<![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/podcastSubstackThu, 08 Oct 2026 22:37:50 GMT<![CDATA[Why Your Marketing Can't Connect If Your Company Isn't Aligned: Justin Brady - Episode # 67]]>https://www.connecttomarket.com/p/why-your-marketing-cant-connect-ifhttps://www.connecttomarket.com/p/why-your-marketing-cant-connect-ifThu, 08 Oct 2026 16:00:14 GMTIn this episode of Connect To Market, host Casey Cheshire sits down with Justin Brady, founder of Cultivate and a PR, communications, and GTM strategist, to explore why internal alignment is the foundation for connecting with your market. Justin argues that before companies worry about campaigns, content, PR, or demand generation, they need to understand their purpose and get everyone moving toward the same destination. When teams are aligned around a shared “peak” and “path,” they can communicate the same core idea in their own voices without sounding scripted or inconsistent.

Justin explains how his “peak and path” framework helps organizations clarify where they’re going, why they’re going there, and how that clarity can shape everything from marketing and sales to recruiting and customer conversations. He also shares why leaders need to listen more closely to the ideas already inside their organizations, using small experiments to build trust instead of dismissing ideas before they’re tested. Along the way, he breaks down why demographics aren’t always the best way to understand an audience, how brands can identify the trust channels their customers already rely on, and why trying to build a following from scratch is often the wrong approach. The conversation closes with a look at authenticity, audience-specific messaging, and how a brand can turn a clear understanding of its audience into a consistent experience at every touchpoint.

Takeaways:

  • Align your team before you market to your audience. Get leadership, sales, marketing, HR, and other teams aligned around a shared purpose and direction. Justin’s “peak and path” framework gives organizations a clear North Star while leaving room to adapt how they get there.

  • Listen to the ideas already inside your organization. Great ideas don’t always need more creativity. They need leaders who are willing to listen, empathize, and build trust. Small experiments can help teams test ideas and prove their value before making a bigger investment.

  • Find where your audience already trusts you. Don’t try to build a following from scratch. Talk to your existing customers and identify the publications, events, communities, people, and other channels they already rely on for information. Understanding your audience’s shared values can be more useful than relying on demographics alone.

  • Keep your message consistent, but make it relevant. Authenticity doesn’t mean saying the exact same thing to everyone. Your company’s core purpose should stay consistent, while the way you communicate it can shift based on who you’re talking to and what matters to them.

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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[What Marketers Can Learn From Improv: Danielle Radden - Episode #66]]>https://www.connecttomarket.com/p/what-marketers-can-learn-from-improvhttps://www.connecttomarket.com/p/what-marketers-can-learn-from-improvThu, 01 Oct 2026 09:03:02 GMTIn this episode of Connect To Market, host Casey Cheshire welcomes Danielle Radden, CMO at Magic Door, to explore why the best way to connect with your market may be to stop assuming you already know what your customers want. Danielle shares her unconventional approach to marketing through the lens of improv, where being open-minded, listening closely, and adapting to what happens in the moment can lead to better customer conversations and stronger strategies.

Danielle explains how marketers can apply the principles of improv by setting aside assumptions, embracing the information customers provide, and using a “yes, and” mindset rather than telling customers what they need. She also shares her approach to “market-led marketing,” from attending industry events and listening to the questions people are asking to building small experiments and following the solutions that gain traction. Plus, Danielle discusses the importance of human connection in building customer advocates, why your network can shape your career, and her cardinal rule for using AI: you can’t use AI to do something you can’t do yourself.

Takeaways:

  • Approach your market with an open mind. Set aside your assumptions and let customers establish the “scene.” Ask questions, listen to what they are experiencing, and adapt your strategy based on what you learn.

  • Use “yes, and” to create better customer conversations. Rather than telling customers what they need, embrace what they tell you and build from there. Marketing should be a reciprocal conversation, not a constant stream of features and messaging.

  • Let the market lead your marketing. Danielle recommends going to industry events, listening to the conversations and questions happening around you, and using those insights to identify problems worth solving. Start small, test an MVP, and follow where your audience leads you.

  • Use AI to amplify your skills, not replace them. AI can help you learn, improve your work, and move faster, but marketers still need to understand the fundamentals behind what they are creating. Without that foundation, it becomes much harder to recognize or fix what AI gets wrong.

Links:

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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[Why Your Brand Sounds Like Everyone Else's AI-Generated Content: Brett Van Buskirk - Episode # 65]]>https://www.connecttomarket.com/p/why-your-brand-sounds-like-everyonehttps://www.connecttomarket.com/p/why-your-brand-sounds-like-everyoneThu, 24 Sep 2026 09:02:00 GMTIs your brand sounding exactly like everyone else’s because AI made “being everywhere” too easy?

In this episode of Connect To Market, host Casey Cheshire sits down with Brett Van Buskirk, VP of Marketing at TrueML, to explore how marketers can connect to their market by staying human and accessible instead of hiding behind the same AI-polished, on-brand talking points as everyone else. Brett argues that AI has erased the old distribution problem, so scale and speed are no longer differentiators. What’s left is authenticity: leaders and brands willing to be curious, show up in person, and represent themselves as people rather than repeating company lines.

Brett walks through why “sounding like a robot” is now a liability, drawing on his time visiting small businesses at Intuit and building one of the first digital mortgage apps at Blend, where his team assumed loan officers wanted to manage deals from their phones while out of the office, only to learn they’d rather just call their team back at the desk. It’s a sharp reminder that even well-researched personas can miss how people actually want to work. He also makes the case for taking bigger creative risks since most of them carry less downside than marketers assume, and shares how he’s applying AI internally for competitive intelligence while still insisting that curiosity and direct customer observation can’t be automated. The conversation closes with Brett’s non-linear path from consulting to product marketing, and his advice for giving yourself permission to grow at your own pace instead of chasing every trend on LinkedIn.

In this episode, we cover:

  • Why AI has removed the old distribution barrier and made “sounding like everyone else” marketing’s biggest new risk

  • How real customer observation, like watching a shopkeeper manage inventory or seeing loan officers actually work in the field, surfaces insights research alone won’t

  • A three-move, no-budget framework for connecting to market: authentic social presence, mining your own customer intelligence, and getting close to product decisions

  • Why marketers systematically overestimate risk, and how to build a career and a brand around calculated, uncomfortable bets

Links:

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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[ Product Marketing in the Age of AI: Beth Barach - Episode #64]]>https://www.connecttomarket.com/p/product-marketing-in-the-age-of-aihttps://www.connecttomarket.com/p/product-marketing-in-the-age-of-aiFri, 18 Sep 2026 09:01:09 GMTIs your product marketing drowning in features your customers never asked for?

In this episode of Connect To Market, host Casey Cheshire sits down with Beth Barach, VP of Product Marketing at Brinqa and a cybersecurity marketing leader, to explore how marketers can connect to their market by escaping the “inside-out” trap of messaging that leads with features instead of customer problems. Beth explains why this trap persists: engineering teams are measured on feature-release velocity, and faster cycles and AI-assisted development only pour more fuel on the fire. Her antidote is to “knit the sweater” by deciding what to market, to whom, and translating technical value into business value.

Beth shares her playbook for ruthless prioritization, making the case that not every feature should be marketed to everyone. She walks through structured customer listening techniques, including in-room prioritization exercises with red, yellow, and green sticky notes that force real tradeoffs and surface true customer needs. The conversation also covers the growing backlash against “AI slop” in content, how Beth uses AI as an assist for competitive intelligence and organizing notes rather than replacing human judgment, and her non-linear career path from English literature into technology marketing.

In this episode, we cover:

  • Why “inside-out” messaging persists and how engineering incentives drive feature bloat in the AI era

  • How to “knit the sweater” by choosing what to market, to whom, and translating technical value into business value

  • Structured customer listening techniques, including sticky-note prioritization exercises that force tradeoffs and reveal true needs

  • Using AI as an assist for competitive intelligence and note organization while avoiding “AI slop” in your content

If you’re a marketing leader watching feature-packed messaging fall flat with buyers, Beth’s framework for prioritized, customer-first product 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 Beth:

Ways to Tune In:

  • Spotify:

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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[What Most B2B Marketers Miss When They Chase Digital Scale: Amy Sitnick - Episode #63]]>https://www.connecttomarket.com/p/what-most-b2b-marketers-miss-whenhttps://www.connecttomarket.com/p/what-most-b2b-marketers-miss-whenThu, 03 Sep 2026 09:01:44 GMTIn this episode of Connect To Market, host Casey Cheshire sits down with Amy Sitnick, VP of Marketing at Viedoc, to talk about what it actually means to bring humanity back into B2B marketing. Amy makes the case that knowing your buyers, your clients, your internal stakeholders, and even the influencers writing about your industry is the real starting point for any go-to-market strategy, and that the fastest way to learn what they need is to sit down with the people who talk to them every day, from client-facing colleagues to the sales reps carrying the target list. She walks through how one conversation with her sales team about a stalled emerging product turned into a direct mail campaign built around a tech-enabled water bottle and a personal note, a play that got some of their most hard-to-reach prospects to respond after everything digital had failed.

Amy also gets into her three-move framework for building a connect-to-market strategy with zero ad budget: interview internal subject matter experts like customer success reps, not just the C-suite, for thought leadership content; partner with the smaller, industry-specific influencers who can actually speak to your buyers; and treat sales enablement as free marketing that just needs the right content behind it. She’s candid about where AI is helping her team, including a branded PowerPoint template that keeps AI-generated content on-brand, and where it’s making marketing noisier, cautioning that without a human in the loop your brand can turn into “a walking em dash.” Amy also opens up about her path from studying Spanish and international relations to running B2B marketing across financial services and now life sciences, and the shift in mission that came with it, from helping people reach their financial goals to giving patients hope.

In this episode, we cover:

  • Where to look inside your own company for the subject matter experts and stories that make thought leadership actually credible

  • Why unique, unexpected outreach can outperform digital channels when it’s backed by real research into a prospect’s pain points

  • How to pick influencer partners based on relevance to your buyers rather than follower count

  • What it takes to scale content production with AI without losing the authenticity that makes a brand trustworthy

  • How tying your team’s work to a greater sense of purpose changes the way marketing shows up day to day

Links:

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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[How to Build an AI-Powered ABM Strategy: Elyssa Steiner - Episode # 062]]>https://www.connecttomarket.com/p/how-to-build-an-ai-powered-abm-strategyhttps://www.connecttomarket.com/p/how-to-build-an-ai-powered-abm-strategyThu, 27 Aug 2026 09:00:35 GMTIn this episode of Connect To Market, host Casey Cheshire sits down with Elyssa Steiner, CMO of Kahua, to explore how B2B marketing leaders can build stronger buyer connection through a mix of field research and AI-driven execution. Elyssa makes the case that AI can scale what you already know, but it can’t invent what you haven’t learned yet, and that field visits, sales call shadowing, and trade show attendance are what turn AI-synthesized data into real buyer insight. She shares how she used her first 60 days as CMO to build ideal customer profile (ICP) frameworks for nine core verticals, why she sends a marketer to every trade show her company exhibits at, and how listening in on sales calls became one of the highest-value habits on her team.

Elyssa walks through how Kahua’s AI adoption evolved from basic custom GPTs to purpose-built AI skills and an account-based marketing (ABM) agent that scaled the team’s target account list from a capacity-constrained “Magic 18” to more than 400 one-to-one and one-to-few accounts. She breaks down why she believes the most critical skill for a modern marketer is being a really good editor, not a really fast prompter, and how her team is shifting from repetitive execution work into real marketing strategy as AI takes over the busy work. She also opens up about her own career path from retail buying to startup sales to CMO, and the philosophy that has shaped her decision-making ever since: hard choices, easy life; easy choices, hard life.

In this episode, we cover:

  • Why closing the physical distance between marketing and the buyer, not just better AI tools, is what actually builds buyer understanding

  • How to build ICP frameworks for multiple verticals in your first 60 days and turn that work into a springboard for AI tools and content strategy

  • How to scale an ABM strategy from a handful of target accounts to hundreds once AI takes the busy work off your team’s plate

  • Why “don’t let comfort make your decisions” is the throughline for marketing leaders moving from individual contributor to CMO

If you’re a marketing leader trying to figure out how AI actually fits into your team’s workflow without losing the human judgment that makes marketing work, Elyssa’s approach to pairing field experience with AI-powered execution 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 Elyssa:

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More About Elyssa:

Elyssa Steiner is Chief Marketing Officer at Kahua and a B2B growth leader with more than 15 years of experience building brands, leading high-performing teams, and developing integrated marketing strategies that drive pipeline, customer engagement, and measurable business growth. At Kahua, she leads the company’s marketing vision and go-to-market strategy across brand, demand generation, product marketing, customer advocacy, and marketing operations. She is also advancing an AI-fluent approach to marketing, using AI to uncover insights, scale execution, and improve efficiency while keeping strategy, creativity, and customer understanding at the center.

Before joining Kahua, Elyssa served as Chief Marketing Officer at Cantaloupe, where she helped guide the company through a period of significant growth and transformation. During her final two years, Cantaloupe grew annual recurring revenue from approximately $250 million to $310 million while she led marketing through multiple acquisitions, portfolio and brand integration, and the company’s eventual sale. Her expertise spans revenue-driven marketing, go-to-market strategy, sales alignment, customer growth, fintech, and emerging technology. She has shared her perspective on The Revenue-Driven CMO, multiple Leaders in Payments episodes, and a live Marketing on Mars CMO panel in San Francisco. Elyssa holds a master’s degree in Communication and Leadership from Gonzaga University and a bachelor’s degree in Business and Marketing from the University of Washington.

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[Scaling Client Relationships Through Community: Paul Jones - Episode #61 (Re-Air)]]>https://www.connecttomarket.com/p/scaling-client-relationships-throughhttps://www.connecttomarket.com/p/scaling-client-relationships-throughThu, 20 Aug 2026 09:02:13 GMTIn this episode of Connect to Market, host Casey Cheshire welcomes Paul Jones, Moderator of the Connect To Market Community & Founder of Bridgio. Paul shares lessons from building over 40 successful communities and explains why real market connection goes beyond launching products or campaigns.

He emphasizes the importance of deeply understanding your Ideal Client Persona (ICP), using empathy to craft resonant messaging, and creating space for meaningful, value-driven interactions. Paul also challenges the overreliance on technology, encouraging marketers to start simple and stay focused on human connection.

In this episode, we cover:
~ The difference between going to market and connecting to it
~ How to understand your ICP beyond the surface level
~ Why low-tech, high-value engagement builds stronger communities
~ Real examples of community-led product and messaging success

If you're looking to engage your audience more meaningfully and build communities that drive real connection, this episode offers practical and inspiring insights.

🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.

Connect with Paul:
LinkedIn: https://www.linkedin.com/in/pauljones101/
Bridgio: https://bridgio.io/

Ways to Tune In:
Spotify:



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/

]]><![CDATA[Turning Live Events into Podcast Magic: Casey Cheshire - Episode # 60]]>https://www.connecttomarket.com/p/turning-live-events-into-podcasthttps://www.connecttomarket.com/p/turning-live-events-into-podcastThu, 13 Aug 2026 09:01:49 GMTIn this special edition of Connect To Market, host Casey Cheshire joins us live from Las Vegas and the Ringmaster Mobile Podcast Studio at Black Hat to share why live events and podcasts can be such a powerful combination for B2B marketers. In between recordings, Casey breaks down how brands can use podcasting to create more human connection, generate buzz around an event, turn conversations into content, and build stronger relationships with prospects and customers.

Casey shares some of the conversations he’s had with members of the Connect To Market community at Black Hat, including discussions around AI, growth, happiness, and the importance of maintaining a human balance in an increasingly noisy digital world. He also walks through several practical ways to bring a podcast to your next event, from capturing quick “hot takes” to using podcast conversations as a reason for prospects to show up for meetings.

The episode also explores how live podcasting can create more authentic customer stories, strengthen relationships, and surface the thought leadership already sitting inside your organization. Casey’s takeaway? As AI-generated content and digital noise continue to increase, genuine human connection becomes even more valuable.

In this episode, we cover:

  • Why live events and podcasts can create a powerful combination for human connection

  • How to use quick “hot takes” to generate buzz and turn event conversations into podcast content

  • Why podcast interviews can give prospects a better reason to show up for meetings

  • How AI and content “slop” are making human connection more important than ever

If you’re heading to a conference or planning your next live event, Casey’s playbook offers simple ways to turn the conversations happening around you into meaningful relationships, content, and opportunities.

🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.

Connect with Casey:

LinkedIn: linkedin.com/in/caseycheshire

Website: ringmaster.com

Ways to Tune In:

  • Spotify:

  • Apple Podcasts:

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[The AI Prompting Masterclass Every Marketer Needs To Hear: Keven Ellison - Episode #59 (RE-AIR)]]>https://www.connecttomarket.com/p/keven-ellison-the-ai-prompting-masterclass-71ehttps://www.connecttomarket.com/p/keven-ellison-the-ai-prompting-masterclass-71eThu, 06 Aug 2026 09:01:49 GMTIn this episode of Connect To Market, host Casey Cheshire welcomes Keven Ellison, Vice President of Marketing at A.I.S., to explore how AI is transforming marketing, content creation, and business systems while still honoring the experience and strategy that drive real results. Keven discusses the rapid advancements in AI and why being proficient in AI is essential for marketers to stay relevant. He shares his journey of learning to prompt effectively and building AI workflows that have drastically increased productivity. The opportunity lies in using AI to scale strategically while keeping messaging aligned with what truly matters to buyers.

He shares why marketers must guide AI tools like a new team member by equipping them with brand knowledge, audience insights, and clear instructions to ensure quality and consistency. From building strong workflows to creating human feedback loops, Keven explains how marketers can accelerate content creation without sacrificing strategy or creativity. He also highlights the future of AI in organizations, predicting the transformation of traditional CRMs and human resource departments into AI-driven systems, and emphasizes the need for marketers to adopt and adapt to AI technologies to lead effectively.

In this episode, we cover:

  • Why marketers must stay ahead of AI trends to remain competitive

  • How to master AI prompts and build scalable workflows

  • How AI is changing the future of work, including CRM and HR systems

  • Why human creativity and business experience remain essential

If you’re a marketing leader looking to leverage AI while strengthening your strategy and creativity, Keven’s insights provide a smart, practical path to modern marketing success.

🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.

Connect with Keven:

https://www.ais-now.com/

Ways to Tune In:

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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[The Pipeline Wake-Up Call Every B2B Marketer Needs to Hear: Randy Brasche - Episode #58]]>https://www.connecttomarket.com/p/the-pipeline-wake-up-call-every-b2b-marketer-needs-to-hearhttps://www.connecttomarket.com/p/the-pipeline-wake-up-call-every-b2b-marketer-needs-to-hearThu, 30 Jul 2026 09:02:10 GMTWhat if the reason marketing keeps getting sidelined is because marketers are measuring the wrong things?

In this episode of Connect To Market, host Casey Cheshire sits down with Randy Brasche, Chief Revenue Officer at Spot-On, Principal at Adaptive B2B Solutions, and author of “Some Assembly Required,” to explore how marketers can connect to their market by getting close to revenue rather than hiding behind conversions and volume metrics. Brasche argues that marketers must understand pipeline coverage multiples, participate in pipeline calls with confidence, and build strategy around ICP definition, account engagement, and the full customer lifecycle, not just top-of-funnel lead generation. He makes the case that the marketers who earn a seat at the revenue table are the ones who can speak the language of pipeline math and tie their work directly to acceleration, churn reduction, and expansion.

Brasche walks through why most marketers default to volume and conversion metrics that don’t resonate with revenue leaders, and how shifting focus to pipeline multiples and lifecycle engagement changes the entire conversation. He breaks down the math behind pipeline coverage, explains how to identify the 10 percent of your market that is actually in-market at any given time, and shares how intent data and ICP refinement can sharpen targeting. The conversation also dives into the AI balance: Brasche outlines how AI can improve ICP definition, context delivery, and messaging quality at scale, but warns that data cleanliness and human oversight are non-negotiable for accuracy.

In this episode, we cover:

  • Why marketers must learn pipeline coverage math and participate in pipeline calls to earn credibility with revenue leaders

  • How to move beyond volume and conversion metrics to focus on lifecycle engagement, churn reduction, and expansion

  • Using AI to sharpen ICP definition and deliver context at scale while maintaining data cleanliness and human oversight

  • Why personal agency, confidence, and conviction are the most important traits for marketers in the AI era

If you’re a marketing leader who feels disconnected from revenue conversations or unsure how to prove your impact beyond MQLs and conversion rates, Brasche’s pipeline-math framework and revenue-proximity mindset is the playbook you need to change the conversation.

🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.

Connect with Randy:

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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[What Most B2B Podcasts Get Wrong About Success Metrics: Ryan Becker - Episode #57]]>https://www.connecttomarket.com/p/what-most-b2b-podcasts-get-wronghttps://www.connecttomarket.com/p/what-most-b2b-podcasts-get-wrongThu, 23 Jul 2026 09:00:57 GMTWhat if the biggest threat to your podcast isn’t your audience, but the people inside your own company?

In this episode of Connect To Market, host Casey Cheshire sits down with Ryan Becker, Founder of Intuitive Podcasting, to explore how marketers can connect to their market by treating internal stakeholders as a primary audience and approaching their podcast like a true product. Ryan makes the case that executives, bosses, and clients control the freedom, trust, and resources marketers need to succeed, and that misalignment with these internal players is the fastest path to burnout. He shares why most marketers neglect internal buy-in, how to document tests when leadership insists on a direction, and how to translate marketing work into business value that resonates beyond the marketing department.

Ryan walks through why traditional podcast analytics are fundamentally flawed and argues that success should be defined by the right audience and tangible outcomes like leads, guest conversions, feedback loops, and revenue, not download counts. He reveals how shows with under 500 downloads can generate millions in pipeline and breaks down the most common mistakes companies make when they forget a podcast is a listener-focused product, from self-celebratory milestone episodes to overly promotional content. He also weighs in on why most brands aren’t equipped to run podcast-driven communities or internal podcasts well, and shares his conviction that as AI floods the content landscape, the premium on authenticity, lived experience, and asking questions only you can ask has never been higher.

In this episode, we cover:

  • Why treating internal stakeholders as your first “target market” unlocks the freedom and resources to do your best work

  • How to redefine podcast success around business outcomes instead of flawed download metrics

  • The most common mistakes that turn a listener-focused product into self-serving content nobody wants

  • Why AI is raising the bar on authenticity and the irreplaceable value of lived-experience questions

If you’re a marketing leader struggling to get executive buy-in for your podcast or wondering why your show isn’t driving real business results, Ryan’s framework for aligning stakeholders and building a listener-first product 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 Ryan:

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  • Spotify:

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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[Karl Van den Bergh: Confident Positioning Stands Out, Playing It Safe Gets Forgotten - Episode #56]]>https://www.connecttomarket.com/p/confident-positioning-stands-outhttps://www.connecttomarket.com/p/confident-positioning-stands-outThu, 16 Jul 2026 09:02:17 GMTIs your brand losing deals because you sound exactly like every other vendor in the market?

In this episode of Connect To Market, host Casey Cheshire sits down with Karl Van den Bergh, Chief Market Officer of Illumio, to explore how marketers can connect to their market by knowing who they are and leading with authenticity in a noisy, AI-saturated landscape. Karl makes the case that the number-one requirement for market connection is self-awareness, arguing that companies fail when they haven’t crystallized their mission, values, and brand, or when they’re afraid to be who they really are. He explains why clear, consistent positioning is the foundation of effective marketing and how trust is built through genuine differentiation, not trend-chasing.

Karl walks through Illumio’s strategic pivot from technology-led messaging around “micro-segmentation” and “zero trust segmentation” to the simpler, more differentiated value proposition of “breach containment,” sharing early campaign traction and the importance of CEO alignment in making bold positioning shifts stick. He also breaks down how bold, opinionated creative helps brands stand out, why AI can enable one-to-one marketing at scale while amplifying human-to-human experiences, and how resilience, experimentation, and a willingness to “break stuff” are essential for marketers who want to push boundaries and grow.

In this episode, we cover:

  • Why knowing yourself as a company and marketer is the foundation for authentic market connection and trust

  • How Illumio shifted from jargon-heavy positioning to the clear, differentiated message of “breach containment” and the early results it drove

  • Using bold, opinionated creative to cut through a crowded market and make your brand memorable

  • How AI enables one-to-one marketing at scale while keeping human-to-human experiences at the center

If you’re a marketing leader struggling to differentiate in a sea of similar-sounding competitors and looking for a framework to simplify your message, own a category, and lead with authenticity, Karl’s approach to positioning and brand courage 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 Karl:

Ways to Tune In:

  • Spotify:

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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[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/

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