader navigating a new or technical category and wondering how to layer AI into your workflow without losing the human judgment that makes your marketing credible, David’s systems-first framework is the reality check you need.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

]]><![CDATA[Aaron Bean: Arm Your Buyer Champion to Win CFO Approval - Episode #45]]>https://www.connecttomarket.com/p/arm-your-buyer-champion-to-win-cfo-approvalhttps://www.connecttomarket.com/p/arm-your-buyer-champion-to-win-cfo-approvalThu, 30 Apr 2026 09:01:37 GMTWhat if your biggest competitor isn’t another vendor, but your buyer’s fear of making the wrong decision?

In this episode of Connect To Market, host Casey Cheshire sits down with Aaron Bean, Co-Founder and Head of Go-to-Market at Supercase.ai, to explore why the most dangerous competitor in B2B isn’t a rival product, but buyer indecision. Aaron makes the case that marketers need to connect to their market by focusing on the late-stage buyer journey, equipping champions to win the internal sale in a room the seller will never be in, especially when the CFO starts asking what the problem is costing and why it can’t be fixed internally.

Aaron shares research showing 61% of deals are lost to indecision and breaks down the three options every buyer weighs: do nothing, build, or buy. He walks through a framework for building decision confidence by quantifying the cost of inaction, creating CFO-credible business cases, and mapping internal advocacy moments into the buyer journey. He also introduces tracking “business case attach rate” as a leading indicator of deal health, and shares lessons from his background in philosophy, entrepreneurship, and global go-to-market work at Lenovo.

In this episode, we cover:

  • Why 61% of B2B deals are lost to buyer indecision, not competitors, and how to fight back

  • How to arm buyer champions with CFO-credible business cases that quantify the cost of doing nothing

  • Adding internal advocacy moments to your buyer-journey map so champions aren’t left unsupported

  • Tracking “business case attach rate” as a leading indicator of deal confidence and close rates

If you’re a B2B marketing leader watching qualified deals stall in committee and losing to “no decision,” Aaron’s framework for building decision confidence and arming your buyer champions is the playbook you’ve been missing.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

]]><![CDATA[Brandon Pittser: Drink Your Own Kool-Aid to Build Marketing That Converts - Episode #44]]>https://www.connecttomarket.com/p/brandon-pittser-drink-your-own-koolhttps://www.connecttomarket.com/p/brandon-pittser-drink-your-own-koolThu, 23 Apr 2026 13:05:20 GMTIs your marketing falling flat because you don’t actually believe in what you’re selling?

In this episode of Connect To Market, host Casey Cheshire sits down with Brandon Pittser, VP of Marketing and Funding Development at Filament Games, to explore how marketers can connect to their market by leading with authenticity instead of automation. Brandon makes the case that the most effective marketing starts with genuinely believing in your organization’s value, and explains why formulaic, AI-templated outreach is eroding trust with buyers. He shares why humility, honesty, and respecting your audience’s intelligence are the real competitive advantages in a landscape flooded with generic messaging.

Brandon walks through his playbook for internalizing a company’s story, from interviewing discipline leaders to synthesizing perspectives and aligning teams around core value. He then breaks down how Filament Games drives growth through a disciplined inbound content engine, including long-running SEO-driven blogging, a structured editorial calendar, and an expanding video strategy built around repurposing livestreams into short-form clips. He also shares how to build modular content campaigns, maintain editorial flexibility, and lean into your organization’s existing strengths to create content that compounds over time.

In this episode, we cover:

  • Why authentic belief in your product is the foundation of marketing that resonates and converts

  • How to align your team around a unified company story by interviewing internal leaders and synthesizing their perspectives

  • Building a disciplined inbound content engine with SEO-driven blogging and a flexible editorial calendar

  • Expanding into short-form video by repurposing livestreams and leaning into organizational strengths

If you’re a marketing leader tired of watching templated outreach fall flat and looking for a more genuine, sustainable approach to content and demand generation, Brandon’s framework for authentic, inbound-first marketing is one worth stealing.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

]]><![CDATA[Max Maurier: Essential Marketing Adaptation Skills in the AI Age - Episode #43]]>https://www.connecttomarket.com/p/max-maurier-essential-marketing-adaptationhttps://www.connecttomarket.com/p/max-maurier-essential-marketing-adaptationThu, 16 Apr 2026 09:01:49 GMTHow 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 success

  • How to align marketing with broader business objectives to increase impact and influence

  • Practical ways to apply AI across marketing teams without over-relying on it

  • How to use data, analytics, and systems to earn trust and a seat at the executive table

If 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.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

]]><![CDATA[Alex Schutte: 6 Ways To Drive Revenue & Earn Executive Trust - Episode #42]]>https://www.connecttomarket.com/p/alex-schutte-6-ways-to-drive-revenuehttps://www.connecttomarket.com/p/alex-schutte-6-ways-to-drive-revenueThu, 09 Apr 2026 09:01:47 GMTWhat 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 strategy

  • How to standardize definitions and build a single source of truth

  • Using a bow tie model to understand growth across the full customer lifecycle

  • Aligning marketing efforts to revenue and using LTV to guide smarter decisions

If 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.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

]]><![CDATA[Melissa Moody: Concentric Circles, Empowering Teams & Customer Success as Marketing - Episode #41]]>https://www.connecttomarket.com/p/melissa-moody-concentric-circleshttps://www.connecttomarket.com/p/melissa-moody-concentric-circlesThu, 02 Apr 2026 09:02:34 GMTWhat 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 landscape

  • Understanding and applying the concentric circles of influence framework

  • Enabling employees and internal stakeholders as authentic brand advocates

  • Leveraging partnerships and customer success as powerful growth drivers

If 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.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

]]><![CDATA[Ian Dowe: Building a Solid Foundation, Embracing Creativity & Data-Driven Decisions - Episode #40]]>https://www.connecttomarket.com/p/ian-dowe-building-a-solid-foundationhttps://www.connecttomarket.com/p/ian-dowe-building-a-solid-foundationThu, 26 Mar 2026 09:02:33 GMTHow 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 campaigns

  • Aligning product, messaging, and GTM strategy using buyer needs and the KANO model

  • Reframing websites as buyer enablement platforms that drive deeper funnel engagement

  • Building scalable marketing systems across MarTech, processes, and revenue metrics

If 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.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

]]><![CDATA[Bill Kenney: Trade Show Masterclass - Episode #39]]>https://www.connecttomarket.com/p/bill-kenney-trade-show-masterclasshttps://www.connecttomarket.com/p/bill-kenney-trade-show-masterclassThu, 19 Mar 2026 09:01:23 GMTHow 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 designs

  • The power of short, strategic conversations over lengthy sales pitches

  • Why cluttered booths and generic giveaways can hurt your brand presence

  • Bill’s framework for turning trade shows into high-performing lead gen channels

If 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!

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

]]><![CDATA[Angela Earl: Honest Conversations, Moving Feedback Through Teams & Using Real Signals - Episode #38]]>https://www.connecttomarket.com/p/angela-earl-honest-conversationshttps://www.connecttomarket.com/p/angela-earl-honest-conversationsThu, 12 Mar 2026 09:02:21 GMTHow 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 feedback

  • Building a shared understanding of the customer across go-to-market teams

  • Capturing and sharing real customer signals through tools and systems

  • Creating a regular feedback cadence to prevent insights from getting stuck in silos

If 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.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

]]><![CDATA[Valerie Zargarpur: Crafting Brand Stories & Cybersecurity Differentiation - Episode #37]]>https://www.connecttomarket.com/p/valerie-zargarpur-crafting-brandhttps://www.connecttomarket.com/p/valerie-zargarpur-crafting-brandThu, 05 Mar 2026 10:01:29 GMTHow 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 them

  • Building a cohesive narrative from customer insights and validated use cases

  • Leveraging origin stories to create brand personality and emotional connection

  • Iterative testing of messaging to ensure clarity, simplicity, and resonance

If 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.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/.

]]><![CDATA[John Rougeux: Category Strategy, Inflection Points & Executive Alignment - Episode #36]]>https://www.connecttomarket.com/p/john-rougeux-category-strategy-inflectionhttps://www.connecttomarket.com/p/john-rougeux-category-strategy-inflectionThu, 26 Feb 2026 10:01:33 GMTHow 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 influence

  • How to define the right problem through customer conversations

  • How category maturity shapes whether you evangelize, niche down, or lead

  • Why strategy must be distilled into a narrative that aligns teams and drives growth

If 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.

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Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

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